ethyl 6-[(2-oxo-1H-quinolin-6-yl)oxy]hexanoate | 87364-42-9

• 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 6-[(2-oxo-1H-quinolin-6-yl)oxy]hexanoate
• CAS: 87364-42-9
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: KLDRIYCNENRYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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 6-[(2-oxo-1H-quinolin-6-yl)oxy]hexanoate 在 羟胺 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.07h， 生成 6-(carbostyril-6-yloxy)hexanoic acid hydroxyamide
  参考文献：
  名称：

  Design and synthesis of novel and highly-active pan-histone deacetylase (pan-HDAC) inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2014.05.001
• 作为产物：
  描述：

  6-羟基-2(1H)-喹啉酮 、 6-溴己酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以88%的产率得到ethyl 6-[(2-oxo-1H-quinolin-6-yl)oxy]hexanoate
  参考文献：
  名称：

  Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. III. N-Cyclohexyl-N-(2-hydroxyethyl)-4-(1,2-dihydro-2-oxo-6-quinolyloxy)butyramide and related compounds.

  摘要：

  合成了一系列 N,N-取代的ω-(1, 2-二氢-2-氧羟喹啉氧基)烷基氨基酸酰胺，并对其在体外对胶原和ADP诱导的兔血小板聚集的抑制活性进行了测试。这些化合物是通过ω-(1, 2-二氢-2-氧羟喹啉氧基)烷酸与各种胺反应，采用混合酸酐法制备的。其中，N-环己基-N-(2-羟乙基)-4-(1, 2-二氢-2-氧-6-喹啉氧基)丁酰胺（IVa1）被发现具有最强的抑制活性。文中讨论了结构-活性关系。

  DOI：

  10.1248/cpb.31.852

文献信息

• NISHI, TAKAO;TABUSA, FUJIO;TANAKA, TATSUYOSHI;UEDA, HIRAKI;SHIMIZU, TAKEF+, CHEM. AND PHARM. BULL., 1983, 31, N 3, 852-860
  作者：NISHI, TAKAO、TABUSA, FUJIO、TANAKA, TATSUYOSHI、UEDA, HIRAKI、SHIMIZU, TAKEF+

  DOI：——

  日期：——