4,6-dibromo-2H-benzimidazole-2-spirocyclohexane | 166904-78-5

• 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: 4,6-dibromo-2H-benzimidazole-2-spirocyclohexane
• 英文别名: 4,6-Dibromospiro[benzimidazole-2,1'-cyclohexane]
• CAS: 166904-78-5
• 化学式: C₁₂H₁₂Br₂N₂
• 分子量: 344.049
• InChiKey: CIFBXHHVUGLVQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-dibromo-2H-benzimidazole-2-spirocyclohexane 在 sodium dithionite 作用下， 以 甲醇 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Iddon, Brian, Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 9, p. 673 - 701

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-dibromo-1,3-dihydro-2H-benzimidazole-2-spirocyclohexane 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到4,6-dibromo-2H-benzimidazole-2-spirocyclohexane
  参考文献：
  名称：

  2 H-苯并咪唑（异苯并咪唑）。第9部分。4,6-二溴-2 H-苯并咪唑-2-螺环己烷的合成与反应

  摘要：

  通过将3，5-二溴-邻-苯二胺10与环己酮缩合并将所得的4，6-二溴-1，3-二氢-2 H-苯并咪唑-2-螺环己烷5与二氧化锰氧化来制备标题化合物1。。用钠2,3- dichlorophenoxide，苯亚磺酸钠，或哌啶它被溴的损失反应，得到6-取代的衍生物2，3，和4，分别。然而，吗啉产生5,7-二溴-4-吗啉代-2 H-苯并咪唑-2-螺环己烷15，而吡啶2（1 H）-硫酮和嘧啶2（1 H）-硫酮得到4-溴-1,3-二氢-6-（吡啶-2-基硫基）-2 H-苯并咪唑-2-螺环己烷6和5,7-二溴-1,3-二氢-4-（嘧啶-2-基硫基）-2 H-苯并咪唑-2-螺环己烷14。在1或2摩尔当量的存在下。甲醇钠似乎发挥作用的芳烃机理，导致形成5-溴-6-甲氧基-11和6-溴-4-甲氧基-2 H-苯并咪唑-2-螺环己烷12或5,6的混合物-二甲氧基-2 H-苯并咪唑-2-螺环己烷13。标题化合物的氧

  DOI：

  10.1016/0040-4020(95)00220-3

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。
• 2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles, particularly 2-substituted benzimidazoles with known or potential anthelminthic activity
  作者：Justine C. Hazelton、Brian Iddon、Hans Suschitzky、Ley H. Woolley

  DOI：10.1016/0040-4020(95)00642-l

  日期：1995.9

  Polysubstiluted o-phenylenediamines were syathesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio-and 2-trifluoromethylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)-benzimidazole and 1 l-(

  通过用连二亚硫酸钠在乙醇水溶液中还原裂解相应的2 H-苯并咪唑-2-螺环己烷，可以中等至高收率合成多取代的邻苯二胺，然后将其转化为甲基苯并咪唑-2-氨基甲酸酯和2-甲硫基和2-三氟甲基苯并咪唑已知或潜在的驱虫活性。还合成了5-（嘧啶-2-基硫基）-苯并咪唑和1l-（吡啶-2-基硫基）二烯并[ a，c ]吩嗪。将2，3-二氨基喹喔啉与环己酮缩合制备的1，3-二氢-2 H -4，9-二氮杂[2，3- d ]咪唑的尝试氧化为标题体系的类似物失败。
• 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.
• US7138530B2
  申请人：——

  公开号：US7138530B2

  公开（公告）日：2006-11-21