5-(2-Ethoxy-5-((4-phenylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one | 1007310-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-(2-Ethoxy-5-((4-phenylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
• 英文别名: 5-[2-ethoxy-5-(4-phenylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• CAS: 1007310-62-4
• 化学式: C₂₇H₃₂N₆O₄S
• 分子量: 536.655
• InChiKey: XDENNBZPJHPBJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-乙氧基苯甲醛 在 氯磺酸 作用下， 以 氯仿 为溶剂， 25.0~120.0 ℃ 、1.7 MPa 条件下， 反应 0.52h， 生成 5-(2-Ethoxy-5-((4-phenylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  磺化氧化石墨烯催化连续流合成吡唑并嘧啶酮、西地那非等PDE-5抑制剂

  摘要：

  磺化氧化石墨烯用于获得取代的吡唑并嘧啶酮的级联缩合和环化反应。此外，通过连续流动化学整合磺化和胺化反应以获得 PDE-5 抑制剂。在此，我们报告了一个简单的连续合成平台，可减少繁琐的手动操作并加速几种有效的 5 型磷酸二酯酶抑制剂的合成。开发的平台使我们能够在 32.3 分钟的反应时间内执行单流程多步骤、多操作过程来合成 PDE-5 抑制剂，如西地那非及其类似物，而人为干预最少，使用单一溶剂。

  DOI：

  10.1039/d1ra08220e

文献信息

• Synthesis and Pharmacological Evaluations of Sildenafil Analogues for Treatment of Erectile Dysfunction
  作者：Haroldo A. Flores Toque、Fernanda B. M. Priviero、Cleber E. Teixeira、Elisa Perissutti、Ferdinando Fiorino、Beatrice Severino、Francesco Frecentese、Raquel Lorenzetti、Juliana S. Baracat、Vincenzo Santagada、Giuseppe Caliendo、Edson Antunes、Gilberto De Nucci

  DOI：10.1021/jm701400r

  日期：2008.5.1

  The 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyll-l-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one, sildenafil, is a cGMP-specific phosphodiesterase-5 (PDE5) inhibitor used for penile erectile dysfunction. In the search for more potent and selective PDE5 inhibitors, new sildenafil analogues (6a-v), characterized by the presence on the sulfonyl group in the 5' position of novel N-4-substituted piperazines or ethylenediamine moiety, were prepared by traditional and micro wave-assisted synthesis and tested in rabbit isolated aorta and corpus cavernosum. Similarly to sildenafil, several analogues showed IC50 values in the nanomolar range. In the in vitro studies, all the tested compounds caused concentration-dependent relaxations in both rabbit isolated aorta and corpus cavernosum. All sildenafil analogues potentiated the nitric oxide-dependent vasodilation in endothelium-intact rabbit aorta. Compound 6f exhibited great pEC(50) value in corpus cavernosum, and compounds 6r and 6u in isolated aorta were found as potent as sildenafil for inhibiting PDE5. Because several analogues were significantly more lipophilic than sildenafil, these compounds may offer a new lead for development of new sildenafil analogues.
• Sulphonated graphene oxide catalyzed continuous flow synthesis of pyrazolo pyrimidinones, sildenafil and other PDE-5 inhibitors
  作者：Vinay Kumar Sthalam、Bhushan Mahajan、Purushotham Reddy Karra、Ajay K. Singh、Srihari Pabbaraja

  DOI：10.1039/d1ra08220e

  日期：——

  Sulphonated graphene oxide was used for cascade condensation and cyclization reactions towards accessing substituted pyrazolo pyrimidinones. Further, sulphonation and amination reactions were integrated through continuous flow chemistry to access PDE-5 inhibitors. Herein, we report a simple continuous synthetic platform that reduce tedious manual operations and accelerate the synthesis of several potent

  磺化氧化石墨烯用于获得取代的吡唑并嘧啶酮的级联缩合和环化反应。此外，通过连续流动化学整合磺化和胺化反应以获得 PDE-5 抑制剂。在此，我们报告了一个简单的连续合成平台，可减少繁琐的手动操作并加速几种有效的 5 型磷酸二酯酶抑制剂的合成。开发的平台使我们能够在 32.3 分钟的反应时间内执行单流程多步骤、多操作过程来合成 PDE-5 抑制剂，如西地那非及其类似物，而人为干预最少，使用单一溶剂。