2-[[(3-氯-2-甲基苯基)磺酰基]氨基]-4-噻唑乙酸 | 376638-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[[(3-氯-2-甲基苯基)磺酰基]氨基]-4-噻唑乙酸
• 英文名称: {2-[(3-Chloro-2-methylbenzene-1-sulfonyl)amino]-1,3-thiazol-4-yl}acetic acid
• 英文别名: 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid
• CAS: 376638-09-4
• 化学式: C₁₂H₁₁ClN₂O₄S₂
• 分子量: 346.815
• InChiKey: SQGWOBDUXQBFJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 2-[[(3-氯-2-甲基苯基)磺酰基]氨基]-4-噻唑乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 以48%的产率得到3-chloro-2-methyl-N-[4-[2-(4-methylpiperazin-4-ium-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]benzenesulfonamide;chloride
  参考文献：
  名称：

  Arylsulfonamidothiazoles as a New Class of Potential Antidiabetic Drugs. Discovery of Potent and Selective Inhibitors of the 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  Novel antidiabetic arylsulfonamidothiazoles are presented that exert action through selective inhibition of the 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) enzyme, thereby attenuating hepatic gluconeogenesis. The diethylamide derivative 2a was shown to potently inhibit human 11beta-HSD1 (IC50 = 52 nM), whereas the N-methylpiperazinamide analogue 2b only inhibited murine 11beta-HSD1 (IC50 = 96 nM). Both compounds showed > 200-fold selectivity over human and murine 11beta-HSD2. 2b was subsequently shown to reduce glucose levels in diabetic KKA(gamma) mice, substantiating the 11beta-HSD1 enzyme as a target for the treatment of type 2 diabetes.(C) 2002 American Chemical Society

  DOI：

  10.1021/jm025530f
• 作为产物：
  描述：

  3-氯-2-甲基苯磺酰氯 在 吡啶 、 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 生成 2-[[(3-氯-2-甲基苯基)磺酰基]氨基]-4-噻唑乙酸
  参考文献：
  名称：

  Arylsulfonamidothiazoles as a New Class of Potential Antidiabetic Drugs. Discovery of Potent and Selective Inhibitors of the 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  Novel antidiabetic arylsulfonamidothiazoles are presented that exert action through selective inhibition of the 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) enzyme, thereby attenuating hepatic gluconeogenesis. The diethylamide derivative 2a was shown to potently inhibit human 11beta-HSD1 (IC50 = 52 nM), whereas the N-methylpiperazinamide analogue 2b only inhibited murine 11beta-HSD1 (IC50 = 96 nM). Both compounds showed > 200-fold selectivity over human and murine 11beta-HSD2. 2b was subsequently shown to reduce glucose levels in diabetic KKA(gamma) mice, substantiating the 11beta-HSD1 enzyme as a target for the treatment of type 2 diabetes.(C) 2002 American Chemical Society

  DOI：

  10.1021/jm025530f

文献信息

• [EN] INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1<br/>[FR] INHIBITEURS DE 11-BETA-HYDROXY-STEROIDE-DESHYDROGENASE DE TYPE 1
  申请人：BIOVITRUM AB

  公开号：WO2001090090A1

  公开（公告）日：2001-11-29

  The present invention relates to compounds with the formula (II) and also to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of thecompounds in medicine and for the preparation of a medicament which acts on the human 11-β-hydroxysteroid dehydrogenase type 1 enzyme.

  本发明涉及式（II）的化合物，以及包含该化合物的药物组合物，以及其制备过程，以及化合物在医学上的应用以及用于制备对人类11-β-羟基类固醇脱氢酶1型酶有作用的药物。
• Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1
  申请人：——

  公开号：US20040224996A1

  公开（公告）日：2004-11-11

  The present invention relates to compounds with the formula (II) and also to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds in medicine and for the preparation of a medicament which acts on the human 11-&bgr;-hydroxysteroid dehydrogenase type 1 enzyme. 1

  本发明涉及式（II）的化合物，以及包含该化合物的制药组合物，其制备过程，以及在医学上使用该化合物以及用于制备对人体11-β-羟基类固醇脱氢酶1型酶起作用的药物。
• INHIBITORS OF 11-BETA-HYDROXY STERIOD DEHYDROGENASE TYPE 1
  申请人：BARF Tjeerd

  公开号：US20100113435A1

  公开（公告）日：2010-05-06

  The present invention relates to compounds with the formula (II) and also to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds in medicine and for the preparation of a medicament which acts on the human 11-β-hydroxysteroid dehydrogenase type 1 enzyme.

  本发明涉及公式（II）的化合物，以及包含这些化合物的制药组合物，它们的制备过程，以及这些化合物在医学上的使用和用于制备对人类11-β-羟基类固醇脱氢酶1型酶起作用的药物。
• INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1
  申请人：BIOVITRUM AB

  公开号：EP1283831A1

  公开（公告）日：2003-02-19
• NEW USE I
  申请人：BIOVITRUM AB

  公开号：EP1638553A1

  公开（公告）日：2006-03-29