(1Z)-1-((E)-1-phenyl-3-p-tolylallylidene)thiosemicarbazide | 1334315-72-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1Z)-1-((E)-1-phenyl-3-p-tolylallylidene)thiosemicarbazide
• 英文别名: (Z)-2-((E)-1-phenyl-3-p-tolylallylidene)hydrazinecarbothioamide；[(Z)-[(E)-3-(4-methylphenyl)-1-phenylprop-2-enylidene]amino]thiourea
• CAS: 1334315-72-8
• 化学式: C₁₇H₁₇N₃S
• 分子量: 295.408
• InChiKey: SHPUVHYBHKPKPR-GANMIEKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 苯乙酮 在 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 (1Z)-1-((E)-1-phenyl-3-p-tolylallylidene)thiosemicarbazide
  参考文献：
  名称：

  Synthesis, molecular modeling and biological evaluation of chalcone thiosemicarbazide derivatives as novel anticancer agents

  摘要：

  A series of novel chalcone thiosemicarbazide derivatives (4a-4x) have been designed, synthesized, structurally determined, and their biological activities were also evaluated as potential EGFR kinase inhibitors. All the synthesized compounds are first reported. Among the compounds, compound 4r showed the most potent biological activity (IC50 = 0.78 +/- 0.05 mu M for HepG2 and IC50 = 0.35 mu M for EGFR), which is comparable to the positive controls. Docking simulation was also performed to position compound 4r into the EGER active site to determine the probable binding model. Antiproliferative assay results demonstrated that some of these compounds possessed good antiproliferative activity against HepG2. Compound 4r with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.016

文献信息

• The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford hydrazones and 2-pyrazolines (4,5-dihydro-1H-pyrazoles): Experimental and theoretical results
  作者：Antonio de la Hoz、Ibon Alkorta、José Elguero

  DOI：10.1016/j.tet.2021.132413

  日期：2021.9

  The reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines was studied using a dissymmetric chalcone (phenyl/p-tolyl) and three hydrazines, hydrazine itself, phenylhydrazine and thiosemicarbazide. Several products were identified, and some reaction paths established thanks to the evolution of 1H and 13C NMR spectra with time. Theoretical calculations on energies and

  使用不对称查耳酮（苯基/对甲苯基）和三种肼（肼本身、苯肼和氨基硫脲）研究了肼与 α,β-不饱和羰基化合物反应生成 2-吡唑啉。由于1 H 和13 C NMR 光谱随时间的演变，确定了几种产物，并建立了一些反应路径。能量和化学位移的理论计算对于确定某些产品的结构至关重要。对于重要的步骤，计算了过渡态，而 IRC 证明需要找到一些意想不到的中间体。