4-(2-chloro-6-methylphenyl)-3-thiosemicarbazide | 122813-71-2

• 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: 4-(2-chloro-6-methylphenyl)-3-thiosemicarbazide
• 英文别名: N1-(2-chloro-6-methylphenyl)hydrazine-1-carbothioamide；1-amino-3-(2-chloro-6-methylphenyl)thiourea
• CAS: 122813-71-2
• 化学式: C₈H₁₀ClN₃S
• 分子量: 215.706
• InChiKey: HILIAIYESTWAIN-UHFFFAOYSA-N

物化性质

• 沸点：
  323.1±52.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)
• 溶解度：
  16.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-chloro-6-methylphenyl)-3-thiosemicarbazide 在 三氯化铁 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N-(2-chloro-6-methylphenyl)-5-pyridin-3-yl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Vio; Mamolo; Laneve, Il Farmaco, 1989, vol. 44, # 2, p. 165 - 172

  摘要：

  DOI：

文献信息

• 3-amino-5-methyl-1H-pyrazole-4-carboxylic acids and esters thereof as anticonvulsants, muscle relaxants and anxiolytics
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0315433A2

  公开（公告）日：1989-05-10

  Pharmaceutical compositions which comprise a compound represented by the formula where R¹ represents a hydrogen atom, a lower alkyl group or a pharmaceutically acceptable cation; R² and R³ independently represent a hydrogen atom, a lower alkyl group, an aryl group, a cycloalkyl group, a lower alkenyl group, a 1-adamantyl group, a hetero­cyclicaminoalkyl group, a diloweralkylaminoloweralkyl group, or R² together with R³ and the adjacent nitrogen atom may form a heterocyclic ring structure; and/or a pharmaceutically acceptable acid salt thereof; the use of such compounds in medicine; and the use of such compounds in the preparation of anticonvul­sant agents, muscle relaxants and anxiolytic agents, are disclosed.

  药物组合物，其中包含由式表示的化合物 其中 R¹ 代表氢原子、低级烷基或药学上可接受的阳离子； R²和R³各自代表氢原子、低级烷基、芳基、环烷基、低级烯基、1-金刚烷基、杂环氨基烷基、稀释烷基氨基低级烷基，或R²与R³及相邻氮原子可形成杂环环结构； 和/或其药学上可接受的酸盐；公开了此类化合物在医药中的用途；以及此类化合物在制备抗惊厥剂、肌肉松弛剂和抗焦虑剂中的用途。
• New barbiturates and thiobarbiturates as potential enzyme inhibitors
  作者：Ashfaq M Qureshi、Saira Mumtaz、Abdul Rauf、Muhammad Ashraf、Rumana Nasar、Zahid H Chohan

  DOI：10.3109/14756366.2014.895717

  日期：2015.1.2

  A series of 27 new barbiturates and thiobarbiturates have been synthesized by a convenient multi-component reaction in overall excellent yields (87-96%). All the synthesized compounds were characterized by H-1, C-13 NMR, EIMS and elemental analysis (C, H, N and S). Furthermore, all compounds were screened for in vitro antioxidant (DPPH radical scavenging), lipoxygenase, chymotrypsin, alpha-glucosidase and anti-urease activities. Out of the series, 23 in DPPH, 14 in lipoxygenase, 2 in chymotrypsin have shown appreciable IC50 values.
• Synthesis, molecular docking studies, and in vitro screening of barbiturates/thiobarbiturates as antibacterial and cholinesterase inhibitors
  作者：Saira Mumtaz、Rashad Hussain、Abdul Rauf、M. Q. Fatmi、H. Bokhari、M. Oelgemöller、A. M. Qureshi

  DOI：10.1007/s00044-013-0847-2

  日期：2014.6

  On the basis of observed biological activity of barbiturates/thiobarbiturates, a set of 13 hydrazinecarboxamide/hydrazinecarbothioamides derivatives were designed and synthesized in good to excellent yield with extensive structural characterization. These compounds were screened for antibacterial and cholinesterase inhibitory activities. Two of the compounds 1 and 2 showed moderate bactericidal activity. Compounds 10 and 4 were found to be the most active acetyl/butyryl cholinesterase inhibitor, respectively (AChEI; 10; IC50 = 40.78 mu M and BChEI; 4; IC50 = 3.31 mu M). In silico molecular docking studies were carried out to identify active interacting sites of drug and enzyme and to establish structure-activity relationships. When predicted cholinesterase binding energies were compared with the experimentally determined inhibitory concentrations (IC50), most active compounds were also found to be the most favorable for binding. The binding scores of compounds 10 and 4 were -10.2 and -9.3 kcal/mol, respectively.
• VIO, L.;MAMOLO, M. G.;LANEVE, A., FARMACO, 44,(1989) N, C. 165-184
  作者：VIO, L.、MAMOLO, M. G.、LANEVE, A.

  DOI：——

  日期：——
• COMPOSITIONS AND USES FOR ENHANCING VIRUS PRODUCTION
  申请人：Ottawa Hospital Research Institute

  公开号：EP2451795B1

  公开（公告）日：2016-07-13