4-(7-bromo-spiro[benzoimidazole-2,1'-cyclohex]e-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester | 631909-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(7-bromo-spiro[benzoimidazole-2,1'-cyclohex]e-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester
• 英文别名: Methyl 4-(7-bromospiro[benzimidazole-2,1'-cyclohexane]-5-yl)sulfonyl-5-methylsulfanylthiophene-2-carboxylate
• CAS: 631909-61-0
• 化学式: C₁₉H₁₉BrN₂O₄S₃
• 分子量: 515.473
• InChiKey: QRDNVCNHRRHMDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(7-bromo-spiro[benzoimidazole-2,1'-cyclohex]e-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester 在 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 生成 4-(3,4-diamino-5-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS
  [FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT

  摘要：

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。

  公开号：

  WO2003099805A1
• 作为产物：
  描述：

  甲基4-氨基-5-(甲硫基)-2-噻吩羧酸酯 在 盐酸 、 亚硝酸特丁酯 、 碳酸氢钠 、 溶剂黄146 、 sodium sulfite 作用下， 以 乙醇 为溶剂， 生成 4-(7-bromo-spiro[benzoimidazole-2,1'-cyclohex]e-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A novel series of arylsulfonylthiophene-2-carboxamidine inhibitors of the complement component C1s

  摘要：

  Inhibiting the classical pathway of complement activation by attenuating the proteolytic activity of the serine protease C1s is a potential strategy for the therapeutic intervention in disease states such as hereditary angioedema, ischemia-reperfusion injury, and acute transplant rejection. A series of arylsulfonylthiophene-2-carboximidine inhibitors of C1s were synthesized and evaluated for C1s inhibitory activity. The most potent compound had a K-i of 10 nM and >1000-fold selectivity over uPA, tPA, FXa, thrombin, and plasmin. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.036

文献信息

• [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS<br/>[FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT
  申请人：DIMENSIONAL PHARM INC

  公开号：WO2003099805A1

  公开（公告）日：2003-12-04

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。
• Novel thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20040009995A1

  公开（公告）日：2004-01-15

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula I 1 or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R 3 , R 4 and R 7 are defined in the specification, Z is SO or SO 2 , and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用公式I的化合物的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中在规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本文中定义的芳香族或杂环芳基。
• A novel series of arylsulfonylthiophene-2-carboxamidine inhibitors of the complement component C1s
  作者：Nalin L. Subasinghe、Jeremy M. Travins、Farah Ali、Hui Huang、Shelley K. Ballentine、Juan José Marugán、Ehab Khalil、Heather R. Hufnagel、Roger F. Bone、Renee L. DesJarlais、Carl S. Crysler、Nisha Ninan、Maxwell D. Cummings、Christopher J. Molloy、Bruce E. Tomczuk

  DOI：10.1016/j.bmcl.2006.01.036

  日期：2006.4

  Inhibiting the classical pathway of complement activation by attenuating the proteolytic activity of the serine protease C1s is a potential strategy for the therapeutic intervention in disease states such as hereditary angioedema, ischemia-reperfusion injury, and acute transplant rejection. A series of arylsulfonylthiophene-2-carboximidine inhibitors of C1s were synthesized and evaluated for C1s inhibitory activity. The most potent compound had a K-i of 10 nM and >1000-fold selectivity over uPA, tPA, FXa, thrombin, and plasmin. (C) 2006 Elsevier Ltd. All rights reserved.