N-(1-methyl-β-caboline-3-carbonyl)-N'-[Boc-(β-OBzl-aspartyl)]-hydrazine | 1346115-05-6

• 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
• 英文名称: N-(1-methyl-β-caboline-3-carbonyl)-N'-[Boc-(β-OBzl-aspartyl)]-hydrazine
• 英文别名: benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[2-(1-methyl-9H-pyrido[3,4-b]indole-3-carbonyl)hydrazinyl]-4-oxobutanoate
• CAS: 1346115-05-6
• 化学式: C₂₉H₃₁N₅O₆
• 分子量: 545.595
• InChiKey: GPXCNKVMSBCQAN-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(1-methyl-β-caboline-3-carbonyl)-N'-[Boc-(β-OBzl-aspartyl)]-hydrazine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以61%的产率得到N-(1-methyl-β-caboline-3-carbonyl)-N'-(β-OBzl-aspartyl)-hydrazine
  参考文献：
  名称：

  A class of novel N-(1-methyl-β-carboline-3-carbonyl)-N′-(aminoacid-acyl)-hydrazines: Aromatization leaded design, synthesis, in vitro anti-platelet aggregation/in vivo anti-thrombotic evaluation and 3D QSAR analysis

  摘要：

  High anti-thrombotic activity of aminoacid modified tetrahydro-beta-carbolines was generally correlated with a small proximity of the side chain of the aminoacid residue to the carboline-cycle. This paper explored that the aromatization of the tetrahydro-beta-carboline-cycle of N-(1-methyl-beta-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines leaded to N-(1-methyl-beta-carboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines and decreased the proximity of the side chain of the aminoacid residue to the carboline-cycle. The in vitro activities of inhibiting pig platelet aggregation induced by PAF, ADP, and AA, as well as the in vivo anti-thrombotic activities of inhibiting rat thrombosis of these aromatized derivatives were generally higher than that of N-(1-methyl-beta-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines. The understanding was also obtained from the 3D QSAR analysis. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.027
• 作为产物：
  描述：

  methyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 N-甲基吗啉 、 potassium permanganate 、 1-羟基苯并三唑 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 N-(1-methyl-β-caboline-3-carbonyl)-N'-[Boc-(β-OBzl-aspartyl)]-hydrazine
  参考文献：
  名称：

  A class of novel N-(1-methyl-β-carboline-3-carbonyl)-N′-(aminoacid-acyl)-hydrazines: Aromatization leaded design, synthesis, in vitro anti-platelet aggregation/in vivo anti-thrombotic evaluation and 3D QSAR analysis

  摘要：

  High anti-thrombotic activity of aminoacid modified tetrahydro-beta-carbolines was generally correlated with a small proximity of the side chain of the aminoacid residue to the carboline-cycle. This paper explored that the aromatization of the tetrahydro-beta-carboline-cycle of N-(1-methyl-beta-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines leaded to N-(1-methyl-beta-carboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines and decreased the proximity of the side chain of the aminoacid residue to the carboline-cycle. The in vitro activities of inhibiting pig platelet aggregation induced by PAF, ADP, and AA, as well as the in vivo anti-thrombotic activities of inhibiting rat thrombosis of these aromatized derivatives were generally higher than that of N-(1-methyl-beta-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines. The understanding was also obtained from the 3D QSAR analysis. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.027

文献信息

• A class of novel N-(1-methyl-β-carboline-3-carbonyl)-N′-(aminoacid-acyl)-hydrazines: Aromatization leaded design, synthesis, in vitro anti-platelet aggregation/in vivo anti-thrombotic evaluation and 3D QSAR analysis
  作者：Chunyu Li、Xiaoyi Zhang、Ming Zhao、Yuji Wang、Jianhui Wu、Jiawang Liu、Meiqing Zheng、Shiqi Peng

  DOI：10.1016/j.ejmech.2011.09.027

  日期：2011.11

  High anti-thrombotic activity of aminoacid modified tetrahydro-beta-carbolines was generally correlated with a small proximity of the side chain of the aminoacid residue to the carboline-cycle. This paper explored that the aromatization of the tetrahydro-beta-carboline-cycle of N-(1-methyl-beta-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines leaded to N-(1-methyl-beta-carboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines and decreased the proximity of the side chain of the aminoacid residue to the carboline-cycle. The in vitro activities of inhibiting pig platelet aggregation induced by PAF, ADP, and AA, as well as the in vivo anti-thrombotic activities of inhibiting rat thrombosis of these aromatized derivatives were generally higher than that of N-(1-methyl-beta-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines. The understanding was also obtained from the 3D QSAR analysis. (C) 2011 Elsevier Masson SAS. All rights reserved.