tert-butyl 2-chloro-5-nitro-1H-benzimidazole-1-carboxylate | 652979-69-6

• 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: tert-butyl 2-chloro-5-nitro-1H-benzimidazole-1-carboxylate
• 英文别名: Tert-butyl 2-chloro-5-nitrobenzimidazole-1-carboxylate
• CAS: 652979-69-6
• 化学式: C₁₂H₁₂ClN₃O₄
• 分子量: 297.698
• InChiKey: VOUNPHBNGRPLSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  螺[异苯并呋喃-1(3H),4'-哌啶]-3-酮盐酸盐 、 tert-butyl 2-chloro-5-nitro-1H-benzimidazole-1-carboxylate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

  摘要：

  Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.018
• 作为产物：
  描述：

  2-氯-5-硝基-1H-1,3-苯并咪唑 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 生成 tert-butyl 2-chloro-5-nitro-1H-benzimidazole-1-carboxylate
  参考文献：
  名称：

  Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

  摘要：

  Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.018

文献信息

• Identification of 2-aminobenzimidazoles as potent melanin-concentrating hormone 1-receptor (MCH1R) antagonists
  作者：Minoru Moriya、Hiroyuki Kishino、Shunji Sakuraba、Toshihiro Sakamoto、Takuya Suga、Hidekazu Takahashi、Takao Suzuki、Masahiko Ito、Junko Ito、Ryuichi Moriya、Norihiro Takenaga、Hisashi Iwaasa、Akane Ishihara、Akio Kanatani、Takehiro Fukami

  DOI：10.1016/j.bmcl.2009.04.147

  日期：2009.7

  A series of 2-aminobenzimidazole-based MCH1R antagonists was identified by core replacement of the aminoquinoline lead 1. Subsequent modi. cation of the 2- and 5-positions led to improvement in potency and intrinsic clearance. Compound 25 exhibited good plasma and brain exposure, and attenuated MCH induced food intake at 30 mg/kg PO in rats. (C) 2009 Elsevier Ltd. All rights reserved.
• ANTAGONIST OF MELANIN-CONCENTRATING HORMONE RECEPTOR COMPRISING BENZIMIDAZOLE DERIVATIVE AS ACTIVE INGREDIENT
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1553089B1

  公开（公告）日：2009-09-30
• Design, syntheses, and structure–activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives
  作者：Yoshio Ogino、Norikazu Ohtake、Yoshikazu Nagae、Kenji Matsuda、Minoru Moriya、Takuya Suga、Makoto Ishikawa、Maki Kanesaka、Yuko Mitobe、Junko Ito、Tetsuya Kanno、Akane Ishihara、Hisashi Iwaasa、Tomoyuki Ohe、Akio Kanatani、Takehiro Fukami

  DOI：10.1016/j.bmcl.2008.08.018

  日期：2008.9

  Design, syntheses, and structure-activity relationships of a novel class of 2-3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.