2-氨基-1,3-噻唑-4-甲酰肼 | 57250-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氨基-1,3-噻唑-4-甲酰肼
• 英文名称: 2-Amino-thiazol-4-carbonsaeure-hydrazid
• 英文别名: 2-Amino-1,3-thiazole-4-carbohydrazide
• CAS: 57250-83-6
• 化学式: C₄H₆N₄OS
• 分子量: 158.184
• InChiKey: KHVLFJLFNMWTBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 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：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-1,3-噻唑-4-甲酰肼 、 2-氯苯甲醛 以61%的产率得到
  参考文献：
  名称：

  GALONS, H.;CAVE, C.;MIOCQUE, M.;RINJARD, P.;TRAN, G.;BINET, P., EUR. J. MED. CHEM., 25,(1990) N, C. 785-788

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基噻唑-4-甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-氨基-1,3-噻唑-4-甲酰肼
  参考文献：
  名称：

  659.微球菌素P的化学。第五部分噻唑的红外吸收光谱

  摘要：

  DOI：

  10.1039/jr9610003381

文献信息

• Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, their Derivatives and Related Compounds^1,2
  作者：Harry L. Yale、Kathryn Losee、Joseph Martins、Mary Holsing、Frances M. Perry、Jack Bernstein

  DOI：10.1021/ja01104a046

  日期：1953.4
• Hydrazidones à action antihypertensive. Étude des 2-chlorobenzylidène hydrazines acylées
  作者：H Galons、C Cavé、M Miocque、P Rinjard、G Tran、P Binet

  DOI：10.1016/0223-5234(90)90198-c

  日期：1990.11

  Antihypertensive actions of hydrazidones: study of acylated 2-cholo benzilidenhydrazines. A series of acylated hydrazones: o-Cl-C6H4-C(R1) = N-NH-CO-R, have been prepared and evaluated on spontaneous hypertensive rats (SHR). The more active compounds present a hydroxyl in position-alpha to the acyl group and R1 is a small alkyl group.
• Fused 3-Hydroxy-3-trifluoromethylpyrazoles Inhibit Mutant Huntingtin Toxicity
  作者：Salvatore La Rosa、Tiziana Benicchi、Laura Bettinetti、Ilaria Ceccarelli、Enrica Diodato、Cesare Federico、Pasquale Fiengo、Davide Franceschini、Ozgun Gokce、Freddy Heitz、Giulia Lazzeroni、Ruth Luthi-Carter、Letizia Magnoni、Vincenzo Miragliotta、Carla Scali、Michela Valacchi

  DOI：10.1021/ml400251g

  日期：2013.10.10

  Here, we describe the selection and optimization of a chemical series active in both a full-length and a fragment-based Huntington's disease (HD) assay. Twenty-four thousand small molecules were screened in a phenotypic HD assay, identifying a series of compounds bearing a 3-hydroxy-3-trifluoromethylpyrazole moiety as able to revert the toxicity induced by full-length mutant Htt by up to 50%. A chemical exploration around the series led to the identification of compound 4f, which demonstrated to be active in a Htt171-82Qrat primary striatal neuron assay and a PC12-Exon-1 based assay. This compound was selected for testing in R6/2 mice, in which it was well-tolerated and showed a positive effect on body weight and a positive trend in preventing ventricular volume enlargment. These studies provide strong rationale for further testing the potential benefits of 3-hydroxy-3-trifluoromethylpyrazoles in treating HD.