2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide | 129841-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide
• 英文别名: 3-phenyl-5-sulfamoyl-1H-indole-2-carbohydrazide；GUZ；2-(hydrazinecarbonyl)-3-phenyl-1H-indole-5-sulfonamide
• CAS: 129841-18-5
• 化学式: C₁₅H₁₄N₄O₃S
• 分子量: 330.367
• InChiKey: PPDLAUCFAOODER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2-(N'-Benzyl-hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonic acid amide
  参考文献：
  名称：

  Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamidoindole derivatives

  摘要：

  Ten new arylidenehydrazides were synthesized by reacting 3-phenyl-5-sulfonamidoindol-2-carboxylic acid hydrazide with various aldehydes and a new N-2-substituted hydrazide was prepared by reduction of 3-phenyl-5-sulfonamidoindole-2-carboxylic acid benzylidene-hydrazide 2 with sodium borohydride. The chemical structures of the compounds were verified by means of their IR, H-1-NMR, E1 mass spectroscopic data and elemental analyses. The antidepressant activity of these compounds were evaluated by the Porsolt forced swimming (behavioral despair) test using tranylcypromine as the standard. 3-Phenyl-5-sulfonamidoindole-2-carboxylic acid 3,4-methylenedioxybenzylidenehydrazide, 3-phenyl-5-sulfonamidoindole-2-carboxylic acid 4-methylbenzylidene- hydrazide, 3-phenyl-5-sulfonamidoindole-2-carboxylic acid 4-nitrobenzylidenehydrazide and 3-phenyl-5-sulfonamidoindole-2-carboxylic acid benzylidenehydrazide showed antidepressant activity at 100 mg/kg. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80039-1
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide
  参考文献：
  名称：

  Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII

  摘要：

  基于新型磺胺基吲哚的酰肼类化合物，具有2-(肼甲酰)-3-苯基-1H-吲哚-5-磺胺酰胺骨架，已经合成并在酶抑制实验中对肿瘤相关的碳酸酐酶同工酶hCA IX和XII以及非靶标hCA I和II进行了测试。这些化合物对hCA IX和XII表现出选择性，优于hCA I和II。六种化合物对hCA IX或XII显示出低于10 nM的KI值。进行了分子建模研究以提出配体与hCA活性位点之间的结合相互作用。

  DOI：

  10.3390/ijms20092354

文献信息

• NA CHANNELS, DISEASE, AND RELATED ASSAYS AND COMPOSITIONS
  申请人：Brown Milton L.

  公开号：US20110230442A1

  公开（公告）日：2011-09-22

  Disclosed are molecules and their synthesis, for use in blocking gated ion channels such as voltage-gated sodium channels (VGSCs) and prostate voltage sodium channels (PVSCs). These inhibitors have superior blocking efficacy, for instance in displacing the radioligand [ 3 H]-Batrachotoxin-B ([ 3 H]-BTX-B) that binds to site 2 of a VGSC. The molecules of the invention comprise a moiety which increases the binding affinity of molecules for the protein binding site in prostate cancer cells (PCs), and which is also fluorescent. In one embodiment the invention molecules are an inhibition system that can be used to target over-abundant or hyperactive VGSCs selectively in pain, epilepsy or prostate cancer, inhibiting the proliferation of PCs. The fluorescent moiety also facilitates screening, tracking, and pharmacodynamic studies of the drug in a biological system both in vitro and in vivo.

  本发明涉及分子及其合成，用于阻断门控离子通道，例如电压门控钠通道（VGSC）和前列腺电压钠通道（PVSC）。这些抑制剂具有卓越的阻断效力，例如在取代结合到VGSC的位点2的放射性配体[3H]-Batrachotoxin-B ([3H]-BTX-B)方面。本发明的分子包括一个基团，增加分子对前列腺癌细胞（PC）中蛋白质结合位点的结合亲和力，并且也是荧光的。在一种实施方式中，本发明的分子是一种抑制系统，可用于选择性地靶向过度丰富或过度活跃的VGSC，从而抑制疼痛、癫痫或前列腺癌的PC的增殖。荧光基团还有助于在体外和体内生物系统中筛选、跟踪和药效学研究药物。
• Novel 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide based thiosemicarbazides as potent and selective inhibitors of tumor-associated human carbonic anhydrase IX and XII: Synthesis, cytotoxicity, and molecular modelling studies
  作者：Kübra Demir-Yazıcı、Muhammed Trawally、Silvia Bua、Dilek Öztürk-Civelek、Atilla Akdemir、Claudiu T. Supuran、Özlen Güzel-Akdemir

  DOI：10.1016/j.bioorg.2024.107096

  日期：2024.3

  In the pursuit of discovering new selective carbonic anhydrase (CA, EC 4.2.1.1) inhibitors, a small collection of novel thiosemicarbazides (5a-5t) were designed and synthesized starting from 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide which was evaluated as a potent inhibitor of different CA isoforms in a previous study. The newly synthesized compounds were examined against four human carbonic

  为了发现新的选择性碳酸酐酶 (CA, EC 4.2.1.1) 抑制剂，从 2-(肼基羰基)-3-苯基-1 H-吲哚开始，设计并合成了一小部分新型氨基硫脲 ( 5a - 5t ) -5-磺酰胺在之前的研究中被评估为不同 CA 亚型的有效抑制剂。新合成的化合物针对四种人碳酸酐酶 (hCA) 进行了检测，即跨膜肿瘤相关的 hCA IX/XII 和胞质广泛脱靶的 hCA I/II。在酶抑制测定中，所有 19 种化合物对 hCA IX/XII 的选择性比脱靶亚型 hCA I/II 高达约 340 倍。四种化合物对肿瘤相关异构体 hCA IX/XII 的酶抑制值 ( K i ) 低于 10 nM，其中包括两种亚纳摩尔范围的化合物（ 5r和5s ；hCA XII； K i ：0.69 和 0.87 nM）。使用整体对接和分子动力学研究研究了最有效的化合物分别针对 hCA IX 和 XII（化合物5s和5
• Carbonic anhydrase inhibitors. Synthesis of 2,4,6-trimethylpyridinium derivatives of 2-(hydrazinocarbonyl)-3-aryl-1H-indole-5-sulfonamides acting as potent inhibitors of the tumor-associated isoform IX and XII
  作者：Özlen Güzel、Alfonso Maresca、Andrea Scozzafava、Aydın Salman、Alexandru T. Balaban、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2009.04.068

  日期：2009.6

  A series of 2-(hydrazinocarbonyl)-3-aryl-1H-indole-5-sulfonamides possessing various 2-, 3- or 4- substituted phenyl groups with methyl-, halogeno- and methoxy-functionalities, or a perfluorophenyl moiety, has been derivatized by reaction with 2,4,6-trimethylpyrylium perchlorate. The new sulfonamides were evaluated as inhibitors of four mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, CA I, II (cytosolic), CA IX and XII (transmembrane, tumor-associated forms). Excellent inhibitory activity was observed against hCA IX with most of these sulfonamides, and against hCA XII with some of the new compounds. These compounds were generally less effective inhibitors of hCA II. Being membrane impermeant, these positively-charged sulfonamides are interesting candidates for targeting the tumor-associated CA IX and XII, as possible diagnostic tools or therapeutic agents. (C) 2009 Elsevier Ltd. All rights reserved.
• Discovery of Low Nanomolar and Subnanomolar Inhibitors of the Mycobacterial β-Carbonic Anhydrases Rv1284 and Rv3273
  作者：Özlen Güzel、Alfonso Maresca、Andrea Scozzafava、Aydın Salman、Alexandru T. Balaban、Claudiu T. Supuran

  DOI：10.1021/jm9004016

  日期：2009.7.9

  A series of 2-(hydrazinocarbonyl)-3-aryl-1H-indole-5-sulfonamides has been derivatized by reaction with 2,4,6-trimethylpyrylium perchlorate, leading to pyridinium derivatives. The new sulfonamides were evaluated as inhibitors of two beta-carbonic anhydrases (CAs, EC 4.2.1.1) from Mycobaterium tuberculosis, Rv1284 and Rv3273. The whole series showed excellent nanomolar inhibitory activity, with several subnanomolar inhibitors being detected. Rv1284 and Rv3273 have potential for developing antimycobacterial agents with an alternate mechanism of action.
• Ergenc; Salman; Gursoy, Pharmazie, 1990, vol. 45, # 5, p. 346 - 347
  作者：Ergenc、Salman、Gursoy、Bankaoglu

  DOI：——

  日期：——