(2S)-2-([(2,3-dichlorophenyl)oxy]methyl)oxirane | 134598-06-4

• 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: (2S)-2-([(2,3-dichlorophenyl)oxy]methyl)oxirane
• 英文别名: (s)-2,3-Dichlorophenyl glycidyl ether；(2S)-2-[(2,3-dichlorophenoxy)methyl]oxirane
• CAS: 134598-06-4
• 化学式: C₉H₈Cl₂O₂
• 分子量: 219.067
• InChiKey: BGOUOFHQLQPABA-LURJTMIESA-N

物化性质

• 沸点：
  308.0±22.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-([(2,3-dichlorophenyl)oxy]methyl)oxirane 、 1-(4-甲氧基苯基)-2-甲基丙烷-2-胺 在 盐酸 作用下， 以 乙醇 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 以60%的产率得到(2S)-1-[(2,3-dichlorophenyl)oxy]-3-((1,1-dimethyl-2-[4-(methyloxy)phenyl]ethyl)amino)-2-propanol
  参考文献：
  名称：

  Antagonists of the Calcium Receptor I. Amino Alcohol-Based Parathyroid Hormone Secretagogues

  摘要：

  Functional screening of the former SmithKline Beecham compound collection against the human calcium receptor (CaR) resulted in the identification of the amino alcohol-based hit 2 (IC50 = 11 mu M)Structure-activity Studies of 2 focused on the optimization of the right- and left-hand side aromatic moieties as well as the amino alcohol linker region. Critical to the optimization of this antagonist template was the discovery that the chirality of the C-2 secondary alcohol played a key role in enhancing both CaR potency as well as selectivity over the beta-adrenergic receptor subtypes. These SAR studies ultimately led to the identification of 38 (NPS 2143; SB-262470A), a potent and orally active CaR antagonist. Pharmacokinetic characterization of 38 in the rat revealed that this molecule had a large volume of distribution (11 L/kg), which resulted in a prolonged systemic exposure, protracted increases in the plasma levels of PTH, and an overall lack of net bone formation effect in a rodent model of osteoporosis.

  DOI：

  10.1021/jm900364m
• 作为产物：
  描述：

  二氯-苯酚 、 (S)-(+)- 间硝基苯磺酸缩水甘油酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以96%的产率得到(2S)-2-([(2,3-dichlorophenyl)oxy]methyl)oxirane
  参考文献：
  名称：

  Antagonists of the Calcium Receptor I. Amino Alcohol-Based Parathyroid Hormone Secretagogues

  摘要：

  Functional screening of the former SmithKline Beecham compound collection against the human calcium receptor (CaR) resulted in the identification of the amino alcohol-based hit 2 (IC50 = 11 mu M)Structure-activity Studies of 2 focused on the optimization of the right- and left-hand side aromatic moieties as well as the amino alcohol linker region. Critical to the optimization of this antagonist template was the discovery that the chirality of the C-2 secondary alcohol played a key role in enhancing both CaR potency as well as selectivity over the beta-adrenergic receptor subtypes. These SAR studies ultimately led to the identification of 38 (NPS 2143; SB-262470A), a potent and orally active CaR antagonist. Pharmacokinetic characterization of 38 in the rat revealed that this molecule had a large volume of distribution (11 L/kg), which resulted in a prolonged systemic exposure, protracted increases in the plasma levels of PTH, and an overall lack of net bone formation effect in a rodent model of osteoporosis.

  DOI：

  10.1021/jm900364m

文献信息

• Calcilytic compounds
  申请人：Del Mar G. Eric

  公开号：US20050032850A1

  公开（公告）日：2005-02-10

  The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

  本发明涉及钙解离化合物。 "钙解离化合物"是指能够抑制钙受体活性的化合物。还描述了使用钙解离化合物来抑制钙受体活性和/或在患者中获得有益效果的方法；以及可用于获得其他钙解离化合物的技术。
• CALCILYTIC COMPOUNDS
  申请人：Del Mar Eric G.

  公开号：US20070249702A1

  公开（公告）日：2007-10-25

  The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

  本发明涉及钙解离化合物。 “钙解离化合物”是指能够抑制钙受体活性的化合物。同时，本发明还描述了使用钙解离化合物来抑制钙受体活性和/或在患者中获得有益效果的方法；以及可用于获得其他钙解离化合物的技术。
• Pyridazinones having cardiotonic and beta blocking activity
  申请人：GLAXO WELLCOME INC.

  公开号：EP0412814A2

  公开（公告）日：1991-02-13

  Pyridazinones of the following formula (I): where R¹-R⁴ are a variety of substituents and L is a linking group, a pharmaceutical composition for treating congestive heart failure, novel intermediates, methods for such treatment and processes for preparing compounds of formula (I).

  下式(I)的哒嗪酮： 其中 R¹-R⁴ 是各种取代基，L 是连接基团；治疗充血性心力衰竭的药物组合物、新型中间体、治疗方法和制备式 (I) 化合物的工艺。
• US5053338A
  申请人：——

  公开号：US5053338A

  公开（公告）日：1991-10-01
• US5096904A
  申请人：——

  公开号：US5096904A

  公开（公告）日：1992-03-17