6-Chloro-1H-benzimidazole-2-sulfonyl chloride | 251921-01-4

• 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: 6-Chloro-1H-benzimidazole-2-sulfonyl chloride
• CAS: 251921-01-4
• 化学式: C₇H₄Cl₂N₂O₂S
• 分子量: 251.093
• InChiKey: ULROCJXAHJCIMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-1H-benzimidazole-2-sulfonyl chloride 在 盐酸 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 44.5h， 生成 1-[[5(6)-chlorobenzoimidazol-2-yl]sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006
• 作为产物：
  描述：

  5-氯苯并咪唑-2-硫醇 在 氯 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.17h， 生成 6-Chloro-1H-benzimidazole-2-sulfonyl chloride
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006

文献信息

• Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06281227B1

  公开（公告）日：2001-08-28

  The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

  本文中的化合物具有有用的药理活性，因此被纳入药物组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是凝血因子Xa活性的抑制剂。本发明涉及具有I式化合物的化合物、含有I式化合物的组合物，以及它们的用途，用于治疗患有或受到生理状况影响的患者，这些生理状况可以通过给予凝血因子Xa活性抑制剂来改善。
• Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds
  申请人：——

  公开号：US20020013310A1

  公开（公告）日：2002-01-31

  The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

  本文中的I式化合物表现出有用的药理活性，因此被纳入制药组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是Factor Xa活性的抑制剂。本发明涉及I式化合物、含有I式化合物的组合物以及它们的使用，用于治疗患有或受到生理状况影响的患者，这些状况可以通过给予Factor Xa活性抑制剂的治疗得到改善。
• Benzimidazoles and isosteric compounds as potent and selective factor Xa inhibitors
  作者：Wei He、Barbara Hanney、Michael R Myers、Stephen Condon、Michael R Becker、Alfred P Spada、Christopher Burns、Karen Brown、Dennis Colussi、Valeria Chu

  DOI：10.1016/s0960-894x(02)00056-2

  日期：2002.3

  Benzimidazoles and their isosteric compounds as factor Xa inhibitors are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Arylsulfonamidopiperidone derivatives as a novel class of factor Xa inhibitors
  作者：Yan Shi、Stephen P. O’Connor、Doree Sitkoff、Jing Zhang、Mengxiao Shi、Sharon N. Bisaha、Ying Wang、Chi Li、Zheming Ruan、R. Michael Lawrence、Herbert E. Klei、Kevin Kish、Eddie C.-K. Liu、Steve M. Seiler、Liang Schweizer、Thomas E. Steinbacher、William A. Schumacher、Jeffrey A. Robl、John E. Macor、Karnail S. Atwal、Philip D. Stein

  DOI：10.1016/j.bmcl.2011.06.098

  日期：2011.12

  The design, synthesis and SAR of a novel class of valerolactam-based arylsulfonamides as potent and selective FXa inhibitors is reported. The arylsulfonamide-valerolactam scaffold was derived based on the proposed bioisosterism to the arylcyanoguanidine-caprolactam core in known FXa inhibitors. The SAR study led to compound 46 as the most potent FXa inhibitor in this series, with an IC50 of 7 nM and EC2xPT of 1.7 mu M. The X-ray structure of compound 40 bound to FXa shows that the sulfonamide-valerolactam scaffold anchors the aryl group in the S1 and the novel acylcytisine pharmacophore in the S4 pockets. (C) 2011 Elsevier Ltd. All rights reserved.
• Solid-phase parallel synthesis of azarene pyrrolidinones as factor Xa inhibitors
  作者：Yong Gong、Michael Becker、Yong Mi Choi-Sledeski、Roderick S Davis、Joseph M Salvino、Valeria Chu、Karen D Brown、Henry W Pauls

  DOI：10.1016/s0960-894x(00)00151-7

  日期：2000.5

  A focused library (4 x 14) prepared from 4-aminopyridine and 4-, 5-, and 6-azoindole templates was synthesized using 14 polymer supported 4-amido-2,3,5,6-tetrafluorophenyl (TFP) sulfonate esters inputs. Several compounds were identified as factor Xa inhibitors (IC(50)less than or equal to 0.1 mu M) helping to establish the SAR among these four series of azarene pyrrolidinones. (C) 2000 Elsevier Science Ltd. All rights reserved.