4-amino-4'-[di(2-chloroethyl)amino]benzophenone | 133041-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-4'-[di(2-chloroethyl)amino]benzophenone
• 英文别名: (4-Aminophenyl)-[4-[bis(2-chloroethyl)amino]phenyl]methanone
• CAS: 133041-73-3
• 化学式: C₁₇H₁₈Cl₂N₂O
• 分子量: 337.249
• InChiKey: NCBWQJGVAATJAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯喹啉 、 4-amino-4'-[di(2-chloroethyl)amino]benzophenone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 [4-[Bis(2-chloroethyl)amino]phenyl]-[4-(quinolin-4-ylamino)phenyl]methanone
  参考文献：
  名称：

  DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards

  摘要：

  A series of 4-anilinoquinoline-linked aniline mustards of widely varying mustard reactivity were prepared and evaluated for their antitumor activity. The compounds were designed as minor groove binding agents, where the aniline mustard ring is itself part of the DNA-binding ligand. While there was a general trend for cytotoxicity to correlate with mustard reactivity, this was much less pronounced than with untargeted mustards. The compounds were much more cytotoxic than the parent diols, and were at least 10-fold more cytotoxic than the corresponding aniline mustards themselves. Comparative cell line studies suggested that the mechanism of cytotoxicity varied with mustard reactivity. The most reactive mustards cross-linked DNA, while cell killing by the less reactive compounds appeared to be by the formation of bulky monoadducts. The compounds were active but not particularly dose-potent against P388 leukemia in vivo. The modest potency may be related to their poor aqueous solubility, since the more soluble methyl quaternary salts were equally active at much lower doses.

  DOI：

  10.1021/jm00109a005
• 作为产物：
  描述：

  氟苯 在 盐酸 、 三氯化铝 、 三乙胺 、 sodium chloride 、 tin(ll) chloride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-amino-4'-[di(2-chloroethyl)amino]benzophenone
  参考文献：
  名称：

  DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards

  摘要：

  A series of 4-anilinoquinoline-linked aniline mustards of widely varying mustard reactivity were prepared and evaluated for their antitumor activity. The compounds were designed as minor groove binding agents, where the aniline mustard ring is itself part of the DNA-binding ligand. While there was a general trend for cytotoxicity to correlate with mustard reactivity, this was much less pronounced than with untargeted mustards. The compounds were much more cytotoxic than the parent diols, and were at least 10-fold more cytotoxic than the corresponding aniline mustards themselves. Comparative cell line studies suggested that the mechanism of cytotoxicity varied with mustard reactivity. The most reactive mustards cross-linked DNA, while cell killing by the less reactive compounds appeared to be by the formation of bulky monoadducts. The compounds were active but not particularly dose-potent against P388 leukemia in vivo. The modest potency may be related to their poor aqueous solubility, since the more soluble methyl quaternary salts were equally active at much lower doses.

  DOI：

  10.1021/jm00109a005

文献信息

• Synthesis of 4β-N-polyaromatic substituted podophyllotoxins: DNA topoisomerase inhibition, anticancer and apoptosis-inducing activities
  作者：Ahmed Kamal、B. Ashwini Kumar、Paidakula Suresh、Satyam Kumar Agrawal、Gousia Chashoo、Shashank K. Singh、A.K. Saxena

  DOI：10.1016/j.bmc.2010.10.042

  日期：2010.12

  A new class of 4β-N-polyaromatic substituted podophyllotoxin congeners have been synthesized and evaluated for their DNA topoisomerase-II (topo-II) inhibition as well as anticancer potential in some human cancer cell lines. The ease of synthesis and interesting biological activities make the present series of polyaromatic-podophyllotoxin congeners as a promising new structure for the development of

  已经合成了新型的4β- N-多芳族取代鬼臼毒素同类物，并评估了它们在某些人类癌细胞系中对DNA拓扑异构酶II（topo-II）的抑制作用以及抗癌潜力。易于合成和有趣的生物学活性使得本系列的多芳基鬼臼毒素同源物成为开发基于鬼臼毒素支架的新型抗癌药的有希望的新结构。
• [EN] NOVEL 4ß-AMINO PODOPHVLLOTOXIN CONGENERS AS ANTI TUMOUR ANTIBIOTICS A PROCESS FOR THE PREPARATION THEREOF<br/>[FR] NOUVEAUX CONGÉNÈRES DE 4ß-AMINO PODOPHYLLOTOXINE UTILISÉS COMME ANTIBIOTIQUES ANTITUMORAUX ET PROCESSUS DE PRÉPARATION DE CEUX-CI
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010052733A1

  公开（公告）日：2010-05-14

  The present invention provises novel β-amino podophyllotoxin congeners of general formula (A); R = CH3, or H; R1 = (a) or (b) or (c) or (d) or (e) or (f). The present invention also provides a process for the preparation of 4β-amino podophyllotoxin congeners useful as antitumour agents.

  本发明提供了一种新的β-氨基鬼臼毒素衍生物，其通式为(A)；其中R = CH3或H；R1 = (a)或(b)或(c)或(d)或(e)或(f)。本发明还提供了一种制备4β-氨基鬼臼毒素衍生物的方法，该衍生物可用作抗肿瘤剂。
• NOVEL 4BETA-AMINO PODOPHYLLOTOXIN CONGENERS AS ANTI TUMOUR ANTIBIOTICS A PROCESS FOR THE PREPARATION THEREOF
  申请人：Ahmed Kamal

  公开号：US20110213165A1

  公开（公告）日：2011-09-01

  The present invention provides novel β-amino podophyllotoxin congeners of general formula (A); R═CH 3 , or H; R 1 =(a) or (b) or (c) or (d) or (e) or (f). The present invention also provides a process for the preparation of 4β-amino podophyllotoxin congeners useful as antitumour agents.

  本发明提供了一种新型β-氨基鬼臼毒素衍生物，其一般式为(A)；其中R═CH3或H；R1＝（a）或（b）或（c）或（d）或（e）或（f）。本发明还提供一种制备4β-氨基鬼臼毒素衍生物的方法，该衍生物对抗肿瘤有用。
• GRAVATT, G. LANCE;BAGULEY, BRUCE C.;WILSON, WILLIAM R.;DENNY, WILLIAM A., J. MED. CHEM., 34,(1991) N, C. 1552-1560
  作者：GRAVATT, G. LANCE、BAGULEY, BRUCE C.、WILSON, WILLIAM R.、DENNY, WILLIAM A.

  DOI：——

  日期：——
• NOVEL 4BETA-AMINO PODOPHVLLOTOXIN CONGENERS AS ANTI TUMOUR ANTIBIOTICS A PROCESS FOR THE PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：EP2346876B1

  公开（公告）日：2013-01-30