1-thiophen-2-ylmethylene-thiocarbonohydrazide | 69050-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-thiophen-2-ylmethylene-thiocarbonohydrazide
• 英文别名: 1-Amino-3-(thiophen-2-ylmethylideneamino)thiourea
• CAS: 69050-04-0
• 化学式: C₆H₈N₄S₂
• 分子量: 200.288
• InChiKey: WKQJSDZSHKXINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-thiophen-2-ylmethylene-thiocarbonohydrazide 、 靛红 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.03h， 以78%的产率得到
  参考文献：
  名称：

  Microwave Assisted Synthesis, Characterization of Some New Isatin and Thiophene Derivatives as Cytotoxic and Chemopreventive Agents

  摘要：

  In obtaining some new cytotoxic and chemopreventive agents with potent antiproliferative activity against cancer cells, a series of new beta-isatin aldehyde-N,N'-thiocarbohydrazone, bis-beta-isatin thiocarbohydrazones, bis-beta-isatin carbohydrazones, N,2-bis(thiophen-2-ylmethylidene) thiocarbohydrazone and N,2-bis(thiophen-2-ylmethylidene) carbohydrazone derivatives was synthesized by microwave oriented reaction and evaluated for their in vitro cytotoxic activity. The newly synthesized compounds were characterized based on spectral (FT-IR, NMR, MS) analyses. The inhibitory effects of synthesized compounds on the proliferation of murine leukemia cells (L1210), human T-lymphocyte cells (CEM) and human cervix carcinoma cells (HeLa) were assayed by using MTT assay. The compounds were also tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). In vitro evaluation of these schiff bases revealed mild to moderate cytotoxic activity in a dose dependent manner. The results of the in vitro inhibitory activities of synthetic compounds against EBV-EA activation with IC50 ranges from 485-535 (mol ratio/32pmol/TPA). Chlorine group containing derivatives did not show increased inhibitory activity against tumor promoter TPA induction. Sulphur containing derivatives also did not show a high inhibitory potency in this system.

  DOI：

  10.2174/157018012804586950
• 作为产物：
  描述：

  2-噻吩甲醛 、 硫代卡巴肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1-thiophen-2-ylmethylene-thiocarbonohydrazide
  参考文献：
  名称：

  作为可能的生物活性剂的硫代碳酰肼和碳酰肼衍生物的合成

  摘要：

  摘要5-取代靛红与硫代卡巴肼或碳酰肼缩合合成了一系列新的β-靛红醛-N、N′-硫代羰腙、双-β-靛红硫代羰腙、双-β-靛红羰腙。新合成化合物的化学结构经FT-IR、1 H NMR和质谱分析证实。评估了合成的化合物对各种 DNA 和 RNA 病毒株的体外抗病毒活性，但与参考化合物相比显示出中等的抗病毒活性。在所有化合物中，6c在两阶段小鼠皮肤致癌试验中表现出最高的化学预防活性。 图形概要

  DOI：

  10.1007/s00044-013-0684-3

文献信息

• Synthesis, characterization, and antiviral activity of novel fluorinated isatin derivatives
  作者：Samir Y. Abbas、Awatef A. Farag、Yousry A. Ammar、Abeer A. Atrees、Aly F. Mohamed、Ahmed A. El-Henawy

  DOI：10.1007/s00706-013-1034-3

  日期：2013.11

  5-fluoroisatin with primary amines, hydrazine hydrate, and thiocarbohydrazides. Thiosemicarbazones were prepared by reacting hydrazone derivatives with isothiocyanates. Upon treatment of thiosemicarbazone derivatives with chloroacetone, the thiazole derivatives were obtained. Some of the prepared compounds exhibited antiviral activity. Graphical abstract

  摘要5-氟靛红与伯胺、水合肼、硫代卡巴肼反应合成了5-氟靛红的新系列席夫碱、腙类、缩氨基硫脲类、噻唑类和硫代卡巴腙类。通过腙衍生物与异硫氰酸酯反应制备氨基硫脲。在用氯丙酮处理氨基硫脲衍生物后，得到噻唑衍生物。一些制备的化合物表现出抗病毒活性。 图形概要
• Kabashima, Shigeru; Okawara, Tadashi; Yamasaki, Tetsuo, Heterocycles, 1990, vol. 31, # 6, p. 1129 - 1139
  作者：Kabashima, Shigeru、Okawara, Tadashi、Yamasaki, Tetsuo、Furukawa, Mitsuru

  DOI：——

  日期：——
• Synthesis of thiocarbohydrazide and carbohydrazide derivatives as possible biologically active agents
  作者：Kiran Gangarapu、Sarangapani Manda、Anvesh Jallapally、Sreekanth Thota、Subhas S. Karki、Jan Balzarini、Erik De Clercq、Harukuni Tokuda

  DOI：10.1007/s00044-013-0684-3

  日期：2014.2

  AbstractA series of new β-isatin aldehyde-N,N′-thiocarbohydrazone, bis-β-isatin thiocarbohydrazones, bis-β-isatin carbohydrazones was synthesized by condensation of 5-substituted isatin with thiocarbohydrazide or carbohydrazide. The chemical structures of the newly synthesized compounds were confirmed by FT-IR, 1H NMR, and mass spectral analysis. The synthesized compounds were evaluated for in vitro antiviral

  摘要5-取代靛红与硫代卡巴肼或碳酰肼缩合合成了一系列新的β-靛红醛-N、N′-硫代羰腙、双-β-靛红硫代羰腙、双-β-靛红羰腙。新合成化合物的化学结构经FT-IR、1 H NMR和质谱分析证实。评估了合成的化合物对各种 DNA 和 RNA 病毒株的体外抗病毒活性，但与参考化合物相比显示出中等的抗病毒活性。在所有化合物中，6c在两阶段小鼠皮肤致癌试验中表现出最高的化学预防活性。 图形概要
• Microwave Assisted Synthesis, Characterization of Some New Isatin and Thiophene Derivatives as Cytotoxic and Chemopreventive Agents
  作者：Kiran Gangarapu、Sarangapani Manda、Sreekanth Thota、Rajeshwar Yerra、Subhas S. Karki、Jan Balzarini、Erik De Clercq、Harukuni Tokuda

  DOI：10.2174/157018012804586950

  日期：2012.12.1

  In obtaining some new cytotoxic and chemopreventive agents with potent antiproliferative activity against cancer cells, a series of new beta-isatin aldehyde-N,N'-thiocarbohydrazone, bis-beta-isatin thiocarbohydrazones, bis-beta-isatin carbohydrazones, N,2-bis(thiophen-2-ylmethylidene) thiocarbohydrazone and N,2-bis(thiophen-2-ylmethylidene) carbohydrazone derivatives was synthesized by microwave oriented reaction and evaluated for their in vitro cytotoxic activity. The newly synthesized compounds were characterized based on spectral (FT-IR, NMR, MS) analyses. The inhibitory effects of synthesized compounds on the proliferation of murine leukemia cells (L1210), human T-lymphocyte cells (CEM) and human cervix carcinoma cells (HeLa) were assayed by using MTT assay. The compounds were also tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). In vitro evaluation of these schiff bases revealed mild to moderate cytotoxic activity in a dose dependent manner. The results of the in vitro inhibitory activities of synthetic compounds against EBV-EA activation with IC50 ranges from 485-535 (mol ratio/32pmol/TPA). Chlorine group containing derivatives did not show increased inhibitory activity against tumor promoter TPA induction. Sulphur containing derivatives also did not show a high inhibitory potency in this system.