2-[2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]acetamido]-3-nitrooxypropanoic acid | 1541831-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]acetamido]-3-nitrooxypropanoic acid
• 英文别名: 2-[[2-[1-(3-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrol-3-yl]acetyl]amino]-3-nitrooxypropanoic acid；2-[[2-[1-(3-fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrol-3-yl]acetyl]amino]-3-nitrooxypropanoic acid
• CAS: 1541831-89-3
• 化学式: C₂₃H₂₂FN₃O₈S
• 分子量: 519.507
• InChiKey: BNBDZFFKPLLERD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-methyl-5-[4-(methylsulfonyl)phenyl]-1-[3-(fluoro)phenyl]-1H-pyrrol-3-acetic acid 、 2-Amino-3-nitrooxypropanoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到2-[2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]acetamido]-3-nitrooxypropanoic acid
  参考文献：
  名称：

  Enhancing the pharmacodynamic profile of a class of selective COX-2 inhibiting nitric oxide donors

  摘要：

  We report herein the development, synthesis, physicochemical and pharmacological characterization of a novel class of pharmacodynamic hybrids that selectively inhibit cyclooxygenase-2 (COX-2) isoform and present suitable nitric oxide releasing properties. The replacement of the ester moiety with the amide group gave access to in vivo more stable and active derivatives that highlighted outstanding pharmacological properties. In particular, the glycine derivative proved to be extremely active in suppressing hyperalgesia and edema. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.008

文献信息

• Enhancing the pharmacodynamic profile of a class of selective COX-2 inhibiting nitric oxide donors
  作者：Mariangela Biava、Claudio Battilocchio、Giovanna Poce、Salvatore Alfonso、Sara Consalvi、Angela Di Capua、Vincenzo Calderone、Alma Martelli、Lara Testai、Lidia Sautebin、Antonietta Rossi、Carla Ghelardini、Lorenzo Di Cesare Mannelli、Antonio Giordani、Stefano Persiani、Milena Colovic、Melania Dovizio、Paola Patrignani、Maurizio Anzini

  DOI：10.1016/j.bmc.2013.12.008

  日期：2014.1

  We report herein the development, synthesis, physicochemical and pharmacological characterization of a novel class of pharmacodynamic hybrids that selectively inhibit cyclooxygenase-2 (COX-2) isoform and present suitable nitric oxide releasing properties. The replacement of the ester moiety with the amide group gave access to in vivo more stable and active derivatives that highlighted outstanding pharmacological properties. In particular, the glycine derivative proved to be extremely active in suppressing hyperalgesia and edema. (C) 2013 Elsevier Ltd. All rights reserved.