methyl 30-phenylcarbamoyl-11-oxo-18β-3,4-secoolean-4(23),12-dien-3-oate | 1158817-94-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 30-phenylcarbamoyl-11-oxo-18β-3,4-secoolean-4(23),12-dien-3-oate
• 英文别名: methyl 3-[(1S,2S,4aR,4bS,6aS,9S,10aR,12aR)-1,4a,4b,6a,9-pentamethyl-12-oxo-9-(phenylcarbamoyl)-2-prop-1-en-2-yl-2,3,4,5,6,7,8,10,10a,12a-decahydrochrysen-1-yl]propanoate
• CAS: 1158817-94-7
• 化学式: C₃₇H₅₁NO₄
• 分子量: 573.816
• InChiKey: JQCNTBJCNYAOBZ-QGWSXVNMSA-N

物化性质

• 熔点：
  149-154 °C
• 沸点：
  677.6±55.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4aR,6aR,7S,8S,10aR,10bS,12aS)-7-(3-methoxy-3-oxopropyl)-3,7,10a,10b,12a-pentamethyl-6-oxo-8-(prop-1-en-2-yl)-1,2,3,4,4a,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid 、 苯胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到methyl 30-phenylcarbamoyl-11-oxo-18β-3,4-secoolean-4(23),12-dien-3-oate
  参考文献：
  名称：

  Synthesis, anti-inflammatory, and antioxidant activities of 18β-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors

  摘要：

  Twenty 18 beta-glycyrrhetic acid (18 beta-GA) derivatives 2-21 including 13 new 18 beta-GA derivatives were synthesized and evaluated as anti-inflammatory and antioxidant agents. Compounds 7 and 20 with a 3,4-seco-structure and compound 6 with a lactone moiety showed potent inhibitory effect on superoxide anion generation in rat neutrophils response to fMLP/CB and PMA, respectively. Compound 6 with a lactone moiety revealed stronger inhibitory effect on XO activity than those of compounds 13 and 14 with a 3,4-seco-struture. Compound 14, a 30-isoproylcarbamoyl seco-compound exhibited potent inhibitory effect on NO accumulation and iNOS protein expression while compounds 3, 10, 13, 15, 17, and 21 revealed potent inhibitory effect on tumor necrosis factor-alpha (TNF-alpha) formation in RAW 264.7 cells in response to lipopolysaccharide (LPS). The cleavage of ring A of 3 attenuated the inhibitory effect on TNF-alpha formation in RAW 264.7 cells in response to LPS except for 17. The present results suggested these compounds were potential to be served as anti-inflammatory and antioxidant agents. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.025

文献信息

• Synthesis, anti-inflammatory, and antioxidant activities of 18β-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors
  作者：Dravidum Maitraie、Chi-Feng Hung、Huang-Yao Tu、Ya-Ting Liou、Bai-Luh Wei、Shyh-Chyun Yang、Jih-Pyang Wang、Chun-Nan Lin

  DOI：10.1016/j.bmc.2009.02.025

  日期：2009.4

  Twenty 18 beta-glycyrrhetic acid (18 beta-GA) derivatives 2-21 including 13 new 18 beta-GA derivatives were synthesized and evaluated as anti-inflammatory and antioxidant agents. Compounds 7 and 20 with a 3,4-seco-structure and compound 6 with a lactone moiety showed potent inhibitory effect on superoxide anion generation in rat neutrophils response to fMLP/CB and PMA, respectively. Compound 6 with a lactone moiety revealed stronger inhibitory effect on XO activity than those of compounds 13 and 14 with a 3,4-seco-struture. Compound 14, a 30-isoproylcarbamoyl seco-compound exhibited potent inhibitory effect on NO accumulation and iNOS protein expression while compounds 3, 10, 13, 15, 17, and 21 revealed potent inhibitory effect on tumor necrosis factor-alpha (TNF-alpha) formation in RAW 264.7 cells in response to lipopolysaccharide (LPS). The cleavage of ring A of 3 attenuated the inhibitory effect on TNF-alpha formation in RAW 264.7 cells in response to LPS except for 17. The present results suggested these compounds were potential to be served as anti-inflammatory and antioxidant agents. (c) 2009 Elsevier Ltd. All rights reserved.