2-aminoquinoline-3-carbohydrazide | 1174524-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-aminoquinoline-3-carbohydrazide
• 英文别名: 2-Aminoquinoline-3-carbohydrazide
• CAS: 1174524-58-3
• 化学式: C₁₀H₁₀N₄O
• 分子量: 202.216
• InChiKey: WKEBFUNCKYHNKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-aminoquinoline-3-carbohydrazide 、 1,3-苯并二唑-5-基异硫氰酸酯 以 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Novel derivatives of 1,3,4-oxadiazoles are potent mitostatic agents featuring strong microtubule depolymerizing activity in the sea urchin embryo and cell culture assays

  摘要：

  A series of novel 1,3,4-oxadiazole derivatives based on structural and electronic overlap with combretastatins have been designed and synthesized. Initially, we tested all new compounds in vivo using the phenotypic sea urchin embryo assay to yield a number of agents with anti-proliferative, anti-mitotic, and microtubule destabilizing activities. The experimental data led to identification of 1,3,4-oxadiazole derivatives with isothiazole (5-8) and phenyl (9-12) pharmacophores featuring activity profiles comparable to that of combretastatins, podophyllotoxin and nocodazole. Cytotoxic effects of the two lead molecules, namely 6 and 12, were further confirmed and evaluated by conventional assays with the A549 human cancer cell line including cell proliferation, cell cycle arrest at the G2/M phase, cellular microtubule distribution, and finally in vitro microtubule assembly with purified tubulin. The modeling results using 3D similarity (ROCS) and docking (FRED) correlated well with the observed activity of the molecules. Docking data suggested that the most potent molecules are likely to target the colchicine binding site. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.072
• 作为产物：
  描述：

  2-氨基喹啉-3-羧酸 在 一水合肼 作用下， 反应 0.17h， 以58%的产率得到2-aminoquinoline-3-carbohydrazide
  参考文献：
  名称：

  A new modification of the Friedländer synthesis. A simple route to 2-aminoquinoline-3-carboxylic acid and its derivatives

  摘要：

  提出了一种新的Friedländer合成2-氨基喹啉-3-羧酸及其衍生物的方法，使用稳定的2-托磺酰氨基苯甲醛或其吗啉。

  DOI：

  10.1007/s11172-008-0065-0

文献信息

• Synthesis of phthalimidines linked to quinoline derivatives by an amide bridge
  作者：L. Yu. Ukhin、K. Yu. Suponitskii、T. N. Gribanova、L. V. Belousova、E. N. Shepelenko

  DOI：10.1007/s11172-010-0199-8

  日期：2010.5

  The reactions of 3-acetoxy-2-acetyl(cyanoacetyl)aminoisoindolin-1-one (1) with o-tosylaminobenzaldehyde and o-mesylaminobenzaldehyde morpholinals lead to a mixture of 2-(2-aminoquinoline-3-carboxamido)-3-morpholinoisoindolin-1-one (3) and 3-cyanoquinolin-2(1H)-one (4). The reaction of 1 with 5-nitro-2-tosylaminobenzaldehyde morpholinal yields a mixture of 2-(2-amino-6-nitroquinoline-carboxamido)-3

  3-乙酰氧基-2-乙酰（氰基乙酰基）氨基异吲哚啉-1-one (1) 与邻甲苯磺酰氨基苯甲醛和邻甲磺酰氨基苯甲醛吗啉醛反应生成 2-(2-氨基喹啉-3-羧酰胺)-3-吗啉异吲哚的混合物-1-一 (3) 和 3-氰基喹啉-2(1H)-一 (4)。1 与 5-nitro-2-tosylaminobenzaldehyde morpholinal 反应生成 2-(2-amino-6-nitroquinoline-carboxamido)-3-morpholinoisoindolin-1-one 和 3-cyano-6-nitroquinolin-2(1H) 的混合物）-一。3-Acetoxy-2-(quinolino[2,3-d]-2-methyl-4-oxopyrimidin-3-yl)isoindolin-1-one (20)由邻甲酰基苯甲酸和2-氨基喹啉缩合制备-3-碳酰肼在 Ac2O 中。通过
• A new modification of the Friedländer synthesis. A simple route to 2-aminoquinoline-3-carboxylic acid and its derivatives
  作者：L. Yu. Ukhin、E. G. Belov

  DOI：10.1007/s11172-008-0065-0

  日期：2008.2

  A new version of the Friedländer synthesis of 2-aminoquinoline-3-carboxylic acid and its derivatives from stable 2-tosylaminobenzaldehyde or its morpholinal was proposed.

  提出了一种新的Friedländer合成2-氨基喹啉-3-羧酸及其衍生物的方法，使用稳定的2-托磺酰氨基苯甲醛或其吗啉。
• Novel derivatives of 1,3,4-oxadiazoles are potent mitostatic agents featuring strong microtubule depolymerizing activity in the sea urchin embryo and cell culture assays
  作者：Alex S. Kiselyov、Marina N. Semenova、Natalya B. Chernyshova、Andrei Leitao、Alexandr V. Samet、Konstantine A. Kislyi、Mikhail M. Raihstat、Tudor Oprea、Heiko Lemcke、Margaréta Lantow、Dieter G. Weiss、Nazli N. Ikizalp、Sergei A. Kuznetsov、Victor V. Semenov

  DOI：10.1016/j.ejmech.2009.12.072

  日期：2010.5

  A series of novel 1,3,4-oxadiazole derivatives based on structural and electronic overlap with combretastatins have been designed and synthesized. Initially, we tested all new compounds in vivo using the phenotypic sea urchin embryo assay to yield a number of agents with anti-proliferative, anti-mitotic, and microtubule destabilizing activities. The experimental data led to identification of 1,3,4-oxadiazole derivatives with isothiazole (5-8) and phenyl (9-12) pharmacophores featuring activity profiles comparable to that of combretastatins, podophyllotoxin and nocodazole. Cytotoxic effects of the two lead molecules, namely 6 and 12, were further confirmed and evaluated by conventional assays with the A549 human cancer cell line including cell proliferation, cell cycle arrest at the G2/M phase, cellular microtubule distribution, and finally in vitro microtubule assembly with purified tubulin. The modeling results using 3D similarity (ROCS) and docking (FRED) correlated well with the observed activity of the molecules. Docking data suggested that the most potent molecules are likely to target the colchicine binding site. (C) 2010 Elsevier Masson SAS. All rights reserved.