4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate | 927181-29-1

• 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: 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate
• 英文别名: 6-acetoxy-4-methylquinolone；(4-methyl-2-oxo-1H-quinolin-6-yl) acetate
• CAS: 927181-29-1
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: DCFQHMRTJXKTMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到ethyl 2-(6-acetoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetate
  参考文献：
  名称：

  Characterization of 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent

  摘要：

  We have studied earlier a membrane bound novel enzyme Acetoxy Drug: protein transacetylase identified as Calreticulin Transacetylase (CRTAase) that catalyzes the transfer of acetyl groups from polyphenolic acetates (PAs) to the receptor proteins and thus modulating their biological activities. In this communication, we have reported for the first time that acetoxy quinolones are endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. The correlation of specificity of platelet CRTAase to various analogues of acetoxy quinolones with intracellular NO and consequent effect on inhibition of platelet aggregation was considered crucial. Among acetoxy quinolones screened, 6-AQ (4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate/6-acetoxyquinolin-2-one, 22) was found to be the superior substrate to platelet CRTAase and emerged as the most active entity to produce antiplatelet action both in vitro and in vivo. 6-AQ caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2) and the inhibition of platelet aggregation. Structural modi. cation of acetoxy quinolones positively correlated with enhancement of intracellular NO and antiplatelet action. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.011
• 作为产物：
  描述：

  2,6-二羟基-4-甲基喹啉 、 乙酸酐 在 溶剂黄146 作用下， 反应 6.0h， 以85%的产率得到4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate
  参考文献：
  名称：

  Characterization of 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent

  摘要：

  We have studied earlier a membrane bound novel enzyme Acetoxy Drug: protein transacetylase identified as Calreticulin Transacetylase (CRTAase) that catalyzes the transfer of acetyl groups from polyphenolic acetates (PAs) to the receptor proteins and thus modulating their biological activities. In this communication, we have reported for the first time that acetoxy quinolones are endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. The correlation of specificity of platelet CRTAase to various analogues of acetoxy quinolones with intracellular NO and consequent effect on inhibition of platelet aggregation was considered crucial. Among acetoxy quinolones screened, 6-AQ (4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate/6-acetoxyquinolin-2-one, 22) was found to be the superior substrate to platelet CRTAase and emerged as the most active entity to produce antiplatelet action both in vitro and in vivo. 6-AQ caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2) and the inhibition of platelet aggregation. Structural modi. cation of acetoxy quinolones positively correlated with enhancement of intracellular NO and antiplatelet action. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.011

文献信息

• [EN] COUMARIN COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS<br/>[FR] COMPOSÉS DE COUMARINE POUR LE TRAITEMENT D'INFECTIONS MYCOBACTÉRIENNES
  申请人：UNIV DELHI

  公开号：WO2012137224A1

  公开（公告）日：2012-10-11

  The present invention relates to method for treating mycobacterial infection/disease by administration of a therapeutically effective amount of compound of formula I.

  本发明涉及通过给予化合物I的治疗有效量来治疗分枝杆菌感染/疾病的方法。