1H NMR (400 MHz) spectra were recorded on a Varian Mercury 400 spectrometer with tetramethylsilane (TMS) as an internal reference. 19F NMR (376 MHz) spectra were recorded on a Varian Mercury 400 spectrometer with CHF3 as an internal reference standard. A 500 MHz Bruker Avance III-HD spectrometer with a microprocessor-controlled gradient unit was used for 31P Solid State NMR spectra. UV-vis spectra were recorded on a Shimadzu UV 2450 spectrophotometer. Mechanical measurement was performed on Discovery HR-3, hybrid rheometer (TA Instrument). The images of gels were recorded by Field-Emission Scanning Electron Microscopy (FE-SEM, Zeiss UltraPlus). The samples were firstly coated with gold using Denton Dest II Sputter Coater for 45 s and then observed by SEM. Gels were freeze-dried before using for SEM.
Mercury 400 spectrometer
Manufactured by Agilent Technologies
Sourced in United States
The Mercury 400 spectrometer is a laboratory instrument designed for high-performance spectroscopic analysis. It features a compact and robust design for reliable operation. The spectrometer is equipped with advanced data acquisition and processing capabilities to support a range of analytical applications.
Automatically generated - may contain errors
Lab products found in correlation
Ultra plus, by Zeiss (1 mentions)
Uv 2450 spectrophotometer, by Shimadzu (1 mentions)
Avance 3 hd spectrometer, by Bruker (1 mentions)
Discovery hybrid rheometer hr 3, by TA Instruments (1 mentions)
Fisher johns apparatus, by Thermo Fisher Scientific (1 mentions)
Microtof 2 spectrometer, by Bruker (1 mentions)
Mercury 300 spectrometer, by Agilent Technologies (1 mentions)
Mercury 300, by Agilent Technologies (1 mentions)
Q ultrapurification system, by Merck Group (1 mentions)
Specord 210 spectrophotometer, by Analytik Jena (1 mentions)
Api 2000 lc ms ms system, by Thermo Fisher Scientific (1 mentions)
Nmr solvents, by Merck Group (1 mentions)
Lsm 800, by Zeiss (1 mentions)
Fv1000, by Olympus (1 mentions)
Uplansapo 100, by Olympus (1 mentions)
Chromaster system, by YMC (1 mentions)
αplan apochromat 100, by Zeiss (1 mentions)
Lc msd tof instrument, by Agilent Technologies (1 mentions)
A549 ddp, by American Type Culture Collection (1 mentions)
Synapt g2, by Waters Corporation (1 mentions)
25 protocols using mercury 400 spectrometer
1
Multi-Spectroscopic Characterization of Gels
2
Physicochemical Characterization of Organic Compounds
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Morin hydrate (M4008), semicarbazide (363634), hydroxylamine hydrochloride (159417), and sodium acetate (236500) were acquired from Aldrich. (Sigma Aldrich, Saint Louis, MO, USA), Melting points were determined on a Fisher-Johns apparatus (Thermo Fisher Scientific Inc., Waltham, MA, USA) and were uncorrected. The 1H and 13C NMR spectra were measured at 400 MHz for 1H and at 100 MHz for 13C using a Varian Mercury 400 spectrometer manufactured by Varian, Inc. (Palo Alto, CA, USA) operating at a field of 9.4 Tesla from DMSO-d6 solutions using tetramethylsilane as the internal reference. Chemical shift values were reported in parts per million and coupling constants (J) in Hz. IR spectra were acquired on a Buck 500 spectrophotometer (Buck Scientific, Norwalk, CT, USA). HRMS spectra were acquired on a Bruker MicroTOF-II spectrometer (Bruker Corp., Billerica, MA, USA). Ultraviolet–visible (UV–Vis) spectra were measured on a Perkin Elmer Lambda (PerkinElmer, Inc., Waltham, Massachusetts, USA) spectrometer at 25 °C using EtOH solution. The molar absorption coefficient data (ε = A(λ)/cl) were given in log ε values.
3
Synthesis and Characterization of TBT, TPT, and TTzT
4
Characterization of Organic Compounds
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General Melting points (m.p.) were determined on a SGWX-4 micro-melting point apparatus and are uncorrected. NMR spectra were recorded on Varian Mercury-300 spectrometer (300 MHz for 1H and 75 MHz for 13C) or Varian Mercury-400 spectrometer (400 MHz for 1H and 100 MHz for 13C), chemical shifts of 1H and 13C spectra were recorded with tetramethylsilane as internal standard (CDC13 δH 7.26, δC 77.2), and coupling constants were reported in hertz. Mass spectra were obtained on a ZAB-2F or JEOLDX-300 spectrometer. Optical rotations were measured on WZZ-3 polarimeter calibrated at the sodium Dline (598 nm). Reactions where exclusion of water was necessary were performed according to Ref. [25 ]. TLC was carried out on silica gel (GF254) under UV light. Column chromatography was run on silica gel (200–300 mesh) or alumina from Qingdao Ocean Chemical Factory.
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General Melting points (m.p.) were determined on a SGWX-4 micro-melting point apparatus and are uncorrected. NMR spectra were recorded on Varian Mercury-300 spectrometer (300 MHz for 1H and 75 MHz for 13C) or Varian Mercury-400 spectrometer (400 MHz for 1H and 100 MHz for 13C), chemical shifts of 1H and 13C spectra were recorded with tetramethylsilane as internal standard (CDC13 δH 7.26, δC 77.2), and coupling constants were reported in hertz. Mass spectra were obtained on a ZAB-2F or JEOLDX-300 spectrometer. Optical rotations were measured on WZZ-3 polarimeter calibrated at the sodium Dline (598 nm). Reactions where exclusion of water was necessary were performed according to Ref. [25 ]. TLC was carried out on silica gel (GF254) under UV light. Column chromatography was run on silica gel (200–300 mesh) or alumina from Qingdao Ocean Chemical Factory.
5
Synthesis and Characterization of mPEG-b-PDLLA Copolymers
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mPEG2000-b-PDLLA1300 was synthesized by the ring-opening polymerization of D,L-lactide in the presence of mPEG2000 homopolymer and a catalyst, as described previously
[35 ,36 (link)]. The molecular weights of copolymers were characterized by nuclear magnetic resonance (NMR) analysis using CDCl3 and a Mercury-400 spectrometer (Varian).
[35 ,36 (link)]. The molecular weights of copolymers were characterized by nuclear magnetic resonance (NMR) analysis using CDCl3 and a Mercury-400 spectrometer (Varian).
6
Synthesis of Compound 1 from Chen et al.
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Example 1
Compound 1 was prepared according to the synthetic methods described in Chen et al., European Journal of Medicinal Chemistry, 2015, 100, 151-161.
All chemicals and solvents were purchased from commercial suppliers and used as received. All reactions were carried out under an atmosphere of dry nitrogen. Reactions were monitored by TLC using Merck 60 F254 silica gel glass backed plates (5×10 cm); and zones were detected visually under ultraviolet irradiation (254 nm) or by spraying with phosphomolybdic acid reagent (Aldrich) followed by heating at 80° C. All flash column is chromatography was performed with Merck Kieselgel 60, No. 9385, 230-400 mesh ASTM silica gel as the stationary phase. Proton CH) nuclear magnetic resonance spectra were measured on a Varian Mercury-300 or Varian Mercury-400 spectrometer. Chemical shifts were recorded in parts per million (ppm) on the delta (δ) scale relative to the resonance of the solvent peak. The following abbreviations were used to describe coupling: s=singlet; d=doublet; t=triplet; q=quartet; quin=quintet; br=broad; and m=multiplet. LCMS data were measured on an Agilent MSD-1100 ESI-MS/MS, Agilent 1200 series LC/MSD VL, and Waters Acquity UPLC-ESI-MS/MS system.
7
Comprehensive Experimental Characterization
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All reagents were purchased from commercial sources (e.g., Sigma) and directly used unless stated otherwise. Solvents were purified by the most used methods. All solutions and buffers were prepared with using metal-free water that was passed through a Millipore-Q ultrapurification system. Elementary analysis was carried out on a Vario EL III elementary analysis instrument. UV-Vis spectra were recorded on an analytik jena Specord 210 spectrophotometer. 1H and 13C NMR spectra were recorded on a Varian Mercury 400 spectrometer at 400 and 100 MHz, respectively. Electrospray ionization mass spectra (ESI-MS) were acquired on an Applied Biosystems API 2000 LC/MS/MS system.
8
Synthetic Characterization and Biological Assays
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All reagents
used for chemical synthesis were purchased from commercially
available sources and used without further purification. Nuclear magnetic
resonance (NMR) solvents were obtained from Sigma-Aldrich. 1H, 13C, and 19F NMR spectra were recorded on
a Varian MERCURY 400 spectrometer (400 MHz for 1H NMR,
101 MHz for 13C NMR, and 376 MHz for 19F NMR).
Chemical shifts (δ) are expressed in parts per million (ppm)
downfield from tetramethylsilane, and deuterated solvent signal was
used as reference. Coupling constants (J) are expressed
in hertz (Hz). Abbreviations used are s = singlet, bs = broad singlet,
d = doublet, dd = doublets of doublets, t = triplet, td = triplets
of doublets, q = quartet, and m = multiplet. Mass spectra were obtained
at the “Centres Científics i Tecnològics de la
Universitat de Barcelona” (CCiTUB). Compounds tested in the
different biological assays were previously diluted to a stock concentration
of 0.5 to 1 M in H2O to perform the experiments.
used for chemical synthesis were purchased from commercially
available sources and used without further purification. Nuclear magnetic
resonance (NMR) solvents were obtained from Sigma-Aldrich. 1H, 13C, and 19F NMR spectra were recorded on
a Varian MERCURY 400 spectrometer (400 MHz for 1H NMR,
101 MHz for 13C NMR, and 376 MHz for 19F NMR).
Chemical shifts (δ) are expressed in parts per million (ppm)
downfield from tetramethylsilane, and deuterated solvent signal was
used as reference. Coupling constants (J) are expressed
in hertz (Hz). Abbreviations used are s = singlet, bs = broad singlet,
d = doublet, dd = doublets of doublets, t = triplet, td = triplets
of doublets, q = quartet, and m = multiplet. Mass spectra were obtained
at the “Centres Científics i Tecnològics de la
Universitat de Barcelona” (CCiTUB). Compounds tested in the
different biological assays were previously diluted to a stock concentration
of 0.5 to 1 M in H2O to perform the experiments.
9
Detailed NMR and Mass Spectrometry Analysis
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Unless stated otherwise, all commercial reagents were used as received. Thin-layer chromatography (TLC) was performed on silica gel 60F254 (Merck). 1H NMR spectra were obtained on a Varian Mercury 400 spectrometer with residual non-deuterated solvents (CD3OD: 3.31 ppm for 1H) as the internal reference. ESI mass spectra were recorded using an Exactive (Thermo Scientific). Reversed-phase HPLC (RP-HPLC) was carried out on a Hitachi Chromaster system equipped with a diode array and YMC-Pack Triart C18 or ODS-A columns. All runs used linear gradients of acetonitrile (ACN) containing 0.1% trifluoroacetic acid (TFA) and 0.1% aqueous TFA. The images of confocal laser scanning microscopy (CLSM) were acquired by a FV1000 (Olympus) and a LSM800 (Carl Zeiss Microscopy). UPlanSApo 100× (1.40 numerical aperture, oil immersion, Olympus), UPlanSApo 4× (0.16 numerical aperture, Olympus), Plan-Apochromat 20× (0.8 numerical aperture, Carl Zeiss), and αPlan-Apochromat 100× (1.46 numerical aperture, Carl Zeiss) were used. The fluorescent intensity of the CLSM images was calculated by Fiji49 (link).
10
Synthesis and Characterization of Piperazine Derivative
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All chemicals were commercially available without further purification. 1H NMR spectra were recorded on the Varian Mercury 400 spectrometer (Figure S1
Compounds 2–4 were synthesized by the reported method.17 (link) Compound 4 (1 mmol) and 1-[(4-methylphenyl) carbonyl] piperazine (1mmol) were added to a solution of acid derivatives (1.2 mmol) in toluene (10 mL). The mixture was refluxed for 8 h. After evaporation, the crude product was purified by flash column chromatography to afford wyc-7-20. Yield: 88%; 1H NMR (400 MHz, CDCl3) δ 9.33 (s, 1H), 8.76 (d, J = 3.6 Hz, 1H), 8.38 (dt, J = 8.0, 1.9 Hz, 1H), 7.48–7.42 (m, 1H), 7.32–7.28 (m, 2H), 7.23–7.18 (m, 2H), 4.00 (s, 2H), 3.70 (d, J = 98.6 Hz, 4H), 2.70 (s, 4H), 2.37 (s, 3H); HR-ESI-MS: m/z calcd for C20H22N5O2+ 364.1773 ([M+H]+), found 364.1776.
Compounds 2–4 were synthesized by the reported method.17 (link) Compound 4 (1 mmol) and 1-[(4-methylphenyl) carbonyl] piperazine (1mmol) were added to a solution of acid derivatives (1.2 mmol) in toluene (10 mL). The mixture was refluxed for 8 h. After evaporation, the crude product was purified by flash column chromatography to afford wyc-7-20. Yield: 88%; 1H NMR (400 MHz, CDCl3) δ 9.33 (s, 1H), 8.76 (d, J = 3.6 Hz, 1H), 8.38 (dt, J = 8.0, 1.9 Hz, 1H), 7.48–7.42 (m, 1H), 7.32–7.28 (m, 2H), 7.23–7.18 (m, 2H), 4.00 (s, 2H), 3.70 (d, J = 98.6 Hz, 4H), 2.70 (s, 4H), 2.37 (s, 3H); HR-ESI-MS: m/z calcd for C20H22N5O2+ 364.1773 ([M+H]+), found 364.1776.
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