N-(4-chlorophenyl)-5-phenyl-1,3,4-thiadiazole-2-amine | 92161-93-8

• 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-(4-chlorophenyl)-5-phenyl-1,3,4-thiadiazole-2-amine
• 英文别名: N-(4-chlorophenyl)-5-phenyl-1,3,4-thiadiazol-2-amine
• CAS: 92161-93-8
• 化学式: C₁₄H₁₀ClN₃S
• 分子量: 287.773
• InChiKey: OZRPBDYWQDSFOY-UHFFFAOYSA-N

物化性质

• 熔点：
  218 °C
• 沸点：
  444.4±47.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酸苯酯 在 硫酸 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 N-(4-chlorophenyl)-5-phenyl-1,3,4-thiadiazole-2-amine
  参考文献：
  名称：

  1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation

  摘要：

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

  DOI：

  10.1021/jm0495632

文献信息

• Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones
  作者：Qing-Hu Teng、Feng-Lai Lu、Kai Wang、Li-Ya Zhou、Dian-Peng Li

  DOI：10.1021/acs.joc.3c00320

  日期：2023.6.2

  A photocatalytic chemodivergent reaction for the selectivity formation of C–S and C–N bonds in a controlled manner was proposed. The reaction medium, either neutral or acidic, is critical to dictate the formation of 2-amino-1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones from isothiocyanates and hydrazones. This is a practical protocol to achieve the chemoselectivity under mild and metal-free conditions

  提出了一种以受控方式选择性形成 C-S 和 C-N 键的光催化化学发散反应。中性或酸性反应介质对于决定从异硫氰酸酯和腙形成 2-氨基-1,3,4-噻二唑和 1,2,4-三唑-3-硫酮至关重要。这是在温和和无金属条件下实现化学选择性的实用方案。
• Design and Synthesis of 1,3,4-Thiadiazole Derivatives as Novel Anticancer and Antitubercular Agents
  作者：D. Chandra Sekhar、D. V. Venkata Rao、A. Tejeswara Rao、U. Lav Kumar、Anjali Jha

  DOI：10.1134/s1070363219040224

  日期：2019.4

  A series of novel 5-phenyl-substituted 1,3,4-thiadiazole-2-amines were designed, synthesized, and screened for their antitumor and antitubercular activities. The target compounds were synthesized starting from isocyanates and acid hydrazides by conventional and microwave-assisted protocols. The structures of the products were confirmed by H-1 NMR, C-13 NMR, high-resolution mass spectrometry, and IR spectroscopy and elemental analysis. Some of the synthesized compounds showed significant invitro antitumor activities against breast cancer and normal human cell lines. Among them, N-benzyl-5-(4-fluorophenyl)-, N-benzyl-5-(4-nitrophenyl)-, and 5-phenyl-N-(p-tolyl)-1,3,4-thiadiazole-2-amines demonstrated higher inhibitory activities against the MDA-MB-231 cell line than the cisplatin control (IC50 3.3 M). N-Benzyl-5-(4-methoxyphenyl)-, 5-phenyl-N-[4-(trifluoromethyl)phenyl]methyl-, N-benzyl-5-(4-fluorophenyl)-, and N-benzyl-5-(4-nitrophenyl)-1,3,4-thiadiazole-2-amines exhibited high inhibitory activities against the HEK293T cell line (IC50 52.63, 42.67, 34.71, and 33.74 M, respectively), which were higher compared to the cisplatin control. In antitubercular activity testing against mycobacterium smegmatis MC155, 5-phenyl-N-[4-(trifluoromethyl)-phenyl]methyl-1,3,4-thiadiazole-2-amine proved to be a more potent agent (MIC 26.46 g/mL) compared to the Isoniazid control (12 g/mL). Potential bioactivities of the synthesized compounds were computed using Molinspiration and Molsoft software tools.
• Srinivasan,V.R.; Ramachander,G., Indian Journal of Chemistry, 1963, vol. 1, p. 234 - 236
  作者：Srinivasan,V.R.、Ramachander,G.

  DOI：——

  日期：——