3-[3-(1H-imidazol-1-yl)butyl]-6-methyl-2,4(1H,3H)-quinazolinedione | 110552-27-7

• 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-[3-(1H-imidazol-1-yl)butyl]-6-methyl-2,4(1H,3H)-quinazolinedione
• 英文别名: 3-(3-Imidazol-1-yl-butyl)-6-methyl-1H-quinazoline-2,4-dione；3-(3-imidazol-1-ylbutyl)-6-methyl-1H-quinazoline-2,4-dione
• CAS: 110552-27-7
• 化学式: C₁₆H₁₈N₄O₂
• 分子量: 298.345
• InChiKey: PNBSAEVXGHYLBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Amino-N-[3-(1H-imidazol-1-yl)butyl]-5-methylbenzamide 在 氢氧化钾 、 乙醇 作用下， 反应 5.0h， 生成 3-[3-(1H-imidazol-1-yl)butyl]-6-methyl-2,4(1H,3H)-quinazolinedione
  参考文献：
  名称：

  Thromboxane synthetase inhibitors and antihypertensive agents. 4. N-[(1H-imidazol-1-yl)alkyl] derivatives of quinazoline-2,4(1H,3H)-diones, quinazolin-4(3H)-ones, and 1,2,3-benzotriazin-4(3H)-ones

  摘要：

  The quinazolinedione, quinazolinone, and 1,2,3-benzotriazinone title compounds were prepared as analogues of N-[(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones which were the subject of a previous report from our laboratories. These compounds were evaluated as thromboxane (TX) synthetase inhibitors and as antihypertensive agents. While each series of compounds had activity both as TX synthetase inhibitors and as antihypertensives, the best compounds were N-[(1H-imidazol-1-yl)alkyl]quinazoline-2,4(1H,3H]-diones (V). In general these compounds were all selective enzyme inhibitors at least equipotent with the standard dazoxiben. These compounds were also very active antihypertensive agents as determined in SHR. The SAR is discussed for both types of activity. Compound 20a was further evaluated for TX formation inhibiting properties in several other platelet types both in vitro and ex vivo and is between 100 and 1000 times more potent than dazoxiben.

  DOI：

  10.1021/jm00395a016

文献信息

• WRIGHT, WILLIAM B. JR.;TOMCUFCIK, ANDREW S.;CHAN, PETER S.;MARSICO, JOSEP+, J. MED. CHEM., 30,(1987) N 12, 2277-2283
  作者：WRIGHT, WILLIAM B. JR.、TOMCUFCIK, ANDREW S.、CHAN, PETER S.、MARSICO, JOSEP+

  DOI：——

  日期：——
• US4684654A
  申请人：——

  公开号：US4684654A

  公开（公告）日：1987-08-04
• Thromboxane synthetase inhibitors and antihypertensive agents. 4. N-[(1H-imidazol-1-yl)alkyl] derivatives of quinazoline-2,4(1H,3H)-diones, quinazolin-4(3H)-ones, and 1,2,3-benzotriazin-4(3H)-ones
  作者：William B. Wright、Andrew S. Tomcufcik、Peter S. Chan、Joseph W. Marsico、Jeffery B. Press

  DOI：10.1021/jm00395a016

  日期：1987.12

  The quinazolinedione, quinazolinone, and 1,2,3-benzotriazinone title compounds were prepared as analogues of N-[(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones which were the subject of a previous report from our laboratories. These compounds were evaluated as thromboxane (TX) synthetase inhibitors and as antihypertensive agents. While each series of compounds had activity both as TX synthetase inhibitors and as antihypertensives, the best compounds were N-[(1H-imidazol-1-yl)alkyl]quinazoline-2,4(1H,3H]-diones (V). In general these compounds were all selective enzyme inhibitors at least equipotent with the standard dazoxiben. These compounds were also very active antihypertensive agents as determined in SHR. The SAR is discussed for both types of activity. Compound 20a was further evaluated for TX formation inhibiting properties in several other platelet types both in vitro and ex vivo and is between 100 and 1000 times more potent than dazoxiben.