3-isobutyl-1,6-dimethyl-3,4-dihydroquinazolin-2(1H)-thione | 1244766-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-isobutyl-1,6-dimethyl-3,4-dihydroquinazolin-2(1H)-thione
• 英文别名: 1,6-dimethyl-3-(2-methylpropyl)-4H-quinazoline-2-thione
• CAS: 1244766-33-3
• 化学式: C₁₄H₂₀N₂S
• 分子量: 248.392
• InChiKey: DEVVLYLHHGRTIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-isobutyl-6-methyl-3,4-dihydroquinazolin-2(1H)-thione 、 碘甲烷 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到3-isobutyl-1,6-dimethyl-3,4-dihydroquinazolin-2(1H)-thione
  参考文献：
  名称：

  Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity

  摘要：

  In order to de. ne the structural requirements of quinazoline-2(1H)-thiones 1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1H)-thiones (3a-h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of alpha-MSH. The anti-melanogenesis activity of 3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.123

文献信息

• Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity
  作者：Pillaiyar Thanigaimalai、Vinay K. Sharma、Ki-Cheul Lee、Cheong-Yong Yun、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2010.06.123

  日期：2010.8

  In order to de. ne the structural requirements of quinazoline-2(1H)-thiones 1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1H)-thiones (3a-h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of alpha-MSH. The anti-melanogenesis activity of 3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.