N-methylphenyl-N'-(2-chlorobenzoyl)thiourea

• 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: N-methylphenyl-N'-(2-chlorobenzoyl)thiourea
• 英文别名: 2-chloro-N-[methyl(phenyl)carbamothioyl]benzamide
• 化学式: C₁₅H₁₃ClN₂OS
• 分子量: 304.8
• InChiKey: CWIHIDXMIRMBAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methylphenyl-N'-(2-chlorobenzoyl)thiourea 、 cobalt(II) diacetate tetrahydrate 以 甲醇 为溶剂， 以80%的产率得到fac-tris[N,N-methylphenyl-N'-(2-chlorobenzoyl)thioureato-κ²O,S]cobalt(III)
  参考文献：
  名称：

  Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Co(III) complexes with N,N,N′-trisubstituted acylthioureas

  摘要：

  The series of cobalt(III) complexes (1a-12a) with N,N,N'-trisubstituted acylthioureas were synthesized and characterized by FT-IR, and multinuclear (H-1 and C-13) NMR spectroscopy and LC-MS combined with elemental analysis. Crystal structure of cobalt(III) chelate of type Co(L-O, S)(3) were determined by single crystal X-ray diffraction analysis. Complexes were adopted to have the octahedral geometry, where the fac-disposed N,N,N'-trisubstituted acylthioureas showed bidentate mode of coordination environment at cobalt centre defined by three O and three S donor atoms. The ligands are coordinated in a chelate fashion, forming three five-membered rings. The synthesized complexes were screened against Jack bean urease. In vitro anticancer activity against lung carcinoma (H-157), and kidney fibroblast (BHK-21) cell lines of the synthesized compounds were also studied and found them potent candidates for drugs. Cytotoxic results revealed that compound 10a was emerged as a leading member with an IC50 value of 0.75 +/- 0.027 mu M against H-157 cell lines. When synthesized compounds were tested for antileishmanial activity against the promastigote forms of Leishmania major, compound 4a was identified as the most potent and lead candidate showed highest inhibition with an IC50 value of 0.45 +/- 0.053 mu M. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.12.027
• 作为产物：
  描述：

  异硫氰酸 2-氯苯甲酰脂 、 N-甲基苯胺 以 四氢呋喃 为溶剂， 60.0~65.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 生成 N-methylphenyl-N'-(2-chlorobenzoyl)thiourea
  参考文献：
  名称：

  2-氯苯甲酰硫脲衍生物的液相微波辅助平行合成、生物学评价和计算机对接研究

  摘要：

  摘要 成功完成了一种高效、简便的微波辅助液相平行合成 38 元 N-芳酰基-N'-芳基硫脲库。这些类似物 (1-38) 是在相同条件下合成的。已经观察到，反应时间从传统方法的 8 到 12 小时急剧减少到仅 10 到 15 分钟。获得的产品纯度超过 98%，通过元素分析以及 FT-IR 和 1H、13C NMR 进行表征。固相结构分析通过单晶XRD分析完成。测试了合成化合物的脲酶抑制潜力，发现化合物以中等至显着的方式抑制脲酶。化合物 17 是最有效的脲酶抑制剂，IC50 值为 0.17 ± 0.1 μM。为了检查衍生物的细胞毒性特征，使用肺癌细胞系。细胞毒性分析显示化合物对测试的肺癌具有显着的毒性，并且化合物由于连接的取代基而表现出抑制活性的变化。进行分子对接研究以鉴定酶活性位点中有效抑制剂的可能结合模式。结果表明，这些化合物可以进一步研究并用于治疗不同的癌症。

  DOI：

  10.1016/j.molstruc.2018.03.056