p-trifluoromethylphenylchlorohydrazone | 1315307-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-trifluoromethylphenylchlorohydrazone
• CAS: 1315307-30-2
• 化学式: C₁₀H₈ClF₃N₂O₂
• 分子量: 280.634
• InChiKey: KPRSQGFMQZRWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.69
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  p-trifluoromethylphenylchlorohydrazone 在 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  新型5-（卤代甲基）-1-芳基-1 H -1,2,4-三唑-3-羧酸盐作为选择性COX-2抑制剂和抗炎剂：设计，合成，生物学评估和对接研究

  摘要：

  通过胺化和杂环化两步反应，从亚胺3a - p合成1,2,4-三唑-3-羧酸5a - p和6的新方法得到了发展。通过光谱技术表征所有1,2,4-三唑-3-羧酸盐5和6。根据SAR的抗炎活性研究，与Celecoxib和消炎痛相比，大多数5a - p对LPS诱导的RAW 264.7细胞（IC 50 <7.0 nM）对NO抑制具有潜在的抗炎活性。几种可能的化合物5b – h，5j，5升，5N和5O进行体外环氧合酶COX-1 / COX-2抑制试验。化合物5d表现出非凡的COX-2抑制作用（IC 50 = 17.9 nM）和最佳选择性（COX-1 / COX-2 = 1080）。此外，与10 mg / kg消炎痛相比，5 mg / kg的化合物5d在体内的抗炎和胃保护作用也更好。已经评估了将5d对接至COX-2结合袋的实验。根据生物活性实验数据，潜在的候选药物5d比消炎痛具有更好的抗炎作用。

  DOI：

  10.1016/j.bioorg.2020.104333

文献信息

• One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition
  作者：Li-Ya Wang、Henry J. Tsai、Hui-Yi Lin、Kimiyoshi Kaneko、Fen-Ying Cheng、Hsin-Siao Shih、Fung Fuh Wong、Jiann-Jyh Huang

  DOI：10.1039/c4ra00113c

  日期：——

  One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition.

  一瓶法合成1,3,5-三取代-1,2,4-三唑，从腈和叠氮酰氯通过1,3-偶极环加成。
• Facile One-Pot Synthesis of Methyl 1-Aryl-1<i>H</i> -1,2,4-triazole-3-carboxylates from Nitrilimines with Vilsmeier Reagent
  作者：Shuo-En Tsai、Kun-Heng Chiang、Ching-Chun Tseng、Nai-Wei Chen、Ching-Yuh Chern、Fung Fuh Wong

  DOI：10.1002/ejoc.201801808

  日期：2019.2.28

  A selective and convenient one‐pot methods have been developed for the synthesis of 1,2,4‐triazoles and methyl 1H‐1,2,4‐triazole‐3‐carboxylates by using hydrazonoyl hydrochlorides (nitrilimines) with Vilsmeier reagent. 2‐Amino‐2‐(2‐arylhydrazono)acetates were prepared from 2‐chloro‐2‐(2‐arylhydrazono)acetates with bis(trimethylsilyl)amine [NH(SiMe3)2] as the isolated intermediates for the further mechanistic

  已经开发了一种选择性方便的单罐方法，该方法是通过使用肼基酰基盐酸盐（硝化亚胺）和Vilsmeier试剂来合成1,2,4-三唑和1 H - 1,2,4-三唑-3-羧酸甲酯。2-氨基-2-（2-芳基肼基）乙酸酯是由2-氯-2-（2-芳基肼基）乙酸酯与双（三甲基甲硅烷基）胺[NH（SiMe 3）2 ]作为分离的中间体制备的，用于进一步的机理研究。
• 1,3-Dipolar Cycloaddition of Carbodiimides and Nitrilimines: Synthesis and Mechanistic Study of 5-Amino-1,2,4-triazoles
  作者：Wan-Ping Yen、Fung-Chun Kung、Fung Fuh Wong

  DOI：10.1002/ejoc.201600240

  日期：2016.5

  An effective 1,3-dipolar cycloaddition was developed for the synthesis of 5-amino-1,2,4-triazoles by reacting hydrazonoyl hydrochlorides (nitrilimines) with carbodiimides in the presence of triethylamine as a base. Both symmetric and asymmetric carbodiimides are compatible with this newly developed reaction; diphenyl carbodiimide is the one exception. Mechanistic studies indicate that alkyl and cycloalkyl

  开发了一种有效的 1,3-偶极环加成反应，通过在三乙胺作为碱的存在下使腙酰盐酸盐（腈亚胺）与碳二亚胺反应来合成 5-氨基-1,2,4-三唑。对称和不对称碳二亚胺都与这种新开发的反应相容；二苯基碳二亚胺是一个例外。机理研究表明，1,2,4-三唑环上季 N+-R 的烷基和环烷基部分作为潜在的离去基团，可以有效地脱离中间体 4,5-二氢-4-烷基-5-亚氨基- 1,2,4-三唑。
• Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties
  作者：Li-Ya Wang、Wen-Che Tseng、Tian-Shung Wu、Kimiyoshi Kaneko、Hiroyuki Takayama、Masayuki Kimura、Wen-Chin Yang、Jin Bin Wu、Shin-Hun Juang、Fung Fuh Wong

  DOI：10.1016/j.bmcl.2011.07.009

  日期：2011.9

  An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoroand trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt(3) as catalytic basic agent to provide the corresponding product in 28-94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine-and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2, 4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.