(E)-N-(4-methoxyphenyl)-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide | 92193-33-4

• 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)-N-(4-methoxyphenyl)-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide
• 英文别名: (E)-4-(4-methoxyphenyl)-1-(pyridin-2-ylmethylene)thiosemicarbazide；pyridine-2-carbaldehyde-[4-(4-methoxy-phenyl)-thiosemicarbazone]；Pyridin-2-carbaldehyd-[4-(4-methoxy-phenyl)-thiosemicarbazon]；1-(4-methoxyphenyl)-3-[(E)-2-pyridylmethyleneamino]thiourea；1-(4-methoxyphenyl)-3-[(E)-pyridin-2-ylmethylideneamino]thiourea
• CAS: 92193-33-4
• 化学式: C₁₄H₁₄N₄OS
• 分子量: 286.357
• InChiKey: ACMYXIUIPBOQHH-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯基 异硫氰酸酯 在 吡咯 、 一水合肼 、 异丙醇 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 (E)-N-(4-methoxyphenyl)-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  二芳基取代氨基硫脲：开发新德里金属-β-内酰胺酶-1抑制剂的有效支架

  摘要：

  由新德里金属-β-内酰胺酶（NDM-1）引起的超级细菌感染已成为一种新兴的公共卫生威胁。由于 NDM-1 在病原菌之间穿梭，因此抑制 NDM-1 已被证明具有挑战性。构建了一种有效的支架，二芳基取代的缩氨基硫脲，并用金属-β-内酰胺酶 (MβLs) 进行了测定。获得的 26 个分子特异性抑制 NDM-1，IC 50 0.038–34.7 µM 范围（1e、2e和3d除外），1c是最有效的抑制剂（IC 50 = 0.038 µM）。合成缩氨基硫脲的构效关系表明，二芳基取代物，特别是 2-吡啶和 2-羟基苯提高了抑制剂的抑制活性。缩氨基硫脲对大肠杆菌-NDM-1表现出协同抗分枝杆菌作用，导致美罗培南的 MIC 降低 2-512 倍，而1c恢复抗生素对临床分离株的 16-256-、16- 和 2 倍的活性ECs、肺炎克雷伯菌和铜绿假单胞菌分别含有 NDM-1。此外，小鼠实验表明，1c与美罗培南具

  DOI：

  10.1016/j.bioorg.2020.104576

文献信息

• [EN] THIOSEMICARBAZONES WITH MDR1 - INVERSE ACTIVITY<br/>[FR] THIOSEMICARBAZONES À ACTIVITÉ ANTI-MDR1
  申请人：US HEALTH

  公开号：WO2012033601A1

  公开（公告）日：2012-03-15

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the structure;Formula (I). Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.

  本文披露了具有MDR逆转活性的药物化合物，因此对多药耐药细胞有效。本文披露的示例化合物具有下列结构；公式（I）。已发现披露的化合物的示例具有直接治疗多药耐药细胞的功效，使多药耐药细胞对其他化疗药物敏感，并在某些情况下逆转多药耐药。
• Fujikawa et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 1231,1233
  作者：Fujikawa et al.

  DOI：——

  日期：——
• Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents
  作者：Xin-Hui Zhang、Bo-Wang、Yuan-Yuan Tao、Qin Ma、Hao-Jie Wang、Zhang-Xu He、Hui-Pan Wu、Yi-Han Li、Bing Zhao、Li-Ying Ma、Hong-Min Liu

  DOI：10.1016/j.ejmech.2020.112349

  日期：2020.8

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.
• COMPOUNDS WITH MDR1-INVERSE ACTIVITY
  申请人：Hall Matthew D.

  公开号：US20100316655A1

  公开（公告）日：2010-12-16

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the structure: Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.
• [EN] COMPOUNDS WITH MDR1-INVERSE ACTIVITY<br/>[FR] COMPOSÉS À ACTIVITÉ MDR1 INVERSE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009102433A2

  公开（公告）日：2009-08-20

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the following structure: (I). Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.