2-溴-1-(3-氯-4-苯基甲氧基苯基)乙酮 | 73898-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-(3-氯-4-苯基甲氧基苯基)乙酮
• 英文名称: 1-[4-(benzyloxy)-3-chlorophenyl]-2-bromoethanone
• 英文别名: 4'-benzyloxy-2-bromo-3'-chloroacetophenone；1-[4-(Benzyloxy)-3-chlorophenyl]-2-bromoethan-1-one；2-bromo-1-(3-chloro-4-phenylmethoxyphenyl)ethanone
• CAS: 73898-28-9
• 化学式: C₁₅H₁₂BrClO₂
• 分子量: 339.616
• InChiKey: JFGYOEJZIYBXRS-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±40.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴-1-(3-氯-4-苯基甲氧基苯基)乙酮 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 sodium ethanolate 作用下， 以 丁酮 为溶剂， 反应 12.0h， 生成 α-(aminomethyl)-(3-chloro-4-hydroxyphenyl)methanol
  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：

  1-(3-氯-4-苯基甲氧基苯基)乙酮 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 以33%的产率得到2-溴-1-(3-氯-4-苯基甲氧基苯基)乙酮
  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

• [EN] 1-'2-(4-HYDROXYPHENYL)-2-HYDROXYETHYL!-PIPERIDIN-4-OL COMPOUNDS AS NMDA RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES DE 1-[2-(4-HYDROXYPHENYL)-2-HYDROXYETHYL]-PIPERIDIN-4-OL EN TANT QU'ANTAGONISTES DU RECEPTEUR DU NMDA
  申请人：PFIZER JAPAN INC

  公开号：WO2005035522A1

  公开（公告）日：2005-04-21

  This invention provides a compound of the formula (I), wherein R1 and R2 independently represents a hydrogen atom or the like; R3 represents an aryl group having from 6 to 10 ring carbon or the like; said aryl groups having from 6 to 10 ring carbon atoms and said heteroaryl groups having from 5 to 10 atoms are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents a; said substituents a are selected from the group consisting of halogen atoms or the like; or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of NMDA NR2B receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了式(I)的化合物，其中R1和R2分别表示氢原子或类似物；R3表示具有6至10个环碳或类似物的芳基基团；所述芳基基团具有6至10个环碳原子和所述杂环芳基基团具有5至10个原子，未经取代或通过从取代基a的群组中选择至少一种取代基而被取代；所述取代基a被选择自卤素原子或类似物的群组；或该化合物的药学上可接受的酯或其药学上可接受的盐。这些化合物对于治疗由NMDA NR2B受体过度激活引起的疾病条件，如疼痛等在哺乳动物中很有用。本发明还提供了包含上述化合物的药物组合物。
• 1-'2-(4-Hydroxyphenyl)-2-hydroxyethyl!-piperidin-4-ol compounds as nmda receptor antagonists
  申请人：Ando Kazuo

  公开号：US20070021414A1

  公开（公告）日：2007-01-25

  This invention provides a compound of the formula (I), wherein R 1 and R 2 independently represents a hydrogen atom or the like; R 3 represents an aryl group having from 6 to 10 ring carbon or the like; said aryl groups having from 6 to 10 ring carbon atoms and said heteroaryl groups having from 5 to 10 atoms are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents a; said substituents a are selected from the group consisting of halogen atoms or the like; or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of NMDA NR2B receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了式(I)的化合物，其中R1和R2独立地表示氢原子或类似物；R3表示具有6至10个环碳或类似物的芳基基团；所述芳基基团具有6至10个环碳原子，所述杂环芳基基团具有5至10个原子，未被取代或被至少一种选择自取代物a的取代基组成的取代；所述取代基a是从卤原子或类似物的组中选择的；或其药学上可接受的酯或药学上可接受的盐。这些化合物对于治疗由NMDA NR2B受体过度激活引起的疾病状态如疼痛等在哺乳动物中具有用处。本发明还提供了包括上述化合物的制药组合物。
• ETHANOLAMINE DERIVATIVES WITH ANTI-POLLAKIURIA ACTIVITY
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0579833B1

  公开（公告）日：1997-08-20
• 1-"2-(4-HYDROXYPHENYL)-2-HYDROXYETHYL]-PIPERIDIN-4-OL COMPOUNDS AS NMDA RECEPTOR ANTAGONISTS
  申请人：Pfizer, Inc.

  公开号：EP1673366A1

  公开（公告）日：2006-06-28
• [EN] ETHANOLAMINE DERIVATIVES WITH ANTI-POLLAKIURIA ACTIVITY
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1992018461A1

  公开（公告）日：1992-10-29

  (EN) This invention relates to new ethanolamine derivatives having gut selective sympathomimetic and anti-pollakiuria activities and represented by general formula (I), wherein R1 is hydrogen or halogen, R2 is halogen, hydroxy, protected hydroxy, aryloxy, lower alkoxy, halo(lower)alkoxy, nitro, cyano, amino or acylamino, R3 is hydrogen or halogen, R4 is hydrogen or lower alkyl, R5 is hydrogen or lower alkyl, R6 is hydrogen, hydroxy or lower alkyl, R7 is hygrogen or lower alkyl, R8 is hydrogen or halogen, R9 is carboxy or esterified carboxy, and A is lower alkylene, provided that R4 is lower alkyl; R5 is lower alkyl; R6 is hydroxy or lower alkyl; or R8 is halogen when R1 is hydrogen, R2 is halogen and R3 is hydrogen, and pharmaceutically acceptable salts thereof, to processes for the preparation thereof and to a pharmaceutical composition comprising the same.(FR) Nouveaux dérivés d'éthanolamine présentant des activités sympathomimétique et anti-pollakiurie à sélectivité intestinale, et répondant à la formule générale (I), dans laquelle R1 représente hydrogène ou halogène; R2 représente halogène, hydroxy, hydroxy protégé, aryloxy, alcoxy inférieur, haloalcoxy inférieur, nitro, cyano, amino ou acylamino; R3 représente hydrogène ou halogène; R4 représente hydrogène ou alkyle inférieur; R5 représente hydrogène ou alkyle inférieur; R6 représente hydrogène, hydroxy ou alkyle inférieur; R7 représente hydrogène ou alkyle inférieur; R8 représente hydrogène ou halogène; R9 représente carboxy ou carboxy estérifié; et A représente alkylène inférieur; à condition que R4 représente alkyle inférieur; que R5 représente alkyle inférieur; que R6 représente hydroxy ou alkyle inférieur; ou que R8 représente halogène lorsque R1 représente hydrogène, que R2 représente halogène et que R3 représente hydrogène; leurs sels pharmaceutiquement acceptables; leurs procédés de préparation; et composition pharmaceutique les contenant.