1-methyl-4-(α-bromoacrylamido)imidazole-2-carboxylic acid | 179983-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-4-(α-bromoacrylamido)imidazole-2-carboxylic acid
• 英文别名: 4-(2-Bromoprop-2-enoylamino)-1-methylimidazole-2-carboxylic acid
• CAS: 179983-41-6
• 化学式: C₈H₈BrN₃O₃
• 分子量: 274.074
• InChiKey: ZVWOUKMQWVWAJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-N-(5-{[(5-{[(3-amino-3-iminopropyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide dihydrochloride 、 1-methyl-4-(α-bromoacrylamido)imidazole-2-carboxylic acid 在 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， 反应 16.0h， 生成 N-(5-{[(5-{[(5-{[(3-amino-3-iminopropyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-4-[(2-bromoacryloyl)amino]-1-methyl-1H-imidazole-2-carboxamide hydrochloride
  参考文献：
  名称：

  Synthesis and antitumor activity of novel distamycin derivatives

  摘要：

  Several distamycin derivatives were synthesized from deformyl distamycin by coupling with different azole carboxylic acids bearing an alkylating moiety. Some of them showed good activities in vitro and in vivo against L 1210 murine leukemia. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00204-1
• 作为产物：
  描述：

  1-甲基-4-硝基-1H-咪唑-2-羧酸 在 palladium on activated charcoal 苄基三乙基氯化铵 、 氢气 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-4-(α-bromoacrylamido)imidazole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and antitumor activity of novel distamycin derivatives

  摘要：

  Several distamycin derivatives were synthesized from deformyl distamycin by coupling with different azole carboxylic acids bearing an alkylating moiety. Some of them showed good activities in vitro and in vivo against L 1210 murine leukemia. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00204-1

文献信息

• Synthesis and growth inhibition activity of α-Bromoacrylic heterocyclic and benzoheterocyclic derivatives of distamycin A modified on the amidino moiety
  作者：Pier Giovanni Baraldi、Italo Beria、Paolo Cozzi、Nicoletta Bianchi、Roberto Gambari、Romeo Romagnoli

  DOI：10.1016/s0968-0896(02)00533-3

  日期：2003.3

  The design, synthesis and in vitro activities of novel alpha-bromoacryloyl pyrazole, imidazole and benzoheterocyclic derivatives of distamycin A, in which the amidino moiety has been replaced by moieties of different physico-chemical features are described, and the structure-activity relationships are discussed. In spite of the relevance of these modifications on the distamycin frame, these derivatives showed significant growth inhibitory activity against mouse leukemia L1210 cells. Therefore, the presence of the amidino moiety, and in general of a basic moiety, is not an absolute requirement for biological activity of alpha-bromoacrylic derivatives of distamycin. (C) 2003 Elsevier Science Ltd. All rights reserved.
• DISTAMYCIN A ANALOGUES AS ANTITUMOUR OR ANTIVIRAL AGENTS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP0722446B1

  公开（公告）日：2002-12-11
• US5753629A
  申请人：——

  公开号：US5753629A

  公开（公告）日：1998-05-19
• US6753316B1
  申请人：——

  公开号：US6753316B1

  公开（公告）日：2004-06-22