13-di-p-tosylamino-12-methoxy-9-oxo-9H-indolo[3,2,1-ij]quino[3,2-c]-1,5-naphthyridine-2-carboxylic acid methyl ester | 1013629-38-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: 13-di-p-tosylamino-12-methoxy-9-oxo-9H-indolo[3,2,1-ij]quino[3,2-c]-1,5-naphthyridine-2-carboxylic acid methyl ester
• 英文别名: Methyl 6-[bis-(4-methylphenyl)sulfonylamino]-7-methoxy-12-oxo-3,13,23-triazahexacyclo[11.10.1.02,11.04,9.014,19.020,24]tetracosa-1(24),2(11),3,5,7,9,14,16,18,20,22-undecaene-22-carboxylate
• CAS: 1013629-38-3
• 化学式: C₃₈H₂₈N₄O₈S₂
• 分子量: 732.794
• InChiKey: BVLBWHFVIQTRFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-[7-di-p-tosylamino-3-hydroxymethyl-6-methoxyquinolin-2-yl]-9H-β-carboline-3-carboxylic acid methyl ester 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 48.0h， 以45%的产率得到13-di-p-tosylamino-12-methoxy-9-oxo-9H-indolo[3,2,1-ij]quino[3,2-c]-1,5-naphthyridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of new lavendamycin analogues

  摘要：

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.016

文献信息

• Synthesis of new lavendamycin analogues
  作者：Arnaud Nourry、Stéphanie Legoupy、François Huet

  DOI：10.1016/j.tet.2007.12.016

  日期：2008.2

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.