CAS: 452-35-7; 6-Ethoxybenzo[d]Thiazole-2-Sulfonamide

该化合物是一种主要用于研究和制药应用的源自磺酰胺的碳己烷酶抑制剂,其主要优势在于它有选择地有效抑制碳氢醚异形,特别是CA-II和CA-IV,使其对研究酶机制和生理过程,如液体分泌和酸基平衡等具有价值;乙氧二氮胺具有高膜渗透性,能够采取有效的细胞内行动;还用于眼科研究,因为它能够减少内压;该化合物具有精细特征的药用动力和稳定性进一步提高其在实验环境中的效用;其特性和可靠性使它成为调查碳氢酶相关途径的首选工具.

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上下游产品

6-ethoxy-2-benzothiazolesulfenamide 6-ethoxy-2-mercaptobenzothiazole 6-ethoxy-benzothiazole-2-carbonitrile 6-hydroxy-2-benzothiazolesulfonamide 2-sulfamoyl-6-benzothiazolyl benzoate (2-sulfamoyl-6-benzothiazolyl) cyclohexanecarboxylate

合成工艺路线路线简述

  • 合成目标产物 6-Ethoxy-2-Benzothiazolesulfonamide 主要起始原料 6-Ethoxy-2-Mercaptobenzothiazole
  • (文献来源)合成步骤主要原料 6-Ethoxy-2-Mercaptobenzothiazole
📜6-乙氧基-2-巯基苯并噻唑置于ammonium Hydroxide,Sodium Hydroxide,Sodium Hypochlorite,Potassium Permanganate,硫酸体系中,用 水,丙酮 作为反应溶剂,化学反应 1.25H,反应生成 依索唑胺
参考文献:局部活性碳酸酐酶抑制剂.1.6-羟基苯并噻唑-2-磺酰胺的o-酰基衍生物.
标题:局部活性碳酸酐酶抑制剂.1.6-羟基苯并噻唑-2-磺酰胺的o-酰基衍生物.
摘要:制备了一系列6-羟基苯并噻唑-2-磺酰胺的o-酰基衍生物(4,L-643,799),并确定了每个系列成员作为眼用碳酸酐酶局部活性抑制剂的潜在用途.体外研究表明,这些酯是眼酯酶的底物,它们在角膜移位过程中释放4.发现最有趣的系列成员2,2-磺氨酰基-6-苯并噻唑基2,2-二甲基丙酸酯(22,L-645,151)以4的前药形式存在,当通过分离的白化兔子角膜递送时,其递送能力提高40倍与母体酚4相比.在兔子中的研究表明22是一种有效的局部活性高眼压性碳酸酐酶抑制剂.
DOI:10.1021/jm00131A011

海关参考信息

专利信息


专利号:US-5847150-A
优先权日:1996-04-24
标题 :Solid phase and combinatorial synthesis of substituted 2-methylene-2, 3-dihydrothiazoles and of arrays of substituted 2-methylene-2, 3-dihydrothiazoles
发明人:DORWALD FLORENCIO ZARAGOZA
权利人:NOVO NORDISK AS
摘要:A solid phase method for the synthesis of a plurality of differently substituted 2-methylenethiazoles with a wide variety of side-chain substituents as compounds of potential therapeutic interest. The 2-methylenethiazoles are prepared by acylation of a substrate-bound primary or secondary amine with cyanoacetic acid and reaction of the resulting cyanoacetamide with an isothiocyanate in the presence of a base. Alkylation with an appropriate alkyl halide under acidic conditions yields differently substituted, support-bound 2-methylene-2,3-dihydrothiazoles. These may be screened on the substrate or cleaved from the substrate and then screened in solution. The efficient synthesis of a wide variety of 2-methylenethiazoles using automated synthesis technology of the present method makes these compounds attractive candidates for the generation and rapid screening of diverse thiazole-based libraries. The method disclosed here provides an easy and fast access to highly diverse heterocyclic compounds of therapeutic interest, amenable to automatization.

专利号:US-10925977-B2
优先权日:2006-10-05
标 题 :Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications
发明人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S
权利人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S; CEIL POINT LLC; UNIV TEXAS
摘要:Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.

专利号:US-2008287407-A1
优先权日:2003-12-10
标题 :Nitric Oxide Releasing Pyruvate Compounds, Compositions and Methods of Use
发明人:GARVEY DAVID S; FANG XINQIN; KHANAPURE SUBHASH P; RANATUNGA RAMANI R; WEY SHIOW-JYI
权利人:NITROMED INC
摘要:The invention describes novel nitrosated and/or nitrosylated pyruvate compounds and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated and/or nitrosylated pyruvate compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one pyruvate compound and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one pyruvate compound, that is optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating diseases resulting from oxidative stress, diabetes, reperfusion injury following ischemia, preservation of tissues, organs, organ parts and/or limbs.

专利号:EP-2054420-B1
优先权日:2006-08-02
标题:Benzimidazo[1,2-c][1,2,3]thiadiazol-7-sulfonamides as inhibitors of carbonic anhydrase and the intermediates for production thereof
发明人:MATULIS DAUMANTAS; DUDUTIENE VIRGINIJA; MATULIENE JURGITA; MISTINAITE LINA
权利人:BIOTECHNOLOGIJOS INST
摘要:The invention is related to novel compounds - benzimidazo[1,2-c][1,2,3]thiadiazole sulfonamides, corresponding to the general formula (I). The compounds can be used in biomedicine as active ingredients in pharmaceutical formulations, because they inhibit enzymes which participate in disease progression such as glaucome. The compounds of formula (I) inhibits enzymes such as carbonic anhydrases and metallo proteinases. This invention is also related to new intermediate compounds which are used for the synthesis of sulfonamides of formula (I).

专利号:US-4975449-A
优先权日:1983-02-04
标 题 :Topical treatment of glaucoma with 2-benzothiazolesulfonamide derivative
发明人:SCHOENWALD RONALD D; BARFKNECHT CHARLES F
权利人:UNIV IOWA RES FOUND
摘要:A topical composition for eye treatment of glaucoma, comprising a small but pharmaceutically effective amount of an analog of benzothiazole-2-sulfonamide. The most preferred compound is 6-chloro-benzothiazole-2-sulfonamide. The invention also relates to a method of topically treating glaucoma with eye drops to reduce intraocular pressure. Finally, disclosed is a method of synthesis of the preferred and highly effective benzothiazole-2-sulfonamide analogs, particularly the 6-chloro-benzothiazole-2-sulfonamide compound.

专利号:US-2008227851-A1
优先权日:2007-03-12
标题 :Laulimalide and laulimalide analogs
发明人:WENDER PAUL A
权利人:WENDER PAUL A
摘要:Novel laulimalide analogs, methods for the treatment of proliferative disease and processes for the synthesis of laulimalide and novel laulimalide analogs are described.

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✅ COA系统入驻 | 共享模式

主要参考文献


1: Ciocci Pardo A, González Arbeláez LF, Fantinelli JC, Álvarez BV, Mosca SM, Swenson ER. Myocardial and mitochondrial effects of the anhydrase carbonic inhibitor ethoxzolamide in ischemia-reperfusion. Physiol Rep. 2021 Nov;9(22):e15093. doi: 10.14814/phy2.15093.
2: Rahman MM, Tikhomirova A, Modak JK, Hutton ML, Supuran CT, Roujeinikova A. Antibacterial activity of ethoxzolamide against Helicobacter pylori strains SS1 and 26695. Gut Pathog. 2020 Apr 15;12:20. doi: 10.1186/s13099-020-00358-5.
3: Modak JK, Tikhomirova A, Gorrell RJ, Rahman MM, Kotsanas D, Korman TM, Garcia-Bustos J, Kwok T, Ferrero RL, Supuran CT, Roujeinikova A. Anti-Helicobacter pylori activity of ethoxzolamide. J Enzyme Inhib Med Chem. 2019 Dec;34(1):1660-1667. doi: 10.1080/14756366.2019.1663416.

合成参考文献


参考文献:10.1021/jm901855h
摘要:Joseph P, Turtaut F, Ouahrani-Bettache S, Montero JL, Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Köhler S, Winum JY, Supuran CT. Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis. J Med Chem. 2010 Mar 11;53(5):2277–85. doi: 10.1021/jm901855h.
参考文献:10.7150/ijms.8.413
摘要:Chang X, Yan X, Zhang Y. Treat ankylosing spondylitis with methazolamide. Int J Med Sci. 2011;8(5):413–9.
参考文献:10.1016/j.bmc.2011.06.038
摘要:Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Supuran CT. Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates. Bioorg Med Chem. 2011 Aug 15;19(16):5023–30. doi: 10.1016/j.bmc.2011.06.038.
参考文献:10.3389/fphar.2011.00034
摘要:Supuran CT. Bacterial carbonic anhydrases as drug targets: toward novel antibiotics Front Pharmacol. 2011;2():34.
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