(E)-2-(naphthalen-2-ylmethylene)hydrazine-1-carbothioamide | 24091-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(naphthalen-2-ylmethylene)hydrazine-1-carbothioamide
• 英文别名: (2E)-2-[(naphthalen-2-yl)methylidene]-hydrazine-1-carbothioamide；2-Naphthaldehyde thiosemicarbazone；[(E)-naphthalen-2-ylmethylideneamino]thiourea
• CAS: 24091-06-3
• 化学式: C₁₂H₁₁N₃S
• 分子量: 229.305
• InChiKey: YGAUDXIKISOSGC-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(naphthalen-2-ylmethylene)hydrazine-1-carbothioamide 、 alpha-溴-4-甲氧基苯乙酮 以32%的产率得到(E)-4-(4-methoxyphenyl)-2-(2-(naphthalen-2-yl-methylene)hydrazinyl)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：

  氨基硫脲 、 2-萘甲醛 反应 8.0h， 以68.88%的产率得到(E)-2-(naphthalen-2-ylmethylene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  一系列与肼碳硫酰胺相连的亚苄基作为酪氨酸酶抑制剂的合成、生物学评价和构效关系

  摘要：

  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。

  DOI：

  10.1002/cbdv.202000285

文献信息

• 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。
• THERAPEUTIC COMPOUNDS
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20190330157A1

  公开（公告）日：2019-10-31

  The invention provides methods for producing analgesia in an animal comprising administering to the animal a compound of the formula Ia′, Ib′, Ic′, and Id′: and pharmaceutically acceptable salts thereof, wherein the variables A, R 6 , R 7 , R 8 , R 9 , R x , L, X, Y, and Z have the meaning as described herein.
• Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase
  作者：Fazal Rahim、Hayat Ullah、Muhammad Tariq Javid、Abdul Wadood、Muhammad Taha、Muhammad Ashraf、Ayesha Shaukat、Muhammad Junaid、Shafqat Hussain、Wajid Rehman、Rashad Mehmood、Muhammad Sajid、Muhammad Naseem Khan、Khalid Mohammed Khan

  DOI：10.1016/j.bioorg.2015.06.006

  日期：2015.10

  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.
• 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。