CAS: 165668-41-7; N-(3-Chloro-1H-Indol-7-yl)Benzene-1,4-Disulfonamide

该化合物是一个小分子,在癌症研究领域引起注意,被归类为磺酰胺化合物,主要用作抗肿瘤剂;Indisulam展示其药理效应,抑制酶碳酸性厌水酶,在包括pH 调节和离子迁移在内的各种生理过程中起着关键作用;这种抑制可能导致细胞代谢改变和癌症细胞的生长抑制;该化合物在临床前研究和早期临床试验中表现出希望,特别是在固态肿瘤的治疗中.Indisulam通常通过静脉注射进行,其半衰期相对较短,需要仔细研究剂量疗法.其安全性特征和潜在副作用仍在调查之中,但与许多止血药剂一样,它可能与宫颈抑制和胃肠炎症的抑制有关.

结构式图片

欧盟法规

C&L通报

上下游产品

N-(1H-Indole-7-yl)-4-Sulfamoylbenzenesulfonamide 165669-28-3
7-氨基-3-氯吲哚 3-Chloro-1H-Indol-7-Amine 165669-13-6
3-氯-7-硝基吲哚 3-Chloro-7-Nitroindole 165669-14-7

合成工艺路线路线简述

    N-(1H-Indole-7-yl)-4-Sulfamoylbenzenesulfonamide置于n-氯代丁二酰亚胺体系中,用 二氯甲烷,N,N-二甲基甲酰胺 用作溶剂,化学反应 1.0H,反应生成2-[n-(2-氰乙基)-4-[(2,6-二氯-4-硝基苯基)偶氮]苯胺基]乙酸乙酯
    参考文献:Ep1813602
    标题:Ep1813602

    专利信息


    专利号:US-7935704-B2
    优先权日:2003-08-01
    标 题 :Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
    发明人:PALLADINO MICHAEL A; LLOYD GEORGE KENNETH; HAYASHI YOSHIO; NICHOLSON BENJAMIN
    权利人:NEREUS PHARMACEUTICALS INC
    摘要:Compounds represented by the following structure (I) are disclosed: n nas are methods for making such compounds, wherein said methods comprise reacting a diacyldiketopiperazine with a first aldehyde to produce an intermediate compound; and reacting the intermediate compound with a second aldehyde to produce the class of compounds with the generic structure, where the first aldehyde and the second aldehydes are selected from the group consisting of an oxazolecarboxaldeyhyde, imidazolecarboxaldehyde, a benzaldehyde, imidazolecarboxaldehyde derivatives, and benzaldehyde derivatives, thereby forming the above compound wherein R 1 , R 1 ′, R 1 ″, R 2 , R 3 , R 4 , R 5 , and R 6 , X 1 and X 2 , Y, Z, Z 1 , Z 2 , Z 3 , and Z 4 may each be separately defined in a manner consistent with the accompanying description. Compositions and methods for treating vascular proliferation are also disclosed.

    专利号:US-7956058-B2
    优先权日:2002-08-02
    标 题:Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
    发明人:HAYASHI YOSHIO; PALLADINO JR MICHAEL A; GRODBERG JENNIFER
    权利人:NEREUS PHARMACEUTICALS INC
    摘要:Compounds represented by the following structure (I) are disclosed: n nas are methods for making such compounds, wherein said methods comprise reacting a diacyldiketopiperazine with a first aldehyde to produce an intermediate compound; and reacting the intermediate compound with a second aldehyde to produce the class of compounds with the generic structure, where the first aldehyde and the second aldehydes are selected from the group consisting of an oxazolecarboxaldeyhyde, imidazolecarboxaldehyde, a benzaldehyde, imidazolecarboxaldehyde derivatives, and benzaldehyde derivatives, thereby forming the above compound wherein R 1 , R 1 ′, R 1 ′, R 2 , R 3 , R 4 , R 5 , and R 6 , X 1 and X 2 , Y, Z, Z 1 , Z 2 , Z 3 , and Z 4 may each be separately defined in a manner consistent with the accompanying description. Compositions and methods for treating cancer and fungal infection are also disclosed.

    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-2023266302-A1
    优先权日:2020-07-24
    标 题:Synthesis and use of n-benzyl sulfonamides
    发明人:LAMAR ANGUS A; SHEAFF ROBERT J
    权利人:THE UNIV OF TULSA
    摘要:Disclosed is a method for preparing N-benzyl sulfonamides. Also disclosed is a composition for treating cancer. The composition includes a N-benzyl sulfonamide and a metabolic inhibitor. Also disclosed is a method for determining the impact on cell ATP levels of a composition containing a N-benzyl sulfonamide with or without a metabolic inhibitor.

    专利号:US-9290529-B2
    优先权日:2011-10-24
    标题:Carbonic anhydrase inhibitors and method of their production
    发明人:BRYNDA JIRI; CIGLER PETR; GRUNER BOHUMIR; MALOY REZACOVA PAVLINA; MADER PAVEL; SICHA VACLAV; BAKARDJIEV MARIO; HOLUB JOSEF; DZUBAK PETR; HAJDUCH MARIAN
    权利人:USTAV ORGANICKE CHEMIE A BIOCHEMIE AKADEMIE VED CESKE REPUBLIKY V V I; USTAV MOLEKULARNI GENETIKY AKADEMIE VED CESKE REPUBLIKY V V I; USTAV ANORGANICKE CHEMIE AKADEMIE VED CESKE REPUBLIKY V V I; UNIV PALACKEHO
    摘要:Derivatives of boron cluster compounds of general formula I and their pharmaceutically acceptable salts and solvates, and their specific inhibition effect on the enzyme carbonic anhydrase IX, a protein overexpressed in cancer tissues. Methods of synthesis and the use of the novel derivatives. These inhibitors of human carbonic anhydrase IX can be used as active compounds of pharmaceuticals for diagnostics and/or therapy of cancer diseases.

    专利号:US-7674903-B2
    优先权日:2002-08-02
    标题:Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
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    主要参考文献


    1: Pogacar Z, Johnson JL, Krenning L, De Conti G, Jochems F, Lieftink C, Velds A, Wardak L, Groot K, Schepers A, Wang L, Song JY, van de Ven M, van Tellingen O, Medema RH, Beijersbergen RL, Bernards R, Leite de Oliveira R. Indisulam synergizes with palbociclib to induce senescence through inhibition of CDK2 kinase activity. PLoS One. 2022 Sep 6;17(9):e0273182. doi: 10.1371/journal.pone.0273182.
    2: Hopkins MD, Witt RC, Flusche AME, Philo JE, Ozmer GL, Purser GH, Sheaff RJ, Lamar AA. Synthesis and biological evaluation of N-alkyl sulfonamides derived from polycyclic hydrocarbon scaffolds using a nitrogen-centered radical approach. Org Biomol Chem. 2022 Aug 24;20(33):6680-6693. doi: 10.1039/d2ob01291j.
    127:106017. doi: 10.1016/j.bioorg.2022.106017. Epub 2022 Jul 9. 5(9):e202101348. doi: 10.26508/lsa.202101348.

    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:10.1016/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.
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