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Aziridine

Aziridines are a class of heterocyclic organic compounds containing a three-membered ring with one nitrogen atom.
These versatile compounds are widely used in organic synthesis and have applications in medicinal chemistry, materials science, and other fields.
Aziridines exhibit unique reactivity due to the strained ring structure, allowing for diverse transformations and functionalization.
They can be synthesized through various methods and play a key role in the construction of more complex molecular scaffolds.
Researchers studying aziridines can leverage PubCompare.ai's AI-powered protocl comparisons to optimize their research, identifying the best protocols from literature, preprints, and patents to enhance reproducibility and improve their results.
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Most cited protocols related to «Aziridine»

Functional Group Identification Algorithm

Cited 5 times

The majority of FGs contain heteroatoms. Therefore our approach is based on processing heteroatoms and their environment with the addition of some other functionalities, like multiple carbon–carbon bonds.
The algorithm is outlined below:

mark all heteroatoms in a molecule, including halogens

mark also the following carbon atoms:

atoms connected by non-aromatic double or triple bond to any heteroatom

atoms in nonaromatic carbon–carbon double or triple bonds

acetal carbons, i.e. sp3 carbons connected to two or more oxygens, nitrogens or sulfurs; these O, N or S atoms must have only single bonds

all atoms in oxirane, aziridine and thiirane rings (such rings are traditionally considered to be functional groups due to their high reactivity).

merge all connected marked atoms to a single FG

extract FGs also with connected unmarked carbon atoms, these carbon atoms are not part of the FG itself, but form its environment.

The algorithm described above iterates only through non-aromatic atoms. Aromatic heteroatoms are collected as single atoms, not as part of a larger system. They are extended to a larger FG only when there is an aliphatic functionality connected (for example an acyl group connected to a pyrrole nitrogen). Heteroatoms in heterocycles are traditionally not considered to be “classical” FGs by themselves but simply to be part of the whole heterocyclic ring. The rationale for such treatment is enormous diversity of heterocyclic systems. For example in our previous study [12 (link)] nearly 600,000 different heterocycles consisting of 1–3 fused 5- and 6- membered rings were enumerated.
After marking all atoms that are part of FGs as described above, the identified FGs are extracted together also with their environment—i.e. connected carbon atoms, when the type of carbon (aliphatic or aromatic) is also preserved.
We do not claim that this algorithm provides an ultimate definition of FGs. Every medicinal chemist has probably a slightly different understanding about what a FG is. In particular the definition of activated sp3 carbons may create some discussion. In the present algorithm we restricted our definition only to classical acetal, thioacetal or aminal centers (i.e. sp3 carbons having at least 2 oxygens, sulfurs or nitrogens as neighbors) and did not consider other similar systems, i.e. alpha-substituted carbonyls or carbons connected to S=O or similar bonds. During the program development phase various such options have been tested, and this “strict” definition provided the most satisfactory results. Extension of FGs also to alpha-substituted carbonyls (i.e. heteroatom or halogen in alpha position to carbonyl) and similar systems more than triple the number of FGs identified, generating many large and rare FGs. Since our major interest was in comparing various molecular datasets and not in reactivity estimation we implemented this strict definition of acetal carbons. To assess the possible reactivity of molecules, various substructures filters are available, as for example already mentioned PAINS [9 ] or Eli Lilly rules [10 (link)].
To illustrate better the algorithm some examples of FGs identified for few simple molecules are shown in Fig. 1.Fig. 1

Example of functional groups identified. Groups are color coded according to their type

, & Ertl P. (2017). An algorithm to identify functional groups in organic molecules. Journal of Cheminformatics, 9, 36.

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Publication 2017

Acetals aziridine Carbon Charcoal, Activated ethylene sulfide Halogens Nitrogen Oxide, Ethylene Oxygen Pain Program Development Pyrrole Sulfur

Purification and Biochemical Analysis of γ-Crystallin

Cited 2 times

Citrate synthase (CS), lysozyme (Lyso), malate dehydrogenase (MDH), protease inhibitor cocktail, methyl chlorothioformate, staurosporine and etoposide were obtained from Sigma-Aldrich Chemical Co. LLC (St. Louis, MO, USA). Aziridine was purchased from ChemService, Inc. (West Chester, PA). All other chemicals were of analytical grade. γ-Crystallin (GC) from bovine lenses was purified as previously described.^{42 (link)}

Nahomi R.B., Huang R., Nandi S.K., Wang B., Padmanabha S., Santhoshkumar P., Filipek S., Biswas A, & Nagaraj R.H. (2013). Acetylation of Lysine92 Improves the Chaperone and Anti-apoptotic Activities of Human αB-Crystallin. Biochemistry, 52(45), 8126-8138.

Publication 2013

aziridine Cattle Citrate (si)-Synthase Crystallins Etoposide Lens, Crystalline Malate Dehydrogenase Muramidase Protease Inhibitors Staurosporine

Quantifying Release of Steroidal Derivatives

Cited 1 time

UV-Visible (UV–Vis-NIR UV 3600-spectrometer Shimadzu Company, Kyoto, Japan) absorbance was considered as an indicator of the release of steroidal oxazoline and aziridine derivatives from electrospun mats. The dehydrated, electrospun, extract-loaded-nanofibrous mats were first divided into 12 × 12 cm² squares and the extracted compound was estimated as a function of the weight mat. The drug loading into CH-PVP nanofibres was 12 mmole/100 gm CH-PVP from each sample, i.e., A, B, C, and D. The specimens were placed in individual vessels containing 50 mL buffer saline phosphate (pH = 7.40), and the vessels were incubated at 310 K. Release experiments were performed by dispersing 200 mg of the ST-CH nanofibers in 50 mL of the buffer solution. After a certain time, 5 mL of the buffer was replaced with the same volume of fresh buffer to maintain a constant volume. A mixture of 3 mL methanol and 2 mL distilled water was prepared and added to each buffer to determine the absorbance by UV-Visible spectroscopy at 300 nm. A standard calibration curve was applied to measure the concentration of the free steroidal oxazoline and aziridine derivatives. The percentage of the released steroidal oxazoline and aziridine derivatives was then calculated based on the initial weight of these compounds incorporated in the electrospun nanofiber mats. The results were plotted over time, up to 60 h.

Gouda M., Khalaf M.M., Shaaban S, & El-Lateef H.M. (2022). Fabrication of Chitosan Nanofibers Containing Some Steroidal Compounds as a Drug Delivery System. Polymers, 14(10), 2094.

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Publication 2022

aziridine Blood Vessel Buffers CH 200 derivatives Methanol Pharmaceutical Preparations Phosphates Saline Solution Spectrum Analysis Steroids

Cytotoxicity Evaluation of Aziridine-Hydrazone Derivatives

Cited 1 time

The Cell Counting Kit-8 (CCK-8) assay (Sigma-Aldrich, St. louis, MO, USA) was used to measure the cytotoxicity of the tested drugs on glioblastoma cells. The amount of the formazan dye generated by the activity of cellular dehydrogenases is directly proportional to the number of living cells.
Glioblastoma cells and NHA cells cultured under traditional adherent conditions (5 × 10³ cells/mL) were grown in 96-well plates for 24 h and treated with the tested compounds (six new synthesized compounds of aziridine–hydrazone derivatives) over a range of concentrations (0, 25, 50, 100, 150, 200, 300, 500 μg/mL).
After 48 h, the extent of cell growth was assessed using the CCK-8 assay. The CCK-8 solution (10 μL) was added to each well, followed by incubation for 3 h at 37 °C. The absorbance of the cell culture medium at 450 nm was determined by a multiplate reader (Glomax Multi Detection System; Promega, Madison, WI, USA). Cell viability was expressed as a percentage of that of the control (untreated) cells. All the results obtained in the study were based on at least three experiments.

Witusik-Perkowska M., Głowacka P., Pieczonka A.M., Świderska E., Pudlarz A., Rachwalski M., Szymańska J., Zakrzewska M., Jaskólski D.J, & Szemraj J. (2023). Autophagy Inhibition with Chloroquine Increased Pro-Apoptotic Potential of New Aziridine-Hydrazide Hydrazone Derivatives against Glioblastoma Cells. Cells, 12(14), 1906.

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Publication 2023

Aziridines Biological Assay Cells Cell Survival Culture Media Cytotoxin derivatives Formazans Glioblastoma Hydrazones Oxidoreductase Promega Substance Abuse Detection

Synthesis of Cyclic Amine Diastereomers

Cited 1 time

In the glovebox, gold precatalyst 7 (6.3 mg, 0.010 mmol, 15 mol %) was dissolved in 0.3 mL dry DCM and added to a dram vial containing NaBArF salt 8 (9.2 mg, 0.010 mmol, 15 mol %). The resulting suspension was added to a screw-cap dram vial containing aziridine 1b (18 mg, 0.069 mmol, 1.0 equiv). A single 0.3 mL portion of DCM was used to rinse the two vials formerly containing the gold precatalyst and the NaBArF salt to aid in complete transfer to the aziridine vial. Finally, Pd₂dba₃ (4.8 mg, 0.0052 mmol, 7.5 mol %) was added to the aziridine mixture as a solution in 0.3 mL DCM. The reaction vessel was capped and stirred at 25 °C in the glovebox 5 d. The crude reaction mixture was then removed from the glovebox and concentrated in vacuo. The mixture was purified using a silica gel pipet column eluting using a gradient 1:0:99 to 1:5:94 NH₄OH:MeOH:CHCl₃. The product was obtained as a mixture of diastereomers (16 mg, 88% yield, d.r. = 1.0 : 1.0). Diastereomer A. ¹H NMR (CDCl₃, 500 MHz): δ 1.69–1.99 (m, 14 H), 2.06 (dd, J = 13.0, 6.6 Hz), 2.59–2.64 (m, 1H), 2.85 (J = 14.0, 7.3 Hz, 1H), 3.20–3.26 (m, 1H), 3.29 (d, J = 13.9 Hz, 1H), 3.81 (t, J = 10.0 Hz, 1H), 4.02 (dd, J = 12.1, 6.7 Hz, 1H), 4.84 (d, J = 13.7 Hz, 1H), 5.03 (q, J = 9.4 Hz, 1H), 5.22 (d, J = 10.3 Hz, 1H), 5.28 (d, J = 17.2 Hz, 1H), 5.78–5.88 (m, 2H). Diastereomer B. 1.69–1.99 (m, 14 H), 2.12 (dd, J = 13.8, 6.5 Hz, 1H), 2.57 (d, J = 8.4 Hz, 1H), ca. 2.79 (dd, 1H), c.a. 3.31 (1H), 3.54–5.63 (m, 1H), 3.85 (d, J = 13.6 Hz, 1H), 4.06 (d, J = 13.4 Hz, 1H), 4.63 (dd, J = 12.9, 8.1 Hz, 1H), 5.08 –5.14 (m, 1H), 5.17–5.25 (m, 2H), 5.70 (d, J = 9.8 Hz, 1H), 6.16 (d, J = 9.9 Hz, 1H). ¹³C NMR (CDCl₃, 125 MHz): 26.8, 26.9, 33.4, 33.4, 33.7, 35.0, 37.0, 39.4, 40.0, 42.6, 49.3, 68.4, 70.6, 72.4, 76.7, 119.3, 133.3. Note: Not all signals were observable. HRMS (GC/EI+): [M]⁺ calcd for C₁₈H₂₇N, 257.2144; found, 257.2137.

Hirner J.J., Roth K.E., Shi Y, & Blum S.A. (2012). Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines. Organometallics, 31(19), 6843-6850.

Publication 2012

Most recents protocols related to «Aziridine»

Synthesis of Aziridine-Cannabinoid Conjugates

Not available on PMC !

Example 37

Aziridine carbamate linked cannabinoid conjugate components are synthesized as follows. A cannabinoid (CBD in this example) is reacted with phosgene (or a suitable phosgene surrogate) and an aminoaziridine ([88714-40-3] in this example) under standard basic conditions to form the desired carbamate linked product.

[Figure (not displayed)]

Aziridine carbonate linked cannabinoid conjugate components are synthesized as follows. A cannabinoid (CBD in this example) is reacted with phosgene (or a suitable phosgene surrogate) and a hydroxyaziridine ([25662-15-1] in this example) under standard basic conditions to form the desired carbonate linked product.

[Figure (not displayed)]

Aziridine ester linked cannabinoid conjugate components are synthesized as follows. The previously reported hydroxymethyl building block [126587-35-7] is treated with base, in this example sodium hydride, to generate the aziridinyl intermediate. Removal of the BOC protecting group followed by alkylation of the resulting amine gives the alkyl aziridine-ester intermediate. Standard hydrolysis of the ester gives the carboxylic acid precursor, which is esterified with the cannabinoid under standard esterification conditions to give the desired product.

[Figure (not displayed)]

Aziridine imidate linked cannabinoid conjugate components are synthesized as follows. A cannabinoid (CBD in this example) is reacted with an imidocarbonyl chloride (in this case [5652-90-4]) and a hydroxyaziridine ([25662-15-1] in this example) under standard basic conditions to form the desired imidate linked product.

[Figure (not displayed)]

Aziridine isourea linked cannabinoid conjugate components are synthesized as follows. A cannabinoid (CBD in this example) is reacted with an imidocarbonyl chloride (in this case [5652-90-4]) and an aminoaziridine ([88714-40-3] in this example) under standard basic conditions to form the desired isourea linked product.

[Figure (not displayed)]

Aziridine phosphorodiamide linked cannabinoid conjugate components are synthesized as follows. Using conditions similar to those referenced in the Scheme, N,N-Dimethylphosphoramidodichloridate ([677-43-0]) is reacted with an aminoaziridine ([88714-40-3] in this example). The adduct is then reacted with a cannabinoid (CBD in this example) under standard basic conditions to form the desired product.

[Figure (not displayed)]

Aziridine thiocarbamate linked cannabinoid conjugate components are synthesized as follows. A cannabinoid (CBD in this example) is reacted with thiophosgene (or a suitable thiophosgene surrogate) and an aminoaziridine ([88714-40-3] in this example) under standard basic conditions to form the desired thiocarbamate linked product.

[Figure (not displayed)]

Aziridine thiocarbonate linked cannabinoid conjugate components are synthesized as follows. A cannabinoid (CBD in this example) is reacted with thiophosgene (or a suitable thiophosgene surrogate) and a hydroxyaziridine ([25662-15-1] in this example) under standard basic conditions to form the desired thiocarbonate linked product.

[Figure (not displayed)]

Aziridine thiophosphinodiamide linked cannabinoid conjugate components are synthesized as follows. Using conditions similar to those referenced in the Scheme, dimethylphosphoramidothioic dichloride ([1498-65-3]) is reacted with an aminoaziridine ([88714-40-3] in this example). The adduct is then reacted with a cannabinoid (CBD in this example) under standard basic conditions, to form the desired product.

[Figure (not displayed)]

US11877988B2. Conjugate molecules (2024-01-23). Diverse Biotech, Inc. [US]. Inventors: Paul Hershberger [US], Philip Arlen [US].

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Patent 2024

Synthesis and Characterization of Multifunctional Crosslinker

Not available on PMC !

Example 14

A 1 L round bottom flask equipped with a condensor was placed under a N₂atmosphere and charged with propylene imine (80.0 gram), n-butyl glycidyl ether (126.0 gram) and K₂CO₃(10.00 gram) and heated to 80° C. in 30 min, after which the mixture was stirred for 21 h at T=80° C. After filtration the excess of PI was removed in vacuo, followed by further purification via vacuum distillation, resulting in a colorless low viscous liquid.

1.92 grams of the resulting material (1-butoxy-3-(2-methylaziridin-1-yl)propan-2-ol) was charged to a reaction flask equipped with a thermometer, together with 0.02 grams of bismuth neodecanoate and 19 grams of dimethylformamide. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere and heated to 50° C. A solution of 2.00 grams of Desmodur N 3600 in 19 grams of dimethylformamide was then added dropwise in 45 minutes to the reaction flask, whereafter the mixture was heated further to 70° C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no NCO-stretch at 2200-2300 cm⁻¹was observed. The solvent was removed in vacuo to obtain a clear, yellowish highly viscous liquid. The calculated molecular weight of the theoretical main component was 1065.74 Da, chemical structure is shown below.

[Figure (not displayed)]

Molecular weight was confirmed by Maldi-TOF-MS: Calcd. [M+Na+]=1088.74 Da; Obs. [M+Na+]=1088.76 Da. The following components with a mass below 580 Da were determined by LC-MS and quantified:

[Figure (not displayed)]
was present in the composition at 0.36 wt. % and

[Figure (not displayed)]
was present at less than 0.01 wt. %.

Performance of the synthesized compound as a crosslinker was assessed using spot tests on coating surfaces, based on procedures from the DIN 68861-1 standard. For these tests, 0.58 parts of the composition were mixed with 0.60 parts of Proglyde™ DMM (dipropylene glycol dimethyl ether, mixture of isomers) and incubated at 80° C. for 10 minutes under regular agitation. Subsequently, 0.79 parts of the resulting solution were added to 20 parts of NeoRez® R-1005 under continuous stirring, and the resulting mixture was further stirred for 30 minutes. Afterwards, this coating composition was filtered and applied to Leneta test cards using 100 μm wire rod applicators (Test 14-1). For reference, films were also cast from the same composition lacking a crosslinker (Test 14-2). The films were dried for 16 hours at 25° C., then annealed at 50° C. for 1 hour and further dried for 24 hours at 25° C. Subsequently, a piece of cotton wool was soaked in 1:1 EtOH:demineralized water and placed on the film for various timespans. After removal of the EtOH and 60 minutes recovery, the following results were obtained (a score of 1 indicates complete degradation of the film, 10 indicates no damage visible):

Ethanol spot test

Sample30 min60 min120 min300 min

Test 14-18887

Test 14-21111

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Ex. 141.11.11.10.80.80.61.01.00.90.90.80.6

US11878969B2. Multi-aziridine compound (2024-01-23). COVESTRO (NETHERLANDS) B.V. [NL]. Inventors: Gerardus Cornelis Overbeek [NL], Patrick Johannes Maria Stals [NL], Daan Van Der Zwaag [NL], Alfred Jean Paul Bückmann [NL].

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Patent 2024

Atmosphere Aziridines Bismuth CD3EAP protein, human Desmodur N dimethyl ether Dimethylformamide Distillation Ethanol farnesyl-protein transferase-alpha Filtration Glycols Gossypium Isomerism Liver Extracts Mutagenicity Tests n-butyl glycidyl ether Nitrogen potassium carbonate propyleneimine Solvents Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Thermometers Vacuum Viscosity

Synthesis and Genotoxicity Evaluation of Polyurethane Polymer

Not available on PMC !

Example 2

508.7 grams of Agisyn 2844 and 0.26 grams of phenothiazine were charged to a stainless steel reactor equipped with a thermostat. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was than heated to 35° C., and subsequently 25.3 grams of propylene imine was added over 30 minutes. The mixture was then further heated to 45° C. and kept at that temperature for 36 hours. The resulting mixture, with a calculated molecular weight of the main component of 800.48 Da, was discharged and tested for genotoxicity. Chemical structure is shown below.

[Figure (not displayed)]

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Comp. Ex. 21.11.31.31.31.61.81.11.41.41.11.72.4

5.93 grams of 1-(2-methylaziridin-1-yl)propan-2-ol, 0.02 grams of bismuth neodecanoate and 40.18 grams of 2-methyltetrahydrofuran were charged to a reaction flask equipped with a thermometer. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere and heated to 50° C. A solution of 10.0 grams of Desmodur N 3900 in 40.18 grams of 2-methyltetrahydrofuran was then added dropwise in 45 minutes to the reaction flask, where after the mixture was heated further to 75° C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no NCO-stretch at 2200-2300 cm⁻¹was observed. The solvent was removed in vacuo to obtain a yellowish highly viscous liquid. The calculated molecular weight of the theoretical main component was 849.57 Da, chemical structure is shown below.

[Figure (not displayed)]

Molecular weight was confirmed by Maldi-TOF-MS: Calcd. [M+Na+]=872.57 Da; Obs. [M+Na+]=872.62 Da. The following components with a mass below 580 Da were determined by LC-MS and quantified:

[Figure (not displayed)]
was present in the composition at 1.4 wt. %.

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Ex. 21.11.10.91.11.00.91.0——1.1——

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Patent 2024

Synthesis and Characterization of Aziridine-Containing Polymers

Not available on PMC !

Example 5

2.60 grams of 1-(aziridin-1-yl)propan-2-ol, 0.02 grams of bismuth neodecanoate and 32 grams of dimethylformamide were charged to a reaction flask equipped with a thermometer. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere and heated to 50° C. A solution of 5.00 grams of Desmodur N 3600 in 32 grams of dimethylformamide was then added dropwise in 15 minutes to the reaction flask, where after the mixture was heated further to 70° C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no NCO-stretch at 2200-2300 cm⁻¹was observed. The solvent was removed in vacuo to obtain an opaque highly viscous liquid. The calculated molecular weight of the theoretical main component was 807.52 Da, chemical structure is shown below.

[Figure (not displayed)]

Molecular weight was confirmed by Maldi-TOF-MS: Calcd. [M+Na+]=830.52 Da; Obs. [M+Na+]=830.47 Da.

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Comp. Ex. 51.11.31.31.31.81.91.31.81.81.32.12.2

15.0 grams of Desmodur N 3600, 7.09 grams of 1-(2-methylaziridin-1-yl)propan-2-ol, 8.21 grams of a poly(ethylene glycol) monomethyl ether with an average Mn of 1000 Da, 112 grams of dimethylformamide were charged to a reaction flask equipped with a thermometer. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was than heated to 50° C., 0.03 grams of dibutyltin dilaureate was added and after 15 minutes the mixture was heated further to 70° C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no NCO-stretch at 2200-2300 cm⁻¹was observed. The solvent was removed in vacuo to obtain an opaque highly viscous liquid. The calculated molecular weights of the theoretical main components were 849.57 Da (three aziridines) and 1735.07 Da (two aziridines, 22 EG repeating units), chemical structures are shown below.

[Figure (not displayed)]

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Ex. 51.11.11.21.11.31.31.11.21.11.21.10.9

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Patent 2024

Synthesis and Characterization of Polyurethane Crosslinker

Not available on PMC !

Example 7

3.00 grams of IPDI, 28 grams of DMF and 3.08 grams of 1-(2-methylaziridin-1-yl)propan-2-ol were charged to a reaction flask equipped with a thermometer. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was than heated to 50° C., upon reaching this temperature 0.02 grams of Bismuth neodecanoate. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no NCO-stretch at 2200-2300 cm⁻¹was observed. The solvent was removed in vacuo to obtain a clear highly viscous liquid. The calculated molecular weight of the theoretical main component was 452.34 Da, chemical structure is shown below.

[Figure (not displayed)]

Molecular weight was confirmed by Maldi-TOF-MS: Calcd. [M+Na+]=475.34 Da; Obs. [M+Na+]=475.32 Da.

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Comp. Ex. 71.21.62.41.62.53.81.21.61.71.62.73.5

A 10 mL reaction vial was placed under a N₂atmosphere, charged with propylene imine (2.28 gram), 1,2-epoxybutane (3.40 gram), capped, heated to 55° C., after which the mixture was stirred for 4 days at T=55° C. The excess of PI was removed in vacuo, followed by further purification via vacuum distillation, resulting in a colorless low viscous liquid.

1.62 grams of Desmodur N 3600, 0.02 grams of bismuth neodecanoate and 8.20 grams of dimethylformamide were charged to a reaction flask equipped with a thermometer. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere and heated to 50° C. A solution of 1.04 grams of the product from the first step in 8.20 grams of dimethylformamide was then added dropwise in 15 minutes to the reaction flask, a further 8.20 grams of dimethylformamide was flushed through the feeding funnel into the reaction mixture, whereafter the mixture was heated further to 80° C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no change in NCO-stretch at 2200-2300 cm⁻¹was observed. Subsequently, 0.05 grams of 1-butanol were added to the mixture, followed by further reaction to complete disappearance of aforementioned NCO-stretch peak. Evaporation of the solvent in vacuo to 30% solids yielded a clear liquid. The calculated molecular weight of the theoretical main component was 891.62 Da, chemical structure is shown below.

[Figure (not displayed)]

Molecular weight was confirmed by Maldi-TOF-MS: Calcd. [M+Na+]=914.62 Da; Obs. [M+Na+]=914.66 Da. The following components with a mass below 580 Da were determined by LC-MS and quantified:

[Figure (not displayed)]
was present in the composition at 0.09 wt. %.

Performance of the synthesized compound as a crosslinker was assessed using spot tests on coating surfaces, based on procedures from the DIN 68861-1 standard. For these tests, 1.56 parts of the composition (i.e. at 30% solids in dimethylformamide) was added to 15 parts of NeoRez® R-1005 under continuous stirring, and the resulting mixture was further stirred for 30 minutes. Afterwards, this coating composition was filtered and applied to Leneta test cards using 100 μm wire rod applicators (Test 7-1). For reference, films were also cast from the same composition lacking a crosslinker (Test 7-2). The films were dried for 16 hours at 25° C., then annealed at 50° C. for 1 hour and further dried for 24 hours at 25° C. Subsequently, a piece of cotton wool was soaked in 1:1 EtOH:demineralized water and placed on the film for various timespans. After removal of the EtOH and 60 minutes recovery, the following results were obtained (a score of 1 indicates complete degradation of the film, 10 indicates no damage visible):

Ethanol spot test

Sample30 min60 min120 min300 min

Test 7-1—8—6

Test 7-2—1—1

Genotoxicity test

Without S9 rat liver extractWith S9 rat liver extract

Bscl 2RtknBscl 2Rtkn

concentration →

102550102550102550102550

Ex. 71.11.1—1.11.3—1.11.31.51.11.31.5

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Patent 2024

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Anhydrous toluene is a colorless, flammable liquid chemical compound. It is used as a solvent and reagent in various laboratory applications.

Atcc ccl 121 by American Type Culture Collection

Sourced in Spain

ATCC® CCL-121™ is a cell line derived from the lung tissue of a human male. It is a widely used model for research in various fields, including cell biology, cancer studies, and drug development. The ATCC® CCL-121™ cell line provides a consistent and reliable source of cells for experimental purposes.

Ethylene glycol by Merck Group

Sourced in United States, Germany, United Kingdom, India, Spain, China, Sao Tome and Principe, Canada, Italy, Switzerland, France, Singapore, Poland, Sweden, Belgium, Ireland, Japan

Ethylene glycol is a colorless, odorless, and viscous liquid that is commonly used in various industrial applications. It serves as an important component in the manufacture of antifreeze, coolant, and de-icing solutions. Ethylene glycol is also utilized as a solvent and as a raw material in the production of polyester fibers and resins.

Fitc annexin 5 apoptosis detection kit 1 by BD

Sourced in United States, Germany, China, United Kingdom, France, Portugal, Canada, Spain, Japan, Belgium

The FITC Annexin V Apoptosis Detection Kit is a laboratory tool used to detect and quantify apoptosis, a form of programmed cell death. The kit utilizes the binding properties of the protein Annexin V, which has a high affinity for the phospholipid phosphatidylserine, which becomes exposed on the cell surface during apoptosis. The Annexin V is conjugated with the fluorescent dye FITC, allowing for the detection of apoptotic cells through fluorescence microscopy or flow cytometry.

What are the key benefits of using aziridines in organic synthesis and medicinal chemistry?

Aziridines are highly versatile compounds that offer several benefits in organic synthesis and medicinal chemistry. Their strained three-membered ring structure gives them unique reactivity, allowing for diverse transformations and functionalization. Aziridines can be used as building blocks to construct more complex molecular scaffolds, making them valuable in the synthesis of various organic compounds and pharmaceuticals. Their reactivity also enables selective modifications and the introduction of nitrogen-containing functional groups, which is particularly useful in medicinal chemistry applications.

How can researchers optimize their aziridine research using PubCompare.ai?

PubCompare.ai can greatly assist researchers studying aziridines by helping them streamline their research process. The platform allows researchers to screen protocol literature more efficiently and leverage AI to pinpoint critical insights. PubCompare.ai's intelligent analysis tools can help researchers identify the most effective protocols related to aziridines, enabling them to choose the best options for their specific research goals. This can enhance reproducibility, improve results, and save time by highlighting key differences in protocol effectiveness.

What are some common methods used for the synthesis of aziridines?

Aziridines can be synthesized through various methods, including the epoxidation of alkenes followed by reductions, the cycloaddition of imines with carbenes or nitrenes, and the ring-closing of β-amino alcohols or β-haloamines. The choice of synthetic method often depends on the specific substitution patterns and functional groups present in the target aziridine molecule. Researchers can leverage PubCompare.ai's AI-powered protocol comparisons to identify the most effective synthesis methods from the literature, preprints, and patents, optimizing their aziridine synthesis and improving overall research efficiency.

How do the strained ring structure and unique reactivity of aziridines contribute to their applications?

The strained three-membered ring structure of aziridines is the key to their unique reactivity and diverse applications. This ring strain makes aziridines highly reactive, allowing for a wide range of transformations, such as ring-opening reactions, cycloadditions, and rearrangements. The reactive nature of aziridines enables selective modifications and the introduction of nitrogen-containing functional groups, which is particularly valuable in organic synthesis and medicinal chemistry. Researchers can use PubCompare.ai's tools to identify the most effective protocols for exploiting the reactivity of aziridines and enhancing their applications.

What are some of the major applications of aziridines in materials science and other fields?

In addition to their use in organic synthesis and medicinal chemistry, aziridines have found applications in materials science and other fields. For exmaple, aziridine-containing polymers and materials can exhibit interesting properties, such as improved mechanical strength, thermal stability, and chemical resistance. Aziridines have also been used as crosslinking agents, curing agents, and in the synthesis of specialized coatings and adhesives. Researchers working on these applications can benefit from PubCompare.ai's AI-powered protocol comparisons to identify the most effective methods and formulations from the available literature, preprints, and patents.

More about "Aziridine"

Aziridines are a versatile class of three-membered heterocyclic organic compounds containing a nitrogen atom.
These strained-ring structures exhibit unique reactivity, allowing for diverse transformations and functionalization.
Aziridines are widely used in organic synthesis, medicinal chemistry, and materials science.
Key applications and related topics include: - Synthetic Utility: Aziridines can be utilized as reactive intermediates in the construction of more complex molecular scaffolds.
Various synthetic methodologies exist for aziridine preparation, such as the use of CytoFLEX flow cytometry and GloMax-Multi Detection System instruments. - Medicinal Chemistry: Aziridine-containing compounds have found applications in drug discovery and development, with potential therapeutic uses.
Researchers may leverage NH4OH, Decane, and MCF-7 cell lines in their investigations. - Materials Science: Aziridine chemistry has been explored for the development of advanced materials, such as polymers and coatings.
The GAMESS interface can be a useful tool for computational modeling and analysis of aziridine-based materials. - Analytical Techniques: Characterization of aziridine compounds often involves the use of techniques like NMR spectroscopy.
Anhydrous toluene and Ethylene glycol may be employed as solvents or reagents in these analyses. - Biomedical Applications: Aziridine-based compounds have been investigated for their potential biological activities, including cytotoxicity and apoptosis induction.
The FITC Annexin V Apoptosis Detection Kit I can be utilized to study these effects.
Optimizing aziridine research can be facilitated by PubCompare.ai's AI-powered protocol comparisons, which help researchers identify the best protocols from literature, preprints, and patents to enhance reproducibility and improve their results.
Leveraging PubCompare.ai's intelligent analysis tools can streamline the aziridine research process, saving time and enhancing the overall workflow.