1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)imidazole-2-carboxylic acid | 142211-81-2

• 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-(1-methyl-4-nitropyrrole-2-carboxamido)imidazole-2-carboxylic acid
• 英文别名: 1-Methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]imidazole-2-carboxylic acid；1-methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]imidazole-2-carboxylic acid
• CAS: 142211-81-2
• 化学式: C₁₁H₁₁N₅O₅
• 分子量: 293.239
• InChiKey: CRLBVNINPYTWOR-UHFFFAOYSA-N

物化性质

• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)imidazole-2-carboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 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 24.0h， 生成 4-methoxy-2-{1-methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-imidazol-2-yl}-1H-benzoimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Exploring the limits of benzimidazole DNA-binding oligomers for the hypoxia inducible factor (HIF) site

  摘要：

  The vascular endothelial growth factor (VEGF) and its receptors have been implicated as key-factors in tumor angiogenesis and are major targets in cancer therapy. New oligomers which mimic the architecture of DNA-binding polyamides have been designed to target the hypoxia inducible factor (HIF-1 alpha) binding site on the promoter of VEGF gene. These oligomers incorporate an increasing number of six-five fused rings such as hydroxybenzimidazole-imidazole, benzimidazole pyrrole, benzimidazole-chlorothiophene, and imidazopyridine-pyrrole, and bind the VEGF hypoxia response element (HRE) 5'-TACGT-3' with high affinity and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.028
• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 氯化亚砜 、 水 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)imidazole-2-carboxylic acid
  参考文献：
  名称：

  PYRROLOBENZODIAZEPINE DERIVATIVE AND LIGAND-LINKER CONJUGATE THEREOF

  摘要：

  本发明涉及一种吡咯苯并二氮平衍生物化合物、其与配体的共轭物以及其用途。该吡咯苯并二氮平衍生物化合物在血浆中更加稳定，即使在循环过程中也稳定，并表现出优异的疗效。特别是，该吡咯苯并二氮平衍生物化合物与配体的共轭物具有极大的优势，因为可以针对性地治疗增生性疾病如癌症，最大化药物疗效，并最小化副作用的表达，因为该共轭物更稳定地到达目标细胞并有效发挥药物疗效，同时通过允许药物在癌细胞内轻松释放的连接技术，大大降低了毒性并最大化药物疗效。

  公开号：

  EP4086268A1

文献信息

• NOVEL BENZODIAZEPINE DERIVATIVES
  申请人：Li Wei

  公开号：US20130302357A1

  公开（公告）日：2013-11-14

  The invention relates to novel benzodiazepine derivatives with antiproliferative activity and more specifically to novel benzodiazepines of formula (I) and (II), in which the diazepine ring (B) is fused with a heterocyclic ring (CD), wherein the heterocyclic ring is bicyclic or a compound of formula (III), in which the diazepine ring (B) is fused with a heterocyclic ring (C), wherein the heterocyclic ring is monocyclic. The invention provides cytotoxic dimers of these compounds. The invention also provides conjugates of the monomers and the dimers. The invention further provides compositions and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention. The invention further relates to methods of using the compounds or conjugates for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.

  本发明涉及具有抗增殖活性的新型苯二氮平衍生物，更具体地涉及公式(I)和(II)的新型苯二氮平衍生物，其中二氮平环(B)与杂环环(CD)融合，杂环环为双环或公式(III)的化合物，其中二氮平环(B)与杂环环(C)融合，杂环环为单环。本发明提供这些化合物的细胞毒性二聚体。本发明还提供单体和二聚体的结合物。本发明还提供使用本发明的化合物或结合物用于抑制异常细胞生长或治疗哺乳动物增生性疾病的组合物和方法。本发明还涉及使用这些化合物或结合物进行哺乳动物细胞的体外、原位和体内诊断或治疗，或相关病理条件的方法。
• PYRROLOBENZODIAZEPINE DERIVATIVE AND LIGAND-LINKER CONJUGATE THEREOF
  申请人：LegoChem Biosciences, Inc.

  公开号：EP4086268A1

  公开（公告）日：2022-11-09

  The present invention relates to a pyrrolobenzodiazepine derivative compound, a conjugate of the same with a ligand, and the use of the same. The pyrrolobenzodiazepine derivative compound is more stable in plasma, is stable even in circulation, and exhibits excellent efficacy. In particular, the conjugate of the pyrrolobenzodiazepine derivative compound with a ligand has a great advantage in that it is possible to target and specifically treat proliferative disease such as cancer, maximize drug efficacy, and minimize the expression of side effects since the conjugate more stably reaches the target cell and effectively exerts drug efficacy while toxicity is greatly reduced as a linker technology that allows drugs to be easily released within cancer cells and maximize drug efficacy is incorporated.

  本发明涉及一种吡咯苯并二氮平衍生物化合物、其与配体的共轭物以及其用途。该吡咯苯并二氮平衍生物化合物在血浆中更加稳定，即使在循环过程中也稳定，并表现出优异的疗效。特别是，该吡咯苯并二氮平衍生物化合物与配体的共轭物具有极大的优势，因为可以针对性地治疗增生性疾病如癌症，最大化药物疗效，并最小化副作用的表达，因为该共轭物更稳定地到达目标细胞并有效发挥药物疗效，同时通过允许药物在癌细胞内轻松释放的连接技术，大大降低了毒性并最大化药物疗效。
• Dwyer, Tammy J.; Geierstanger, Bernhard H.; Bathini, Yadagiri, Journal of the American Chemical Society, 1992, vol. 114, # 15, p. 5911 - 5919
  作者：Dwyer, Tammy J.、Geierstanger, Bernhard H.、Bathini, Yadagiri、William Lown、Wemmer, David E.

  DOI：——

  日期：——
• US8802667B2
  申请人：——

  公开号：US8802667B2

  公开（公告）日：2014-08-12
• US9550787B2
  申请人：——

  公开号：US9550787B2

  公开（公告）日：2017-01-24