(1-(chloromethyl)-1,2-dihydropyrrolo[3,2-e]indol-3(6H)-yl)(5-methoxy-1H-indol-2-yl)methanone | 454691-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1-(chloromethyl)-1,2-dihydropyrrolo[3,2-e]indol-3(6H)-yl)(5-methoxy-1H-indol-2-yl)methanone
• 英文别名: ICT2700；[8-(chloromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indol-6-yl]-(5-methoxy-1H-indol-2-yl)methanone
• CAS: 454691-95-3
• 化学式: C₂₁H₁₈ClN₃O₂
• 分子量: 379.846
• InChiKey: ZHFAARVXMYJTEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl 5-amino-4-bromo-1H-indole-1-carboxylate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 sodium hydride 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 32.08h， 生成 (1-(chloromethyl)-1,2-dihydropyrrolo[3,2-e]indol-3(6H)-yl)(5-methoxy-1H-indol-2-yl)methanone
  参考文献：
  名称：

  Re-engineering of the Duocarmycin Structural Architecture Enables Bioprecursor Development Targeting CYP1A1 and CYP2W1 for Biological Activity

  摘要：

  A library of duocarmycin bioprecursors based on the CPI and CBI scaffolds was synthesized and used to probe selective activation by cells expressing CYP1A1 and 2W1, CYPs known to be expressed in high frequency in some tumors. Several CPI-based compounds were pM-nM potent in CYP1A1 expressing cells. CYP2W1 was also shown to sensitize proliferating cells to several compounds, demonstrating its potential as a target for tumor selective activation of duocarmycin bioprecursors.

  DOI：

  10.1021/jm4000209

文献信息

• MINOR GROOVE BINDER PHOSPHORAMIDITES AND METHODS OF USE
  申请人：Vorobiev Alexei

  公开号：US20130030166A1

  公开（公告）日：2013-01-31

  Minor groove binder phosphoramidites having unique structures have been synthesized according to particular methods. These minor groove binder phosphoramidites are useful in the preparation of oligonucleotide conjugates, particularly those for use as probes and primers.

  根据特定方法合成了具有独特结构的小沟结合剂磷酰胺酰胺。这些小沟结合剂磷酰胺酰胺在制备寡核苷酸共轭物中很有用，特别是用作探针和引物的情况。
• Pyrrolo-indole and pyrrolo-quinoline derivatives as prodrugs for tumour treatment
  申请人：——

  公开号：US20040157873A1

  公开（公告）日：2004-08-12

  Compounds of the general formula (I) or (IA) in which X is H, Y is a leaving group, R 1 and optionally also R 3 preferably being an aromatic DNA binding subunit are prodrug analogues of duocarmycin. The compounds are expected to be hydroxylated at the carbon atom to which X is joined, by cytochrome P450, in particular by CYP1B1, expressed at high levels in tumours. The prodrug is expected to be activated preferentially in tumour cells, where it will act as a DNA alkylating agent preventing cell division. 1

  通式（I）或（IA）的化合物中，X为H，Y为离开基团，R1和可选的R3优选为芳香族DNA结合亚基，是二元环霉素的前药类似物。这些化合物预计将在连接X的碳原子上被细胞色素P450，特别是CYP1B1水解，而在肿瘤中表达高水平。预计前药将优先在肿瘤细胞中被激活，从而作为DNA烷基化剂防止细胞分裂。
• PYRROLO-INDOLE AND PYRROLO-QUINOLINE DERIVATIVES AS PRODRUGS FOR TUMOUR TREATMENT
  申请人：THE SCHOOL OF PHARMACY, UNIVERSITY OF LONDON

  公开号：EP1409480B1

  公开（公告）日：2007-11-14
• Synthesis of Duocarmycin Analogues
  申请人：University of East Anglia

  公开号：US20160347753A1

  公开（公告）日：2016-12-01

  A novel Fmoc protected duocarmycin subunit and utilisation as a reagent in solid phase protein synthesis methodology. Also provided is a novel method of solid phase peptide synthesis, and in particular a method for the production of novel intermediates and novel monomeric and extended duocarmycin analogues having amino acid substituents.
• US7626026B2
  申请人：——

  公开号：US7626026B2

  公开（公告）日：2009-12-01