3-[2-(3,4-dimethoxyphenyl)ethylamino]-1,2-propanediol | 66781-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[2-(3,4-dimethoxyphenyl)ethylamino]-1,2-propanediol
• 英文别名: 3-<<2-(3,4-dimethoxyphenyl)ethyl>amino>-1,2-propanediol；3-(3,4-dimethoxyphenethylamino)-1,2-propanediol；1,2-dihydroxy-3-(3,4-dimethoxyphenethylamino)propane；3-[2-(3,4-dimethoxyphenyl)ethylamino]1,2-propanediol；3-(3,4-dimethoxyphenethyl)amino-1,2-propanediol；1,2-Dihydroxy-3-(3,4-dimethoxyphenylethylamino)-propan；3-[2-(3,4-dimethoxyphenyl)ethylamino]propane-1,2-diol
• CAS: 66781-19-9
• 化学式: C₁₃H₂₁NO₄
• mdl: MFCD16472171
• 分子量: 255.314
• InChiKey: MXBYDXCALGSKTG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.3±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  71
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(3,4-dimethoxyphenyl)ethylamino]-1,2-propanediol 在 吡啶 、 盐酸 、 sodium acetate 、 sodium hydride 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 27.5h， 生成 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[4-(5-methyl-1H-imidazol-2-yl)phenoxy]propan-2-ol
  参考文献：
  名称：

  .beta.1-Selective adrenoceptor antagonists: examples of the 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazole class

  摘要：

  A series of 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazoles is described. The compounds were investigated in vitro for beta-adrenoceptor antagonism, and several examples were found to be selective for the beta 1-adrenoceptor. The structure--activity relationship exhibited by this series of compounds is discussed. (S)-2-[p-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-2-hydroxypropoxy]phenyl]-4-(2 -thienyl)imidazole [(S)-13] was over 100 times more selective than atenolol for the beta 1-adrenergic receptor and has been selected for in-depth studies.

  DOI：

  10.1021/jm00361a004
• 作为产物：
  描述：

  缩水甘油 、 3,4-二甲氧基苯乙胺 生成 3-[2-(3,4-dimethoxyphenyl)ethylamino]-1,2-propanediol
  参考文献：
  名称：

  [(Arylcarbonyl)oxy]propanolamines. 1. Novel .beta.-blockers with ultrashort duration of action

  摘要：

  Novel [(arylcarbonyl)oxy]propanolamines were synthesized and investigated as potential ultrashort-acting beta-adrenergic receptor blockers. Many of these analogues exhibited good potency and short duration. The N-ureidoalkyl analogue 85 (ACC-9089) has a potency equal to propranolol and a duration of action of about 21 min in the dog. It has been selected as a candidate for further clinical study. Structure-activity relationships and structure-duration relationships for these new beta-blockers are also discussed.

  DOI：

  10.1021/jm00374a013

文献信息

• Process for preparing alkoxyalkyl-idenehydrazinopyridazine derivatives
  申请人：I.S.F. Socièta per Azioni

  公开号：EP0274409A3

  公开（公告）日：1989-06-07

  A process for preparing a compound of the formula (4): is described wherein R3 and R4 are both hydrogen or together are =CR1R2, where R1 is hydrogen or C1-3alkyl and R2 is Cl-3alkyl, carboxy or phenyl, which comprises reducing a compound of the formula (5) : wherein Ph is phenyl, X is WN or O wherein W is 3,4-di(MeO)Ph(CH2)2-; Y and Z are both hydrogen or together are a protecting group and thereafter : i) removing the triphenylmethyl group and any other protecting groups; il) when X is WN optionally reacting with R1R2CO or when X is O reacting with R1R2CO and converting the product so formed to an epoxide of the formula (9) : which is reacted with 3,4-dimethoxyphenethylamine, and thereafter optionally removing the CR1R2 group by hydrolysis.

  描述了一种制备化合物的过程，其化学式为(4)：其中R3和R4都是氢或者一起是=CR1R2，其中R1是氢或者C1-3烷基，R2是Cl-3烷基、羧基或苯基，包括还原化合物的过程的化学式为(5)：其中Ph是苯基，X是WN或O，其中W是3,4-二甲氧基苯基(CH2)2-；Y和Z都是氢或者一起是保护基，然后：i)去除三苯甲基基团和其他保护基；ii)当X是WN时，可以选择与R1R2CO反应，当X是O时，与R1R2CO反应并将产物转化为化学式(9)的环氧化合物：然后与3,4-二甲氧基苯乙胺反应，然后通过水解可选择去除CR1R2基团。
• N-Aralkyl containing cyanopyridines
  申请人：Merck & Co., Inc.

  公开号：US04208416A1

  公开（公告）日：1980-06-17

  N-Aralkylamino-OR-propoxycyanopyridines having pharmacological activity are disclosed.

  揭示了具有药理活性的N-芳基氨基-OR-丙氧基氰吡啶。
• Thieno[3,2-c]pyridines
  申请人：Sandoz Ltd.

  公开号：US04165374A1

  公开（公告）日：1979-08-21

  This invention provides compounds of formula I ##STR1## wherein R.sub.1 is (i) hydrogen or alkyl of 1 to 4 carbon atoms, or (ii) chlorine or bromine, in the 2, 3 or 7 position, or (iii) fluorine, cyano or COOB, wherein B is alkyl of 1 to 4 carbon atoms, in the 2 or 3 position, R.sub.2 is (i) hydrogen or alkyl of 1 to 4 carbon atoms, or (ii) chlorine or bromine, in the 2, 3 or 7 position, or (iii) fluorine, in the 2 or 3 position, either R.sub.3 is a group --COR.sub.4, wherein R.sub.4 is alkyl of 1 to 17 carbon atoms, phenyl, phenyl monosubstituted by nitro, phenyl mono- or disubstituted by alkyl of 1 to 4 carbon atoms or halogen with an atomic number of 9 to 35, phenyl mono-, di- or trisubstituted by alkoxy of 1 to 4 carbon atoms, or a group D--COOH, wherein D is ethylene or trimethylene, and R is phenylalkyl of 8 to 10 carbon atoms, phenylalkyl of 8 to 10 carbon atoms monosubstituted in the phenyl radical by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen with an atomic number of 9 to 35, or phenylalkyl of 8 to 10 carbon atoms disubstituted in the phenyl radical by alkoxy of 1 to 4 carbon atoms, the phenyl ring of each of the phenylalkyl radicals being separated by at least 2 carbon atoms from the nitrogen atom to which R is bound, alkyl of 3 to 7 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkyl of 3 to 7 carbon atoms monosubstituted by alkyl of 1 to 4 carbon atoms, .alpha.-dialkylpropinyl of 5 to 9 carbon atoms, .alpha.-dialkylallyl of 5 to 9 carbon atoms, or phenoxyalkyl of 8 to 11 carbon atoms, the oxygen atom of the phenoxyalkyl radical being separated by at least two carbon atoms from the nitrogen atom to which R is bound, or R.sub.3 is hydrogen and R is phenylalkyl of 8 to 10 carbon atoms, phenylalkyl of 8 to 10 carbon atoms monosubstituted in the phenyl radical by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen with an atomic number of 9 to 35, or phenylalkyl of 8 to 10 carbon atoms disubstituted in the phenyl radical by alkoxy of 1 to 4 carbon atoms, the phenyl ring of each of the phenylalkyl radicals being separaed by at least 2 carbon atoms from the nitrogen atom to which R is bound, with the general proviso that, when R.sub.1 is cyano or COOB, R.sub.2 is other than fluorine, chlorine or bromine, in the 2 or 3 position, useful in the treatment of heart diseases, hyperlipoidemia and hyperglycemia.

  本发明提供了式I的化合物：##STR1## 其中R.sub.1是（i）1至4个碳原子的氢或烷基，或（ii）在2,3或7位上的氯或溴，或（iii）在2或3位上的氟，氰或COOB，其中B是1至4个碳原子的烷基；R.sub.2是（i）1至4个碳原子的氢或烷基，或（ii）在2,3或7位上的氯或溴，或（iii）在2或3位上的氟；R.sub.3是一个基团，--COR.sub.4，其中R.sub.4是1至17个碳原子的烷基，苯基，被硝基单取代的苯基，被1至4个碳原子的烷基或原子序数为9至35的卤素单取代的苯基，被1至4个碳原子的烷氧基单、双或三取代的苯基，或一个基团D--COOH，其中D是乙烯或三亚甲基；R是8至10个碳原子的苯基烷基，被1至4个碳原子的烷基、1至4个碳原子的烷氧基或原子序数为9至35的卤素单取代的8至10个碳原子的苯基烷基，或被1至4个碳原子的烷氧基双取代的8至10个碳原子的苯基烷基，每个苯基烷基基团的苯环与R所结合的氮原子之间至少相隔2个碳原子；3至7个碳原子的烷基，3至7个碳原子的环烷基，被1至4个碳原子的烷基单取代的3至7个碳原子的环烷基，5至9个碳原子的.alpha.-二烷基丙炔基，5至9个碳原子的.alpha.-二烷基烯基，或8至11个碳原子的苯氧基烷基，其中苯氧基烷基的氧原子与R所结合的氮原子之间至少相隔2个碳原子；或者R.sub.3是氢，R是8至10个碳原子的苯基烷基，被1至4个碳原子的烷基、1至4个碳原子的烷氧基或原子序数为9至35的卤素单取代的8至10个碳原子的苯基烷基，或被1至4个碳原子的烷氧基双取代的8至10个碳原子的苯基烷基，每个苯基烷基基团的苯环与R所结合的氮原子之间至少相隔2个碳原子。其中一般规定，当R.sub.1是氰或COOB时，R.sub.2不是2或3位上的氟、氯或溴，则该化合物可用于治疗心脏疾病、高脂血症和高血糖症。
• 3-Amino-2-hydroxypropoxyaryl imidazole derivatives
  申请人：Merck & Co., Inc.

  公开号：US04440774A1

  公开（公告）日：1984-04-03

  Novel substituted imidazoles of the formula ##STR1## and methods for their preparation are disclosed. These imidazoles, and their salts, exhibit pharmacological activity which includes antihypertensive activity and .beta.-adrenergic blocking activity.

  本发明揭示了式子##STR1##的新型取代咪唑衍生物及其制备方法。这些咪唑衍生物及其盐具有药理活性，包括抗高血压活性和β-肾上腺素能阻滞活性。
• .beta.-Adrenergic 2-[4-(3-amino-2-hydroxypropoxy)phenyl]imidazoles
  申请人：Merck & Co., Inc.

  公开号：US04567276A1

  公开（公告）日：1986-01-28

  Novel substituted imidazoles and methods for their preparation are disclosed. These imidazoles, and their salts, exhibit pharmacological activity which includes antihypertensive activity and .beta.-adrenergic blocking activity.

  本发明揭示了一种代替咪唑的新型咪唑化合物及其制备方法。这些咪唑化合物及其盐具有药理活性，包括抗高血压活性和β-肾上腺素能阻滞活性。