ethyl 4-hydroxy-5-methylquinoline-3-carboxylate | 228728-31-2

• 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: ethyl 4-hydroxy-5-methylquinoline-3-carboxylate
• 英文别名: ethyl 5-methyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 228728-31-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: YPDDUVLTNPUAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-5-methylquinoline-3-carboxylate 在 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 ethyl 4-chloro-5-methylquinoline-3-carboxylate
  参考文献：
  名称：

  一种四环内酰胺类化合物及其制备方法和用途

  摘要：

  本发明涉及一种四环内酰胺类化合物,或其互变异构体、立体异构体、外消旋体、对映异构体的非等量混合物、几何异构体、溶剂化物、药学上可接受的盐或前药,以及包含该化合物的药物组合物。本发明还公开了这类化合物及其药物组合物作为药物,尤其是作为抗菌、抗病毒及抗寄生虫等药物的用途。

  公开号：

  CN108623589A
• 作为产物：
  描述：

  3-硝基甲苯 在 铁粉 、 碳酸氢钠 、 氯化铵 、 三氯氧磷 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 ethyl 4-hydroxy-5-methylquinoline-3-carboxylate
  参考文献：
  名称：

  Quinolone–Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity

  摘要：

  Recent publications report in vitro activity of quinolone 3-esters against the bc(1) protein complex of Plasmodium falciparum and the parasite. Docking studies performed in silica at the yeast Q(o) Site established a key role for the 4-oxo and N-H groups in drug-target interactions. Thus, the possibility of 4-oxoquinoline/4-hydroxyquinoline tautomerism may impact in pharmacologic profiles and should be investigated. We describe the synthesis, structure, photochemistry, and activity against multidrug-resistant P. falciparum strain Dd2 of ethyl 4-oxo-7-methylquinoline-3-carboxylate (7Me-OQE) and ethyl 4-hydroxy-5-methylquinoline-3-carboxylate (5Me-HQE), obtained from diethyl 2-[((3-methylphenyl)amino)methylene]malonate. Theoretically (B3LYP/6-311+ +G(d,p)), 5Me-HQE and 7Me-OQE show clear preference for the hydroxyquinoline form. The difference between the lowest energy hydroxyquinoline and quinolone forms is 27 and 38 kJ mol(-1), for 5Me-HQE and 7Me-OQE, respectively. Calculations of atomaticity indexes show that in 5Me-HQE,both rings are aromatic, while in the corresponding oxo tautomers the nitrogen-containing ring is essentially non-aromatic. The structure of monomeric 5Me-HQE was studied using matrix-isolation coupled to FTIR spectroscopy. No traces of 4-oxoquinoline tautomers were found in the experimental IR spectra, revealing that:the species present in the crystal, 5Me-HQE center dot HCl, was lost HCl upon sublimation but did not tautomerize. Continuous broadband irradiation (lambda > 220 nm; 130 min) of the matrix led to only partial photodecomposition of 5Me-HQE (ca. 1/3).

  DOI：

  10.1021/acs.joc.5b02169

文献信息

• MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
  申请人：Sheth Urvi

  公开号：US20120309758A1

  公开（公告）日：2012-12-06

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及调节ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节蛋白，以及相关的组合物和方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。
• 一种含内酰胺的四环衍生物及其制备方法和应用
  申请人：中国海洋大学

  公开号：CN108623588A

  公开（公告）日：2018-10-09

  本发明涉及一类含内酰胺的四环衍生物,或其互变异构体、立体异构体、外消旋体、对映异构体的非等量混合物、几何异构体、溶剂化物、药学上可接受的盐或前药,以及包含该化合物的药物组合物。本发明还公开了这类化合物及其药物组合物在农业领域作为杀虫剂、杀菌剂、除草剂的用途。
• Modulators of ATP-Binding Cassette Transporters
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20130165442A1

  公开（公告）日：2013-06-27

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜电导调节器、其组成物以及使用它们的方法。本发明还涉及使用这种调节剂治疗ABC转运蛋白介导的疾病的方法。
• Modulators of ATP-binding cassette transporters
  申请人：Van Goor Fredrick

  公开号：US08354427B2

  公开（公告）日：2013-01-15

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜导电调节因子、其组合物以及使用这些调节剂的方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。
• Modulators of ATP-Binding Cassette transporters
  申请人：Sheth Urvi

  公开号：US08802700B2

  公开（公告）日：2014-08-12

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节因子，以及其组合物和方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。