11-[3-(dimethylamino)propyl]-11H-pyrido[2,3-b][1,4]benzodiazepin-6(5H)-one | 108295-83-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 11-[3-(dimethylamino)propyl]-11H-pyrido[2,3-b][1,4]benzodiazepin-6(5H)-one
• 英文别名: 5,11-dihydro-11-[3-(dimethylamino)propyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one；11-[3-(dimethylamino)propyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
• CAS: 108295-83-6
• 化学式: C₁₇H₂₀N₄O
• 分子量: 296.372
• InChiKey: RBNXMPWKJNXZHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二甲基-3-氯丙胺 、 5,11-二氢-6H-吡啶并[2,3-B][1,4]苯并二氮杂-6-酮 在 正丁基锂 作用下， 生成 11-[3-(dimethylamino)propyl]-11H-pyrido[2,3-b][1,4]benzodiazepin-6(5H)-one
  参考文献：
  名称：

  Tricyclic compounds as selective antimuscarinics. 1. Structural requirements for selectivity towards the muscarinic acetylcholine receptor in a series of pirenzepine and imipramine analogs

  摘要：

  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.

  DOI：

  10.1021/jm00391a019

文献信息

• Process for the preparation of aryl-pyrido(1,4) benzodiazepines
  申请人：A. H. Robins Company, Incorporated

  公开号：US04749788A1

  公开（公告）日：1988-06-07

  A process is described wherein pyrido[1,4]benzodiazepines having the formula: ##STR1## wherein Q is NR.sup.1 R.sup.2 or ##STR2## are prepared from unsubstituted pyridobenzodiazepinones by alkylation reaction with halo-alkyl-Q followed by acylation of the other nitrogen; breaking the ring with an aryl Grignard reagent and recyclizing to add the aryl radical and form the azepine ring. Novel intermediates are thereby disclosed.

  描述了一种过程，其中通过烷基化反应与卤代烷基-Q反应制备具有以下化学式的吡啶并[1,4]苯二氮杂环己烯类化合物：其中Q是NR^1R^2或；然后通过对另一氮进行酰化反应；用芳基格氏试剂打破环，并再循环加入芳基自由基并形成环氮杂烯环。因此，揭示了新颖的中间体。
• Process for the preparation of benzodiazepines
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0288201A1

  公开（公告）日：1988-10-26

  A process is described wherein pyrido[1,4]benzo­diazepines having the formula: wherein Q is NR¹R² or are prepared from unsubstituted pyridobenzodiazepinones by alkylation reaction with halo-alkyl-Q followed by acylation of the other nitrogen; breaking the ring with an aryl Grignard reagent and recyclizing to add the aryl radical and form the azepine ring. Novel intermediates are thereby disclosed.

  描述了一种工艺，其中吡啶并[1,4]苯并二氮杂卓具有以下式子： 其中 Q 为 NR¹R² 或 由未取代的吡啶并二氮杂卓通过以下方法制备：与卤代烷基-Q 进行烷基化反应，然后对另一个氮进行酰化；用芳基格氏试剂破环，然后再反应以加入芳基并形成氮杂卓环。由此揭示了新型中间体。
• 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：——
• US4749788A
  申请人：——

  公开号：US4749788A

  公开（公告）日：1988-06-07
• 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.