2-Amino-5-(2-bromo-1-hydroxyethyl)-3-chlorobenzonitrile | 213009-04-2

• 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: 2-Amino-5-(2-bromo-1-hydroxyethyl)-3-chlorobenzonitrile
• CAS: 213009-04-2
• 化学式: C₉H₈BrClN₂O
• 分子量: 275.532
• InChiKey: DZLQJROGEHPGHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-5-(2-bromo-1-hydroxyethyl)-3-chlorobenzonitrile 在 吡啶 作用下， 反应 24.0h， 生成 [(1R)-1-(4-amino-3-chloro-5-cyanophenyl)-2-bromoethyl] acetate
  参考文献：
  名称：

  Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol by lipase mediated enantioselective alcoholysis, hydrolysis and acylation

  摘要：

  Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol has been achieved by ethanol enantio-selective lipase-catalysed alcoholysis, hydrolysis and acylation. Although a good enantioselectivity was observed in the three reactions, the best results were obtained by hydrolysis. This alpha-bromohydrin is an intermediate in the synthesis of a new adrenergic agent. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00252-3
• 作为产物：
  描述：

  2-amino-5-(2-bromoacetyl)-3-chlorobenzonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以68%的产率得到2-Amino-5-(2-bromo-1-hydroxyethyl)-3-chlorobenzonitrile
  参考文献：
  名称：

  Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol by lipase mediated enantioselective alcoholysis, hydrolysis and acylation

  摘要：

  Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol has been achieved by ethanol enantio-selective lipase-catalysed alcoholysis, hydrolysis and acylation. Although a good enantioselectivity was observed in the three reactions, the best results were obtained by hydrolysis. This alpha-bromohydrin is an intermediate in the synthesis of a new adrenergic agent. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00252-3

文献信息

• Discovery of β-arrestin-biased β2-adrenoceptor agonists from 2-amino-2-phenylethanol derivatives
  作者：Anthony Yiu-Ho Woo、Xin-yue Ge、Li Pan、Gang Xing、Yong-mei Mo、Rui-juan Xing、Xiao-ran Li、Yu-yang Zhang、Irving W. Wainer、Mao-sheng Cheng、Rui-ping Xiao

  DOI：10.1038/s41401-018-0200-x

  日期：2019.8

  modulate GPCR signal transduction in such a way that desirable signals are enhanced to produce therapeutic effects while undesirable signals of the same GPCR are suppressed to avoid side effects. In the present study, we evaluated agonist bias for compounds developed along a drug discovery project of β2-adrenoceptor agonists. About 150 compounds, including derivatives of fenoterol, 2-amino-1-phenylethanol

  β-Arrestins 是一小类蛋白质，对 G 蛋白偶联受体 (GPCR) 的信号转导很重要。β-Arrestins 参与 GPCR 的脱敏。最近，出现了在激活单个 GPCR 下游的 G 蛋白与 β-抑制蛋白依赖性信号方面具有不同功效的偏向配体，可用于选择性调节 GPCR 信号转导，从而增强所需信号以产生治疗效果，同时抑制相同 GPCR 的不良信号以避​​免副作用。在本研究中，我们评估了沿 β2-肾上腺素受体激动剂药物发现项目开发的化合物的激动剂偏倚。获得或合成了大约 150 种化合物，包括非诺特罗的衍生物、2-氨基-1-苯乙醇和 2-氨基-2-苯乙醇，并最初在豚鼠气管平滑肌松弛试验或心肌细胞收缩试验中筛选其 β-肾上腺素受体介导的活性。使用 HTRF cAMP 测定和 PathHunter β-抑制蛋白测定进一步评估了 19 种生物活性化合物。他们在刺激 cAMP 合成和 β-arrestin
• [EN] NEW ETHANOLAMINE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES D'ETHANOLAMINE
  申请人：LABORATORIOS ALMIRALL, S.A.

  公开号：WO1996031466A1

  公开（公告）日：1996-10-10

  (EN) A compound which is an ethanolamine derivative of formula (I), wherein R1 is a pyridyl or NR2R3 group, wherein R2 is hydrogen or a C1-C4 alkyl or methanesulphonyl group and R3 is a C2-C4 alkanoyl group, an unsubstituted phenyl group or a phenyl group substituted by a carbamoyl group; m is from 4 to 8; and n is 2 or 3; or a pharmacologically acceptable salt thereof, has agonist activity on the adrenergic $g(b)-receptors of the bronchus.(FR) La présente invention décrit un composé qui est un dérivé d'éthanolamine de formule (I), dans laquelle R1 est un pyridyle ou un groupe NR2R3, dans lequel R2 représente un hydrogène ou un alkyle C1-C4 ou un groupe méthanesulphuryle et R3 représente un groupe alkanoyle C2-C4, un groupe phényle non substitué ou un groupe phényle substitué par un groupe carbamoyle; m est compris entre 4 et 8; et n vaut 2 ou 3; ou un de ses sels pharmaceutiquement acceptables, comporte une activité agoniste sur les récepteurs $g(b) adrénergiques des bronches.
• Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol by lipase mediated enantioselective alcoholysis, hydrolysis and acylation
  作者：Santiago Conde、Marta Fierros、Marı́a Isabel Rodrı́guez-Franco、Carles Puig

  DOI：10.1016/s0957-4166(98)00252-3

  日期：1998.7

  Resolution of 1-(4-amino-3-chloro-5-cyanophenyl)-2-bromo-1-ethanol has been achieved by ethanol enantio-selective lipase-catalysed alcoholysis, hydrolysis and acylation. Although a good enantioselectivity was observed in the three reactions, the best results were obtained by hydrolysis. This alpha-bromohydrin is an intermediate in the synthesis of a new adrenergic agent. (C) 1998 Elsevier Science Ltd. All rights reserved.