4-氯-2-氧代-1H-喹啉-3-羧酸乙酯 | 99429-64-8

• 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
• 中文名称: 4-氯-2-氧代-1H-喹啉-3-羧酸乙酯
• 英文名称: ethyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 4-chloro-2-oxo-1H-quinoline-3-carboxylate
• CAS: 99429-64-8
• 化学式: C₁₂H₁₀ClNO₃
• mdl: MFCD00572655
• 分子量: 251.669
• InChiKey: KTFCVAZGXKEUSN-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  431.5±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氯-2-氧代-1H-喹啉-3-羧酸乙酯 在 sodium ethanolate 、 sodium hydride 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 86.17h， 生成 2-[4-({[3-methoxy-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydro-1H-pyrrolo[3,2-c]quinolin-2-yl]carbonyl}amino)piperidin-1-yl]-2-oxoethyl acetate
  参考文献：
  名称：

  Discovery of pyrrolo[3,2-c]quinoline-4-one derivatives as novel hedgehog signaling inhibitors

  摘要：

  The Hedgehog (Hh) signaling pathway plays a significant role in the regulation of cell growth and differentiation during embryonic development. Since activation of the Hh signaling pathway is implicated in several types of human cancers, inhibitors of this pathway could be promising anticancer agents. Using high throughput screening, thieno[3,2-c] quinoline-4-one derivative 9a was identified as a compound of interest with potent in vitro activity but poor metabolic stability. Our efforts focused on enhancement of in vitro inhibitory activity and metabolic stability, including core ring conversion and side chain optimization. This led to the discovery of pyrrolo[3,2-c] quinoline-4-one derivative 12b, which has a structure distinct from previously reported Hh signaling inhibitors. Compound 12b suppressed stromal Gli1 mRNA expression in a murine model and demonstrated antitumor activity in a murine medulloblastoma allograft model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.039
• 作为产物：
  描述：

  2,4-二羟基喹啉-3-甲酸乙酯 在 甲烷磺酸 、 水 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 4-氯-2-氧代-1H-喹啉-3-羧酸乙酯
  参考文献：
  名称：

  4-azido-2-oxoquinoline-3-羧酸盐和4-azidocoumarin-3羧酸盐的闭环和重排反应† ‡

  摘要：

  通过相应的4-羟基衍生物1经由4-甲苯磺酸酯2或4-氯化合物4从相应的4-羟基衍生物1中获得4-叠氮基-2-氧代喹啉-3-羧酸盐和4-叠氮杂多古灵-3-羧酸盐6，将它们在热解后环化成3-烷氧基异恶唑[ 4,3- c ]喹啉-4（5 H）-或相应的香豆素8，而在稍高的温度下，发生3- O，4- O重排，得到4-烷氧基-异恶唑[4]。 ，3- c ]-喹啉-3-酮和相应的香豆素9.借助差示扫描量热法可以容易地获得必要的反应条件。

  DOI：

  10.1002/jhet.5570350322

文献信息

• Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones
  作者：Isabelle Tomassoli、Guillaume Herlem、Fabien Picaud、Mohamed Benchekroun、Oscar M. Bautista-Aguilera、Vincent Luzet、María-Luisa Jimeno、Tijani Gharbi、Bernard Refouvelet、Lhassane Ismaili

  DOI：10.1007/s00706-016-1660-7

  日期：2016.6

  AbstractThe condensation of hydrazine, N-methylhydrazine, and N-phenylhydrazine with ethyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate derivatives has been investigated. As a result, 12 new antioxidant pyrazolo[4,3-c]quinolin-3,4-diones were obtained with good to high yields. When two cross-products could be possible, only one isomer bearing the methyl or the phenyl group at the N1 position is

  摘要已经研究了肼，N-甲基肼和N-苯基肼与4-氯-2-氧代-1,2-二氢喹啉-3-羧酸乙酯衍生物的缩合。结果，以良好至高产率获得了12种新的抗氧化剂吡唑并[4，3 - c ]喹啉-3，4-二酮。当可能产生两种交叉产物时，仅分离出一个在N1位置带有甲基或苯基的异构体，并使用1D和2D NMR技术，FT-IR和燃烧分析对其进行明确表征。在皮尔逊硬质软酸碱骨架中进行了反应机理的DFT分析，确认了所观察到的吡唑并[4,3- c]的结构。]喹啉-3,4-二酮。这些计算表明，与其可能的区域异构体相比，合成的吡唑并[4,3 - c ]喹啉-3,4-二酮具有良好的动力学控制。 图形概要
• Inhibitors of macrophage migration inhibitory factor and methods for identifying the same
  申请人：——

  公开号：US20030195194A1

  公开（公告）日：2003-10-16

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: 1 including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF的抑制剂，对治疗各种疾病具有实用性，包括与MIF活性相关的病理条件的治疗。MIF的抑制剂具有以下结构：包括立体异构体、前药和其药用盐，其中n、R1、R2、R3、R4、X、Y和Z如本文所定义。还提供了含有MIF抑制剂的组合物，与药用载体结合，以及使用方法。
• FUSED HETEROCYCLIC DERIVATIVE AND USE THEREOF
  申请人：FUJII Nobuhiro

  公开号：US20090227561A1

  公开（公告）日：2009-09-10

  The present invention provides a compound having a superior Smo inhibitory activity and lower toxicity, which is sufficiently satisfactory as a pharmaceutical product. The present invention provides a compound represented by the formula wherein ring A is 5- to 7-membered ring optionally having substituent(s), where substituents are optionally bonded to each other to form a ring; X is O, S or NR 1 (R 1 is a hydrogen atom or a hydrocarbon group optionally having substituent(s)); R 2 is carbamoyl optionally having substituent(s); and R 3 is hydroxy optionally having substituent(s), or a salt thereof.

  本发明提供了一种具有优异的Smo抑制活性和较低毒性的化合物，该化合物作为药物产品是完全令人满意的。本发明提供了一种由下式表示的化合物： 其中，环A是5-至7-成员环，可选择地具有取代基，其中取代基可选择地与彼此结合形成环；X是O、S或NR1（R1是氢原子或具有取代基的碳氢基团）；R2是氨基甲酰，可选择地具有取代基；R3是羟基，可选择地具有取代基，或其盐。
• Facile Synthesis of 4-Substituted-2-quinolinone-3-carboxylic Acid Ethyl Esters
  作者：Lijuan Zhang、Yu Luo、Shanbao Yu、Wei Lu

  DOI：10.1002/jhet.967

  日期：2012.9

  An efficient route for the synthesis of 4‐substituted‐2‐quinolinone‐3‐carboxylic acid ethyl esters has been developed through Suzuki or Sonogashira reactions. The advantages of the method include high yields, operational simplicity, and suitability for medicinal modification of 4‐substituted quinolinones and their derivatives.

  通过Suzuki或Sonogashira反应，已经开发出一种有效的合成4-取代-2-喹啉酮-3-羧酸乙酯的途径。该方法的优点包括高收率，操作简便以及适用于4取代的喹啉酮及其衍生物的药物修饰。
• INHIBITORS OF MACROPHASE MIGRATION INHIBITORY FACTOR AND METHODS FOR IDENTIFYING THE SAME
  申请人：Gaeta C.A. Federico

  公开号：US20060094727A1

  公开（公告）日：2006-05-04

  Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

  提供了MIF抑制剂，其在治疗各种疾病方面具有用途，包括治疗与MIF活性相关的病理状况。MIF抑制剂具有以下结构：包括立体异构体，前药和其药学上可接受的盐，其中n，R1，R2，R3，R4，X，Y和Z如本文所定义。还提供了含有MIF抑制剂和药学上可接受的载体的组合物，以及使用它们的方法。