3,5-bis(4-chlorophenyl)-4,5-dihydropyrazole-1-carbothioamide | 153332-07-1

• 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: 3,5-bis(4-chlorophenyl)-4,5-dihydropyrazole-1-carbothioamide
• 英文别名: 3-(4-chlorophenyl)-5-(4-chlorophenyl)-4,5-dihydropyrazole-1-carbothioamide；1-thiocarbamoyl-3,5-bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol；3,5-bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide；3,5-bis(4-chlorophenyl)-3,4-dihydropyrazole-2-carbothioamide
• CAS: 153332-07-1
• 化学式: C₁₆H₁₃Cl₂N₃S
• 分子量: 350.271
• InChiKey: ABVLEDJVQBYJHS-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C(Solvent: Acetone; Ethanol)
• 沸点：
  494.2±55.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3,5-bis(4-chlorophenyl)-4,5-dihydropyrazole-1-carbothioamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole-5-carbonyl)-2H-chromen-2-one
  参考文献：
  名称：

  Triad pyrazole–thiazole–coumarin heterocyclic core effectively inhibit HSP and drive cancer cells to apoptosis

  摘要：

  DOI：

  10.1080/07391102.2023.2181643
• 作为产物：
  描述：

  4-氯苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3,5-bis(4-chlorophenyl)-4,5-dihydropyrazole-1-carbothioamide
  参考文献：
  名称：

  Novel pyrazoline linked acyl thiourea pharmacophores as antimicrobial, urease, amylase and α-glucosidase inhibitors: design, synthesis, SAR and molecular docking studies

  摘要：

  新合成的吡唑啉酰基硫脲类化合物的 IC50 值显示，5b 和 5g 是强效的脲酶抑制剂。化合物 5b 是一种强效的 α-葡萄糖苷酶抑制剂，化合物 5f 是一种强效的淀粉酶抑制剂，化合物 5b 则是一种强效的抗氧化剂。

  DOI：

  10.1039/d3ra06812a

文献信息

• Synthesis and Selective Inhibitory Activity Against Human COX-1 of Novel 1-(4-Substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline Derivatives
  作者：Simone Carradori、Daniela Secci、Adriana Bolasco、Celeste De Monte、Matilde Yáñez

  DOI：10.1002/ardp.201200249

  日期：2012.12

  (compounds 5, 6, 13, 16, and 17) displayed promising selectivity against hCOX‐1 in the micromolar range and were shown to have a selectivity index similar or better than the reference drugs (indometacin, diclofenac). The introduction of a phenyl or a 4‐F‐phenyl ring on the C5 associated with a 4‐substituted phenyl or a heteroaryl group on the C3 of (4‐substituted‐thiazol‐2‐yl)pyrazoline derivatives improved

  3,5-二(杂)芳基-1-硫代氨基甲酰基-2-反应得到新型1-(4-乙基羧酸酯-噻唑-2-基)-3,5-二(杂)芳基-2-吡唑啉衍生物吡唑啉与α-溴-丙酮酸乙酯。合成的化合物通过光谱数据得到证实，并进行了分析，以评估它们在体外抑制人类环氧合酶 (hCOX) 两种异构体的能力。一些衍生物（化合物 5、6、13、16 和 17）在微摩尔范围内对 hCOX-1 显示出有希望的选择性，并且显示出与参考药物（吲哚美辛、双氯芬酸）相似或更好的选择性指数。在（4-取代-噻唑-2-基）吡唑啉衍生物的 C3 上与 4-取代苯基或杂芳基相连的 C5 上引入苯基或 4-F-苯环提高了对 hCOX-的活性1.
• Recurrent π–π stacking motifs in three new 4,5-dihydropyrazolyl–thiazole–coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
  作者：Murtaza Madni、Muhammad Naeem Ahmed、Muhammad Hafeez、Muhammad Ashfaq、Muhammad Nawaz Tahir、Diego M. Gil、Bartomeu Galmés、Shahid Hameed、Antonio Frontera

  DOI：10.1039/d0nj02931a

  日期：——

  The synthesis and X-ray characterization of three new 4,5-dihydropyrazolylthiazole–coumarin hybrids (1–3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) and 3-(2-(3-(4-chlorophenyl)-4,5-dihydro-5-p-tolylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one

  本文报道了三种新的4,5-二氢吡唑基噻唑-香豆素杂化物（1-3）的合成和X射线表征，即3-（2-（3,5-双（4-氯苯基）-4,5-二氢吡唑） -1-基）噻唑-4-基）-2 H-铬-2- （1），3-（2-（5-（4-氯苯基）-4,5-二氢-3-苯基吡唑-1- yl）thiazol-4-yl）-2 H -chromen-2-one（2）和3-（2-（3-（4-chlorophenyl）-4,5-dihydro-5- p -tolylpyrazol-1-yl ）噻唑-4-基）-2 H-铬-2--2-（3）。还报告了非共价相互作用的详细结构分析及其使用Hirshfeld表面分析的评估，证明了C–H⋯O和π–π相互作用的重要性。最后，DFT计算以及分子静电势（MEP）和NCIplot指数分析已被用于大力评估这些相互作用，并研究了两种不同的π堆积模式的相对重要性，这些模式是循环结合基序在固体结构中的相对重要性。三个复合体。
• Synthesis and Crystal Structure of New Thiazolyl-Pyrazoline Derivatives Bearing 1,2,4-Triazole Moiety
  作者：Yong-Ming Zeng、Sheng-Qin Chen、Fang-Ming Liu

  DOI：10.1007/s10870-011-0198-0

  日期：2012.1

  The title compounds 1-(4-aryl-5-triazolyl-2-thiazolyl)-3,5-diaryl-2-pyrazoline derivatives (3a–c) were synthesized by reacting 3,5-diaryl1-thiocarbamoyl -2-pyrazoline 1 with 2-bromo-1-aryl-2-(1H-1,2,4-triazol-1-yl) ethanones 2 in boiling ethanol. Their structures were characterized by IR, 1H-NMR, MS spectroscopic data and elementary analyses. The structure of compound (3a), C26H18Cl2N6S, was conclusively established with X-ray crystal structure analysis. It crystallizes in the Orthorhombic space group Pna2(1), with a = 17.8160(5), b = 18.9125(7), c = 14.7926(4), α = 90°, β = 90°, γ = 90°and Dc = 1.379 mg/m3 for Z = 8, V = 4984.3(3) Å, μ(Mo–Kα) = 0.372 mm, λ = 0.71070 Å, the final R = 0.0527 and wR = 0.1307 for 43309 observed reflections with I > 2σ(I). The structure is stabilized by weak C–H···N intramolecular hydrogen bonds and C–H···Cg p-ring intermolecular interactions and gives support to molecular packing stability in the unit cell. The title compounds 1-(4-aryl-5-triazolyl-2-thiazolyl)-3,5-diaryl-2–pyrazoline derivatives (3a-c) were synthesized by reacting 3,5-diaryl1-thiocarbamoyl-2- pyrazoline 1 with 2-bromo-1-aryl-2-(1H-1,2,4-triazol-1-yl) ethanones 2. Their structures were characterized by IR, 1H-NMR, MS spectroscopic data and elementary analyses. The structure of compound (3a) was conclusively established with X-ray crystal structure analysis.

  标题化合物 1-(4-芳基-5-三唑基-2-噻唑基)-3,5-二芳基-2-吡唑啉衍生物 (3a-c) 是由 3,5- 二芳基-1-硫代氨基甲酰基-2-吡唑啉 1 与 2-溴-1-芳基-2-(1H-1,2,4-三唑-1-基) 乙酮 2 在沸腾的乙醇中反应合成的。通过红外光谱、1H-NMR、MS 光谱数据和基本分析对它们的结构进行了表征。化合物 (3a) C26H18Cl2N6S 的结构是通过 X 射线晶体结构分析确定的。它结晶于正交空间群 Pna2(1)，a = 17.8160(5), b = 18.9125(7), c = 14.7926(4), α = 90°, β = 90°, γ = 90°and Dc = 1.379 mg/m3 for Z = 8, V = 4984.3(3) Å, μ(Mo-Kα) = 0.372 mm, λ = 0.71070 Å, 最终 R = 0.0527 and wR = 0.1307 for 43309 observed reflections with I > 2σ(I).该结构通过微弱的 C-H-N 分子内氢键和 C-H-Cg p-ring 分子间相互作用而稳定，并支持单元胞中的分子堆积稳定性。标题化合物 1-(4-芳基-5-三唑基-2-噻唑基)-3,5-二芳基-2-吡唑啉衍生物（3a-c）是由 3,5-二芳基-1-硫代氨基甲酰基-2-吡唑啉 1 与 2-溴-1-芳基-2-(1H-1,2,4-三唑-1-基)乙酮 2 反应合成的。通过红外光谱、1H-NMR、MS 光谱数据和基本分析对它们的结构进行了表征。化合物 (3a) 的结构通过 X 射线晶体结构分析得以确定。
• 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.
• Synthesis and Spectral Characterization of Some New Thiazolyl-Pyrazolines Bearing 1,2,4-Triazole Moiety
  作者：Sheng-Qin Chen、Yi-Chao Zhang、Fang-Ming Liu

  DOI：10.1080/10426507.2010.497519

  日期：2011.1.31