1-n-propyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid | 129686-99-3

• 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: 1-n-propyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 1-propyl-4-quinolone-3-carboxylic acid；1,4-Dihydro-4-oxo-1-n-propylquinoline-3-carboxylic acid；4-Oxo-1-propyl-1,4-dihydroquinoline-3-carboxylic acid；4-oxo-1-propylquinoline-3-carboxylic acid
• CAS: 129686-99-3
• 化学式: C₁₃H₁₃NO₃
• mdl: MFCD11557449
• 分子量: 231.251
• InChiKey: YUXVAHFIXDDTAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  oxalic acid dihydrate 、 (1S,5R)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine 、 1-n-propyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 、 二苯基次膦酰氯 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-4-oxo-1-n-propylquinoline-3-carboxamide
  参考文献：
  名称：

  Pharmacologically active amides and esters containing an

  摘要：

  式为##STR1##的化合物，其中R.sup.1是氢或一个或多个指定的取代基，X是--O--或--NR.sup.2 --，其中R.sup.2是较低的烷基、较低的烯基、较低的炔基、芳基或指定的取代的较低烷基，或R.sup.2代表一个连接到芳香环的8位的--Z--基团，以形成5至7个环成员的杂环环，Y是O或NR.sup.3，其中R.sup.3是氢或较低的烷基，B是饱和的氮杂双环环（例如环丙基或喹诺啉基）或其酸盐，它们是5-HT.sub.3拮抗剂，可用于治疗神经精神障碍。

  公开号：

  US05096901A1
• 作为产物：
  描述：

  1-n-propyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 1-n-propyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of N-Alkyl-1,4-Dihydro-4-Oxo-3-Quinolinecarboxylic Acidvia2-(2',2',2'-Tri-Chloro)Ethylidene-3-Oxo-3-(2''-Chlorophenyl)Propionate

  摘要：

  A clay catalyzed synthesis of 2-(2',2',2'-trichloro)ethylidene-3-oxo-3-(2"-chlorophenyllpropionate (2) and its application for the preparation of various N-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids (5a-e) has been described.

  DOI：

  10.1080/00397910008087417

文献信息

• Structural development of a type-1 ryanodine receptor (RyR1) Ca2+-release channel inhibitor guided by endoplasmic reticulum Ca2+ assay
  作者：Shuichi Mori、Hiroto Iinuma、Noriaki Manaka、Mari Ishigami-Yuasa、Takashi Murayama、Yoshiaki Nishijima、Akiko Sakurai、Ryota Arai、Nagomi Kurebayashi、Takashi Sakurai、Hiroyuki Kagechika

  DOI：10.1016/j.ejmech.2019.06.076

  日期：2019.10

  Type-1 ryanodine receptor (RyRI) is a calcium-release channel localized on sarcoplasmic reticulum (SR) of the skeletal muscle, and mediates muscle contraction by releasing Ca2+ from the SR. Genetic mutations of RyRI are associated with skeletal muscle diseases such as malignant hyperthermia and central core diseases, in which over-activation of RyRI causes leakage of Ca2+ from the SR. We recently developed an efficient high-throughput screening system based on the measurement of Ca2+ in endoplasmic reticulum, and used it to identify oxolinic acid (1) as a novel RyRI channel inhibitor. Here, we designed and synthesized a series of quinolone derivatives based on 1 as a lead compound. Derivatives bearing a long alkyl chain at the nitrogen atom of the quinolone ring and having a suitable substituent at the 7-position of quinolone exhibited potent RyR1 channel-inhibitory activity. Among the synthesized compounds, 14h showed more potent activity than dantrolene, a known RyR1 inhibitor, and exhibited high RyR1 selectivity over RyR2 and RyR3. These compounds may be promising leads for clinically applicable RyRI channel inhibitors. (C) 2019 Elsevier Masson SAS. All rights reserved.
• HETEROCYCLIC COMPOUNDS
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0494978A1

  公开（公告）日：1992-07-22
• US5096901A
  申请人：——

  公开号：US5096901A

  公开（公告）日：1992-03-17
• US5225419A
  申请人：——

  公开号：US5225419A

  公开（公告）日：1993-07-06
• US5362734A
  申请人：——

  公开号：US5362734A

  公开（公告）日：1994-11-08