pirenzepine | 108295-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: pirenzepine
• 英文别名: 5-[(4-methyl-piperazin-1-yl)-acetyl]-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one；11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-benzo[b][1,4]benzodiazepin-6-one
• CAS: 108295-86-9
• 化学式: C₂₀H₂₂N₄O₂
• 分子量: 350.42
• InChiKey: RYIVUUNQOYFPOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,10-二氢-二苯并[b,e][1,4]二氮杂卓-11-酮 在 N,N-二甲基苯胺 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 pirenzepine
  参考文献：
  名称：

  Van Hijfte, Luc; Zerr, Veronique; Richards, Mary H., Medicinal Chemistry Research, 1996, vol. 6, # 3, p. 190 - 196

  摘要：

  DOI：

文献信息

• Tricyclic compounds as selective antimuscarinics. 1. Structural requirements for selectivity towards the muscarinic acetylcholine receptor in a series of pirenzepine and imipramine analogs
  作者：Wolfgang G. Eberlein、Guenter Trummlitz、Wolfhard W. Engel、Guenther Schmidt、Helmut Pelzer、Norbert Mayer

  DOI：10.1021/jm00391a019

  日期：1987.8

  The M1-selective antiulcer drug pirenzepine (1) is a tricyclic compound with close resemblance to tricyclic psychotropic agents such as imipramine (2). Despite this fact, pirenzepine is devoid of any psychotropic effects, exhibiting measurable antagonistic effects in biochemical assays and receptor binding studies only toward the muscarinic receptor system. To understand how different groups in these tricyclic molecules affect binding affinities, a set of nine compounds structurally related to pirenzepine (1) and imipramine (2) has been selected for analysis, comprising three different tricycles and three different side chains. The compounds were tested for their affinity to the imipramine and muscarinic receptors in homogenized rat cortex tissue. The result of these studies suggests that it is the nature and placement of accessory groups that determine the differences in receptor recognition and the binding process. In the case of pirenzepine (1), preferential binding toward the muscarinic receptor is brought about by the endocyclic amide group, by the positioning of the protonated N atom of the side chain, and to a minor extent by the exocyclic amide group. From these findings a putative model for the explanation of selective binding of pirenzepine (1) to the muscarinic receptor has been derived.
• EBERLEIN, W. G.;TRUMMLITZ, G.;ENGEL, W. W.;SCHMIDT, G.;PELZER, H.;MAYER, +, J. MED. CHEM., 30,(1987) N 8, 1378-1382
  作者：EBERLEIN, W. G.、TRUMMLITZ, G.、ENGEL, W. W.、SCHMIDT, G.、PELZER, H.、MAYER, +

  DOI：——

  日期：——
• Van Hijfte, Luc; Zerr, Veronique; Richards, Mary H., Medicinal Chemistry Research, 1996, vol. 6, # 3, p. 190 - 196
  作者：Van Hijfte, Luc、Zerr, Veronique、Richards, Mary H.、Moser, Paul、Hibert, Marcel F.、Van Giersbergen, Paul L.M.

  DOI：——

  日期：——