Methyl 3-(7-methoxy-4,5-dihydropyrazolo[1,5-a]quinolin-3-yl)prop-2-enoate | 1202520-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 3-(7-methoxy-4,5-dihydropyrazolo[1,5-a]quinolin-3-yl)prop-2-enoate
• 英文别名: methyl 3-(7-methoxy-4,5-dihydropyrazolo[1,5-a]quinolin-3-yl)prop-2-enoate
• CAS: 1202520-55-5
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: LYBDNUUJHKPCEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3-(7-methoxy-4,5-dihydropyrazolo[1,5-a]quinolin-3-yl)prop-2-enoate 在 palladium on carbon 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 palladium(II) hydroxide 、 三溴化硼 、 双(三甲基硅烷基)氨基钾 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 生成 2-[[2-Amino-3-(7-hydroxy-4,5-dihydropyrazolo[1,5-a]quinolin-3-yl)propanoyl]amino]benzoic acid
  参考文献：
  名称：

  The discovery of high affinity agonists of GPR109a with reduced serum shift and improved ADME properties

  摘要：

  Amino-anthranilic acid derivatives have been identified as a new class of low serum shifted, high affinity full agonists of the human orphan G-protein-coupled receptor GPR109a with improved ADME properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.116
• 作为产物：
  描述：

  2-溴-5-甲氧基溴苄 在 盐酸 、 copper(l) iodide 、 2,2,6,6-四甲基哌啶氧化物 、 乙酸酐 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 肼 、 N,N'-二甲基乙二胺 、 亚氨基二乙酸 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 生成 Methyl 3-(7-methoxy-4,5-dihydropyrazolo[1,5-a]quinolin-3-yl)prop-2-enoate
  参考文献：
  名称：

  The discovery of high affinity agonists of GPR109a with reduced serum shift and improved ADME properties

  摘要：

  Amino-anthranilic acid derivatives have been identified as a new class of low serum shifted, high affinity full agonists of the human orphan G-protein-coupled receptor GPR109a with improved ADME properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.116

文献信息

• Discovery of Novel Tricyclic Full Agonists for the G-Protein-Coupled Niacin Receptor 109A with Minimized Flushing in Rats
  作者：Hong C. Shen、Fa-Xiang Ding、Qiaolin Deng、Larissa C. Wilsie、Mihajlo L. Krsmanovic、Andrew K. Taggart、Ester Carballo-Jane、Ning Ren、Tian-Quan Cai、Tsuei-Ju Wu、Kenneth K. Wu、Kang Cheng、Qing Chen、Michael S. Wolff、Xinchun Tong、Tom G. Holt、M. Gerard Waters、Milton L. Hammond、James R. Tata、Steven L. Colletti

  DOI：10.1021/jm900151e

  日期：2009.4.23

  Tricyclic analogues were rationally designed as the high affinity niacin receptor G-protein-coupled receptor 109A (GPR109A) agonists by overlapping three lead structures. Various tricyclic anthranilide and cycloalkene carboxylic acid full agonists were discovered with excellent in vitro activity. Compound 2g displayed a good therapeutic index regarding free fatty acids (FFA) reduction and vasodilation effects in rats, with very weak cytochrome P450 2C8 (CYP2C8) and cytochrome P450 2C9 (CYP2C9) inhibition, and a good mouse pharmacokinetics (PK) profile.
• The discovery of high affinity agonists of GPR109a with reduced serum shift and improved ADME properties
  作者：Jason E. Imbriglio、Daniel DiRocco、Rena Bodner、Subharekha Raghavan、Weichun Chen、Daria Marley、Craig Esser、Tom G. Holt、Michael S. Wolff、Andrew K.P. Taggart、M. Gerard Waters、James R. Tata、Steven L. Colletti

  DOI：10.1016/j.bmcl.2010.11.116

  日期：2011.5

  Amino-anthranilic acid derivatives have been identified as a new class of low serum shifted, high affinity full agonists of the human orphan G-protein-coupled receptor GPR109a with improved ADME properties. (C) 2010 Elsevier Ltd. All rights reserved.