(E)-2-(4-(benzyloxy)benzylidene)hydrazinecarbothioamide | 101091-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-(4-(benzyloxy)benzylidene)hydrazinecarbothioamide
• 英文别名: 4-benzyloxy-benzaldehyde-thiosemicarbazone；4-Benzyloxy-benzaldehyd-thiosemicarbazon；Benzaldehyde, 4-benzyloxy-, thiosemicarbazone；[(E)-(4-phenylmethoxyphenyl)methylideneamino]thiourea
• CAS: 101091-29-6
• 化学式: C₁₅H₁₅N₃OS
• 分子量: 285.37
• InChiKey: XVIITPGJQGFFIP-LICLKQGHSA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  459.8±47.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-(benzyloxy)benzylidene)hydrazinecarbothioamide 、 2'-溴-4-氯苯乙酮 以81%的产率得到(E)-2-(2-(4-(benzyloxy)benzylidene)hydrazinyl)-4-(4-chlorophenyl)thiazole
  参考文献：
  名称：

  Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

  摘要：

  A series of thiazole derivatives 1-21 were prepared, characterized by EI-MS and H-1 NMR and evaluated for alpha-glucosidase inhibitory potential. All twenty one derivatives showed good alpha-glucosidase inhibitory activity with IC50 value ranging between 18.23 +/- 0.03 and 424.41 +/- 0.94 mu M when compared with the standard acarbose (IC50, 38.25 +/- 0.12 mu M). Compound (8) (IC50, 18.23 +/- 0.03 mu M) and compound (7) (IC50 = 36.75 +/- 0.05 mu M) exhibited outstanding inhibitory potential much better than the standard acarbose (IC50, 38.25 +/- 0.12 mu M). All other analogs also showed good to moderate enzyme inhibition. Molecular docking studies were carried out in order to find the binding affinity of thiazole derivatives with enzyme. Studies showed these thiazole analogs as a new class of a-glucosidase inhibitors. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.06.006
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 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-(4-(benzyloxy)benzylidene)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

• Hydrazine clubbed 1,3-thiazoles as potent urease inhibitors: design, synthesis and molecular docking studies
  作者：Pervaiz Ali Channar、Aamer Saeed、Saira Afzal、Dilawar Hussain、Markus Kalesse、Syeda Aaliya Shehzadi、Jamshed Iqbal

  DOI：10.1007/s11030-020-10057-7

  日期：2021.5

  motifs has been demonstrated in terms of their strong urease inhibition activity. The results of in vitro study revealed that all the compounds are the potent inhibitors of urease. The IC50 (ranging in between 110 and 440 nM) values were higher as compared to that of standard, i.e., thiourea (IC50 = 490 ± 10 nM). The synthesized compounds were docked at the active sites of the Jack bean urease enzyme in

  通过在回流乙醇中将 hydrazine-1-carbothioamides (3a-k) 与 α-氯或溴苯乙酮 (4a-d) 反应，合成了一系列新型肼棒状 1,3-噻唑 (5a-m)良率至极好 (65-86%)。结构确认基于光谱技术，例如 1H-NMR、13C-NMR、FT-IR 和质谱。这些基序的生物学应用已在它们强烈的脲酶抑制活性方面得到证明。体外研究结果表明，所有化合物都是脲酶的强抑制剂。与标准品（即硫脲）相比，IC50（介于 110 和 440 nM 之间）值更高（IC50 = 490 ± 10 nM）。将合成的化合物对接在杰克豆脲酶的活性位点上，以探索酶-配体复合物可能的结合相互作用；结果加强了体外生物活性结果。
• [EN] METHODS OF TREATING OR PREVENTING A PROTEOPATHY<br/>[FR] MÉTHODES POUR TRAITER OU PRÉVENIR UNE PROTÉOPATHIE
  申请人：USHER III INITIATIVE INC

  公开号：WO2016201266A1

  公开（公告）日：2016-12-15

  Methods for the treatment or prevention of a proteopathy are described herein.

  本文描述了一种治疗或预防蛋白质病的方法。
• [EN] TREATMENT OF CANCER, INFLAMMATORY DISEASES AND AUTOIMMUNE DISEASES<br/>[FR] TRAITEMENT DU CANCER, DE MALADIES INFLAMMATOIRES ET DE MALADIES AUTO-IMMUNES
  申请人：USHER III INITIATIVE INC

  公开号：WO2022011091A1

  公开（公告）日：2022-01-13

  The present disclosure relates to methods for the treatment or prevention of cancer, an inflammatory disease or an autoimmune disease with compounds of the invention as disclosed herein. The present disclosure also relates to methods for reducing risk of developing cancer, an inflammatory disease or an autoimmune disease with compounds of the invention as disclosed herein.

  本公开涉及使用本文所披露的化合物治疗或预防癌症、炎症性疾病或自身免疫疾病的方法。本公开还涉及使用本文所披露的化合物降低患癌症、炎症性疾病或自身免疫疾病风险的方法。
• Thiosemicarbazones as anti-virals and immunopotentiators
  申请人：Barsanti A. Paul

  公开号：US20050069555A1

  公开（公告）日：2005-03-31

  The present invention is directed to novel immune potentiators, novel vaccine adjuvants, novel compounds and pharmaceutical compositions, novel methods for treating viral infections, including HCV, by administering the compounds, and novel methods for modulating an immune response by administering the compounds.

  本发明涉及新型免疫增强剂、新型疫苗佐剂、新型化合物和药物组合物、通过给予该化合物治疗包括HCV在内的病毒感染的新方法，以及通过给予该化合物调节免疫反应的新方法。
• Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents
  作者：Fazal Rahim、Khalid Zaman、Hayat Ullah、Muhammad Taha、Abdul Wadood、Muhammad Tariq Javed、Wajid Rehman、Muhammad Ashraf、Reaz Uddin、Imad Uddin、Humna Asghar、Aftab Ahmad Khan、Khalid M. Khan

  DOI：10.1016/j.bioorg.2015.10.005

  日期：2015.12

  4-Thiazolidinone analogs 1-20 were synthesized, characterized by H-1 NMR and EI-MS and investigated for urease inhibitory activity. All twenty (20) analogs exhibited varied degree of urease inhibitory potential with IC50 values 1.73-69.65 mu M, if compared with standard thiourea having IC50 value of 21.25 +/- 0.15 mu M. Among the series, eight derivatives 3, 6, 8, 10, 15, 17, 19, and 20 showed outstanding urease inhibitory potential with IC50 values of 9.34 +/- 0.02, 14.62 +/- 0.03, 8.43 +/- 0.01, 7.3 +/- 0.04, 2.31 +/- 0.002, 5.75 +/- 0.003, 8.81 +/- 0.005, and 1.73 +/- 0.001 mu M, respectively, which is better than the standard thiourea. The remaining analogs showed good to excellent urease inhibition. The binding interactions of these compounds were confirmed through molecular docking studies. (C) 2015 Elsevier Inc. All rights reserved.