N-{4-[bis(2-chloroethyl)amino]phenyl}-N'-(2-methyl-4-quinolinyl)urea | 1038623-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-{4-[bis(2-chloroethyl)amino]phenyl}-N'-(2-methyl-4-quinolinyl)urea
• 英文别名: 1-{4-[bis(2-chloroethyl)amino]phenyl}-3-(2-methylquinolin-4-yl)urea；1-[4-[bis(2-chloroethyl)amino]phenyl]-3-(2-methylquinolin-4-yl)urea
• CAS: 1038623-43-6
• 化学式: C₂₁H₂₂Cl₂N₄O
• 分子量: 417.338
• InChiKey: QFFYHGSWSSUPEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基喹哪啶 、 p-isocyanophenyl mustard 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到N-{4-[bis(2-chloroethyl)amino]phenyl}-N'-(2-methyl-4-quinolinyl)urea
  参考文献：
  名称：

  Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard–quinoline conjugates having a urea or hydrazinecarboxamide linker

  摘要：

  A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic than the corresponding urea counterparts in inhibiting human lymphoblastic leukemia and various solid tumor cell growths in culture. The therapeutic efficacy against human tumor xenografts in animal model was studied. It was shown that complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft by 17a, i and 18c, d was achieved. In the present study, it was revealed that both linkers are able to lower the chemically reactive N-mustard pharmacophore and thus the newly synthesized conjugates possess a long half-life in rat plasma. Moreover, the new N-mustard derivatives are able to induce DNA cross-linking either by modified comet assay or by alkaline agarose gel shift assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.061

文献信息

• Aniline or phenol mustards linked to DNA-affinic molecules or water-soluble aromatic rings and their use as cancer therapeutic agents
  申请人：Su Tsann-Long

  公开号：US20080171765A1

  公开（公告）日：2008-07-17

  New aniline or phenol N-mustards linked to DNA-affinity carriers (such as 9-anilinoacridines, acridines and quinolines), aminobenzamides or aminophenol ethers by a urea, carbamic acid, carbanic acid ester, hydrazineurea, hydrazinecarbamic acid ester, phenoxyurea, phenoxycarbamic acid ester linkage with improved chemical stability and anti-tumor therapeutic efficacy are provided.

  提供了与DNA亲和载体（如9-苯胺基吖啶、吖啶和喹啉）、氨基苯甲酰胺或氨基酚醚通过脲、碳酸酯、碳酸酯、叠氮脲、叠氮碳酸酯、苯氧基脲、苯氧基碳酸酯链接的新苯胺或酚N-芥子素，具有改善的化学稳定性和抗肿瘤治疗效果。
• PHENYL N-MUSTARD LINKED TO DNA-AFFINIC MOLECULES OR WATER-SOLUBLE ARYL RINGS, METHOD AND THEIR USE AS CANCER THERAPEUTIC AGENTS
  申请人：SU Tsann-Long

  公开号：US20130178494A1

  公开（公告）日：2013-07-11

  The present disclosure relates to new DNA-directed alkylating agents and water-soluble N-mustard agents with improved chemical stability and anti-tumor therapeutic efficacy.

  本公开涉及新的DNA定向烷基化剂和具有改善化学稳定性和抗肿瘤治疗效果的水溶性N-芥子剂。
• Phenyl N-mustard linked to DNA-affinic molecules or water-soluble aryl rings, method and their use as cancer therapeutic agents
  申请人：Su Tsann-Long

  公开号：US09193687B2

  公开（公告）日：2015-11-24

  The present disclosure relates to new DNA-directed alkylating agents and water-soluble N-mustard agents with improved chemical stability and anti-tumor therapeutic efficacy.

  本公开涉及新的DNA定向烷基化剂和水溶性N-芥子剂，具有改善的化学稳定性和抗肿瘤治疗效果。
• US8222297B2
  申请人：——

  公开号：US8222297B2

  公开（公告）日：2012-07-17
• US9193687B2
  申请人：——

  公开号：US9193687B2

  公开（公告）日：2015-11-24