4-[2-methoxy-5-(4-methylpiperazin-1-ylsulfonyl)-6-pentadecylbenzamido]-1-methyl-3-n-propylpyrazole-5-carboxamide | 485387-01-7

• 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: 4-[2-methoxy-5-(4-methylpiperazin-1-ylsulfonyl)-6-pentadecylbenzamido]-1-methyl-3-n-propylpyrazole-5-carboxamide
• CAS: 485387-01-7
• 化学式: C₃₆H₆₀N₆O₅S
• 分子量: 688.976
• InChiKey: PYZFEUMQRJSZJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  48.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  139.86
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-[2-methoxy-5-(4-methylpiperazin-1-ylsulfonyl)-6-pentadecylbenzamido]-1-methyl-3-n-propylpyrazole-5-carboxamide 在 N,N'-二环己基碳二亚胺 作用下， 以 xylene 为溶剂， 以25%的产率得到5-[2-methoxy-5-(4-methylpiperazin-1-ylsulfonyl)-6-pentadecylphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Synthesis of Sildenafil Analogues from Anacardic Acid and Their Phosphodiesterase-5 Inhibition

  摘要：

  Anacardic acid (6-pentadecylsalicylic acid), a major component of cashew nut shell liquid, consists of a heterogeneous mixture of monoenes, dienes, and trienes. The enes mixture of anacardic acid was hydrogenated to a saturated compound. Using saturated anacardic acid as a starting material, analogues of sildenafil [a potent phosphodiesterase-5 (PDE5) inhibitor and an orally active drug for the treatment of erectile dysfunction] were synthesized, to observe the effect of the pentadecyl side chain on PDE5 inhibition. The synthesized compounds were characterized by spectral studies and tested for PDE5 inhibition, and the results were compared With those obtained with sildenafil.

  DOI：

  10.1021/jf0258050
• 作为产物：
  描述：

  2-methoxy-6-pentadecylbenzoic acid 在 氯磺酸 、 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 4-[2-methoxy-5-(4-methylpiperazin-1-ylsulfonyl)-6-pentadecylbenzamido]-1-methyl-3-n-propylpyrazole-5-carboxamide
  参考文献：
  名称：

  Synthesis of Sildenafil Analogues from Anacardic Acid and Their Phosphodiesterase-5 Inhibition

  摘要：

  Anacardic acid (6-pentadecylsalicylic acid), a major component of cashew nut shell liquid, consists of a heterogeneous mixture of monoenes, dienes, and trienes. The enes mixture of anacardic acid was hydrogenated to a saturated compound. Using saturated anacardic acid as a starting material, analogues of sildenafil [a potent phosphodiesterase-5 (PDE5) inhibitor and an orally active drug for the treatment of erectile dysfunction] were synthesized, to observe the effect of the pentadecyl side chain on PDE5 inhibition. The synthesized compounds were characterized by spectral studies and tested for PDE5 inhibition, and the results were compared With those obtained with sildenafil.

  DOI：

  10.1021/jf0258050