N,N-bis[(4-dimethylaminophenyl)methylidene]carbothioic dihydrazide | 7155-10-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis[(4-dimethylaminophenyl)methylidene]carbothioic dihydrazide
• 英文别名: 1,5-bis(p-dimethylaminobenzaldehyde)dithiocarbohydrazone；p-dimethylaminobenzaldehyde thiocarbodihydrazone；N',2-Bis{[4-(dimethylamino)phenyl]methylidene}hydrazine-1-carbothiohydrazide；1,3-bis[[4-(dimethylamino)phenyl]methylideneamino]thiourea
• CAS: 7155-10-4
• 化学式: C₁₉H₂₄N₆S
• 分子量: 368.506
• InChiKey: MBUQGKAMDXBKEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  87.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-苯基-2-丙炔-1-酮 、 N,N-bis[(4-dimethylaminophenyl)methylidene]carbothioic dihydrazide 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到1,7-bis(p-dimethylaminophenyl)-4-(2-benzoylvinylthio)-2,3,5,6-tetraaza-1,3,6-heptatriene
  参考文献：
  名称：

  Reactions of terminal acylacetylenes with thiocarbohydrazones

  摘要：

  The reactions of terminal acylacetylenes with thiocarbohydrazones give 2-(2-acyl-vinyl)thiocarbohydrazones or 2,2-bis(2-acylvinyl)thiocarbohydrazones depending on the reagent ratio. Benzoylacetylene reacts with thiocarbohydrazone of p-dimethylaminobenzaldehyde to form S-[2-(p-dimethylaminobenzoyl)vinyl]isothiocarbodihydrazone.

  DOI：

  10.1007/bf02494526
• 作为产物：
  描述：

  硫代卡巴肼 、 对二甲氨基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以87%的产率得到N,N-bis[(4-dimethylaminophenyl)methylidene]carbothioic dihydrazide
  参考文献：
  名称：

  Synthesis of Thiocarbohydrazones and Evaluation of their in vitro Antileishmanial Activity

  摘要：

  背景：利什曼病是一种原生动物寄生虫病媒传染病，在 88 个热带国家流行。受感染的沙蝇是这种疾病的主要传播媒介，同时还有其他几种传播媒介、寄生虫和储库参与这种疾病的传播。 唐氏利什曼原虫、婴儿利什曼原虫和查加斯利什曼原虫是常见的致病物种，通过沙蝇传播。利什曼病是一种被忽视的热带疾病，具有广泛的临床表现。皮肤利什曼病在包括巴基斯坦在内的许多国家都很流行。 方法：在乙酸作为催化剂的存在下，通过一锅法将硫代酰肼与不同取代的苯甲醛在乙醇中回流合成了硫代酰肼（1-20）。结果：化合物 5-8、11、14、16、17、19 和 20 早先已有报道，而化合物 2-4、9、10、12、13 和 15 则被鉴定为衍生物。与标准药物喷他脒（IC50 = 5.09 ± 0.04 µM）相比，化合物 1-20 具有抗利什曼病活性，IC50 值介于 1.63 ± 0.05 - 64.82 ± 0.17 µM。化合物 2（IC50 = 1.63 ± 0.05 µM）、11（IC50 = 2.33 ± 0.01 µM）、4（IC50 = 11.03 ± 0.20 µM）和 10（IC50 = 11.63 ± 0.06 µM）显示出与标准药物喷他脒相当的抗利什曼活性。然而，IC50 值分别为 36.95 ± 0.025、64.82 ± 0.17、64.27 ± 0.38、62.34 ± 0.38 和 40.47 ± 0.05 µM 的化合物 13、15-17 和 20 显示出中等程度的抗利什曼病活性。结论：在硫代羧腙衍生物中，芳基部分的不同取代基可能是体外抗利什曼活性不同的原因。因此，这些化合物可能有潜力作为一类新的抗利什曼病药进行进一步研究。

  DOI：

  10.2174/1573406414666180115094630

文献信息

• SYNTHESIS AND CHARACTERIZATION OF SOME DITHIOCARBOHYDRAZONES
  作者：Anjiang Zhang、Yunlong Hou、Lixue Zhang、Yi Xiong

  DOI：10.1081/scc-120015405

  日期：2002.1.1

  Three bisthiocarbohydrazones had been synthesized and characterized. The structures of the three compounds were determined by elemental analysis, IR, MS, (HNMR)-H-1 and (CNMR)-C-13. The crystal structure of one of the compounds was determined by X-ray single crystal diffraction techniques.
• Synthesis of Thiocarbohydrazones and Evaluation of their in vitro Antileishmanial Activity
  作者：Munira T. Muhammad、Nida Ghouri、Khalid M. Khan、Arshia、Muhammad I. Choudhary、Shahnaz Perveen

  DOI：10.2174/1573406414666180115094630

  日期：2018.10.3

  Background: Leishmaniasis is a protozoan parasitic vector-borne disease which is endemic in 88 tropical countries. Infected sandfly is the main vector of this disease, while there are several other vectors, parasites, and reservoirs involved in the transmission of this disease. Leishmania donovani, L. infantum, and L. chagasi are common disease causing species, transmitted through sandflies. Leishmaniasis is a neglected tropical disease with broad spectrum of clinical manifestations. Cutaneous leishmaniasis is prevalent in many countries, including Pakistan. Methods: Thiocarbohydrazones (1-20) were synthesized through one pot method by refluxing thiocarbahydrazide with different substituted benzaldehydes in ethanol in the presence of acetic acid as a catalyst. These synthetic compounds were evaluated for their potential antileishmanial activity in vitro against Leishmania major promastigotes. Results: Compounds 5-8, 11, 14, 16, 17, 19 and 20 were reported earlier, while compounds 2-4, 9, 10, 12, 13 and 15 were identified as were derivatives. Compounds 1-20 demonstrated antileishmanial activities with IC50 values between 1.63 ± 0.05 - 64.82 ± 0.17 µM, as compared to the standard drug pentamidine (IC50 = 5.09 ± 0.04 µM). Compounds 2 (IC50 = 1.63 ± 0.05 µM), 11 (IC50 = 2.33 ± 0.01 µM), 4 (IC50 = 11.03 ± 0.20 µM), and 10 (IC50 = 11.63 ± 0.06 µM) displayed comparable antileishmanial activities to the standard drug pentamidine. However, compounds 13, 15-17, and 20 with IC50 values 36.95 ± 0.025, 64.82 ± 0.17, 64.27 ± 0.38, 62.34 ± 0.38, and 40.47 ± 0.05 µM, respectively, showed a moderate antileishmanial activity. In contrast, compounds 1, 3, 5-9, 12, 14, 18, and 19 demonstrated less than 50% growth inhibition of promestigotes of L. major, and thus considered as inactive. Conclusion: In thiocarbohydrazone derivatives, different substituents at aryl part may be responsible for a varying degree of antileishmanial activity in vitro. Consequently, these compounds might have a potential for further studies as a new class of antileishmanial agents.

  背景：利什曼病是一种原生动物寄生虫病媒传染病，在 88 个热带国家流行。受感染的沙蝇是这种疾病的主要传播媒介，同时还有其他几种传播媒介、寄生虫和储库参与这种疾病的传播。 唐氏利什曼原虫、婴儿利什曼原虫和查加斯利什曼原虫是常见的致病物种，通过沙蝇传播。利什曼病是一种被忽视的热带疾病，具有广泛的临床表现。皮肤利什曼病在包括巴基斯坦在内的许多国家都很流行。 方法：在乙酸作为催化剂的存在下，通过一锅法将硫代酰肼与不同取代的苯甲醛在乙醇中回流合成了硫代酰肼（1-20）。结果：化合物 5-8、11、14、16、17、19 和 20 早先已有报道，而化合物 2-4、9、10、12、13 和 15 则被鉴定为衍生物。与标准药物喷他脒（IC50 = 5.09 ± 0.04 µM）相比，化合物 1-20 具有抗利什曼病活性，IC50 值介于 1.63 ± 0.05 - 64.82 ± 0.17 µM。化合物 2（IC50 = 1.63 ± 0.05 µM）、11（IC50 = 2.33 ± 0.01 µM）、4（IC50 = 11.03 ± 0.20 µM）和 10（IC50 = 11.63 ± 0.06 µM）显示出与标准药物喷他脒相当的抗利什曼活性。然而，IC50 值分别为 36.95 ± 0.025、64.82 ± 0.17、64.27 ± 0.38、62.34 ± 0.38 和 40.47 ± 0.05 µM 的化合物 13、15-17 和 20 显示出中等程度的抗利什曼病活性。结论：在硫代羧腙衍生物中，芳基部分的不同取代基可能是体外抗利什曼活性不同的原因。因此，这些化合物可能有潜力作为一类新的抗利什曼病药进行进一步研究。
• Reactions of terminal acylacetylenes with thiocarbohydrazones
  作者：T. N. Komarova、A. S. Nakhmanovich、T. E. Glotova、V. A. Lopyrev

  DOI：10.1007/bf02494526

  日期：1998.10

  The reactions of terminal acylacetylenes with thiocarbohydrazones give 2-(2-acyl-vinyl)thiocarbohydrazones or 2,2-bis(2-acylvinyl)thiocarbohydrazones depending on the reagent ratio. Benzoylacetylene reacts with thiocarbohydrazone of p-dimethylaminobenzaldehyde to form S-[2-(p-dimethylaminobenzoyl)vinyl]isothiocarbodihydrazone.