6-乙酰基-3,4-二氢-2(1h)-喹啉酮 | 62245-12-9

• 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
• 中文名称: 6-乙酰基-3,4-二氢-2(1h)-喹啉酮
• 英文名称: 6-acetyl-3,4-dihydro-1H-quinolin-2-one
• 英文别名: 6-acetyl-3,4-dihydro-2(1H)-quinolinone；6-acetyl-3,4-dihydroquinolin-2(1H)-one；6-acetyl-3,4-dihydrocarbostyril
• CAS: 62245-12-9
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD09034969
• 分子量: 189.214
• InChiKey: FXPPYJRCOQZMIL-UHFFFAOYSA-N

物化性质

• 熔点：
  161.0-162.0 °C
• 沸点：
  429.2±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  6-乙酰基-3,4-二氢-2(1h)-喹啉酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3,4-dihydro-6-(1-hydroxyethyl)-2(1H)-quinolinone
  参考文献：
  名称：

  3,4-Dihydroquinolin-2(1H)-ones as combined inhibitors of thromboxane A2 synthase and cAMP phosphodiesterase

  摘要：

  A series of 1H-imidazol-1-yl- and 3-pyridyl-substituted 3,4-dihydroquinolin-2(1H)-ones was designed and synthesized as combined inhibitors of thromboxane (TXA2) synthase and cAMP phosphodiesterase (PDE) in human blood platelets. A number of structures, e.g. 4b, 7a, 7e, 13a, and 21-25, were superior to dazoxiben 26 as inhibitors of TXA2 synthase in in vitro ADP-induced aggregation experiments with human blood platelets. The TXA2 synthase inhibitory activity was confirmed by measurement of the prostanoid metabolites derived from C-14-labeled arachidonic acid. Three compounds (7a, 7e, and 25) demonstrated in vitro inhibition of human platelet cAMP PDE at micromolar concentrations in conjunction with their TXA2 synthase inhibitory activity. Synergistic enhancement of antiaggregatory and antithrombotic actions was expected when simultaneous stimulation of adenylate cyclase (through increased PGI2 production) and inhibition of platelet cAMP PDE were possible from the same compound. Ex vivo and in vivo experiments were conducted in rats and mice, respectively, to evaluate the effects of compounds 7e and 23 on platelet aggregation and thrombotic events within these animals. Compound 7e, which has a comparable level of TXA2 synthase (IC50 1.2-mu-M) and human platelet cAMP PDE (IC50 6.4-mu-M) inhibitory activities, was found to be orally bioavailable with a long duration of action and offered effective protection against mortality in a collagen-epinephrine-induced pulmonary thromboembolism model in mice. Significant blood pressure and heart rate effects were observed for several compounds, e.g. 7e, 9e, 13a, 13d, 18, 20, 21, and 23, when dosed orally in conscious spontaneously hypertensive rats.

  DOI：

  10.1021/jm00082a002
• 作为产物：
  描述：

  3,4-二氢-2(1H)-喹啉酮 生成 6-乙酰基-3,4-二氢-2(1h)-喹啉酮
  参考文献：
  名称：

  WALKER, KEITH A. M.;BRUNO, JOHN J.;MARTINEZ, GREGORY R.

  摘要：

  DOI：

文献信息

• Synthesis of Five-, Six-, and Seven-Membered Ring Lactams by Cp*Rh Complex-Catalyzed Oxidative N-Heterocyclization of Amino Alcohols
  作者：Ken-ichi Fujita、Yoshinori Takahashi、Maki Owaki、Kazunari Yamamoto、Ryohei Yamaguchi

  DOI：10.1021/ol0489954

  日期：2004.8.1

  pentamethylcyclopentadienyl) for the lactamization of amino alcohols has been developed. As an example, the reaction of 3-(2-aminophenyl)-1-propanol in the presence of [CpRhCl(2)](2) (5.0% Rh) and K(2)CO(3) (10%) in acetone gives 3,4-dihydro-2(1H)-quinolinone in an isolated yield of 80%. A variety of five-, six-, and seven-membered benzo-fused lactams are synthesized by this catalytic system. [reaction:

  开发了一种新的有效催化体系，由[CpRhCl（2）]（2）/ K（2）CO（3）（Cp =五甲基环戊二烯基）进行氨基醇内酰胺化。例如，在[CpRhCl（2）]（2）（5.0％Rh）和K（2）CO（3）（10％）的存在下，3-（2-氨基苯基）-1-丙醇的反应丙酮得到3,4-二氢-2（1H）-喹啉酮，分离产率为80％。通过该催化体系合成了五元​​，六元和七元的苯并稠合内酰胺。[反应：看文字]
• [EN] 2-OXO-3,4-DIHYDROQUINOLINE COMPOUNDS AS PLANT GROWTH REGULATORS<br/>[FR] COMPOSÉS 2-OXO-3,4-DIHYDROQUINOLÉINE À UTILISER EN TANT QUE RÉGULATEURS DE CROISSANCE DES PLANTES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2016128317A1

  公开（公告）日：2016-08-18

  The present invention relates to novel sulfonamide derivatives of formula (I), to processes and intermediates for preparing them, to plant growth regulator compositions comprising them and to methods of using them for controlling the growth of plants, improving plant tolerance to abiotic stress (including environmental and chemical stresses), inhibiting seed germination and/or safening a plant against phytotoxic effects of chemicals.

  本发明涉及公式(I)的新型磺胺衍生物，以及制备它们的过程和中间体，包括植物生长调节剂组合物和使用它们控制植物生长、提高植物对非生物胁迫（包括环境和化学胁迫）的耐受性、抑制种子萌发和/或保护植物免受化学物质的毒害作用的方法。
• &lsqb;3-(C5-14ALKYL-2-OXO-1,2,3,4-TETRAHYDRO-QUINOLIN-6-YL)-3-OXO-PROPENYL&rsqb;-PHENYL AND &lsqb;3-(C5-14ALKYL-2-OXO-1,2,3,4- TETRAHYDRO-QUINOLIN-6-YL)-3-OXO-PROPENYL&rsqb;-HETEROARYL DERIVATIVES HAVING ANTI-TUMOR ACTIVITY
  申请人：Allergan, Inc.

  公开号：US06683092B1

  公开（公告）日：2004-01-27

  Compounds of the formula where the variables have the meaning defined in the specification have anti-tumor activity.

  式中变量的含义在说明书中定义，这些化合物具有抗肿瘤活性。
• Design, Synthesis, and Pharmacology of New Triazole-Containing Quinolinones as CNS Active Agents
  作者：Wennan Zhao、Mingxia Song、Yi Hua、Yangnv Zhu、Wenli Liu、Qishan Xia、Xianqing Deng、Yushan Huang

  DOI：10.3390/molecules28041987

  日期：——

  disorder are the two of the most common central nervous system (CNS) diseases. Clinicians and patients call for new antidepressants, antiseizure medicines, and in particular drugs for depression and epilepsy comorbidities. In this work, a dozen new triazole-quinolinones were designed, synthesized, and investigated as CNS active agents. All compounds reduced the immobility time significantly during

  癫痫和重度抑郁症是两种最常见的中枢神经系统 (CNS) 疾病。临床医生和患者需要新的抗抑郁药、抗癫痫药，尤其是治疗抑郁症和癫痫合并症的药物。在这项工作中，设计、合成和研究了十几种新的三唑-喹啉酮类化合物作为中枢神经系统活性剂。在 50 mg/kg 的剂量下，所有化合物在小鼠强迫游泳试验 (FST) 期间显着减少不动时间。化合物 3f-3j 在 FST 中表现优于氟西汀，不动时间减少更多。化合物 3g 在尾部悬吊试验 (TST) 中以 50 mg/kg 的剂量也显着减少了不动时间，尽管其抗不动活性不如氟西汀。进行了旷场试验，消除了3g在FST和TST中的假阳性可能性，补充支持了3g的抗抑郁活性。我们还发现，除 3k 外，几乎所有化合物在 100 或 300 mg/kg 的最大电休克发作 (MES) 模型中均表现出抗癫痫活性。化合物 3c、3f 和 3g 的 ED50 分别为 63.4、78.9
• 一种N-取代的喹啉酮衍生物及其制备方法和应用
  申请人：井冈山大学

  公开号：CN116813592A

  公开（公告）日：2023-09-29

  本发明提供一种N‑取代的喹啉酮衍生物及其制备方法和应用，其结构通式如下式(I)所示。该化合物具有显著的抗抑郁与抗癫痫活性，从而使其能够应用于癫痫与抑郁疾病治疗领域。#imgabs0#