- Synthetic method for drug intermediate 1,3,4-thiadiazole-2-acetamido-5-sulfonyl chloride
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The invention discloses a synthetic method for the drug intermediate 1,3,4-thiadiazole-2-acetamido-5-sulfonyl chloride. The synthetic method comprises the following steps: adding 2-acetamido-5-thiomethyl-1,3,4-thiadiazole into a reaction vessel, controlling a temperature, adding a potassium nitrate solution, controlling a stirring speed and carrying out a reaction; and adding lanthanum nitrate inbatches, controlling the temperature, adding a 3-chlorophenol solution in batches within a certain period of time, continuing the reaction, adjusting the pH of value the obtained solution, allowing asolid to be precipitated, washing the solid with a sodium sulfate solution a plurality of times, then washing the solid with a cyclobutane solution a plurality of times, then washing the solid with amethylamine solution a plurality of times, carrying out recrystallization in a t-butanol solution, and then carrying out dehydration with a dehydrating agent so as to obtain the finished 1,3,4-thiadiazole-2-acetamido-5-sulfonyl chloride.
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Paragraph 0017-0018; 0021-0022; 0023-0026
(2018/07/30)
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- Preparation process for intermediate of acetazolamide
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The invention especially relates to a preparation process for an intermediate of acetazolamide, belonging to the field of medicine synthesis. The process comprises the following steps: with thiosemicarbazide and carbon disulfide as reactants and a mixture of pyridine and piperidine as a solvent, carrying out a reaction; and then successively carrying out purification and drying so as to obtain 2-amino-5-mercapto-1,3,4-thiadiazole, i.e., the intermediate of acetazolamide.
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Paragraph 0051
(2017/09/13)
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- Key intermediate aqiang 2-acetyl-5-chlorosulfonyl -1, 3, 4-thiadiazole method for preparing the non-chlorine (by machine translation)
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The invention discloses a preparation method of non-chlorine gas of acetazolamide key intermediate 2-acetamido-5-chlorosulfonyl-1, 3, 4-thiadiazole. The preparation method comprises the steps of firstly adding hydrochloric acid into a reactor and then dropwise adding hydrogen peroxide to perform reaction so as to obtain a reaction solution; adding 2-acetamido-5-sulfydryl-1, 3, 4-thiadiazole into the obtained reaction solution in batch to perform reaction and obtaining a reactant after reaction is completed; directly conducting suction filtration, washing and drying on the reactant and performing drying to obtain the intermediate 2-acetamido-5-chlorosulfonyl-1, 3, 4-thiadiazole. The preparation method is more moderate in operate and more environment-friendly, and the obtained intermediate 2-acetamido-5-chlorosulfonyl-1, 3, 4-thiadiazole is good in color and luster and high in purity.
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Paragraph 0029
(2017/01/02)
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- GIAO/DFT 13C NMR Chemical Shifts of 1,3,4-thiadiazoles
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1H, 13C and 15N NMR spectra of 2-acetylamino-1,3,4-thiadiazole and its 5-substituted derivatives have been measured and assigned based on reference data, as well as homo- and heteronuclear 2 D NMR experiments. In addition, the GIAO/DFT approach at the B3LYP level of theory using the 6-311G basis set was used to calculate the 13C NMR chemical shifts. Although this method gives reliable results for 2-arylhydrazones of 1,3-diphenylpropanetrione, 2-phenacylpyridines, (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines, 4-fluoroanilines, (1Z,3Z)-1,4-di(pyridin-2-yl)buta-1,3-dienediols and their tautomeric forms, the calculated chemical shifts for the 1,3,4-thiadiazoles studied are less satisfactory. Presence of the sulfur atom(s) seems to be responsible for such behavior.
- Loghmani-Khouzani, Hossein,Rauckyte, Teresa,Osmialowski, Borys,Gawinecki, Ryszard,Kolehmainen, Erkki
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p. 2217 - 2225
(2008/02/10)
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- Synthesis, antibacterial and?antitubercular activities of?some?7-[4-(5-amino-[1,3,4]thiadiazole-2-sulfonyl)-piperazin -1-yl] fluoroquinolonic derivatives
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In the present study, a series of 7-[4-(5-amino-1,3,4 thiadiazole-2-sulfonyl)]-1-piperazinyl fluoroquinolonic derivatives VIIa-d were synthesized in good yields and characterized by IR, 1H-NMR, 13C-NMR, FAB Mass spectral and elemental analyses. The compounds were evaluated for their preliminary in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria and selected compounds VIIa, b were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth dilution assay method. The antibacterial data of the tested N-sulfonylfluoroquinolones VIIa-d indicated that all the synthesized compounds showed better activity against Gram-positive bacteria S.?aureus, E.?faecelis, Bacillus sp. (MIC = 1-5?μg?ml-1, respectively) compared to reference drugs. The MIC values of tested derivatives connotes that the sparfloxacin and gatifloxacin derivatives VIIc, d were most active against the tested Gram-positive bacterial strains (MIC = 1-5?μg?ml-1). All the tested compounds VIIa-d showed poor activity against the Gram-negative bacteria. The in vitro antitubercular activity reports of selected compounds VIIa, b against M.?tuberculosis strain H37Rv showed moderate activity at MIC of 10?μg?ml-1.
- Talath,Gadad
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p. 918 - 924
(2007/10/03)
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- Synthesis of certain diarylsulfonylureas as antitumor agents
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A new series of N-aryl-N′-heteroaryl or N,N′-diheteroaryl sulfonylurea or sulfonylthiourea was synthesized and screened for their antitumor activity at the National Cancer Institute (NCI). N-(3-Chlorophenyl)-N′-(6-methyl-uracil-2-sulfonyl)urea (28) with GI50, TGI, LC50 (MG-MID) values of 66.1, 83.2, 93.3 μM, respectively is the most active compound in this study. It showed a remarkable activity more than sulofenur against HL-60 (TB) and RPMI-8226 leukemia, HOP-92 Non small lung cancer, KM12 colon cancer, SF-295 CNS cancer, PC-3 prostate cancer, OVCAR-4 Ovarian cancer, CAKI-1 and UO-31 Renal cancer, and MDA-MB-435 Breast cancer with GI50 values of 0.3, 2.7, 6.9, 14.7, 8.2, 9.3, 2.0, 2.1, 3.4, 11.3 μM, respectively.
- Youssef,Al-Abdullah,El-Khamees
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p. 404 - 418
(2007/10/03)
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- Synthesis and investigation of inhibition effects of new carbonic anhydrase inhibitors
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Three new derivatives of 2-substituted 1,3,4-thiadiazole-5-sulfonamide have been synthesized. These compounds are 2-(3-chloropropionylamino)- 1,3,4-thiadiazole-5-sulfonamide (1); 2-(2,2-dichloroacetylamino)-1,3,4-thiadiazole-5-sulfonamide (2); and 2-(3-phenylpropionylamino)-1,3,4-thiadiazole-5-sulfonamide (3). Inhibition effects of these compounds on carbonic anhydrase I and II have been investigated. By comparing 150 and K(i) values of the compounds, it has been found that compound 1 is a more potent inhibitor than acetazolamide (b) on carbonic anhydrase II.
- Arslan, Oktay,Kuefrevioglu, Oe. Irfan,Nalbantoglu, Barbaros
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p. 515 - 518
(2007/10/03)
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- Aminosulfonylthiadiazolylureas
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Disclosed are compounds of the formula STR1 wherein R1 is alkyl, R2 is selected from the group consisting of hydrogen and alkyl; or R1 and R2 together with the nitrogen atom form a cyclic ring structure having 4 or 5 carbon atoms; m is the integer 0 or 1; when m is 1, R4 and R5 are each independently selected from the group consisting of hydrogen and alkyl or up to 3 carbon atoms; when m is 0, R4 is hydrogen and R5 is the same as defined above; R3, R6, R7, R8, R9 are each independently selected from the group consisting of hydrogen and alkyl; n is an integer from 0 to 2; and Z1 and Z2 are each independently selected from the group consisting of oxygen and sulfur. These compounds are useful as herbicides.
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