2-(4-ethyl-1-piperazinyl)-4-phenylquinoline | 72320-59-3

• 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: 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline
• 英文别名: 2-(4-ethyl-piperazin-1-yl)-4-phenyl-quinoline；Quinoline, 2-(4-ethyl-1-piperazinyl)-4-phenyl-, dihydrochloride；2-(4-ethylpiperazin-1-yl)-4-phenylquinoline
• CAS: 72320-59-3
• 化学式: C₂₁H₂₃N₃
• 分子量: 317.434
• InChiKey: PHOZLMDTTWWBAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-ethyl-1-piperazinyl)-4-phenylquinoline 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以80%的产率得到1-ethyl-4-(4-phenylquinoline-2-yl)piperazine 1-oxide
  参考文献：
  名称：

  Synthesis and antiulcar activity of the metabolites of 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline dimaleate (AS-2646), a novel gastric antisecretory and antiulcer agent.

  摘要：

  合成了 2-(4-乙基-1-哌嗪基)-4-苯基喹啉二马来酸酯 (AS-2646, 1) 的代谢物 3 和 4，作为胃抗分泌和抗溃疡药物的候选药物，以确认所提出的结构。测定了代谢物2-4对应激诱发的溃疡的作用。

  DOI：

  10.1248/cpb.37.190
• 作为产物：
  描述：

  (Z)-but-2-enedioic acid;2-(4-ethylpiperazin-1-yl)-4-phenylquinoline 生成 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline
  参考文献：
  名称：

  HINO, KATSUHIKO;KAWASHIMA, KATSUYOSHI;OKA, MAKOTO;UNO, HITOSHI;MATSUMOTO,+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 190-192

  摘要：

  DOI：

文献信息

• 4-Phenyl-2-(1-piperazinyl)quinolines with potent antidepressant activity.
  作者：KATSUHIKO HINO、KIYOSHI FURUKAWA、YASUTAKA NAGAI、HITOSHI UNO

  DOI：10.1248/cpb.28.2618

  日期：——

  A series of 2-amino-4-phenylquinolines was synthesized and the effects of these compounds on the central nervous system were evaluated pharmacologically in mice. Among these compounds, many 2-(substituted piperazinyl) derivatives exhibited a potent antagonism to hypothermia and catalepsy induced by reserpine, as well as some inhibitory effect on locomotor activity. Some compounds were found to possess activity to inhibit tremorine-induced tremor.

  合成了一系列2-氨基-4-苯基喹啉，并在小鼠中药理评估了这些化合物对中枢神经系统的影响。在这些化合物中，许多2-(取代哌嗪基)衍生物表现出对美克洛西丁诱导的低体温和植物人状态的显著拮抗作用，同时对运动活动也有一定的抑制效果。一些化合物被发现具有抑制颤动素诱发的震颤的活性。
• A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines.
  作者：Katsuhiko HINO、Katsuyoshi KAWASHIMA、Makoto OKA、Yasutaka NAGAI、Hitoshi UNO、Jun-ichi MATSUMOTO

  DOI：10.1248/cpb.37.110

  日期：——

  The synthesis of a novel class of antiulcer agents, the substituted 4-phenyl-2-(1-piperazinyl)quinolines, and their pharmacological activities (inhibitory effects on hypothermia induced by reserpine and on gastric ulcers induced by stress or ethanol) are described. These compounds can be classified into three groups (a group predominantly effective on the stress-induced ulcer, one effective on both the stress- and ethanol-induced ulcers, and one selectively effective on the ethanol-induced ulcer), with regard to antiulcer activity. The inhibitory effect on stress-induced ulcer was found to be in close relation to the antagonism of hypothermia. The structure-activity relationships in these compounds are described. Among the compounds, 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline dimaleate (9, AS-2646) showed a potent inhibition of stress-induced ulcer and gastric acid secretion, possively through action on the central nervous system, and it was selected for clinical evaluation.

  描述了一类新型抗溃疡药物的合成，即取代的4-苯基-2-(1-哌嗪基)喹啉，以及它们的药理活性（对由雷沙平引起的低温及由压力或乙醇引起的胃溃疡的抑制作用）。这些化合物可根据抗溃疡活性分为三类（针对压力诱导溃疡具有主导效应的一类、对压力和乙醇诱导的溃疡均有效的一类，以及对乙醇诱导溃疡选择性有效的一类）。在压力诱导的溃疡中，抑制作用与对低温的拮抗作用密切相关。描述了这些化合物的结构-活性关系。在这些化合物中，2-(4-乙基-1-哌嗪基)-4-苯基喹啉二马来酸盐（9，AS-2646）对压力诱导的溃疡和胃酸分泌表现出显著抑制作用，可能通过对中枢神经系统的作用实现，因此被选中进行临床评估。
• Anti-peptic ulcer agent
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04677107A1

  公开（公告）日：1987-06-30

  Use of a compound of the formula: ##STR1## wherein R is hydrogen atom or ethyl group, or a pharmaceutically acceptable salt thereof for prophylaxis and/or treatment of peptic ulcer, and a method for prophylaxis and/or treatment of peptic ulcer disease which comprises administering an effective amount of the above-mentioned compound to warm blooded aninal, especially human. Said active compounds have excellent pharmacological activities such as inhibition of ulceration and inhibition of gastric secretion, and hence, are useful as an anti-peptic ulcer agent.

  使用公式为##STR1##的化合物，其中R为氢原子或乙基基团，或其药学上可接受的盐，用于预防和/或治疗消化性溃疡，并提供一种预防和/或治疗消化性溃疡疾病的方法，该方法包括向温血动物，特别是人类，给予上述化合物的有效量。所述活性化合物具有卓越的药理活性，如抑制溃疡和抑制胃分泌，因此，它们可用作抗消化性溃疡药物。
• 2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline, process for preparation
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04237135A1

  公开（公告）日：1980-12-02

  2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline and its pharmaceutically acceptable acid addition salts, which are useful as antidepressant agents in the treatment of depression or depressive state in mammals including humans, and processes for the preparation thereof.

  2-(4-乙基-1-哌嗪基)-4-苯基喹啉及其药学上可接受的酸加盐，可用于治疗哺乳动物包括人类的抑郁症或抑郁状态，是一种抗抑郁药物，以及其制备方法。
• 2-(1-PIPERAZINYL)-4-SUBSTITUTED PHENYLQUINOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND MEDICINAL COMPOSITION CONTAINING SAME
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0204003A1

  公开（公告）日：1986-12-10

  Compounds represented by the general formula (1), (wherein R1 represents a fluorine atom in p-position, a chlorine atom in p-position, a methyl group in p-position or a trifluoromethyl group in p- or m-position, and R2 represents a hydrogen atom, a methyl group, an ethyl group, a 2-hydroxyethyl group or a 3-hydroxypropyl group, provided that R2 represents an ethyl group, a 2-hydroxyethyl group or a 3-hydroxypropyl group when R, represents a fluorine atom in p-position, a methyl group in p-position or a trifluoromethyl group in p-position), physiologically acceptable salts thereof, process for their preparation, and medicinal composition. These compounds and salts possess an excellent mucous membrane-protecting effect, and are useful for prophylaxis and treatment of peptic ulcer and inflammatory diseases of gastrointestinal tracts.

  通式(1)所代表的化合物，（其中 R1 代表 p 位的氟原子、p 位的氯原子、p 位的甲基或 p 位或 m 位的三氟甲基，R2 代表氢原子、甲基、乙基、2-羟乙基或 3-羟丙基、当 R 代表 p 位的氟原子、p 位的甲基或 p 位的三氟甲基时，R2 代表乙基、2-羟乙基或 3-羟丙基）、其生理上可接受的盐、其制备方法和药物组合物。这些化合物和盐具有良好的粘膜保护作用，可用于预防和治疗消化性溃疡和胃肠道炎症性疾病。