2-(3,4-methylenedioxyphenyl)-3-phenyl-5-phenylamino-1,3,4-thiadiazolium chloride | 1029101-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(3,4-methylenedioxyphenyl)-3-phenyl-5-phenylamino-1,3,4-thiadiazolium chloride
• 英文别名: 5-(1,3-benzodioxol-5-yl)-N,4-diphenyl-1,3,4-thiadiazol-4-ium-2-amine;chloride
• CAS: 1029101-24-3
• 化学式: C₂₁H₁₆N₃O₂S*Cl
• 分子量: 409.896
• InChiKey: ULGDAHJBNSCKFG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  75.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒醛 、 1,4-二苯氨基硫脲 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 以92%的产率得到2-(3,4-methylenedioxyphenyl)-3-phenyl-5-phenylamino-1,3,4-thiadiazolium chloride
  参考文献：
  名称：

  新型胡椒醛1,3,4-噻二唑-2-苯基胺类中性离子衍生物：合成，酪氨酸酶抑制评价和HSA结合研究

  摘要：

  合成了一系列新的胡椒基中离子衍生物（PMI 1-6）。在PMI-1，-2，-3，-4，-5和-6存在下酪氨酸酶抑制作用以及人血清白蛋白（HSA）与PMI-5和PMI-6的结合研究是通过光谱和理论方法完成的。中离子化合物PMI-5是最有前途的酪氨酸酶抑制剂，具有非竞争性抑制机制，IC 50  = 124μmolL -1。根据动力学曲线，分子对接结果表明PMI-5能够与包含底物分子L-DOPA的酪氨酸酶活性位点良好相互作用，并与Val-247，Phe-263和Val-282残基相互作用。HSA：PMI-5和HSA：PMI-6相互作用的光谱结果表明，这些中离子化合物可以在基态下与HSA缔合，并且能量转移的可能性很高。结合是中等的，自发的，并且可以显着干扰白蛋白的二级结构。分子对接结果表明，PMI-5和PMI-6能够被容纳在HSA的Sudlow位点I内，与疏水和亲水氨基酸残基相互作用。

  DOI：

  10.1016/j.ijbiomac.2018.02.050

文献信息

• Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: Chemical and biological studies
  作者：Welisson da Silva Ferreira、Leonardo Freire-de-Lima、Víctor Barbosa Saraiva、Frederico Alisson-Silva、Lucia Mendonça-Previato、José Osvaldo Previato、Aurea Echevarria、Marco Edilson Freire de Lima

  DOI：10.1016/j.bmc.2007.12.049

  日期：2008.3.15

  We herein describe the synthesis and characterization of nine new 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine. We evaluate their toxic effects against the different evolutive forms of Trypanosoma cruzi, and the host cell (murine macrophages). The results obtained show that mesoionic hydrochloride MI possesses the best activity profile. Compound MI may be a prototype for use in the development of a new chemotherapeutic agent with high efficiency, which may be employed in the treatment of Chagas' disease. (C) 2008 Elsevier Ltd. All rights reserved.
• Improved synthesis of 1,3,4-thiadiazolium-2-phenylamines using microwave and ultrasound irradiation and investigation of their cytotoxic activity
  作者：Camilla Moretto dos Reis、Juliana Echevarria-Lima、Amanda Fraga Miranda、Aurea Echevarria

  DOI：10.1590/s0103-50532011000800014

  日期：——

  A new and efficient synthesis of eight 1,3,4-thiadiazolium-2-phenylamine derivatives (1-8, where 8 is novel in the literature) was performed using thionyl chloride or trimethylsilyl chloride as catalysts under microwave or ultrasound irradiation. The target compounds were obtained in good yields and remarkably short times, 5 min under microwave irradiation and 10 min under ultrasound irradiation, where compared to traditional methodology (24 to 48 h at room temperature standing). The best yields were obtained using the microwave irradiation and, in general way, using thionyl chloride instead trimethylsilyl chloride. The cytotoxicity against K562 human leukemia and Daudi lymphoma lines was evaluated and showed promising results from the 4-phenyl-5-(4'-nitro-styryl)-1,3,4-thiadiazolium-2-phenylamine chloride derivative.
• Novel piperonal 1,3,4-thiadiazolium-2-phenylamines mesoionic derivatives: Synthesis, tyrosinase inhibition evaluation and HSA binding study
  作者：Natália Drumond Lopes、Otávio Augusto Chaves、Márcia C.C. de Oliveira、Carlos Mauricio R. Sant'Anna、Danilo Sousa-Pereira、José Carlos Netto-Ferreira、Aurea Echevarria

  DOI：10.1016/j.ijbiomac.2018.02.050

  日期：2018.6

  A novel series of piperonal mesoionic derivatives (PMI 1–6) was synthesized. Tyrosinase inhibition in the presence of PMI-1, −2, −3, −4, −5 and −6 as well as human serum albumin (HSA) binding studies with PMI-5 and PMI-6 were done by spectroscopic and theoretical methods. The mesoionic compound PMI-5 is the most promising tyrosinase inhibitor with a noncompetitive inhibitory mechanism and an IC50 = 124 μmol L−1

  合成了一系列新的胡椒基中离子衍生物（PMI 1-6）。在PMI-1，-2，-3，-4，-5和-6存在下酪氨酸酶抑制作用以及人血清白蛋白（HSA）与PMI-5和PMI-6的结合研究是通过光谱和理论方法完成的。中离子化合物PMI-5是最有前途的酪氨酸酶抑制剂，具有非竞争性抑制机制，IC 50  = 124μmolL -1。根据动力学曲线，分子对接结果表明PMI-5能够与包含底物分子L-DOPA的酪氨酸酶活性位点良好相互作用，并与Val-247，Phe-263和Val-282残基相互作用。HSA：PMI-5和HSA：PMI-6相互作用的光谱结果表明，这些中离子化合物可以在基态下与HSA缔合，并且能量转移的可能性很高。结合是中等的，自发的，并且可以显着干扰白蛋白的二级结构。分子对接结果表明，PMI-5和PMI-6能够被容纳在HSA的Sudlow位点I内，与疏水和亲水氨基酸残基相互作用。