3-(3-bromophenyl)-2-(hydrazinocarbonyl)-1H-indole-5-sulfonamide | 1091602-15-1

• 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: 3-(3-bromophenyl)-2-(hydrazinocarbonyl)-1H-indole-5-sulfonamide
• 英文别名: 3-(3-bromophenyl)-2-(hydrazinecarbonyl)-1H-indole-5-sulfonamide
• CAS: 1091602-15-1
• 化学式: C₁₅H₁₃BrN₄O₃S
• 分子量: 409.263
• InChiKey: LOUMFRZBAXRSLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 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：

  3-(3-bromophenyl)-2-(hydrazinocarbonyl)-1H-indole-5-sulfonamide 、 2,4,6-三甲基吡喃鎓高氯酸盐 在 高氯酸 作用下， 以 甲醇 、 水 为溶剂， 生成 1-({[5-(aminosulfonyl)-3-(3-bromophenyl)-1H-indol-2-yl]carbonyl}amino)-2,4,6-trimethylpyridinium perchlorate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.04.068
• 作为产物：
  描述：

  ethyl 3-(3-bromophenyl)-5-sulfamoyl-1H-indole-2-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以64%的产率得到3-(3-bromophenyl)-2-(hydrazinocarbonyl)-1H-indole-5-sulfonamide
  参考文献：
  名称：

  碳酸酐酶抑制剂：用一系列2-（肼基羰基）-3-取代的苯基-1H-吲哚-5-磺酰胺对哺乳动物同工型I-XV的合成和抑制研究。

  摘要：

  一系列2-（肼羰基）-3-取代的苯基-1H-吲哚-5-磺酰胺，具有各种带有甲基，卤代和甲氧基官能团的2-，3-或4-取代的苯基，以及全氟苯基部分已合成并评估了它们作为13种具有催化活性的哺乳动物碳酸酐酶（CA，EC 4.2.1.1）同工型的抑制剂，即CA I-CA XV（人类（人类）或鼠类（人类）来源）的抑制剂。新化合物是同工酶hCA III，hCA IV，hCA VA，hCA VB，hCA VI和mCA XIII的无效抑制剂，hCA I，hCA VII，hCA IX和mCA XV的中度抑制剂以及hCA的优异的低纳摩尔抑制剂II和hCA XIV。在该系列磺酰胺中，吲哚环的3-位上的芳族基团的取代模式影响了生物活性和同工酶抑制谱。

  DOI：

  10.1016/j.bmc.2008.09.032

文献信息

• 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.
• Carbonic anhydrase inhibitors: Synthesis and inhibition studies against mammalian isoforms I–XV with a series of 2-(hydrazinocarbonyl)-3-substituted-phenyl-1H-indole-5-sulfonamides
  作者：Özlen Güzel、Alessio Innocenti、Andrea Scozzafava、Aydın Salman、Seppo Parkkila、Mika Hilvo、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2008.09.032

  日期：2008.10

  A series of 2-(hydrazinocarbonyl)-3-substitutedphenyl-1H-indole-5-sulfonamides possessing various 2-, 3- or 4- substituted phenyl groups with methyl-, halogeno- and methoxy- functionalities, as well as the perfluorophenyl moiety have been synthesized and evaluated as inhibitors of 13 catalytically active, mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, CA I-CA XV (of human (h) or murine

  一系列2-（肼羰基）-3-取代的苯基-1H-吲哚-5-磺酰胺，具有各种带有甲基，卤代和甲氧基官能团的2-，3-或4-取代的苯基，以及全氟苯基部分已合成并评估了它们作为13种具有催化活性的哺乳动物碳酸酐酶（CA，EC 4.2.1.1）同工型的抑制剂，即CA I-CA XV（人类（人类）或鼠类（人类）来源）的抑制剂。新化合物是同工酶hCA III，hCA IV，hCA VA，hCA VB，hCA VI和mCA XIII的无效抑制剂，hCA I，hCA VII，hCA IX和mCA XV的中度抑制剂以及hCA的优异的低纳摩尔抑制剂II和hCA XIV。在该系列磺酰胺中，吲哚环的3-位上的芳族基团的取代模式影响了生物活性和同工酶抑制谱。
• 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.