2-Hydroxy-5-[[bis(phenylmethyl)amino]acetyl]benzoic acid, methyl ester, hydrochloride | 24099-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hydroxy-5-[[bis(phenylmethyl)amino]acetyl]benzoic acid, methyl ester, hydrochloride
• 英文别名: Methyl 5-[2-(dibenzylamino)acetyl]-2-hydroxybenzoate;hydrochloride
• CAS: 24099-13-6
• 化学式: C₂₄H₂₃NO₄*ClH
• 分子量: 425.912
• InChiKey: PIDGASBUYKWVIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-5-[[bis(phenylmethyl)amino]acetyl]benzoic acid, methyl ester, hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 98.0h， 生成 methyl 5-(2-amino-1-hydroxyethyl)-2-hydroxybenzoate hydrochloride
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008
• 作为产物：
  描述：

  阿司匹林 在 盐酸 、 三氯化铝 、 1,4-dioxane dibromide 、 硫酸 作用下， 以 1,4-二氧六环 、 乙醚 、 硝基苯 、 丁酮 为溶剂， 反应 39.0h， 生成 2-Hydroxy-5-[[bis(phenylmethyl)amino]acetyl]benzoic acid, methyl ester, hydrochloride
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008

文献信息

• 4-Hydroxy-1,3-benzenedimethanol derivatives
  申请人：Allen & Hanburys Limited

  公开号：US04160036A1

  公开（公告）日：1979-07-03

  Compounds of the general formula (I): ##STR1## in which one or more substituents R.sub.1 may be present and in which: R.sub.1 represents a halogen atom, preferably fluorine or chlorine, or a trifluoromethyl group or a group --NR.sub.5 R.sub.6 in which R.sub.5 and R.sub.6 which may be the same or different represent a hydrogen atom, or an alkyl group containing from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms or an acyl group, preferably the residue of a C.sub.1 -C.sub.6 alkanoic acid; X represents a straight or branched chain alkyl group containing 2 to 6 carbon atoms; and R.sub.2 and R.sub.3 which may be the same or different each represent a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, preferably a methyl group; and R.sub.4 represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, are provided together with processes for the production thereof. They have a .beta..sub.2 -stimulant activity.

  通式（I）的化合物：##STR1## 其中一个或多个取代基R.sub.1可能存在，其中：R.sub.1代表卤素原子，最好是氟或氯，或三氟甲基基团或基团--NR.sub.5 R.sub.6，其中R.sub.5和R.sub.6可以相同也可以不同，代表氢原子，或含有1至6个碳原子的烷基基团，最好是1至4个碳原子或酰基团，最好是C.sub.1 -C.sub.6烷酸的残基；X代表含有2至6个碳原子的直链或支链烷基基团；R.sub.2和R.sub.3可以相同也可以不同，每个代表1至4个碳原子的氢原子或烷基基团，最好是甲基基团；R.sub.4代表氢原子或含有1至4个碳原子的烷基基团，以及它们的生产方法一起提供。它们具有β2-受体激动剂活性。
• Saligenin analogs of sympathomimetic catechol amines
  作者：David T. Collin、David. Hartley、David. Jack、Lawrence H. C. Lunts、J. C. Press、Alexander C. Ritchie、Paul. Toon

  DOI：10.1021/jm00298a022

  日期：1970.7.1
• SHANG YUN; WANG YIJUN; FENG JUNCAI; ZHANG NANXIAN; CHEN WEIXING; GAO RUIQ+, NANTSZIN DASYUEH SYUEHBAO TSZYZHAN KEHSYUEH, NANJING DAXUE XUE BAO, J. NA+
  作者：SHANG YUN、 WANG YIJUN、 FENG JUNCAI、 ZHANG NANXIAN、 CHEN WEIXING、 GAO RUIQ+

  DOI：——

  日期：——