(6-methoxy-quinolin-2-yl)-acetic acid methyl ester | 73387-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (6-methoxy-quinolin-2-yl)-acetic acid methyl ester
• 英文别名: Methyl 2-(6-methoxyquinolin-2-yl)acetate
• CAS: 73387-71-0
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: NYLIVRJQHUNUSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6-methoxy-quinolin-2-yl)-acetic acid methyl ester 在 sodium hydride 、 4-乙酰氨基苯磺酰叠氮 作用下， 以 四氢呋喃 、 petroleum oil 为溶剂， 反应 3.5h， 以20%的产率得到Methyl 7-methoxytriazolo[1,5-a]quinoline-3-carboxylate
  参考文献：
  名称：

  Discovery of Novel Tricyclic Full Agonists for the G-Protein-Coupled Niacin Receptor 109A with Minimized Flushing in Rats

  摘要：

  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.

  DOI：

  10.1021/jm900151e
• 作为产物：
  描述：

  6-甲氧基-2-甲基喹啉 、 氯甲酸甲酯 在 正丁基锂 、 二异丙胺 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.08h， 以41%的产率得到(6-methoxy-quinolin-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Discovery of Novel Tricyclic Full Agonists for the G-Protein-Coupled Niacin Receptor 109A with Minimized Flushing in Rats

  摘要：

  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.

  DOI：

  10.1021/jm900151e

文献信息

• Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines
  作者：Ze-Peng Yang、Qing-Feng Wu、Wen Shao、Shu-Li You

  DOI：10.1021/jacs.5b10440

  日期：2015.12.23

  The first Ir-catalyzed intramolecular asymmetric allylic dearomatization reaction of pyridines, pyrazines, quinolines, and isoquinolines has been developed. Enabled by in situ formed chiral Ir-catalyst, the dearomatized products were isolated in high levels of yield (up to 99% yield) and enantioselectivity (up to 99% ee). It is worth noting that the Me-THQphos ligand is much more efficient than other

  已开发出第一个 Ir 催化的吡啶、吡嗪、喹啉和异喹啉的分子内不对称烯丙基脱芳构化反应。通过原位形成的手性 Ir 催化剂，脱芳构化产物以高产率（高达 99% 的产率）和对映选择性（高达 99% ee）分离。值得注意的是，对于吡嗪和某些喹啉的脱芳构化，Me-THQphos 配体比其他测试的配体更有效。进行了脱芳构化反应的机理研究，结果表明了以形成喹啉作为关键中间体的替代方法的可行性。机理研究结果使该反应成为 Reissert 型反应化学中尚不为人知的类型。此外，
• [EN] NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT<br/>[FR] AGONISTES DES RECEPTEURS DE NIACINE, COMPOSITIONS CONTENANT LESDITS COMPOSES ET METHODES DE TRAITEMENT
  申请人：MERCK & CO INC

  公开号：WO2006052555A3

  公开（公告）日：2006-06-22
• SCHROEDER E.; LEHMANN M.; BOETTCHER I., EUR. J. MED. CHEM.-CHIM. THER., 1979, 14, NO 6, 499-506 D2#105#; #99# #10+
  作者：SCHROEDER E.、 LEHMANN M.、 BOETTCHER I.

  DOI：——

  日期：——
• 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.