1-((2-chloro-8-methylquinolin-3-yl)methylene)thiosemicarbazide | 104827-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-((2-chloro-8-methylquinolin-3-yl)methylene)thiosemicarbazide
• 英文别名: 2-((2-chloro-8-methylquinolin-3-yl)methylene)hydrazinecarbothioamide；[(2-Chloro-8-methylquinolin-3-yl)methylideneamino]thiourea；[(2-chloro-8-methylquinolin-3-yl)methylideneamino]thiourea
• CAS: 104827-57-8
• 化学式: C₁₂H₁₁ClN₄S
• mdl: MFCD20927434
• 分子量: 278.765
• InChiKey: XGRVWQISSFSUAV-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  468.9±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((2-chloro-8-methylquinolin-3-yl)methylene)thiosemicarbazide 在 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.5h， 生成 3-chloro-4-(2-chloro-8-methylquinolin-3-yl)-1-(4-phenylthiazol-2-ylamino)azetidin-2-one
  参考文献：
  名称：

  Desai; Harsora, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 7, p. 1011 - 1019

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-8-甲基喹啉-3-甲醛 、 氨基硫脲 以 水 为溶剂， 生成 1-((2-chloro-8-methylquinolin-3-yl)methylene)thiosemicarbazide
  参考文献：
  名称：

  Facile synthesis of novel quinoline derivatives as anticancer agents

  摘要：

  Convenient and efficient synthesis of novel N-(4-acetyl-4,5-dihydro-5-(7,8,9-substituted-tetrazolo[1,5-a]-quinolin-4-yl)-1,3,4-thiadiazol-2-yl)acetamides 4a-j and their in vitro anticancer activity against two cell lines viz., human breast cancer cell line MCF7 and human cervix cancer cell line HeLa were carried out. GI50, LC50, TGI values were evaluated. Two of the compounds 4e and 4i with halogen substituent at 7th position of the target molecules have shown potent activity against human cervix cancer cell line HeLa. DNA cleavage studies revealed that most of these compounds show partial cleavage and few of them show complete cleavage of DNA.

  DOI：

  10.1007/s00044-013-0855-2

文献信息

• 3-(1,3,4-Thiadiazole-2-yl)quinoline derivatives: Synthesis, characterization and anti-microbial activity
  作者：Abdul R. Bhat、Tazeem、Amir Azam、Inho Choi、Fareeda Athar

  DOI：10.1016/j.ejmech.2011.04.013

  日期：2011.7

  A new series of thiadiazoles and intermediate thiosemicarbazones were synthesized from the chloroquinone molecule, with an aim to explore their effect on in vitro growth of microorganisms causing microbial infection. The chemical structures of the compound were elucidated by elemental analysis, FTIR, 1H and 13C NMR and ESI-MS spectral data. In vitro anti-microbial activity was performed against Staphylococcus aureus, Streptococcus pyogenes, Salmonella typhimurium, and Escherichia coli. The MIC was detected using the double dilution method. The results were compared by calculating percent inhibit area/mu g of the compounds and the standard "amoxicillin". The selected compounds were tested for cytotoxic results using MIT assay H9c2 cardiac myoblasts cell line and the results showed that all the compounds offered remarkable >80% viability to a concentration of 200 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Facile synthesis of novel quinoline derivatives as anticancer agents
  作者：Sheetal Babu Marganakop、Ravindra Ramappa Kamble、Joy Hoskeri、D. Jagadish Prasad、Gangadhar Yamanappa Meti

  DOI：10.1007/s00044-013-0855-2

  日期：2014.6

  Convenient and efficient synthesis of novel N-(4-acetyl-4,5-dihydro-5-(7,8,9-substituted-tetrazolo[1,5-a]-quinolin-4-yl)-1,3,4-thiadiazol-2-yl)acetamides 4a-j and their in vitro anticancer activity against two cell lines viz., human breast cancer cell line MCF7 and human cervix cancer cell line HeLa were carried out. GI50, LC50, TGI values were evaluated. Two of the compounds 4e and 4i with halogen substituent at 7th position of the target molecules have shown potent activity against human cervix cancer cell line HeLa. DNA cleavage studies revealed that most of these compounds show partial cleavage and few of them show complete cleavage of DNA.
• Desai; Harsora, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 7, p. 1011 - 1019
  作者：Desai、Harsora

  DOI：——

  日期：——