methyl 7-methoxyisoquinoline-3-carboxylate | 224321-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: methyl 7-methoxyisoquinoline-3-carboxylate
• 英文别名: 7-methoxyisoquinoline-3-carboxylic acid methyl ester
• CAS: 224321-74-8
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: BOWIWICTINXXDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 7-methoxyisoquinoline-3-carboxylate 在 氢氧化钾 、 乙醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 methyl (8S)-8-(chloromethyl)-4-hydroxy-6-[5-[(7-methoxyisoquinoline-3-carbonyl)amino]-1H-indole-2-carbonyl]-2-(trifluoromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups

  摘要：

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.

  DOI：

  10.1021/jm980668c
• 作为产物：
  描述：

  6-amino-7-methoxyisoquinoline-3-carboxylic acid methyl ester 在 次磷酸 、 溶剂黄146 、 sodium nitrite 作用下， 反应 2.5h， 以65%的产率得到methyl 7-methoxyisoquinoline-3-carboxylate
  参考文献：
  名称：

  Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone

  摘要：

  An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-L-tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.118

文献信息

• Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups
  作者：Yasumichi Fukuda、Hirosuke Furuta、Yoshie Kusama、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.1021/jm980668c

  日期：1999.4.22

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.
• Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone
  作者：Jörn Carstens、Markus R. Heinrich、Wolfgang Steglich

  DOI：10.1016/j.tetlet.2013.07.118

  日期：2013.10

  An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-L-tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus. (C) 2013 Elsevier Ltd. All rights reserved.