6-chloro-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester | 638192-18-4

• 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-chloro-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-chloro-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate；methyl 6-chloro-4-hydroxy-2-oxo-1H-quinoline-3-carboxylate
• CAS: 638192-18-4
• 化学式: C₁₁H₈ClNO₄
• 分子量: 253.642
• InChiKey: GAIZDOQZWXZGST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 4-(1-Benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamino)-6-chloro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  鉴定和表征氨基哌啶喹诺酮类和喹唑啉酮类作为MCHr1拮抗剂。

  摘要：

  已合成和评估了几种衍生自喹啉2（1H）-和喹唑啉-2（1H）-的功能强大的功能性MCHr1拮抗剂。喹诺酮1位上的吡啶基甲基取代导致衍生物具有较低的nM结合力和相对于hERG结合的良好选择性。

  DOI：

  10.1016/j.bmcl.2006.02.044
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸甲酯 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 6-chloro-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and In vitro evaluation of potent, novel, small molecule inhibitors of plasminogen activator inhibitor-1

  摘要：

  We have synthesized and evaluated a series of tetramic acid-based and hydroxvquinolinone-based inhibitors of plasminogen activator inhibitor-1 (PAI-1). These studies resulted in the identification of several compounds which showed excellent potency against PAI-1. The design, synthesis and SAR of these compounds are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00078-1

文献信息

• Antagonists of melanin concentrating hormone receptor
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20040106645A1

  公开（公告）日：2004-06-03

  This invention provides compounds that are antagonists of melanin concentrating hormone receptor-1 (MCH-R1). The compounds are represented by formula I: 1 where m is zero or one, n is zero to two, Y is oxygen or —N(R 9 )—, R 1 , R 2 , R 3 , R 4 , R 5 , R 9 and Ring A are defined in the specification. Coumarin and quinolone compounds where R 1 and R 2 together form a fused benzo ring are preferred. The invention also provides compounds of formula VI where the coumarin moiety is replaced by a quinazolinone ring. The compounds are useful for treating MCH-R1-related disorders, particularly overweight conditions including obesity.

  这项发明提供了一些与黑色素浓集激素受体-1 (MCH-R1) 相对抗的化合物。这些化合物由公式 I 表示：其中 m 为零或一，n 为零至二，Y 为氧或 —N(R9)—，R1、R2、R3、R4、R5、R9 和环 A 在说明书中有定义。偏好使用 R1 和 R2 结合形成融合苯环的香豆素和喹啉类化合物。该发明还提供了公式 VI 的化合物，其中香豆素基团被喹嗪酮环替换。这些化合物可用于治疗与 MCH-R1 相关的疾病，特别是超重症，包括肥胖症。
• [EN] ANTAGONISTS OF MELANIN CONCENTRATING HORMONE RECEPTOR<br/>[FR] ANTAGONISTES DU RECEPTEUR DE L'HORMONE DE MELANO-CONCENTRATION
  申请人：——

  公开号：WO2003106452A3

  公开（公告）日：2004-04-08
• US6921821B2
  申请人：——

  公开号：US6921821B2

  公开（公告）日：2005-07-26
• Identification and characterization of amino-piperidinequinolones and quinazolinones as MCHr1 antagonists
  作者：Christopher Blackburn、Matthew J. LaMarche、James Brown、Jennifer Lee Che、Courtney A. Cullis、Sujen Lai、Martin Maguire、Thomas Marsilje、Bradley Geddes、Elizabeth Govek、Vivek Kadambi、Colleen Doherty、Brian Dayton、Sevan Brodjian、Kennan C. Marsh、Christine A. Collins、Philip R. Kym

  DOI：10.1016/j.bmcl.2006.02.044

  日期：2006.5

  Several potent, functionally active MCHr1 antagonists derived from quinolin-2(1H)-ones and quinazoline-2(1H)-ones have been synthesized and evaluated. Pyridylmethyl substitution at the quinolone 1-position results in derivatives with low-nM binding potency and good selectivity with respect to hERG binding.

  已合成和评估了几种衍生自喹啉2（1H）-和喹唑啉-2（1H）-的功能强大的功能性MCHr1拮抗剂。喹诺酮1位上的吡啶基甲基取代导致衍生物具有较低的nM结合力和相对于hERG结合的良好选择性。
• Design, synthesis and In vitro evaluation of potent, novel, small molecule inhibitors of plasminogen activator inhibitor-1
  作者：Adrian Folkes、S.David Brown、Lynne E. Canne、Jocelyn Chan、Erin Engelhardt、Sergey Epshteyn、Richard Faint、Julian Golec、Art Hanel、Patrick Kearney、James W. Leahy、Morrison Mac、David Matthews、Michael P. Prisbylla、Jason Sanderson、Reyna J. Simon、Zerom Tesfai、Nigel Vicker、Shouming Wang、Robert R. Webb、Peter Charlton

  DOI：10.1016/s0960-894x(02)00078-1

  日期：2002.4

  We have synthesized and evaluated a series of tetramic acid-based and hydroxvquinolinone-based inhibitors of plasminogen activator inhibitor-1 (PAI-1). These studies resulted in the identification of several compounds which showed excellent potency against PAI-1. The design, synthesis and SAR of these compounds are described. (C) 2002 Elsevier Science Ltd. All rights reserved.