6-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• 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-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 6-Benzyl-1-(2-hydroxyethyl)-4-oxo-quinoline-3-carboxylic acid；6-benzyl-1-(2-hydroxyethyl)-4-oxoquinoline-3-carboxylic acid
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: NNFYVCXXTFQCIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以54%的产率得到RuCl(η6-p-cymene)(6-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid) monohydrate
  参考文献：
  名称：

  Ruthenium arene complexes as HIV-1 integrase strand transfer inhibitors

  摘要：

  The quinolone HL1 and the hydroxypyrimidine-carboxamide HL2 were designed and synthesized as models of the HIV integrase strand transfer inhibitors Elvitegravir and Raltegravir (brand name Isentress), with the aim to study their complexing behavior and their biological activity. The Ru(arene) complexes [RuCl(eta(6)-p-cym)L-1], [RuCl(eta(6)-p-cym)L-2] and [RuCl(hexamethylbenzene)(L)2] were also synthesized and spectroscopically characterized and their X-ray diffraction structures were discussed. The ligands and the complexes showed inhibition potency in the sub/low-micromolar concentration range in anti-HIV-1 integrase enzymatic assays, with selectivity toward strand transfer catalytic process, without any significant cytotoxicity on cancer cells. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.09.021
• 作为产物：
  描述：

  6-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate ethyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以97%的产率得到6-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Ruthenium arene complexes as HIV-1 integrase strand transfer inhibitors

  摘要：

  The quinolone HL1 and the hydroxypyrimidine-carboxamide HL2 were designed and synthesized as models of the HIV integrase strand transfer inhibitors Elvitegravir and Raltegravir (brand name Isentress), with the aim to study their complexing behavior and their biological activity. The Ru(arene) complexes [RuCl(eta(6)-p-cym)L-1], [RuCl(eta(6)-p-cym)L-2] and [RuCl(hexamethylbenzene)(L)2] were also synthesized and spectroscopically characterized and their X-ray diffraction structures were discussed. The ligands and the complexes showed inhibition potency in the sub/low-micromolar concentration range in anti-HIV-1 integrase enzymatic assays, with selectivity toward strand transfer catalytic process, without any significant cytotoxicity on cancer cells. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.09.021

文献信息

• 4-OXOQUINOLINE COMPOUND AND USE THEREOF AS PHARMACEUTICAL AGENT
  申请人：Japan Tobacco Inc.

  公开号：US20150174117A1

  公开（公告）日：2015-06-25

  An anti-HIV agent containing, as an active ingredient, a 4-oxoquinoline compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. The compound of the present invention has HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compound can become a more effective anti-HIV agent. Since the compound has high inhibitory activity specific for integrases, it can provide a safe pharmaceutical agent with a fewer side effects for human.

  一种抗HIV剂，其活性成分为以下式[I]所代表的4-氧喹啉化合物，其中每个符号在规范中定义，或其药学上可接受的盐。本发明的化合物具有HIV整合酶抑制作用，并且可用作预防或治疗艾滋病的抗HIV剂。此外，通过与其他抗HIV剂（如蛋白酶抑制剂，逆转录酶抑制剂等）的联合使用，该化合物可以成为更有效的抗HIV剂。由于该化合物具有高度特异性的整合酶抑制活性，因此可以提供一种对人体副作用较少的安全药物。
• 4-OXOQUINOLINE COMPOUND AND USE THEREOF AS HIV INTEGRASE INHIBITOR
  申请人：SATOH Motohide

  公开号：US20130172344A1

  公开（公告）日：2013-07-04

  An anti-HIV agent containing, as an active ingredient, a 4-oxoquinoline compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. The compound of the present invention has HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compound can become a more effective anti-HIV agent. Since the compound has high inhibitory activity specific for integrases, it can provide a safe pharmaceutical agent with a fewer side effects for human.

  一种抗HIV药剂，其含有以下式[I]所表示的4-氧喹啉化合物作为活性成分，其中每个符号如规范中所定义，或其药学上可接受的盐。本发明的化合物具有HIV整合酶抑制作用，可用于预防或治疗艾滋病的抗HIV药剂。此外，与其他抗HIV药剂（如蛋白酶抑制剂、反转录酶抑制剂等）联合使用，该化合物可以成为更有效的抗HIV药剂。由于该化合物具有针对整合酶的高抑制活性，因此可以提供一种对人体副作用更少的安全药物。
• 4-oxoquinoline compound and use thereof as hiv integrase inhibitor
  申请人：Japan Tobacco Inc.

  公开号：EP2161258A2

  公开（公告）日：2010-03-10

  An anti-HIV agent containing, as an active ingredient, a 4-oxoquinoline compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. The compound of the present invention has HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compound can become a more effective anti-HIV agent. Since the compound has high inhibitory activity specific for integrases, it can provide a safe pharmaceutical agent with a fewer side effects for human.

  一种抗HIV剂，其包含一个由以下式[I]表示的4-氧喹啉化合物作为活性成分，其中每个符号如规范中所定义，或其药学上可接受的盐。本发明的化合物具有HIV整合酶抑制作用，并且可用作预防或治疗艾滋病的抗HIV剂。此外，与其他抗HIV剂（如蛋白酶抑制剂，逆转录酶抑制剂等）的联合使用，该化合物可以成为更有效的抗HIV剂。由于该化合物具有特异性高的整合酶抑制活性，因此可以提供一种具有更少副作用的安全药物。
• 4-Oxoquinoline compound and use thereof as HIV integrase inhibitor
  申请人：Japan Tobacco, Inc.

  公开号：EP2272516A2

  公开（公告）日：2011-01-12

  An anti-HIV agent containing, as an active ingredient, a 4-oxoquinoline compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. The compound of the present invention has HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compound can become a more effective anti-HIV agent. Since the compound has high inhibitory activity specific for integrases, it can provide a safe pharmaceutical agent with a fewer side effects for human.

  一种抗艾滋病毒制剂，其活性成分含有下式[I]代表的 4-氧代喹啉化合物 其中各符号如说明书中所定义，或其药学上可接受的盐。本发明的化合物具有抑制艾滋病毒整合酶的作用，可用作预防或治疗艾滋病的抗艾滋病毒药物。此外，通过与蛋白酶抑制剂、逆转录酶抑制剂等其他抗艾滋病毒药物联合使用，本发明化合物可以成为更有效的抗艾滋病毒药物。由于该化合物对整合酶具有较高的特异性抑制活性，因此可以为人类提供一种安全的、副作用较小的药物制剂。
• 4-OXOQUINOLINE COMPOUNDS AND UTILIZATION THEREOF AS HIV INTEGRASE INHIBITORS
  申请人：Japan Tobacco Inc.

  公开号：EP1564210B9

  公开（公告）日：2010-03-31