beta-D-吡喃葡萄糖醛酸 1-[6-(4-氯苯基)-2,3-二氢-2,2-二甲基-7-苯基-1H-吡咯里嗪-5-乙酸酯] | 1033702-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: beta-D-吡喃葡萄糖醛酸 1-[6-(4-氯苯基)-2,3-二氢-2,2-二甲基-7-苯基-1H-吡咯里嗪-5-乙酸酯]
• 中文别名: beta-D-吡喃葡萄糖醛酸1-[6-(4-氯苯基)-2,3-二氢-2,2-二甲基-7-苯基-1H-吡咯里嗪-5-乙酸酯]；BETA-D-吡喃葡萄糖醛酸 1-[6-(4-氯苯基)-2,3-二氢-2,2-二甲基-7-苯基-1H-吡咯里嗪-5-乙酸酯]
• 英文名称: Licofelone glucuronide
• 英文别名: Licofelone Acyl-|A-D-glucuronide；(2S,3S,4S,5R,6S)-6-[2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1033702-58-7
• 化学式: C₂₉H₃₀ClNO₈
• 分子量: 556.012
• InChiKey: WHKFJCYVPLCOGR-NLMMERCGSA-N

物化性质

• 沸点：
  738.4±60.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苄基beta-D-吡喃葡糖苷酸甲酯三乙酸酯 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 KH₂PO₄ buffer 、 偶氮二甲酸二异丙酯 、 氢氟酸 、 氢气 、 sodium methylate 、 氯磷酸二乙酯 、 三乙胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 144.5h， 生成 beta-D-吡喃葡萄糖醛酸 1-[6-(4-氯苯基)-2,3-二氢-2,2-二甲基-7-苯基-1H-吡咯里嗪-5-乙酸酯]
  参考文献：
  名称：

  Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000

  摘要：

  The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid gamma-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled with 1 under Mitsunobu conditions. Deprotection, i. e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of alpha- and beta-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00123-6

文献信息

• Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000
  作者：Andreas Kirschning、Monika Ries、Silvie Domann、Wolfgang Martin、Wolfgang Albrecht、Peter Arnold、Stefan Laufer

  DOI：10.1016/s0960-894x(97)00123-6

  日期：1997.1

  The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid gamma-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled with 1 under Mitsunobu conditions. Deprotection, i. e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of alpha- and beta-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis. (C) 1997 Elsevier Science Ltd.