methyl (1R,4R,12S)-4-methyl-3,7-dioxo-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate | 179239-42-0

• 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: methyl (1R,4R,12S)-4-methyl-3,7-dioxo-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate
• CAS: 179239-42-0
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: IAGKGIMYZAXFHL-RILORBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1R,4R,12S)-4-methyl-3,7-dioxo-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate 在 吡啶 、 氢溴酸 、 sodium hydride 作用下， 生成 (2R,8S)-8-Bromomethyl-4-dimethylcarbamoyloxy-6-(5-methoxycarbonylamino-1H-indole-2-carbonyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of novel duocarmycin derivatives

  摘要：

  A series of Duocarmycin B-2 analogs bearing simplified right hand segments (Seg-Bs) with the protected phenolic hydroxyl group in left hand segment (Seg-A) was synthesized. Among them, the cinnamoyl derivatives 6c and 6d exhibited potent antitumor activity against in vivo murine tumor models in the wider range of doses without detectable toxic effects than DUMB(2). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00203-x
• 作为产物：
  描述：

  (2R,8S)-8-(溴甲基)-4-羟基-2-甲基-1-氧代-6-(5,6,7-三甲氧基1h-吲哚-2-羰基)-7,8-二氢-3H-吡咯并[3,2-e]吲哚-2-羧酸甲酯 在 sodium methylate 作用下， 生成 methyl (1R,4R,12S)-4-methyl-3,7-dioxo-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel duocarmycin derivatives

  摘要：

  A series of Duocarmycin B-2 analogs bearing simplified right hand segments (Seg-Bs) with the protected phenolic hydroxyl group in left hand segment (Seg-A) was synthesized. Among them, the cinnamoyl derivatives 6c and 6d exhibited potent antitumor activity against in vivo murine tumor models in the wider range of doses without detectable toxic effects than DUMB(2). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00203-x

文献信息

• Sequence-Specific DNA Alkylation by Hybrid Molecules between Segment A of Duocarmycin A and Pyrrole/Imidazole Diamide
  作者：Zhi-Fu Tao、Tsuyoshi Fujiwara、Isao Saito、Hiroshi Sugiyama

  DOI：10.1002/(sici)1521-3773(19990301)38:5<650::aid-anie650>3.0.co;2-o

  日期：1999.3.1

  In the absence of distamycin A (Dist), hybrids 1 (X=N, CH) selectively alkylate the 3' end of adenine in AT-rich DNA sequences. However, these hybrids can form a heterodimer with Dist to alkylate G residues of predetermined DNA sequences efficiently and with high selectivity.
• Novel indole derivative for alkylating specific base sequence of dna and alkylating agent and drug containing the derivative
  申请人：Sugiyama Hiroshi

  公开号：US20070191260A1

  公开（公告）日：2007-08-16

  There is provided a novel pyrrole-imidazole polyamide compound for alkylating the specific base sequence of DNA, the polyamide compound being capable of being synthesized through fewer reaction steps than known hybrid molecules and having a combination of a high reactivity in DNA alkylation and the ability to recognize a sequence. Furthermore, there is provided an alkylating agent and a molecule serving as a drug, the alkylating agent and the molecule containing the polyamide compound. An indole derivative is represented by general formula (1): wherein R 1 represents a functional group for alkylating DNA; R 2 represents a hydrogen atom, an alkyl group, or an acyl group; and X represents a divalent group having one constitutional unit or having two or more constitutional units which may be the same or different, the constitutional unit being represented by the following formula: (wherein m is an integer of 0 to 10), wherein among the constitutional units, a terminal constitutional unit adjacent to R 2 may be a constitutional unit represented by the following formula: (wherein k is an integer of 0 to 10).
• US7745473B2
  申请人：——

  公开号：US7745473B2

  公开（公告）日：2010-06-29
• Synthesis and antitumor activity of novel duocarmycin derivatives
  作者：Akira Asai、Satoru Nagamura、Eiji Kobayashi、Katushige Gomi、Hiromitsu Saito

  DOI：10.1016/0960-894x(96)00203-x

  日期：1996.6

  A series of Duocarmycin B-2 analogs bearing simplified right hand segments (Seg-Bs) with the protected phenolic hydroxyl group in left hand segment (Seg-A) was synthesized. Among them, the cinnamoyl derivatives 6c and 6d exhibited potent antitumor activity against in vivo murine tumor models in the wider range of doses without detectable toxic effects than DUMB(2). Copyright (C) 1996 Elsevier Science Ltd