1-[5-Amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-3-yl]-3-(3-methoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-[5-Amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-3-yl]-3-(3-methoxyphenyl)prop-2-en-1-one
• 化学式: C₂₃H₂₁ClN₂O₂
• 分子量: 392.9
• InChiKey: VRBJCJNVLXEKKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

文献信息

• Processes for preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3h-[ring fused indol-5-yl-(amine- derived)] compounds and analogues thereof, and to products obtained therefrom
  申请人：Denny Alexander William

  公开号：US20050148651A1

  公开（公告）日：2005-07-07

  The invention provides processes of preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3H-[ring fused indol-5-yl(amine-derived)] compounds of formula (I) and its analogues, or a physiologically functional derivative thereof, (I), wherein A and B together may represent a fused optionally substituted benezene, naphthalene, pyridine, furan or a pyrrole ring, where the optional substituents are represented by Y; X is halogen or OSO 2 R, and W is selected from NO 2 , NHOH, N(R 3 ) 2 NHR 3 , NHCO 2 R 3 , N(phthaloyl) or NH 2 , or W is further selected from the group (a), wherein J is selected from OH or R, and P is a group which is a substrate suitable for a nitroreductase or carboxypeptidase enzyme. The invention is also directed to the use of compounds of formula (I) prepared by the processes of the invention as cytotoxins for cancer therapy and as prodrugs for gene-directed enzyme-prodrug therapy (GDEPT) and antibody-directed enzyme-prodrug therapy (ADEPT).

  本发明提供了制备式(I)及其类似物或其生理功能衍生物的3-取代-1-(氯甲基)-1,2-二氢-3H-[环融合吲哚-5-基(氨基衍生)]化合物的过程，其中A和B在一起可以表示为融合的可选取代苯、萘、吡啶、呋喃或吡咯环，其中可选的取代基由Y表示；X是卤素或OSO2R，W从NO2、NHOH、N(R3)2NHR3、NHCO2R3、N(phthaloyl)或NH2中选择，或者W进一步从(a)组中选择，其中J从OH或R中选择，P是适用于硝基还原酶或羧肽酶酶的底物基团。本发明还涉及使用通过本发明的方法制备的式(I)化合物作为癌症治疗的细胞毒素以及基因导向酶前药治疗(GDEPT)和抗体导向酶前药治疗(ADEPT)的前药。
• CYCLOPROPYLINDOLE COMPOUNDS AND THEIR USE AS PRODRUGS
  申请人：AUCKLAND UNISERVICES LIMITED

  公开号：EP0938474B1

  公开（公告）日：2005-11-23
• US6130237A
  申请人：——

  公开号：US6130237A

  公开（公告）日：2000-10-10
• US7235578B2
  申请人：——

  公开号：US7235578B2

  公开（公告）日：2007-06-26