(5-Chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid | 104189-86-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5-Chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid
• 英文别名: 1H-Benzimidazole-1-aceticacid, 5-chloro-2,3-dihydro-2-oxo-；2-(5-chloro-2-oxo-3H-benzimidazol-1-yl)acetic acid
• CAS: 104189-86-8
• 化学式: C₉H₇ClN₂O₃
• 分子量: 226.619
• InChiKey: OJSZGAKDLNMAHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5'-amino-3-methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione 、 (5-Chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid 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 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(5-chloro-2-oxo-3H-benzimidazol-1-yl)-N-[(2R)-1'-methyl-2',4'-dioxospiro[1,3-dihydroindene-2,5'-imidazolidine]-5-yl]acetamide
  参考文献：
  名称：

  Potent benzimidazolone-based CGRP receptor antagonists

  摘要：

  The previously disclosed spirohydantoin-based CGRP receptor antagonists were optimized for potency through modi. cation of the benzimidazolone substituents. Compounds were identified which had minimal shift in the cAMP functional assay containing 50% human serum. Blockade of CGRP-mediated vasodilation was observed with these compounds in a rhesus pharmacodynamic assay and the in vivo potency correlated with the in vitro activity in the serum-shifted functional assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.019
• 作为产物：
  描述：

  sodium;6-chloro-1-prop-1-en-2-ylbenzimidazol-3-id-2-one 在 盐酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 10.0h， 生成 (5-Chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid
  参考文献：
  名称：

  Synthesis of N-carboxylalkylbenzimidazolin-2-ones

  摘要：

  DOI：

  10.1007/bf00515223

文献信息

• Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand
  作者：Gerd Dannhardt、Beate K. Kohl

  DOI：10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5

  日期：2000.5

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.
• XALIKOV, S. S.;KADYROV, CH. SH.;AYUPOVA, A. T.;MOLCHANOV, L. V., XIMIYA GETEROTSIKL. SOEDIN., 1985, N 11, 1517-1520
  作者：XALIKOV, S. S.、KADYROV, CH. SH.、AYUPOVA, A. T.、MOLCHANOV, L. V.

  DOI：——

  日期：——
• Synthesis of N-carboxylalkylbenzimidazolin-2-ones
  作者：S. S. Khalikov、Ch. Sh. Kadyrov、A. T. Ayupova、L. V. Molchanov

  DOI：10.1007/bf00515223

  日期：1985.11
• Potent benzimidazolone-based CGRP receptor antagonists
  作者：Cory R. Theberge、Rodney A. Bednar、Ian M. Bell、Halea A. Corcoran、John F. Fay、James C. Hershey、Victor K. Johnston、Stefanie A. Kane、Scott Mosser、Christopher A. Salvatore、Theresa M. Williams、C. Blair Zartman、Xu-Fang Zhang、Samuel L. Graham、Joseph P. Vacca

  DOI：10.1016/j.bmcl.2008.10.019

  日期：2008.12

  The previously disclosed spirohydantoin-based CGRP receptor antagonists were optimized for potency through modi. cation of the benzimidazolone substituents. Compounds were identified which had minimal shift in the cAMP functional assay containing 50% human serum. Blockade of CGRP-mediated vasodilation was observed with these compounds in a rhesus pharmacodynamic assay and the in vivo potency correlated with the in vitro activity in the serum-shifted functional assay. (C) 2008 Elsevier Ltd. All rights reserved.