5-dihydro-3,5-diphenylpyrazole-1-carbothioamide | 1333466-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-dihydro-3,5-diphenylpyrazole-1-carbothioamide
• 英文别名: 5-(4-Bromophenyl)-3-(4-methoxyphenyl)-3,4-dihydropyrazole-2-carbothioamide
• CAS: 1333466-20-8
• 化学式: C₁₇H₁₆BrN₃OS
• 分子量: 390.304
• InChiKey: QMGTWVOSENBPHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-dihydro-3,5-diphenylpyrazole-1-carbothioamide 、 溴乙酸 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以86%的产率得到2-(3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors

  摘要：

  A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 mu M for EGFR and IC50 = 1.07 mu M for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 mu M, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.051
• 作为产物：
  描述：

  4-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 5-dihydro-3,5-diphenylpyrazole-1-carbothioamide
  参考文献：
  名称：

  吡唑基-噻唑衍生物的晶体工程：π-堆积和σ-空穴相互作用的结构指导作用

  摘要：

  1-（2-（3-（4-溴苯基）-5-（4-甲氧基苯基）-4,5-二氢-1 H-吡唑-1-基）-4-甲基噻唑-的合成及X射线表征5-基）乙酮（7），2-（5-（4-溴苯基）-3-（4-氯苯基）-4,5-二氢吡唑-1-基）噻唑-4-羧酸乙酯（8）和2- （5-（4-氯苯基）-3-苯基-4,5-二氢-1 H-吡唑-1-基）-N '-（2-羟基-3-甲氧基亚苄基）噻唑-4-碳酰肼（10）在本手稿中进行了介绍。使用DFT计算和Hirshfeld表面分析，对各种非共价相互作用的结构指导作用进行了有力的分析。此外，已经通过使用分子中原子的量子理论和非共价相互作用指数（NCIplot）分析了卤素和硫族元素键相互作用的存在和重要性。

  DOI：

  10.1039/d1ce00256b

文献信息

• Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives as EGFR TK inhibitors and potential anticancer agents
  作者：Peng-Cheng Lv、Dong-Dong Li、Qing-Shan Li、Xiang Lu、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2011.07.010

  日期：2011.9

  Fourty-two thiazolyl-pyrazoline derivatives were synthesized to screen for their EGFR kinase inhibitory activity. Compound 4-(4-chlorophenyl)-2-(3-(3,4-dimethylphenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl) thiazole (11) displayed the most potent EGFR TK inhibitory activity with IC(50) of 0.06 mu M, which was comparable to the positive control. Molecular docking results indicated that compound 11 was nicely bound to the EGFR kinase. Compound 11 also showed significant antiproliferative activity against MCF-7 with IC(50) of 0.07 mu M, which would be a potential anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
  作者：Ke-Ming Qiu、Hai-Hong Wang、Li-Ming Wang、Yin Luo、Xian-Hui Yang、Xiao-Ming Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.01.051

  日期：2012.3

  A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 mu M for EGFR and IC50 = 1.07 mu M for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 mu M, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.
• Crystal engineering with pyrazolyl-thiazole derivatives: structure-directing role of π-stacking and σ-hole interactions
  作者：Muhammad Naeem Ahmed、Murtaza Madni、Shaista Anjum、Saiqa Andleeb、Shahid Hameed、Abdul Majeed Khan、Muhammad Ashfaq、Muhammad Nawaz Tahir、Diego M. Gil、Antonio Frontera

  DOI：10.1039/d1ce00256b

  日期：——

  The synthesis and X-ray characterization of 1-(2-(3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazol-5-yl)ethanone (7), ethyl 2-(5-(4-bromophenyl)-3-(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazole-4-carboxylate (8) and 2-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N′-(2-hydroxy-3-methoxybenzylidene)thiazole-4-carbohydrazide (10) are described in this

  1-（2-（3-（4-溴苯基）-5-（4-甲氧基苯基）-4,5-二氢-1 H-吡唑-1-基）-4-甲基噻唑-的合成及X射线表征5-基）乙酮（7），2-（5-（4-溴苯基）-3-（4-氯苯基）-4,5-二氢吡唑-1-基）噻唑-4-羧酸乙酯（8）和2- （5-（4-氯苯基）-3-苯基-4,5-二氢-1 H-吡唑-1-基）-N '-（2-羟基-3-甲氧基亚苄基）噻唑-4-碳酰肼（10）在本手稿中进行了介绍。使用DFT计算和Hirshfeld表面分析，对各种非共价相互作用的结构指导作用进行了有力的分析。此外，已经通过使用分子中原子的量子理论和非共价相互作用指数（NCIplot）分析了卤素和硫族元素键相互作用的存在和重要性。