(1-benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone | 374633-43-9

• 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-benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone
• 英文别名: 1-(3,4-Methylenedioxyphenyl)-2-[5-(3-trifluoromethylphenyl)furoyl]-2,3,4,9-tetrahydro-1H-β-carboline；(1-Benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone；[1-(1,3-benzodioxol-5-yl)-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl]-[5-[3-(trifluoromethyl)phenyl]furan-2-yl]methanone
• CAS: 374633-43-9
• 化学式: C₃₀H₂₁F₃N₂O₄
• 分子量: 530.503
• InChiKey: XBWMHHZJSVNSTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1-benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone 在 potassium superoxide 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以26%的产率得到3-benzo[1,3]dioxol-5-yl-2-[5-(3-trifluoromethyl-phenyl)-furan-2-carbonyl]-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one
  参考文献：
  名称：

  过氧化钾可作为温特费尔德氧化β-咔啉的替代试剂。

  摘要：

  研究了过氧化钾作为温特费尔特反应的替代氧化剂。发现KO（2）优于原始的Winterfeldt协议用于碱敏底物。[反应-见文字]

  DOI：

  10.1021/ol0271279
• 作为产物：
  描述：

  色胺 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (1-benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone
  参考文献：
  名称：

  过氧化钾可作为温特费尔德氧化β-咔啉的替代试剂。

  摘要：

  研究了过氧化钾作为温特费尔特反应的替代氧化剂。发现KO（2）优于原始的Winterfeldt协议用于碱敏底物。[反应-见文字]

  DOI：

  10.1021/ol0271279

文献信息

• beta-carboline derivatives useful as inhibitors of phosphodiesterase
  申请人：——

  公开号：US20020010189A1

  公开（公告）日：2002-01-24

  The present invention relates to novel &bgr;-carboline derivatives of the general formula 1 wherein all the variables are as described within the specification, useful as phosphodiesterase inhibitors. The present invention further relates to use of the described derivatives for the treatment of diseases and conditions related to PDE, for example male erectile dysfunction.

  本发明涉及一种新颖的β-咔啉衍生物，其通式如下，其中所有变量如规范中所述，用作磷酸二酯酶抑制剂。本发明还涉及所述衍生物用于治疗与PDE相关的疾病和病况，例如男性勃起功能障碍。
• Beta-carboline derivatives useful as inhibitors of phosphodiesterase
  申请人：——

  公开号：US20030166641A1

  公开（公告）日：2003-09-04

  The present invention relates to novel &bgr;-carboline derivatives of the general formula 1 wherein all the variables are as described within the specification, useful as phosphodiesterase inhibitors. The present invention further relates to use of the described derivatives for the treatment of diseases and conditions related to PDE, for example male erectile dysfunction.

  本发明涉及新颖的β-咔啉衍生物，其通式为1，其中所有变量如规范中所述，可用作磷酸二酯酶抑制剂。本发明还涉及所述衍生物用于治疗与PDE相关的疾病和病状，例如男性勃起功能障碍。
• Benzo[4,5]thieno[2,3-c]pyridine and Benzo[4,5]furo[2,3-c]pyridine Derivatives Useful as Inhibitors of Phosphodiesterase
  申请人：Sui Zhihua

  公开号：US06864253B2

  公开（公告）日：2005-03-08

  The present invention relates to novel β-carboline derivatives of the general formula wherein all the variables are as described within the specification, useful as phosphodiesterase inhibitors. The present invention further relates to use of the described derivatives for the treatment of diseases and conditions related to PDE, for example male erectile dysfunction.

  本发明涉及新的β-咔唑啉衍生物，其一般式如下： 其中，所有变量均如规范中所述，可用作磷酸二酯酶抑制剂。本发明还涉及所述衍生物用于治疗与PDE相关的疾病和病情，例如男性勃起功能障碍。
• &bgr;-carboline derivatives useful as inhibitors of phosphodiesterase
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06492358B2

  公开（公告）日：2002-12-10

  The present invention relates to novel &bgr;-carboline derivatives of the general formula wherein all the variables are as described within the specification, useful as phosphodiesterase inhibitors. The present invention further relates to use of the described derivatives for the treatment of diseases and conditions related to PDE, for example male erectile dysfunction.

  本发明涉及一种新的&bgr;-咔啉衍生物，其通式中的所有变量均如规范中所述，可用作磷酸二酯酶抑制剂。本发明还涉及所述衍生物用于治疗与PDE相关的疾病和病症，例如男性勃起功能障碍。
• 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.