3-ethyl-4(1H)-quinolone | 143494-68-2

• 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: 3-ethyl-4(1H)-quinolone
• 英文别名: 3-ethyl-1H-quinolin-4-one
• CAS: 143494-68-2
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: OYCKIBTUGGCAPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethyl-4(1H)-quinolone 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4'-<(3-ethyl-1,4-dihydro-4-oxoquinolinyl)methyl>biphenyl-2-carboxylic acid
  参考文献：
  名称：

  New nonpeptide angiotensin II receptor antagonists. 2. Synthesis, biological properties, and structure-activity relationships of 2-alkyl-4-(biphenylylmethoxy)quinoline derivatives

  摘要：

  A novel series of nonpeptidic angiotensin II (AII) receptor antagonists is reported, derived from linkage of the biphenylcarboxylic acid or biphenylyltetrazole moiety found in previously described antagonists via a methyleneoxy chain to the 4-position of a 2-alkyl quinoline. When evaluated in an in vitro binding assay using a guinea pig adrenal membrane preparation, compounds in this series generally gave IC50 values in the range 0.01-1 muM. Structure-activity studies showed the quinoline nitrogen atom and a short alkyl chain at the quinoline 2-position to be essential for receptor binding. On intravenous administration in a normotensive rat model, the more potent compounds inhibited the AII-induced pressor response with ED50 values in the range 0.1-2.0 mg/kg. One of the compounds, 2-ethyl-4-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methoxy]quinoline (5g), demonstrated good oral activity in two rat models. At doses in the range 1-10 mg/kg in AII-infused, normotensive rats, the compound exhibited a dose-related inhibition of the pressor response with a good duration of action at the higher doses. In a renal hypertensive rat model, compound 5g showed a rapid and sustained lowering of blood pressure at a dose of 5 mg/kg. On the basis of its profile, this compound, designated ICID8731, has been selected for clinical evaluation.

  DOI：

  10.1021/jm00100a007
• 作为产物：
  描述：

  ethyl 3-ethyl-1,4-dihydro-4-oxoquinoline-2-carboxylate 在 sodium hydroxide 、 正十二烷基苯 作用下， 反应 2.08h， 生成 3-ethyl-4(1H)-quinolone
  参考文献：
  名称：

  New nonpeptide angiotensin II receptor antagonists. 2. Synthesis, biological properties, and structure-activity relationships of 2-alkyl-4-(biphenylylmethoxy)quinoline derivatives

  摘要：

  A novel series of nonpeptidic angiotensin II (AII) receptor antagonists is reported, derived from linkage of the biphenylcarboxylic acid or biphenylyltetrazole moiety found in previously described antagonists via a methyleneoxy chain to the 4-position of a 2-alkyl quinoline. When evaluated in an in vitro binding assay using a guinea pig adrenal membrane preparation, compounds in this series generally gave IC50 values in the range 0.01-1 muM. Structure-activity studies showed the quinoline nitrogen atom and a short alkyl chain at the quinoline 2-position to be essential for receptor binding. On intravenous administration in a normotensive rat model, the more potent compounds inhibited the AII-induced pressor response with ED50 values in the range 0.1-2.0 mg/kg. One of the compounds, 2-ethyl-4-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methoxy]quinoline (5g), demonstrated good oral activity in two rat models. At doses in the range 1-10 mg/kg in AII-infused, normotensive rats, the compound exhibited a dose-related inhibition of the pressor response with a good duration of action at the higher doses. In a renal hypertensive rat model, compound 5g showed a rapid and sustained lowering of blood pressure at a dose of 5 mg/kg. On the basis of its profile, this compound, designated ICID8731, has been selected for clinical evaluation.

  DOI：

  10.1021/jm00100a007

文献信息

• TRPV1 Antagonists
  申请人：AbbVie Inc.

  公开号：US20130158067A1

  公开（公告）日：2013-06-20

  Disclosed herein are compounds of formula (I): or pharmaceutically acceptable salts thereof, wherein X 1 , L, R x , R y , R z , A, m, n, p, q, s, and positions a and b are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

  披露于此的是公式（I）的化合物： 或其药用可接受的盐，其中X 1 ，L，R x ，R y ，R z ，A，m，n，p，q，s，以及位置a和b如说明书所述定义。还披露了包含此类化合物的组合物以及使用此类化合物和组合物治疗状况和失调的方法。
• 4(1H)-Quinolones Having Antimalarial Activity With Reduced Chemical Resistance
  申请人：Manetsch Roman

  公开号：US20130123258A1

  公开（公告）日：2013-05-16

  Provided are 4(1H)-quinolone derivatives effective in inhibiting or eliminating the viability of at least one of the stages in the life-cycle of the malarial parasite, and to show a reduced propensity to induce resistance to the compound by the target parasite. In particular, the compounds can be derivatives of phenoxyethoxy-quinolones, and including, but not only, 7-(2-phenoxyethoxy)quinolin derivatives. These compounds may be administered by themselves, with at least one other derivative compound, or with other antimalarial compounds, to an animal or human subject. The therapeutic compositions can be and formulated to reduce the extent of a Plasmodium infection in the recipient subject, or to reduce the likelihood of the onset or establishment of a Plasmodium infection if administered prior to the parasite contacting the subject. The therapeutic compositions can be formulated to provide an effective single dose amount of an antimalarial compound or multiple doses for administering over a period of time.

  提供了4(1H)-喹啉酮衍生物，能有效抑制或消除疟原虫生命周期中至少一个阶段的生存能力，并且显示出减少目标寄生虫对化合物产生抗药性的倾向。具体来说，这些化合物可以是苯氧乙氧基喹啉酮的衍生物，包括但不限于7-(2-苯氧乙氧基)喹啉衍生物。这些化合物可以单独或与至少另一种衍生物化合物或其他抗疟疾化合物一起，向动物或人类受试者施用。治疗组合物可以配制成减少受试者体内疟原虫感染程度的程度，或者在寄生虫接触受试者之前施用，以减少疟原虫感染的可能性。治疗组合物可以配制成提供有效的单剂量抗疟疾化合物或多剂量，以在一段时间内施用。
• TRPV1 ANTAGONISTS
  申请人：AbbVie Inc.

  公开号：US20130172334A1

  公开（公告）日：2013-07-04

  Disclosed herein are compounds of formula (I): or pharmaceutically acceptable salts thereof, wherein X 1 , L, R x , R y , G, Z, A, m, n, and p are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

  本文公开了公式(I)的化合物：或其药学上可接受的盐，其中X1，L，Rx，Ry，G，Z，A，m，n和p如规范中定义。还公开了包含这些化合物的组合物以及使用这些化合物和组合物治疗疾病和疾病的方法。
• US8859584B2
  申请人：——

  公开号：US8859584B2

  公开（公告）日：2014-10-14
• US8877752B2
  申请人：——

  公开号：US8877752B2

  公开（公告）日：2014-11-04