5-((R)-3-Dimethylamino-pyrrolidine-1-sulfonyl)-2-propoxy-benzoic acid methyl ester | 252233-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-((R)-3-Dimethylamino-pyrrolidine-1-sulfonyl)-2-propoxy-benzoic acid methyl ester
• 英文别名: methyl 5-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]sulfonyl-2-propoxybenzoate
• CAS: 252233-59-3
• 化学式: C₁₇H₂₆N₂O₅S
• 分子量: 370.47
• InChiKey: DAOYOMXINALMNU-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-((R)-3-Dimethylamino-pyrrolidine-1-sulfonyl)-2-propoxy-benzoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-5-[(3-(dimethylamino)pyrrolidinyl)sulfonyl]-2-propoxybenzoic acid
  参考文献：
  名称：

  Optimization of Substituted N-3-Benzylimidazoquinazolinone Sulfonamides as Potent and Selective PDE5 Inhibitors

  摘要：

  A previous report from these laboratories identified the N-3-benzylimidazoquinazolinone nucleus as a more selective PDE5 inhibitor template compared to the pyrazolopyrimidine of sildenafil. This paper describes in detail the structure-activity relationships of a set of sulfonamide analogues, several of which are both more potent and more selective PDE5 inhibitors in vitro than sildenafil. The synthesis, in vitro enzyme activity and selectivity, and in vitro functional and preclinical pharmacokinetic assessment of molecules in this series are described.

  DOI：

  10.1021/jm000336j
• 作为产物：
  描述：

  2-n-丙基氧基苯甲酸甲酯 在 氯磺酸 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-((R)-3-Dimethylamino-pyrrolidine-1-sulfonyl)-2-propoxy-benzoic acid methyl ester
  参考文献：
  名称：

  Optimization of Substituted N-3-Benzylimidazoquinazolinone Sulfonamides as Potent and Selective PDE5 Inhibitors

  摘要：

  A previous report from these laboratories identified the N-3-benzylimidazoquinazolinone nucleus as a more selective PDE5 inhibitor template compared to the pyrazolopyrimidine of sildenafil. This paper describes in detail the structure-activity relationships of a set of sulfonamide analogues, several of which are both more potent and more selective PDE5 inhibitors in vitro than sildenafil. The synthesis, in vitro enzyme activity and selectivity, and in vitro functional and preclinical pharmacokinetic assessment of molecules in this series are described.

  DOI：

  10.1021/jm000336j

文献信息

• [EN] QUINAZOLINONE INHIBITORS OF cGMP PHOSPHODIESTERASE<br/>[FR] INHIBITEURS QUINAZOLINONE DE LA PHOSPHODIESTERASE cGMP
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999064004A1

  公开（公告）日：1999-12-16

  (EN) Novel quinazolinone compounds, methods of using such compounds in the treatment of cGMP-associated conditions such as erectile dysfunction, and pharmaceutical compositions containing such compounds.(FR) Nouveaux composés quinazolinone, procédés d'utilisation desdits composés dans le traitement d'états pathologiques associés à l'acide guanosine-3'5'-monosphosphate cyclique (cGMP), tels que les troubles de l'érection, et compositions pharmaceutiques contenant lesdits composés.

  （中文）一种新型的喹唑啉酮化合物，以及在治疗与cGMP相关的疾病，如勃起功能障碍方面使用这种化合物的方法和含有这种化合物的制药组合物。
• QUINAZOLINONE INHIBITORS OF cGMP PHOSPHODIESTERASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1085871A1

  公开（公告）日：2001-03-28
• EP1085871A4
  申请人：——

  公开号：EP1085871A4

  公开（公告）日：2001-10-04
• US6087368A
  申请人：——

  公开号：US6087368A

  公开（公告）日：2000-07-11