N-(benzyloxy)carbonyl-2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetic acid | 1363375-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(benzyloxy)carbonyl-2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetic acid
• 英文别名: N-(benzyloxycarbonyl)-2-amino-2-[1-(3-fluorophenyl)-2-methyl-5-(4-methylsulphonyl phenyl)-1H-pyrrol-3-yl]-acetic acid；2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-(benzyloxycarbonyl)aminoacetic acid；(R,S)-N-(benzyloxycarbonyl)-2-amino-2-[1-(3-fluorophenyl)-2-methyl-5-(4-methylsulphonyl phenyl)-1H-pyrrol-3-yl]acetic acid；2-[1-(3-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrol-3-yl]-2-(phenylmethoxycarbonylamino)acetic acid；2-[1-(3-fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrol-3-yl]-2-(phenylmethoxycarbonylamino)acetic acid
• CAS: 1363375-45-4
• 化学式: C₂₈H₂₅FN₂O₆S
• 分子量: 536.581
• InChiKey: RJBUKWGEZBGXAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(benzyloxy)carbonyl-2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetic acid 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 甲酸铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 20.0~80.0 ℃ 、1.17 MPa 条件下， 反应 12.08h， 生成 N-(3-hydroxypropyl)-2-amino-2-(1-(3-fluorophenyl)-2-methyl-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-3-yl)acetamide
  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
• 作为产物：
  描述：

  1-[4-(methylsulfonyl)phenyl]pentane-1,4-dione 在 甲酸 、 盐酸羟胺 、 水 、 sodium acetate 、 四氯化钛 、 sodium carbonate 、 对甲苯磺酸 、 sodium hydroxide 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 160.0 ℃ 、1.03 MPa 条件下， 反应 65.75h， 生成 N-(benzyloxy)carbonyl-2-[1-(3-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetic acid
  参考文献：
  名称：

  Improving the solubility of a new class of antiinflammatory pharmacodynamic hybrids, that release nitric oxide and inhibit cycloxygenase-2 isoenzyme

  摘要：

  The development of a novel class of pharmacodynamic hybrids that inhibits COX-2 isoform is reported. These molecules display enhanced nitric oxide releasing properties due to the presence of an ionisable moiety. The in vivo analgesic/anti-inflammatory activity was maintained in relation to the parent compounds. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.014

文献信息

• Improving the solubility of a new class of antiinflammatory pharmacodynamic hybrids, that release nitric oxide and inhibit cycloxygenase-2 isoenzyme
  作者：Mariangela Biava、Claudio Battilocchio、Giovanna Poce、Salvatore Alfonso、Sara Consalvi、Giulio Cesare Porretta、Silvia Schenone、Vincenzo Calderone、Alma Martelli、Lara Testai、Carla Ghelardini、Lorenzo Di Cesare Mannelli、Lidia Sautebin、Antonietta Rossi、Antonio Giordani、Paola Patrignani、Maurizio Anzini

  DOI：10.1016/j.ejmech.2012.10.014

  日期：2012.12

  The development of a novel class of pharmacodynamic hybrids that inhibits COX-2 isoform is reported. These molecules display enhanced nitric oxide releasing properties due to the presence of an ionisable moiety. The in vivo analgesic/anti-inflammatory activity was maintained in relation to the parent compounds. (c) 2012 Elsevier Masson SAS. All rights reserved.
• 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.