1-Methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carbonyl chloride | 188847-78-1

• 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: 1-Methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carbonyl chloride
• CAS: 188847-78-1
• 化学式: C₁₂H₁₁ClN₄O₄
• 分子量: 310.697
• InChiKey: PJLOBQLZYCUPGR-UHFFFAOYSA-N

物化性质

• 沸点：
  420.8±45.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-O-demethyl-4β-(p-aminoanilino)-4-desoxypodophyllotoxin 、 1-Methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carbonyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[4-[[(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]phenyl]-1-methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carboxamide
  参考文献：
  名称：

  Antitumor agents. 1771. Design, syntheses, and biological evaluation of novel etoposide analogs bearing pyrrolecarboxamidino group as DNA topoisomerase II inhibitors

  摘要：

  Novel water-soluble 4 beta-amino-4'-O-demethylepipodophyllotoxin derivatives (6-12), designed to enhance minor groove binding ability, were synthesized and screened against NCI's in vitro disease-oriented human tumor cells. Among them, 4'-O-demethyl-4 beta-[N-(1 triple prime-methyl-4 triple prime-nitro-pyrrole-2 triple prime-carbonyl)-4 ''-aminoanilino]-4-desoxypodophyllotoxin (10) and its HCl salt (11) were found to exhibit potent cytotoxic activities (average log GI(50) = -6.91, -7.00, and -5.01 for 10, 11, and etoposide, respectively). Compounds 10 and 12 were further tested for their inhibitory activities against DNA topoisomerase II. Compound 10 again exhibited a superior activity profile compared to that of etoposide, displaying increased cytotoxicity against KB and KB-7d cells (ID50/LD(50) = 0.04/0.15 and 0.2/0.25 for KB and KB-7d cells, respectively), topoisomerase II inhibitory activity (12.5 mu M), and cellular protein DNA complex formation (225%). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)00060-7
• 作为产物：
  描述：

  4-氨基-1-甲基-1H-吡咯-2-羧酸 在 氯化亚砜 作用下， 生成 1-Methyl-4-[(1-methyl-4-nitropyrrole-2-carbonyl)amino]pyrrole-2-carbonyl chloride
  参考文献：
  名称：

  Antitumor agents. 1771. Design, syntheses, and biological evaluation of novel etoposide analogs bearing pyrrolecarboxamidino group as DNA topoisomerase II inhibitors

  摘要：

  Novel water-soluble 4 beta-amino-4'-O-demethylepipodophyllotoxin derivatives (6-12), designed to enhance minor groove binding ability, were synthesized and screened against NCI's in vitro disease-oriented human tumor cells. Among them, 4'-O-demethyl-4 beta-[N-(1 triple prime-methyl-4 triple prime-nitro-pyrrole-2 triple prime-carbonyl)-4 ''-aminoanilino]-4-desoxypodophyllotoxin (10) and its HCl salt (11) were found to exhibit potent cytotoxic activities (average log GI(50) = -6.91, -7.00, and -5.01 for 10, 11, and etoposide, respectively). Compounds 10 and 12 were further tested for their inhibitory activities against DNA topoisomerase II. Compound 10 again exhibited a superior activity profile compared to that of etoposide, displaying increased cytotoxicity against KB and KB-7d cells (ID50/LD(50) = 0.04/0.15 and 0.2/0.25 for KB and KB-7d cells, respectively), topoisomerase II inhibitory activity (12.5 mu M), and cellular protein DNA complex formation (225%). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)00060-7

文献信息

• DEBART, FRANCOISE;PERIGAUD, CHRISTIAN;GOSSELIN, GILLES;MRANI, DRISS;RAYNE+, J. MED. CHEM., 32,(1989) N, C. 1074-1083
  作者：DEBART, FRANCOISE、PERIGAUD, CHRISTIAN、GOSSELIN, GILLES、MRANI, DRISS、RAYNE+

  DOI：——

  日期：——
• Antitumor agents. 1771. Design, syntheses, and biological evaluation of novel etoposide analogs bearing pyrrolecarboxamidino group as DNA topoisomerase II inhibitors
  作者：Zheng Ji、Hui-Kang Wang、Kenneth F. Bastow、Xiao-Kang Zhu、Sung Jin Cho、Yung-Chi Cheng、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(97)00060-7

  日期：1997.3

  Novel water-soluble 4 beta-amino-4'-O-demethylepipodophyllotoxin derivatives (6-12), designed to enhance minor groove binding ability, were synthesized and screened against NCI's in vitro disease-oriented human tumor cells. Among them, 4'-O-demethyl-4 beta-[N-(1 triple prime-methyl-4 triple prime-nitro-pyrrole-2 triple prime-carbonyl)-4 ''-aminoanilino]-4-desoxypodophyllotoxin (10) and its HCl salt (11) were found to exhibit potent cytotoxic activities (average log GI(50) = -6.91, -7.00, and -5.01 for 10, 11, and etoposide, respectively). Compounds 10 and 12 were further tested for their inhibitory activities against DNA topoisomerase II. Compound 10 again exhibited a superior activity profile compared to that of etoposide, displaying increased cytotoxicity against KB and KB-7d cells (ID50/LD(50) = 0.04/0.15 and 0.2/0.25 for KB and KB-7d cells, respectively), topoisomerase II inhibitory activity (12.5 mu M), and cellular protein DNA complex formation (225%). (C) 1997 Elsevier Science Ltd. All rights reserved.