ethyl 2-(bezyloxy)-5-(2-bromoacetyl)benzoate | 56443-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(bezyloxy)-5-(2-bromoacetyl)benzoate
• 英文别名: Ethyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoate；ethyl 5-(2-bromoacetyl)-2-phenylmethoxybenzoate
• CAS: 56443-71-1
• 化学式: C₁₈H₁₇BrO₄
• 分子量: 377.235
• InChiKey: FCHBGPAUYQMKKC-UHFFFAOYSA-N

物化性质

• 熔点：
  116.5-117.5 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  510.8±45.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(bezyloxy)-5-(2-bromoacetyl)benzoate 在 palladium on activated charcoal 甲醇 、 sodium tetrahydroborate 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 377.5h， 生成 N-<2-<<2-hydroxy-2-<4-hydroxy-3-(hydroxymethyl)phenyl>ethyl>amino>ethyl>-2-methylpropanamide
  参考文献：
  名称：

  .beta.-Adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols

  摘要：

  Parallel series of 2-[(2-amidoethyl)amino]-1-arylethanols and 1-[(2-amidoethyl)amino]-3-(aryloxy)-2-propanols have been prepared, and the compounds were tested as beta-adrenoceptor stimulants on the heart and circulation of the dog. The corresponding 2-(alkylamino)-1-arylethanols and 3-(alkylamino)-2-propanols have been tested for comparison and the structure-activity relationships (SAR) examined. The arylethanols are potent full agonists, showing selectivity for the heart relative to blood vessels, while the (aryloxy)propanols are even more cardioselective and are partial agonists. Within a narrow series of 1-[(amidoethyl)amino]-3-(4-hydroxyphenoxy)-2-propanols, careful examination of the SAR of the amide group showed that great variation in cardioselectivity and degree of agonism may be produce. From this study ICI 118587, N-[20[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide, was selected for its high cardioselectivity and 50% agonist properties. This compound in under clinical evaluation as a cardiac stimulant.

  DOI：

  10.1021/jm00135a015
• 作为产物：
  描述：

  ethyl 5-acetylsalicylate 在 溴 、 potassium carbonate 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 ethyl 2-(bezyloxy)-5-(2-bromoacetyl)benzoate
  参考文献：
  名称：

  2-（β-芳基乙基氨基）-和4-（β-芳基乙基氨基）喹唑啉作为磷酸二酯酶抑制剂。

  摘要：

  具有不同动力学特性的几种形式的cAMP磷酸二酯酶的存在表明开发这种酶的组织选择性抑制剂的可行性。该观察在开发用于治疗可逆性阻塞性气道疾病的治疗剂中特别重要。本报告描述了一系列在2或4位具有β-芳基乙胺取代基的6,7-二甲氧基喹唑啉衍生物的设计，合成和药理学表征。喹唑啉核旨在赋予磷酸二酯酶高度的抑制活性，而β-芳基乙胺部分则旨在为肾上腺素能神经支配的组织提供选择性。本研究的目标化合物6和7 通过从适当的氯喹唑啉中间体取代氯的β-芳基乙胺制备氯乙烯。评价所得产物松弛豚鼠气管平滑肌和作为磷酸二酯酶抑制剂的能力。

  DOI：

  10.1021/jm00379a004

文献信息

• MILLEN, J.;RILEY, T. N.;WATERS, I. W.;HAMRICK, M. E., J. MED. CHEM., 1985, 28, N 1, 12-17
  作者：MILLEN, J.、RILEY, T. N.、WATERS, I. W.、HAMRICK, M. E.

  DOI：——

  日期：——
• US4021485A
  申请人：——

  公开号：US4021485A

  公开（公告）日：1977-05-03
• 2-(.beta.-Arylethylamino)- and 4-(.beta.-arylethylamino)quinazolines as phosphodiesterase inhibitors
  作者：J. Millen、Thomas N. Riley、I. W. Waters、M. E. Hamrick

  DOI：10.1021/jm00379a004

  日期：1985.1

  report describes the design, synthesis and pharmacological characterization of a series of 6,7-dimethoxyquinazoline derivatives having beta-arylethylamine substituents at the 2- or 4-positions. The quinazoline nucleus is intended to confer a high degree of inhibitory activity for phosphodiesterase while the beta-aryethylamine moieties are designed to provide selectivity for adrenergically innervated tissue

  具有不同动力学特性的几种形式的cAMP磷酸二酯酶的存在表明开发这种酶的组织选择性抑制剂的可行性。该观察在开发用于治疗可逆性阻塞性气道疾病的治疗剂中特别重要。本报告描述了一系列在2或4位具有β-芳基乙胺取代基的6,7-二甲氧基喹唑啉衍生物的设计，合成和药理学表征。喹唑啉核旨在赋予磷酸二酯酶高度的抑制活性，而β-芳基乙胺部分则旨在为肾上腺素能神经支配的组织提供选择性。本研究的目标化合物6和7 通过从适当的氯喹唑啉中间体取代氯的β-芳基乙胺制备氯乙烯。评价所得产物松弛豚鼠气管平滑肌和作为磷酸二酯酶抑制剂的能力。
• .beta.-Adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols
  作者：Jeffrey J. Barlow、Brian G. Main、H. Michael Snow

  DOI：10.1021/jm00135a015

  日期：1981.3

  Parallel series of 2-[(2-amidoethyl)amino]-1-arylethanols and 1-[(2-amidoethyl)amino]-3-(aryloxy)-2-propanols have been prepared, and the compounds were tested as beta-adrenoceptor stimulants on the heart and circulation of the dog. The corresponding 2-(alkylamino)-1-arylethanols and 3-(alkylamino)-2-propanols have been tested for comparison and the structure-activity relationships (SAR) examined. The arylethanols are potent full agonists, showing selectivity for the heart relative to blood vessels, while the (aryloxy)propanols are even more cardioselective and are partial agonists. Within a narrow series of 1-[(amidoethyl)amino]-3-(4-hydroxyphenoxy)-2-propanols, careful examination of the SAR of the amide group showed that great variation in cardioselectivity and degree of agonism may be produce. From this study ICI 118587, N-[20[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide, was selected for its high cardioselectivity and 50% agonist properties. This compound in under clinical evaluation as a cardiac stimulant.