5-(2',3'-dihydrobenzofuran-7'-yl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one | 258270-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 5-(2',3'-dihydrobenzofuran-7'-yl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
• 英文别名: 5-(2,3-dihydro-7-benzofuryl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidine-7-one；5-(2,3-dihydro-1-benzofuran-7-yl)-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• CAS: 258270-59-6
• 化学式: C₁₇H₁₈N₄O₂
• 分子量: 310.356
• InChiKey: YNSOQGLXJSQMGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2',3'-dihydrobenzofuran-7'-yl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 以 氯磺酸 为溶剂， 生成 5-(5'-chlorosulfonyl-2',3'-dihydrobenzofuran-7'-yl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Compounds and pharmaceutical compositions containing the same

  摘要：

  本发明涉及新型化合物和含有它们的药物组合物。所揭示的化合物可用于治疗勃起功能障碍等疾病。它们由通式（I）表示。

  公开号：

  US06242444B1
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 正丁基锂 、 氯化亚砜 、 四甲基乙二胺 、 potassium tert-butylate 、 三乙胺 作用下， 以 环己烷 、 叔丁醇 、 苯 为溶剂， 反应 14.0h， 生成 5-(2',3'-dihydrobenzofuran-7'-yl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Voelter, Wolfgang; El-Abadelah, Mustafa M.; Sabri, Salim S., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1999, vol. 54, # 11, p. 1469 - 1473

  摘要：

  DOI：

文献信息

• Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues
  作者：Dae-Kee Kim、Namkyu Lee、Ju Young Lee、Do Hyun Ryu、Jae-Sun Kim、Suk-Ho Lee、Jin-Young Choi、Kieyoung Chang、Young-Woo Kim、Guang-Jin Im、Won-Son Choi、Tae-Kon Kim、Je-Ho Ryu、Nam-Ho Kim、Kyoungrim Lee

  DOI：10.1016/s0968-0896(01)00055-4

  日期：2001.6

  New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a-d and 7a-d, were efficiently synthesized from the readily available starting materials, 1a-d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarity of the molecule. The torsional angles were calculated to be 2-3 degrees for the 5-membered cyclic ether derivatives, 6a, 6c, 7a, and 7c, and 12-16 degrees for the 6-membered ones, 6b, 6d, 7b, and 7d. On the other hand, sildenafil showed the least co-planarity with the torsional angle of 23 degrees compared with the target compounds, 6a-d and 7a-d. In the enzyme assay, however, the in Vitro PDE 5 inhibitory activity was found out to be inversely related to the degree of coplanarity. In other words, the least planar sildenafil showed the highest activity, and the most planar 5-membered cyclic ether derivatives were least active by 100-200-fold compared with sildenafil. Our study clearly demonstrated that the open chain 2'-alkoxy group of the phenyl ring, although less effective for inducing the co-planarity, seemed to act as a much better lipophilic requirement than the cyclic alkoxy moiety. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Novel compounds and pharmaceutical compositions containing the same
  申请人：The Jordanian Pharmaceutical Manufacturing and Medical Equipment Co.Ltd.

  公开号：EP1057829B1

  公开（公告）日：2002-11-20
• US6242444B1
  申请人：——

  公开号：US6242444B1

  公开（公告）日：2001-06-05