1-thiocarbamoyl-3-phenyl-4-methyl-4,5-dihydropyrazole | 888955-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-thiocarbamoyl-3-phenyl-4-methyl-4,5-dihydropyrazole
• 英文别名: 4-Methyl-5-phenyl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 888955-68-8
• 化学式: C₁₁H₁₃N₃S
• 分子量: 219.31
• InChiKey: BZXQICQSIIQUBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-thiocarbamoyl-3-phenyl-4-methyl-4,5-dihydropyrazole 、 2,3-二氯喹喔啉 以 乙醇 为溶剂， 以63%的产率得到2-(4-Methyl-5-phenyl-3,4-dihydropyrazol-2-yl)-[1,3]thiazolo[4,5-b]quinoxaline
  参考文献：
  名称：

  Synthesis, characterization and antiamoebic activity of 1-(thiazolo[4,5-b]quinoxaline-2-yl)-3-phenyl-2-pyrazoline derivatives

  摘要：

  A new series of 1-N-thiocarboxamide-3-phenyl-2-pyrazolines 1-6 was synthesized by cyclization of different Mannich bases with unsubstituted thiosemicarbazide. The reaction of cyclized pyrazoline derivatives 1-6 with 2,3-dichloroquinoxaline afforded the title compounds 7-12. The structures of the new compounds were confirmed by elemental analyses as well as H-1, C-13 NMR, IR and electronic spectral data. The HM1:IMSS strain of Entamoeba histolytica parasite was cultured in vitro and the sensitivity of the parasite to the synthesized compounds was evaluated using the microdilution method. Among all the pyrazoline derivatives 1-6, none was found to be a better inhibitor as compared to the reference drug, metronidazole. The quinoxaline derivatives, 9, 11 and 12 were found to be potent inhibitors of E. histolytica. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.116
• 作为产物：
  描述：

  苯丙酮 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-thiocarbamoyl-3-phenyl-4-methyl-4,5-dihydropyrazole
  参考文献：
  名称：

  Synthesis, characterization and antiamoebic activity of 1-(thiazolo[4,5-b]quinoxaline-2-yl)-3-phenyl-2-pyrazoline derivatives

  摘要：

  A new series of 1-N-thiocarboxamide-3-phenyl-2-pyrazolines 1-6 was synthesized by cyclization of different Mannich bases with unsubstituted thiosemicarbazide. The reaction of cyclized pyrazoline derivatives 1-6 with 2,3-dichloroquinoxaline afforded the title compounds 7-12. The structures of the new compounds were confirmed by elemental analyses as well as H-1, C-13 NMR, IR and electronic spectral data. The HM1:IMSS strain of Entamoeba histolytica parasite was cultured in vitro and the sensitivity of the parasite to the synthesized compounds was evaluated using the microdilution method. Among all the pyrazoline derivatives 1-6, none was found to be a better inhibitor as compared to the reference drug, metronidazole. The quinoxaline derivatives, 9, 11 and 12 were found to be potent inhibitors of E. histolytica. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.116

文献信息

• Synthesis of new 3-aryl-4,5-dihydropyrazole-1-carbothioamide derivatives. An investigation on their ability to inhibit monoamine oxidase
  作者：E. Maccioni、S. Alcaro、F. Orallo、M.C. Cardia、S. Distinto、G. Costa、M. Yanez、M.L. Sanna、S. Vigo、R. Meleddu

  DOI：10.1016/j.ejmech.2010.07.009

  日期：2010.10

  investigate their monoamine oxidase inhibitory activity. The chemical structures of the compounds have been characterized by means of their IR, 1H NMR, 13C NMR spectroscopic data and elemental analyses. All the active compounds showed a selective activity towards the B isoform of the enzyme, regardless of the substitution on the heterocyclic ring. The inhibition of the enzymatic activity was measured on

  为了研究它们对单胺氧化酶的抑制活性，已经合成了一些不同取代的3-芳基-4,5-二氢吡唑-1-碳硫代酰胺。化合物的化学结构已通过其IR，1 H NMR，13 C NMR光谱数据和元素分析进行了表征。不论杂环上的取代如何，所有活性化合物均显示出对酶B同工型的选择性活性。测定了在杆状病毒感染的BTI昆虫细胞中表达的人重组MAO同工型对酶活性的抑制。进行对接实验的目的是合理化抑制最具活性和选择性的化合物的机理。
• Novel Pd(II) complexes of 1-N-substituted 3-phenyl-2-pyrazoline derivatives and evaluation of antiamoebic activity
  作者：Kakul Husain、Mohammad Abid、Amir Azam

  DOI：10.1016/j.ejmech.2007.03.021

  日期：2008.2

  Cyclization of Mannich base with N(4)-substituted thiosemicarbazides by different aliphatic, aromatic and cyclic amines afforded a series of new 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones (PYZ-TSC) 1-10. Reaction of [Pd(DMSO)(2)Cl(2)] with pyrazoline derivatives led to new palladium(II) complexes [Pd(PYZ-TSC)Cl(2)] 1a-10a. The structures of all the compounds were characterized by spectroscopic methods. It was concluded that the pyrazoline thiosemicarbazone derivatives have two chelating arms, one attached at the 2-position of the pyrazole ring (that is, N donor) and other (S donor) linked to the thiosemicarbazone branch. The determination of antiamoebic activity of all the compounds was done using HM1:-IMSS strain of Entamoeba histolytica, among all the complexes, 8a showed the most promising IC(50) = 0.37 mu M vs. IC(50) = 1.81 mu M of metronidazole, the reference drug. MTT assay showed that the compounds are non-toxic to human kidney epithelial cell line. (c) 2007 Elsevier Masson SAS. All rights reserved.