3-(2-adamantan-1-ylethyl)-2-(3,4,5-trimethoxyphenyl)thiazolidin-4-one | 1118763-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-adamantan-1-ylethyl)-2-(3,4,5-trimethoxyphenyl)thiazolidin-4-one
• 英文别名: 3-[2-(1-Adamantyl)ethyl]-2-(3,4,5-trimethoxyphenyl)thiazolidin-4-one；3-[2-(1-adamantyl)ethyl]-2-(3,4,5-trimethoxyphenyl)-1,3-thiazolidin-4-one
• CAS: 1118763-20-4
• 化学式: C₂₄H₃₃NO₄S
• 分子量: 431.596
• InChiKey: WMKTXIZTDHHJSP-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C(Solvent: Heptane)
• 沸点：
  584.8±50.0 °C(predicted)
• 密度：
  1.199±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-C-乙基氨基金刚烷 、 3,4,5-三甲氧基苯甲醛 、 巯基乙酸 以 甲苯 为溶剂， 以78%的产率得到3-(2-adamantan-1-ylethyl)-2-(3,4,5-trimethoxyphenyl)thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones

  摘要：

  A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 mu M). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 mu M) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 mu M, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 mu M, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.039

文献信息

• Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones
  作者：Jan Balzarini、Barbara Orzeszko-Krzesińska、Jan K. Maurin、Andrzej Orzeszko

  DOI：10.1016/j.ejmech.2008.02.039

  日期：2009.1

  A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 mu M). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 mu M) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 mu M, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 mu M, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones. (C) 2008 Elsevier Masson SAS. All rights reserved.