4-(2-benzo[b]thienyl)-2-chloroquinazoline

• 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: 4-(2-benzo[b]thienyl)-2-chloroquinazoline
• 英文别名: 4-(1-Benzothiophen-2-yl)-2-chloroquinazoline
• 化学式: C₁₆H₉ClN₂S
• 分子量: 296.78
• InChiKey: QXXABHLNSIOGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 4-(2-benzo[b]thienyl)-2-chloroquinazoline 反应 2.0h， 以58%的产率得到4-(1-Benzothiophen-2-yl)-2-(4-methylpiperazin-1-yl)quinazoline
  参考文献：
  名称：

  Structure-activity relationship studies of CNS agents. Part 29. N-Methylpiperazino-substituted derivatives of quinazoline, phthalazine and quinoline as novel α1, 5-HT1A and 5-HT2A receptor ligands

  摘要：

  New N-methylpiperazino-substituted quinazolines 8 and 9, phthalazine 13, and quinoline 19 have been synthesized. The receptor binding profiles (alpha(1), 5-HT1A, 5-HT2A) of these compounds and their analogs (7-22) have been determined. It has been demonstrated that orientation of a local dipole moment of the heteroaromatic ring system affects both the alpha(1) and 5-HT2A affinity of the investigated class of ligands. Distortion of the coplanar unfused heteroaromatic ring system results in a decreased 5-HT2A affinity. 4-(4-Methylpiperazino)-2-(2-thienyl)quinoline 18 is the most active and selective alpha(1) ligand (K-i = 4.9 nM) with a much lower affinity for 5-HT1A (K-i = 3420 nM) and 5-HT2A (K-i = 211 nM) receptors.

  DOI：

  10.1016/s0223-5234(97)86176-4
• 作为产物：
  描述：

  benzothiophen-2-yllithium 、 2,4-二氯喹唑啉 以56%的产率得到4-(2-benzo[b]thienyl)-2-chloroquinazoline
  参考文献：
  名称：

  Structure-activity relationship studies of CNS agents. Part 29. N-Methylpiperazino-substituted derivatives of quinazoline, phthalazine and quinoline as novel α1, 5-HT1A and 5-HT2A receptor ligands

  摘要：

  New N-methylpiperazino-substituted quinazolines 8 and 9, phthalazine 13, and quinoline 19 have been synthesized. The receptor binding profiles (alpha(1), 5-HT1A, 5-HT2A) of these compounds and their analogs (7-22) have been determined. It has been demonstrated that orientation of a local dipole moment of the heteroaromatic ring system affects both the alpha(1) and 5-HT2A affinity of the investigated class of ligands. Distortion of the coplanar unfused heteroaromatic ring system results in a decreased 5-HT2A affinity. 4-(4-Methylpiperazino)-2-(2-thienyl)quinoline 18 is the most active and selective alpha(1) ligand (K-i = 4.9 nM) with a much lower affinity for 5-HT1A (K-i = 3420 nM) and 5-HT2A (K-i = 211 nM) receptors.

  DOI：

  10.1016/s0223-5234(97)86176-4

文献信息

• Structure-activity relationship studies of CNS agents. Part 29. N-Methylpiperazino-substituted derivatives of quinazoline, phthalazine and quinoline as novel α1, 5-HT1A and 5-HT2A receptor ligands
  作者：JL Mokrosz、B Duszyńska、S Charakchieva-Minol、AJ Bojarski、MJ Mokrosz、RL Wydra、L Janda、L Strekowski

  DOI：10.1016/s0223-5234(97)86176-4

  日期：1996.1

  New N-methylpiperazino-substituted quinazolines 8 and 9, phthalazine 13, and quinoline 19 have been synthesized. The receptor binding profiles (alpha(1), 5-HT1A, 5-HT2A) of these compounds and their analogs (7-22) have been determined. It has been demonstrated that orientation of a local dipole moment of the heteroaromatic ring system affects both the alpha(1) and 5-HT2A affinity of the investigated class of ligands. Distortion of the coplanar unfused heteroaromatic ring system results in a decreased 5-HT2A affinity. 4-(4-Methylpiperazino)-2-(2-thienyl)quinoline 18 is the most active and selective alpha(1) ligand (K-i = 4.9 nM) with a much lower affinity for 5-HT1A (K-i = 3420 nM) and 5-HT2A (K-i = 211 nM) receptors.