9H-吡啶并[3,4-b]吲哚-1-乙酸甲酯 | 138428-34-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 中文名称: 9H-吡啶并[3,4-b]吲哚-1-乙酸甲酯
• 英文名称: 1-methoxycarbonylmethyl-β-carboline
• 英文别名: Infractin；9H-Pyrido[3,4-b]indole-1-acetic acid, methyl ester；methyl 2-(9H-pyrido[3,4-b]indol-1-yl)acetate
• CAS: 138428-34-9
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: JRTQEVZKQDRWFT-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±30.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9H-吡啶并[3,4-b]吲哚-1-乙酸甲酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 β-carboline potassium salt
  参考文献：
  名称：

  The use of the Ramberg–Bäcklund rearrangement for the formation of aza-macrocycles: a total synthesis of manzamine C

  摘要：

  A total synthesis of the marine alkaloid manzamine C has been accomplished. A Ramberg-Backlund reaction was used as a key step to construct the required azacycloundecene ring.

  DOI：

  10.1139/cjc-78-8-1060
• 作为产物：
  描述：

  6-氟-DL-色氨酸 在 potassium dichromate 、 硫酸 、 溶剂黄146 作用下， 反应 12.1h， 生成 9H-吡啶并[3,4-b]吲哚-1-乙酸甲酯
  参考文献：
  名称：

  β-Carbolines as specific inhibitors of cyclin-Dependent kinases

  摘要：

  Harmine (3), 7-fluoro-1-methyl beta-carboline (35) and 1-(5-methyl-imidazol-4-yl) beta-carboline (41) were potent and specific inhibitors of cyclin-dependent kinases. The degree of aromaticity of the tricyclic ring and the positioning of substituents are important for inhibitory activity. While most beta-carbolines inhibited CDK2 and CDK5 to the same extent. selective inhibition against CDK2 was observed in 1-(2-chlorophenyl)- (12), 1-(2-fluorophenyl)- (15), and 1-(2-chloro-5-nitrophenyl)- (28) beta-carbolines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00094-x

文献信息

• A total synthesis of manzamine C and its geometrical isomer
  作者：Yasuhiro Torisawa、Akihiro Hashimoto、Masako Nakagawa、Hiroko Seki、Ritsuko Hara、Tohru Hino

  DOI：10.1016/s0040-4020(01)91003-8

  日期：1991.9

  Manzamine C (1) has been synthesized from silyloxyscetylene (3) along the line: 4→5→8→18→1. The overall yields is 21%. Thr β-carboline segment (11) was obtained by the Bischler-Napieralski reaction of 14 followed by dehydregenation. By the similar procedure, the trans isomer 2 and dihydromanzamine C (21) have been synthesized.

  Manzamine C（1）是由甲硅烷基氧乙烯（3）沿以下路线合成的：4→5→8→18→1。总产率为21％。通过14的Bischler-Napieralski反应，然后进行脱水，可得到Thrβ-咔啉链段（11）。通过类似的步骤，已经合成了反式异构体2和二氢马扎明C（21）。
• Nowak, Wolfgang; Gerlach, Hans, Liebigs Annalen der Chemie, 1993, # 2, p. 153 - 160
  作者：Nowak, Wolfgang、Gerlach, Hans

  DOI：——

  日期：——
• β-Carbolines as specific inhibitors of cyclin-Dependent kinases
  作者：Yongcheng Song、Jian Wang、Su Fern Teng、Djohan Kesuma、Yu Deng、Jinao Duan、Jerry H. Wang、Robert Zhong Qi、Mui Mui Sim

  DOI：10.1016/s0960-894x(02)00094-x

  日期：2002.4

  Harmine (3), 7-fluoro-1-methyl beta-carboline (35) and 1-(5-methyl-imidazol-4-yl) beta-carboline (41) were potent and specific inhibitors of cyclin-dependent kinases. The degree of aromaticity of the tricyclic ring and the positioning of substituents are important for inhibitory activity. While most beta-carbolines inhibited CDK2 and CDK5 to the same extent. selective inhibition against CDK2 was observed in 1-(2-chlorophenyl)- (12), 1-(2-fluorophenyl)- (15), and 1-(2-chloro-5-nitrophenyl)- (28) beta-carbolines. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The use of the Ramberg–Bäcklund rearrangement for the formation of aza-macrocycles: a total synthesis of manzamine C
  作者：David I. MaGee、Ellen J. Beck

  DOI：10.1139/cjc-78-8-1060

  日期：——

  A total synthesis of the marine alkaloid manzamine C has been accomplished. A Ramberg-Backlund reaction was used as a key step to construct the required azacycloundecene ring.