1-(3,4-methylenedioxyphenyl)-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline | 374633-67-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3,4-methylenedioxyphenyl)-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 1-Benzo[1,3]dioxol-5-yl-2-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-beta-carboline；1-(1,3-benzodioxol-5-yl)-2-[5-(4-methoxyphenyl)pyrimidin-2-yl]-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 374633-67-7
• 化学式: C₂₉H₂₄N₄O₃
• 分子量: 476.535
• InChiKey: KVVNILHEEWTMAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4-methylenedioxyphenyl)-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline 在 sodium hydride 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以25%的产率得到1,2,3,4-Tetrahydro-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one
  参考文献：
  名称：

  嘧啶基吡咯并喹诺酮类药物是治疗勃起功能障碍的高效和选择性PDE5抑制剂。

  摘要：

  发现了一系列N-嘧啶基吡咯并喹诺酮类是非常有效和选择性的PDE5抑制剂。代表性化合物在狗勃起功能障碍模型中显示出体内功效，并且可以口服生物利用。

  DOI：

  10.1021/jm025545d
• 作为产物：
  描述：

  5-(4-methoxy-phenyl)-1-methyl-1H-pyrimidin-2-one 在 N,N-二异丙基乙胺 、 三氯氧磷 、 三氯化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(3,4-methylenedioxyphenyl)-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Synthesis and biological activities of novel β-Carbolines as PDE5 inhibitors

  摘要：

  A series of N-2-furoyl and N(2)pyrimidinyl beta-carbolines was discovered to possess potent inhibitors activity against PDE5. During the synthesis we developed a tandem resin quenching protocol. which allowed us to synthesize large number of target compounds in a rapid fashion. Representative Compounds exhibit superior selectivity to sildenafil versus other isozymes of PDEs. and demonstrated in vivo efficacy in increasing introcavernosal pressure in dogs. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01036-3

文献信息

• Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors
  申请人：——

  公开号：US20020010183A1

  公开（公告）日：2002-01-24

  The invention relates to novel pyrrolopyridinone derivatives of the formula (I) or (II): 1 pharmaceutical compositions containing the compounds and their use for the treatment of sexual dysfunction.

  这项发明涉及公式(I)或(II)的新型吡咯吡啶酮衍生物： 1 含有这些化合物的药物组合物及其用于治疗性功能障碍的用途。
• SUBSTITUTED PYRROLOPYRIDINONE DERIVATIVES USEFUL AS PHOSPHODIESTERASE INHIBITORS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1296981B1

  公开（公告）日：2004-10-06
• US6635638B2
  申请人：——

  公开号：US6635638B2

  公开（公告）日：2003-10-21
• US6818646B2
  申请人：——

  公开号：US6818646B2

  公开（公告）日：2004-11-16
• Synthesis and biological activities of novel β-Carbolines as PDE5 inhibitors
  作者：Zhihua Sui、Jihua Guan、Mark J. Macielag、Weiqin Jiang、Yuhong Qiu、Patricia Kraft、Sheela Bhattacharjee、T.Matthew John、Elizabeth Craig、Donna Haynes-Johnson、Joanna Clancy

  DOI：10.1016/s0960-894x(02)01036-3

  日期：2003.2

  A series of N-2-furoyl and N(2)pyrimidinyl beta-carbolines was discovered to possess potent inhibitors activity against PDE5. During the synthesis we developed a tandem resin quenching protocol. which allowed us to synthesize large number of target compounds in a rapid fashion. Representative Compounds exhibit superior selectivity to sildenafil versus other isozymes of PDEs. and demonstrated in vivo efficacy in increasing introcavernosal pressure in dogs. (C) 2003 Elsevier Science Ltd. All rights reserved.