4-氨基-2-甲基喹啉-3-羧酸乙酯 | 163455-37-6

• 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-氨基-2-甲基喹啉-3-羧酸乙酯
• 英文名称: 4-amino-2-methylquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-amino-2-methylquinoline-3-carboxylate；4-amino-3-carboxyethyl-2-methylquinoline；ethyl-4-amino-2-methylquinoline-3-carboxylate
• CAS: 163455-37-6
• 化学式: C₁₃H₁₄N₂O₂
• mdl: MFCD13976403
• 分子量: 230.266
• InChiKey: LRXJUYOPYYMLFD-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C
• 沸点：
  362.5±37.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  4-氨基-2-甲基喹啉-3-羧酸乙酯 在 六氯乙烷 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 生成 2-(4-chloro-3-methylphenoxy)-3-(4-fluorophenyl)-5-methylpyrimido[5,4-c]quinolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of pyrimido[5,4-c]quinoline-4-(3H)-one derivatives

  摘要：

  A series of pyrimido[5,4-c]quinoline-4-(3H)-one derivatives variously substituted at positions 2 and 3 were synthesized and evaluated for their in vitro antiproliferative activities against a panel of six human cancer cell lines. Biological evaluation revealed that the vast majority of derivatives exhibited moderate tumor growth inhibitory activities. In particular, compound 7e showed effective anti-tumor activity with broad-spectrum toward numerous cell lines and the most active member in this study. This derivative displaying significant activity against KB (IC50: 4.9 mu M), CNE2 (IC50: 13.8 mu M), MGC-803 (IC50: 4.8 mu M), GLC-82 (IC50: 7.88 mu M), MDA-MB-453 (IC50: 18.2 1.1 mu M) and MCF-7 (IC50: 10.1 mu M) cell lines could be considered as the most promising and useful template for future development to obtain more potent anti-tumor agent(s). 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.044
• 作为产物：
  描述：

  5-甲基-3-(2-硝基苯基)-1,2-恶唑-4-羧酸乙酯 在 镍 氢气 作用下， 以 乙醇 为溶剂， 以88%的产率得到4-氨基-2-甲基喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Jensen, Soeren; Torssell, Kurt B. G., Acta Chemica Scandinavica, 1995, vol. 49, # 1, p. 53 - 56

  摘要：

  DOI：

文献信息

• Chitosan-SO3H: an efficient, biodegradable, and recyclable solid acid for the synthesis of quinoline derivatives via Friedländer annulation
  作者：B.V. Subba Reddy、A. Venkateswarlu、G. Niranjan Reddy、Y.V. Rami Reddy

  DOI：10.1016/j.tetlet.2013.07.165

  日期：2013.10

  Chitosan-SO3H is found to catalyze the Friedländer condensation/annulation reaction of 2-aminoaryl ketones with α-methyleneketones to produce the corresponding quinoline derivatives in high yields in short reaction times. The use of recyclable and biodegradable chitosan-SO3H makes this method quite simple, more convenient, and economically viable compared to acid catalyzed methods reported in the literature

  发现壳聚糖-SO 3 H催化2-氨基芳基酮与α-亚甲基酮的Friedländer缩合/环化反应，从而在较短的反应时间内以高收率生产相应的喹啉衍生物。与文献中报道的酸催化方法相比，可回收和可生物降解的壳聚糖-SO 3 H的使用使该方法相当简单，方便和经济。
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• Synthesis and structure elucidation of five new pyrimido[5,4-c]quinoline-4(3H)-one derivatives using 1D and 2D NMR spectroscopy
  作者：Yong Ai、Guangzhong Yang、Jianchao Liu、Yu Chen、Lu Liu、Xinxiang Lei

  DOI：10.1002/mrc.2689

  日期：2010.12

  Five new 2‐(amino/aroxy)‐5‐methylpyrimido[5,4‐c]quinolin‐4(3H)‐one derivatives have been designed and synthesized via an aza‐Wittig reaction, and the structure elucidation was accomplished using extensive 1D (1H, 13C) and 2D NMR spectroscopic studies (COSY, HSQC and HMBC experiments). Copyright © 2010 John Wiley & Sons, Ltd.

  通过 aza-Wittig 反应设计并合成了五种新的 2-(氨基/芳氧基)-5-甲基嘧啶并[5,4-c]喹啉-4(3H)-one衍生物，并使用广泛的1D完成了结构解析(1H, 13C) 和 2D NMR 光谱研究（COSY、HSQC 和 HMBC 实验）。版权所有 © 2010 John Wiley & Sons, Ltd.
• SWEET FLAVOR MODIFIER
  申请人：TACHDJIAN Catherine

  公开号：US20110245353A1

  公开（公告）日：2011-10-06

  The present invention includes compounds having structural formula (I), or pharmaceutically acceptable salts, solvate, and/or ester thereof. These compounds are useful as sweet flavor modifiers. The present invention also includes compositions comprising the present compounds and methods of enhancing the sweet taste of ingestible compositions. Furthermore, the present invention provides methods for preparing the compounds.

  本发明包括具有结构式(I)的化合物，或其药用可接受的盐、溶剂合物和/或酯。这些化合物可用作甜味调节剂。本发明还包括包含本发明的化合物的组合物以及增强可食用组合物甜味的方法。此外，本发明提供了制备这些化合物的方法。
• Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles
  作者：Keith C. Coffman、Vy Duong、Alex L. Bagdasarian、James C. Fettinger、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1002/ejoc.201403065

  日期：2014.12

  A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc via a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one

  利用 ZnO 或 FeO 粉尘和 HOAc，通过还原杂环化过程，由取代的 3-(2-硝基苯基)异恶唑合成了多种喹啉-4-胺。起始异恶唑是由容易获得的起始材料合成的。对这种还原性杂环化中耐受的官能团进行了简要调查，并发现了几种 10-氨基-3,4-二氢苯并[b][1,6]萘啶-1(2H)-酮和 9-氨基-3,4-二氢吖啶-1(2H)-合成了一个实例。