(E)-2-(3,4-dimethoxybenzylidene)hydrazinecarbothioamide | 6292-77-9

• 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: (E)-2-(3,4-dimethoxybenzylidene)hydrazinecarbothioamide
• 英文别名: (2E)-2-[(3,4-dimethoxyphenyl)methylidene]-hydrazine-1-carbothioamide；Veratraldehyde (8CI), thiosemicarbazone；[(E)-(3,4-dimethoxyphenyl)methylideneamino]thiourea
• CAS: 6292-77-9
• 化学式: C₁₀H₁₃N₃O₂S
• 分子量: 239.298
• InChiKey: QUQXICHUDASLHF-WUXMJOGZSA-N

物化性质

• 熔点：
  193.2-195 °C
• 沸点：
  383.6±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,4-dimethoxybenzylidene)hydrazinecarbothioamide 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 以76%的产率得到ethyl 2-[(E)-2-[(3,4-dimethoxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

  摘要：

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.054
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (E)-2-(3,4-dimethoxybenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  芳基腙连接噻唑基香豆素杂化物作为潜在的脲酶抑制剂

  摘要：

  通过遵循“一锅”两步反应方案制备带有噻唑基香豆素杂化物1-32的芳基腙。各种芳醛在酸性条件下与氨基硫脲反应形成芳基氨基氨基硫脲中间体，该中间体又在碱性条件下用 3-溴乙酰香豆素处理，得到噻唑基香豆素杂化物 1-32。所有杂种均通过 EI-和 HREI-MS 以及 1H-和 13C-NMR 光谱技术进行识别。筛选化合物 1-32 对脲酶的体外抑制活性，并在 IC50 = 16.29 ± 1.1-256.30 ± 1.4 µM 范围内显示出良好至中等的抑制潜力。值得指出的是，化合物 21 (IC50 = 16.29 ± 1.1 µM) 被确定为比标准乙酰氧肟酸 (IC50 = 27.0 ± 0.5 µM) 更有效的脲酶抑制剂。衍生物 19 (IC50 = 77.67 ± 1. 5 µM) 和 30 (IC50 = 71.21 ± 1.6 µM) 被发现具有中度活性。构效关系表明-F、-Cl、-

  DOI：

  10.1007/s13738-021-02377-8

文献信息

• A Series of Benzylidenes Linked to Hydrazine‐1‐carbothioamide as Tyrosinase Inhibitors: Synthesis, Biological Evaluation and Structure−Activity Relationship
  作者：Hona Hosseinpoor、Aida Iraji、Najmeh Edraki、Somayeh Pirhadi、Mahshid Attarroshan、Mahsima Khoshneviszadeh、Mehdi Khoshneviszadeh

  DOI：10.1002/cbdv.202000285

  日期：2020.8

  and enzymatic browning of vegetables and fruits. In the present article, 12 small molecules of benzylidene-hydrazinecarbothioamide were designed, synthesized and evaluated for their anti-tyrosinase activities followed by molecular docking and pharmacophore-based screening. Among synthesized thiosemicarbazone derivatives, 3d is the strongest inhibitor of mushroom tyrosinase with IC 50 of 0.05 µM which

  酪氨酸酶是一种 3 型铜酶，可导致皮肤色素沉着障碍、皮肤癌以及蔬菜和水果的酶促褐变。在本文中，设计、合成了 12 个小分子亚苄基肼碳硫酰胺并评估了它们的抗酪氨酸酶活性，然后进行了分子对接和基于药效团的筛选。在合成的氨基硫脲衍生物中，3d 是最强的蘑菇酪氨酸酶抑制剂，IC 50 为 0.05 µM，与阳性对照相比，其效力提高了 128 倍。动力学研究还揭示了 3d 的混合类型抑制。对接研究证实合成的化合物完全适合酪氨酸酶活性位点。
• Aryl thiosemicarbazones for the treatment of trypanosomatidic infections
  作者：Pasquale Linciano、Carolina B. Moraes、Laura M. Alcantara、Caio H. Franco、Bruno Pascoalino、Lucio H. Freitas-Junior、Sara Macedo、Nuno Santarem、Anabela Cordeiro-da-Silva、Sheraz Gul、Gesa Witt、Maria Kuzikov、Bernhard Ellinger、Stefania Ferrari、Rosaria Luciani、Antonio Quotadamo、Luca Costantino、Maria Paola Costi

  DOI：10.1016/j.ejmech.2018.01.043

  日期：2018.2

  interesting activity against the same organisms. The compounds were particularly effective against T. brucei and T. cruzi. Among the 28 synthesized compounds, the best one was (E)-2-(4-((3.4-dichlorobenzyl)oxy)benzylidene) hydrazinecarbothioamide (A14) yielding a comparable anti-parasitic activity against the three parasitic species (TbEC50 = 2.31 μM, LiEC50 = 6.14 μM, TcEC50 = 1.31 μM) and a Selectivity Index

  基于显示出抗锥虫病活性的噻二唑衍生物库，我们已经考虑了噻二唑的开放形式和反应中间体硫代半脲类化合物，作为针对布鲁氏锥虫（Tb），婴儿利什曼原虫（Li）和克氏锥虫（Tc）。相似的化合物已经显示出对相同生物的有趣活性。该化合物对T. brucei和T. cruzi特别有效。在这28种合成的化合物中，最好的一种是（E）-2-（4-（（3.4-二氯苄基）氧基）亚苄基）肼基甲硫代酰胺（A14）针对三种寄生物（Tb EC 50  = 2.31μM，Li EC 50  = 6.14μM，Tc EC 50  = 1.31μM ）产生可比的抗寄生虫活性，并且相对于人类巨噬细胞的选择性指数高于10，因此显示泛抗锥虫病活动。（E）-2-（（（3'.4'-二甲氧基-[1.1'-联苯] -3-基]甲基）甲基）肼基甲硫代酰胺（A12）和（E）-2-（4-（（3.4-二氯苄基）氧基）苯亚甲基）肼硫代甲酰胺（A14）在组
• Synthesis of 1,3-Thiazolidin-4-Ones; Reactivity of the Thiosemicarbazone Function towards Dimethyl Acetylenedicarboxylate
  作者：Alaa A. Hassan、Shaaban K. Mohamed、Nasr K. Mohamed、Kamal M. El-Shaieb、Ahmed T. Abdel-Aziz、Joel T. Mague、Mehmet Akkurt

  DOI：10.3184/174751916x14552868764580

  日期：2016.3

  Aryl thiosemicarbazones react rapidly in a facile procedure with dimethyl acetylene-dicarboxylate to give substituted (ylidene) hydrazono(4-oxothiazolidin-5-ylidene) acetates in high yields. The synthesised compounds were characterised by spectroscopic methods and the structures confirmed by single crystal X-ray crystallography. Several mechanistic options involving nucleophilic interaction are presented

  芳基缩氨基硫脲以简便的方法与乙炔-二羧酸二甲酯快速反应，以高产率得到取代的（亚基）腙（4-氧噻唑烷-5-亚基）乙酸酯。合成的化合物通过光谱方法进行表征，并通过单晶 X 射线晶体学确认其结构。介绍了涉及亲核相互作用的几种机械选择。
• HUSAIN M. I.; SRIVASTAV G. C., J. INDIAN CHEM. SOC., 1979, 56, NO 9, 938-940
  作者：HUSAIN M. I.、 SRIVASTAV G. C.

  DOI：——

  日期：——
• HUSAIN, M. I.;SRIVASTAVA, V. P., ACTA PHARM. JUGOSL., 1984, 34, N 1, 21-26
  作者：HUSAIN, M. I.、SRIVASTAVA, V. P.

  DOI：——

  日期：——