4-aminoisothiazole-3-carboxylic acid amide | 4592-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-aminoisothiazole-3-carboxylic acid amide
• 英文别名: 4-Amino-3-carbamoyl-isothiazol；4-Aminoisothiazol-3-carboxamid；4-aminoisothiazole-3-carboxamide；4-Amino-1,2-thiazole-3-carboxamide
• CAS: 4592-54-5
• 化学式: C₄H₅N₃OS
• mdl: MFCD02598858
• 分子量: 143.169
• InChiKey: UOMSIZYOTADNJO-UHFFFAOYSA-N

物化性质

• 熔点：
  143-145 °C(Solv: benzene (71-43-2))
• 沸点：
  211.7±33.0 °C(Predicted)
• 密度：
  1.537±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-aminoisothiazole-3-carboxylic acid amide 在 一水合肼 作用下， 以 水 为溶剂， 反应 3.0h， 以70%的产率得到4-aminoisothiazole-3-carboxylic acid hydrazide
  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：

  4-nitro-isothiazole-3-carboxylic acid amide 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 4-aminoisothiazole-3-carboxylic acid amide
  参考文献：
  名称：

  1337.异噻唑。第九部分 异噻唑并嘧啶

  摘要：

  DOI：

  10.1039/jr9650007277

文献信息

• Gewald,K.; Bellmann,P., Liebigs Annalen der Chemie, 1979, p. 1534 - 1546
  作者：Gewald,K.、Bellmann,P.

  DOI：——

  日期：——
• Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines
  作者：Xiaohu Ouyang、Evgueni L. Piatnitski、Vatee Pattaropong、Xiaoling Chen、Hai-Ying He、Alexander S. Kiselyov、Avdhoot Velankar、Joel Kawakami、Marc Labelle、Leon Smith、Julia Lohman、Sui Ping Lee、Asra Malikzay、James Fleming、Jason Gerlak、Ying Wang、Robin L. Rosler、Kai Zhou、Stan Mitelman、Margarita Camara、David Surguladze、Jacqueline F. Doody、M. Carolina Tuma

  DOI：10.1016/j.bmcl.2005.11.094

  日期：2006.3

  Oxadiazole derivatives were synthesized and evaluated for their ability to inhibit tubulin polymerization and to cause mitotic arrest in tumor cells. The most potent compounds inhibited tubulin polymerization at concentrations below 1 mu M. Lead analogs caused mitotic arrest of A431 human epidermoid cells and cells derived from multi-drug resistant tumors (10, EC50 = 7.8 nM). Competition for the colchicine binding site and pharmacokinetic properties of selected potent compounds were also investigated and are reported herein, along with structure-activity relationships for this novel series of antimitotic agents. (C) 2005 Elsevier Ltd. All rights reserved.
• GEWALD K.; BELLMANN P., LIEBIGS ANN. CHEM., 1979, NO 10, 1534-1546
  作者：GEWALD K.、 BELLMANN P.

  DOI：——

  日期：——