ethyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrate | 58900-56-4

• 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-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrate
• 英文别名: 6-(3'-Ethoxycarbonyl)propoxy-3,4-dihydrocarbostyril；ethyl 4-[(2-oxo-3,4-dihydro-1H-quinolin-6-yl)oxy]butanoate
• CAS: 58900-56-4
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: QOQVKCLJMBKWCA-UHFFFAOYSA-N

物化性质

• 熔点：
  121-121.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  485.3±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 propyl 4-[(2-oxo-3,4-dihydro-1H-quinolin-6-yl)oxy]butanoate
  参考文献：
  名称：

  2-氧代喹啉衍生物作为血小板聚集抑制剂的研究。I.4-（2-氧代-1,2,3,4-四氢-6-喹啉基氧基）丁酸酯和相关化合物。

  摘要：

  合成并测试了许多烷基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯及相关化合物对体外血小板聚集的抑制活性。其中，乙基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯显示出最强的抑制活性。讨论了构效关系。

  DOI：

  10.1248/cpb.31.798
• 作为产物：
  描述：

  6-羟基-3,4-二氢-2(1H)-喹诺酮 、 4-溴丁酸乙酯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到ethyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrate
  参考文献：
  名称：

  2-氧代喹啉衍生物作为血小板聚集抑制剂的研究。I.4-（2-氧代-1,2,3,4-四氢-6-喹啉基氧基）丁酸酯和相关化合物。

  摘要：

  合成并测试了许多烷基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯及相关化合物对体外血小板聚集的抑制活性。其中，乙基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯显示出最强的抑制活性。讨论了构效关系。

  DOI：

  10.1248/cpb.31.798

文献信息

• NISHI, TAKAO;YAMAMOTO, KATSUYOSHI;SHIMIZU, TAKEFUMI;KANBE, TOSHIMI;KIMURA+, CHEM. AND PHARM. BULL., 1983, 31, N 3, 798-810
  作者：NISHI, TAKAO、YAMAMOTO, KATSUYOSHI、SHIMIZU, TAKEFUMI、KANBE, TOSHIMI、KIMURA+

  DOI：——

  日期：——
• US4070470A
  申请人：——

  公开号：US4070470A

  公开（公告）日：1978-01-24
• Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. I. Alkyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrates and related compounds.
  作者：TAKAO NISHI、KATSUYOSHI YAMAMOTO、TAKEFUMI SHIMIZU、TOSHIMI KANBE、YUKIO KIMURA、KAZUYUKI NAKAGAWA

  DOI：10.1248/cpb.31.798

  日期：——

  Many alkyl 4-(2-oxo-1, 2, 3, 4-tetrahydro-6-quinolyloxy) butyrates and related compounds were synthesized and tested for inhibitory activity against blood platelet aggregation in vitro. Among them, ethyl 4-(2-oxo-1, 2, 3, 4-tetrahydro-6-quinolyloxy) butyrate was found to have the most potent inhibitory activity. The structure-activity relationships are discussed.

  合成并测试了许多烷基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯及相关化合物对体外血小板聚集的抑制活性。其中，乙基4-(2-氧代-1, 2, 3, 4-四氢-6-喹啉氧基)丁酸酯显示出最强的抑制活性。讨论了构效关系。
• Design and synthesis of novel and highly-active pan-histone deacetylase (pan-HDAC) inhibitors
  作者：Toshihiko Tashima、Hiroaki Murata、Hidehiko Kodama

  DOI：10.1016/j.bmc.2014.05.001

  日期：2014.7

  Histone deacetylase (HDAC) inhibitions are known to elicit anticancer effects. We designed and synthesized several HDAC inhibitors. Among these compounds, compound 40 exhibited a more than 10-fold stronger inhibitory activity compared with that of suberoylanilide hydroxamic acid (SAHA) against each human HDAC isozyme in vitro (IC50 values of 40: HDAC1, 0.0038μM; HDAC2, 0.0082μM; HDAC3, 0.015μM; HDAC8, 0.0060μM; HDAC4, 0.058μM; HDAC9, 0.0052μM; HDAC6, 0.058μM). The dose of the administered HDAC inhibitors that contain hydroxamic acid as the zinc-binding group may be reduced by 40. Because the carbostyril subunit is a time-tested structural component of drugs and biologically active compounds, 40 most likely exhibits good absorption, distribution, metabolism, excretion, and toxicity (ADMET). Thus, compound 40 is expected to be a promising therapeutic agent or chemical tool for the investigation of life process.