2-[4-(2-溴乙基)苯氧基]-2-甲基丙酸乙酯 | 167213-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[4-(2-溴乙基)苯氧基]-2-甲基丙酸乙酯
• 英文名称: ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropionate
• 英文别名: ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoate；ethyl 2-[4-(2-bromoethyl)phenoxy]isobutyrate；2-[4-(2-bromoethyl)phenoxy]-2-methylpropionic ethyl ester
• CAS: 167213-40-3
• 化学式: C₁₄H₁₉BrO₃
• 分子量: 315.207
• InChiKey: BSARASXZMNRHDV-UHFFFAOYSA-N

物化性质

• 沸点：
  359.2±22.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-(2-溴乙基)苯氧基]-2-甲基丙酸乙酯 在 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-[4-(2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl)phenoxy]-2-methylpropionic acid
  参考文献：
  名称：

  β3-Adrenoceptor agonists for the treatment of frequent urination and urinary incontinence: 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acid

  摘要：

  In a search for novel analogues of beta (3)-adrenoceptor (AR) agonists relaxing the bladder for treatment of urinary dysfunction, 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acids (1a-e), into which a fibrate-like structure ha been incorporated, were synthesised. Compound la was found to be a selective beta (3)-AR agonist in functional assays using the ferret detrusor (VAR), rat uterus (beta (2)-AR), and rat atrium (beta (1)-AR): beta (3): EC50 = 7.8 nM, beta (2): IC50 = 7,300 nM, beta (1): EC20 = 23,000 nM. The introduction of a chlorine atom or methyl substituent at the ortho-position on the phenyl ring of la further improved VAR selectivity. In an in vivo study, la lowered intrabladder pressure (ED50 = 31 mug/kg) in rats, without increasing heart rate, in keeping with the in vitro results. Consequently, it is proposed that la and its analogues (1b e), possess beta (3)-AR agonistic activity in the absence of undesirable beta (1)- or beta (2)-AR mediated actions. and may be useful for clinical treatment and pharmacological studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00240-1
• 作为产物：
  描述：

  2-甲基-2-(苯氧基)丙酸乙酯 在 三乙基硅烷 、 三氯化铝 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-[4-(2-溴乙基)苯氧基]-2-甲基丙酸乙酯
  参考文献：
  名称：

  β3-Adrenoceptor agonists for the treatment of frequent urination and urinary incontinence: 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acid

  摘要：

  In a search for novel analogues of beta (3)-adrenoceptor (AR) agonists relaxing the bladder for treatment of urinary dysfunction, 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acids (1a-e), into which a fibrate-like structure ha been incorporated, were synthesised. Compound la was found to be a selective beta (3)-AR agonist in functional assays using the ferret detrusor (VAR), rat uterus (beta (2)-AR), and rat atrium (beta (1)-AR): beta (3): EC50 = 7.8 nM, beta (2): IC50 = 7,300 nM, beta (1): EC20 = 23,000 nM. The introduction of a chlorine atom or methyl substituent at the ortho-position on the phenyl ring of la further improved VAR selectivity. In an in vivo study, la lowered intrabladder pressure (ED50 = 31 mug/kg) in rats, without increasing heart rate, in keeping with the in vitro results. Consequently, it is proposed that la and its analogues (1b e), possess beta (3)-AR agonistic activity in the absence of undesirable beta (1)- or beta (2)-AR mediated actions. and may be useful for clinical treatment and pharmacological studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00240-1

文献信息

• SUBSTITUTED IMIDAZOLONE DERIVATIVES, PREPARATIONS AND USES
  申请人：Bouey Edith

  公开号：US20100004159A1

  公开（公告）日：2010-01-07

  The present invention relates to polysubstituted imidazolone derivatives, to the pharmaceutical compositions comprising them and to the therapeutic uses thereof in the human and animal health fields. The present invention also relates to a process for preparing these derivatives.

  本发明涉及多取代咪唑酮衍生物，包括它们的药物组合物以及在人类和动物健康领域中的治疗用途。本发明还涉及一种制备这些衍生物的方法。
• BETA-3 RECEPTOR LIGANDS AND THEIR USE IN THERAPY
  申请人：Scilimati Antonio

  公开号：US20100075977A1

  公开（公告）日：2010-03-25

  The present invention relates to new compounds, ligands of the beta-3 adrenergic receptor, their preparation and their use in therapy or as research tools for said receptor; the invention also relates to a process for the preparation of the compounds of the invention and the use of inverse agonists of the beta-3 adrenergic receptor as medicaments.

  本发明涉及新化合物，β-3肾上腺素受体的配体，它们的制备以及它们在治疗或作为该受体的研究工具中的使用；该发明还涉及一种制备本发明化合物的方法以及将β-3肾上腺素受体的反向激动剂用作药物的用途。
• Stereospecific synthesis and bio-activity of novel β3-adrenoceptor agonists and inverse agonists
  作者：Maria Grazia Perrone、Ernesto Santandrea、Laura Bleve、Paola Vitale、Nicola Antonio Colabufo、Ralf Jockers、Ferdinando Maria Milazzo、Anna Floriana Sciarroni、Antonio Scilimati

  DOI：10.1016/j.bmc.2007.11.060

  日期：2008.3

  towards beta(3)-adrenoceptor and their affinity for beta(1)- and beta(2)-adrenergic receptors. Stereochemical features were found to play a crucial role in determining the behaviour of such compounds. In particular, alpha-racemic, (alphaR)- and (alphaS)-2-4-[2-(2-hydroxy-2-phenylethylamino)ethyl]phenoxy}-2- methylpropanoic acid, (alpha-rac, beta-rac)-, (alphaR, betaS)- and (alphaR, betaR)- 2-4-[2-(2-

  由于β（3）-肾上腺素能受体广泛分布于体内，因此正成为治疗多种疾病的诱人靶标，例如肥胖，2型糖尿病，代谢综合征，恶病质，膀胱过度活动症，肠道溃疡性炎症，早产，焦虑和抑郁症以及心力衰竭。以高收率制备属于具有一个或两个立体生成中心的芳基乙醇胺类的新化合物，为外消旋体和旋光形式。然后，评估他们对β（3）-肾上腺素受体的内在活性以及对β（1）-和β（2）-肾上腺素受体的亲和力。发现立体化学特征在确定此类化合物的行为中起关键作用。特别是，α-外消旋，（alphaR）-和（alphaS）-2- 4- [2-（2-（2-羟基-2-苯基乙基氨基）乙基]苯氧基} -2-甲基丙酸，（alpha-rac，beta-rac）-，（alphaR，发现βS）-和（αR，βR）-2- 4- [2-（2-（2-羟基-2-苯基乙基氨基）乙基]苯氧基}丙酸具有β（3）-肾上腺素受体激动活性。而（alphaS，betaS）-和（alphaS，betaR）-2-
• Substituted phenoxyisobutyric acids and esters
  申请人：Adir et Compagnie

  公开号：US05512595A1

  公开（公告）日：1996-04-30

  New substituted phenoxyisobutyric acids and esters that can be used as medicaments and correspond to the formula: ##STR1## wherein X, A, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and Z are as defined in the description. Those compounds and their physiologically tolerable salts can be used therapeutically.

  新的替代苯氧异丁酸及其酯，可用作药物，符合以下公式：##STR1## 其中X、A、R、R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、R.sub.6、R.sub.7和Z如描述中定义。这些化合物及其生理耐受盐可用于治疗。
• 2-methylpropionic acid derivatives and pharmaceutical compositions comprising the same
  申请人：KISSEI PHARMACEUTICAL CO., LTD.

  公开号：US20030166719A1

  公开（公告）日：2003-09-04

  The present invention provides novel 2-methylpropionic acid derivatives represented by the general formula: 1 (wherein R 1 represents a hydroxy group, a lower alkoxy group or an aralkyl group; R 2 represents a hydroxy group, a lower alkyl group or a halogen atom; A represents an oxygen atom or an imino group; the carbon atom marked with (R) represents a carbon atom in R configuration; and the carbon atom marked with (S) represents a carbon atom in S configuration) and pharmaceutically acceptable salts thereof, which have excellent &bgr; 3 -adrenoceptor stimulating effects and are useful as agents for the prevention or treatment of obesity, hyperglycemia, the diseases caused by intestinal hypermotility, pollakiuria, urinary incontinence, depression, or the diseases caused by biliary calculi or hypermotility of biliary tract.

  本发明提供了一种新的2-甲基丙酸衍生物，其通式表示为：1（其中R1代表一个羟基、一个较低的烷氧基或一个芳基烷基；R2代表一个羟基、一个较低的烷基或一个卤原子；A代表一个氧原子或一个亚胺基；标有（R）的碳原子代表R构型中的一个碳原子；标有（S）的碳原子代表S构型中的一个碳原子），以及其药学上可接受的盐，具有优异的β3-肾上腺素受体刺激效应，可用作预防或治疗肥胖、高血糖、由肠道过度运动引起的疾病、尿频、尿失禁、抑郁症或胆结石或胆道过度运动引起的疾病的药剂。