8-benzyloxy-5-(2,3-epoxypropoxy)-3,4-dihydro-2(1H)-quinolinone | 59826-17-4

• 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: 8-benzyloxy-5-(2,3-epoxypropoxy)-3,4-dihydro-2(1H)-quinolinone
• 英文别名: 8-phenylmethoxy-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril；5-(2',3'-epoxy)propoxy-8-benzyloxy-3,4-dihydrocarbostyril；8-benzyloxy-(5S)-5-oxiranylmethoxy-3,4-dihydro-1H-quinolin-2-one；5-(2,3-Epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyril；5-(oxiran-2-ylmethoxy)-8-phenylmethoxy-3,4-dihydro-1H-quinolin-2-one
• CAS: 59826-17-4
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: FTOLVSJSPXVSGL-UHFFFAOYSA-N

物化性质

• 熔点：
  106.5-107 °C
• 沸点：
  572.6±50.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  60.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-benzyloxy-5-(2,3-epoxypropoxy)-3,4-dihydro-2(1H)-quinolinone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 5-[3-(1,1-Dimethyl-2-phenyl-ethylamino)-2-hydroxy-propoxy]-8-hydroxy-3,4-dihydro-1H-quinolin-2-one; compound with oxalic acid
  参考文献：
  名称：

  Syntheses and .BETA.-adrenergic blocking activities of carbostyril derivatives.

  摘要：

  许多5-(3-氨基-2-羟基丙氧基)-8-烷氧基和酰氧基-3,4-二氢羰基苯并吡喃和5-(3-氨基-2-羟基丙氧基)-8-烷氧基羰基苯并吡喃是由5,8-二羟基-3,4-二氢羰基苯并吡喃合成的，并对其β-肾上腺素阻断活性进行了研究。其中，8-乙酰氧基-5-[3-(3,4-二甲氧基苯乙胺基)-2-羟基丙氧基]-3,4-二氢羰基苯并吡喃盐酸盐水合物（IVh）被证明具有强效的β1选择性肾上腺素阻断活性。

  DOI：

  10.1248/cpb.29.2166
• 作为产物：
  描述：

  8-benzyloxy-5-hydroxy-3,4-dihydrocarbostyril 生成 8-benzyloxy-5-(2,3-epoxypropoxy)-3,4-dihydro-2(1H)-quinolinone
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• 3,4-Dihydrocarbostyril derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04072683A1

  公开（公告）日：1978-02-07

  Novel (3'-alkylamino-2'-hydroxy)propoxy-3,4-dihydrocarbostyril derivatives having .beta.-adrenergic nerves blocking activity and hypotensive activity and useful as a remedy for angina pectoris, irregular pulse and hypertension, etc., represented by the formula, ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or aralkyl and R.sub.2 is C.sub.1 -C.sub.4 alkyl, are prepared by reacting a 3,4-dihydrocarbostyril derivative represented by the formula, ##STR2## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl or aralkyl, with an epihalogenohydrin represented by the formula, ##STR3## wherein X is halogen, reacting the resulting product with an alkylamine represented by the formula, R.sub.2 -- NH.sub.2 wherein R.sub.2 is as defined above, and, if necessary, reducing the resulting product.

  具有β-肾上腺能神经阻滞活性和降压活性的新型(3'-烷基氨基-2'-羟基)丙氧基-3,4-二氢咔波斯蒂尔衍生物，可用作治疗心绞痛、心律不齐和高血压等疾病的药物，其化学式为，其中R1为氢、C1-C4烷基或芳基烷基，R2为C1-C4烷基。通过将化学式所代表的3,4-二氢咔波斯蒂尔衍生物与化学式所代表的环氧卤水合物反应，然后将得到的产物与化学式所代表的烷基胺反应，其中R2为如上定义的烷基，必要时，还可以还原得到的产物。
• Substituted 2- (S) -hydroxy-3- (piperidin-4-yl-methylamino) -propyl ethers and substituted 2-aryl-2- (R) - hydroxy-1- (piperidin-4-yl-methyl) -ethylamine beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020037907A1

  公开（公告）日：2002-03-28

  This invention provides compounds of Formula I having the structure 1 wherein A, B, Z, R and R 1 are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  这项发明提供了具有结构式1的化合物，其中A、B、Z、R和R1如前文所定义，或其药学上可接受的盐，用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠道疾病、神经炎症、青光眼、眼压增高和频繁排尿；特别适用于治疗或抑制2型糖尿病。
• Carbostyril compounds connected via an oxyalkyl group with a piperidine
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05082847A1

  公开（公告）日：1992-01-21

  Carbostyril derivatives of Formula I: ##STR1## wherein: m is 0, 1, or 2; n is 0, 1, or 2; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is hydrogen, halogen, hydroxy, lower alkyl, lower alkoxy, aralkoxy, or acyloxy; R.sup.3 is hydrogen, halogen, lower alkyl, or lower alkoxy; R.sup.4 is hydrogen, hydroxy, lower alkyl, acyloxy, provided that when R.sup.4 is hydroxy or acyloxy, m and n are both 1; R.sup.5 is hydrogen or lower alkyl; and R.sup.6 is alkyl, hydroxyalkyl, alkoxyalkyl, or (dialkylamino)alkyl; and the pharmaceutically acceptable acid addition salts and N-oxides (at the carbostyril nitrogen) thereof, and compositions containing them, are useful in treating cardiovascular diseases, particularly arrhythmias. Methods of preparing intermediates, the compounds, their formulations and methods of treatment therewith are also disclosed.

  Carbostyril衍生物的化学式I: ##STR1## 其中：m为0、1或2；n为0、1或2；R.sup.1为氢或较低烷基；R.sup.2为氢、卤素、羟基、较低烷基、较低烷氧基、芳基氧基或酰氧基；R.sup.3为氢、卤素、较低烷基或较低烷氧基；R.sup.4为氢、羟基、较低烷基、酰氧基，但当R.sup.4为羟基或酰氧基时，m和n均为1；R.sup.5为氢或较低烷基；R.sup.6为烷基、羟基烷基、烷氧基烷基或（二烷基氨基）烷基；以及它们的药学可接受的酸盐和N-氧化物（在carbostyril氮上），以及含有它们的组合物，在治疗心血管疾病，特别是心律失常方面是有用的。还公开了制备中间体、化合物、它们的配方和治疗方法的方法。
• Studies on positive inotropic agents. IV. Synthesis of 5-(3-amino-2-hydroxypropoxy)-3,4-dihydro-8-hydroxy-2(1H)-quinolinone derivatives.
  作者：MICHIAKI TOMINAGA、HIDENORI OGAWA、EIYU YO、SHUJI YAMASHITA、YOUICHI YABUUCHI、KAZUYUKI NAKAGAWA

  DOI：10.1248/cpb.35.3699

  日期：——

  Many 5- (3-amino-2-hydroxypropoxy) -3, 4-dihydro-8-hydroxy-2 (1H) -quinolinone derivatives were synthesized and examined for positive inotropic activity on the canine heart. These compounds were prepared by the reaction of 8-alkoxy-5- (2, 3-epoxypropoxy) -2 (1H) -quinolinone derivatives and various amines. Among them, 3, 4-dihydro-8-hydroxy-5-[3- (1, 1, 3, 3-tetramethylbutylamino) propoxy] -2 (1H) -quinolinone hydrochloride (IIIf) was found to have potent positive inotropic activity with a relatively minor increase in heart rate.

  研究人员合成了许多 5-（3-氨基-2-羟基丙氧基）-3，4-二氢-8-羟基-2 (1H) -喹啉酮衍生物，并考察了它们对犬心脏的正性肌力活性。这些化合物由 8-烷氧基-5-（2，3-环氧丙氧基）-2 (1H) -喹啉酮衍生物和各种胺反应制备而成。其中，3, 4-二氢-8-羟基-5-[3-（1, 1, 3, 3-四甲基丁氨基）丙氧基] -2 (1H) -喹啉酮盐酸盐（IIIf）具有强效的正性肌力活性，心率增加相对较小。
• Carbostyril compounds
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04302588A1

  公开（公告）日：1981-11-24

  Carbostyril compounds represented by the formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom or an alkyl group; R.sub.2 represents a hydrogen atom, an alkyl group or a phenylalkyl group; R.sub.3 represents a hydrogen atom and R.sub.4 represents a phenylalkyl group or a phenoxyalkyl group; the 3,4-bond of the carbostyril nucleus represents a single or double bond, pharmaceutically acceptable acid addition salts thereof, and process for preparing the same.

  化合物的Carbostyril化合物由公式(I)表示：##STR1##其中R.sub.1代表氢原子或烷基；R.sub.2代表氢原子、烷基或苯基烷基；R.sub.3代表氢原子，R.sub.4代表苯基烷基或苯氧基烷基；Carbostyril核的3,4-键表示单键或双键，其药学上可接受的酸盐加成物，以及其制备过程。