Methyl 7-methoxytriazolo[1,5-a]quinoline-3-carboxylate | 1146205-98-2

• 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: Methyl 7-methoxytriazolo[1,5-a]quinoline-3-carboxylate
• CAS: 1146205-98-2
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: PHEUJIVXZXMXQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 7-methoxytriazolo[1,5-a]quinoline-3-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (7-Methoxytriazolo[1,5-a]quinolin-3-yl)methanol
  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-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

文献信息

• [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
• 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.