4-(3-phenyl-2-oxooxazolidin-5-yl)methoxyaniline | 154872-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-phenyl-2-oxooxazolidin-5-yl)methoxyaniline
• 英文别名: 5-((4-Aminophenoxy)methyl)-3-phenyloxazolidin-2-one；5-[(4-aminophenoxy)methyl]-3-phenyl-1,3-oxazolidin-2-one
• CAS: 154872-76-1
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: KBDYFHAVKBISDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-phenyl-2-oxooxazolidin-5-yl)methoxyaniline 、 4-[3-(4-chlorophenyl)-2-oxooxazolidin-5-yl]methoxyaniline 在 氢溴酸 作用下， 生成 methyl 3-[4-(3-phenyl-2-oxooxazolidin-5-yl)methoxyphenyl]-2-chloropropionate 、 methyl 3-{4-[3-(4-chlorophenyl)-2-oxooxazolidin-5-yl]methoxyphenyl}-2-chloropropionate
  参考文献：
  名称：

  Oxazolidine derivatives and pharmaceutically acceptable salts thereof

  摘要：

  一种由化学式（I）表示的噁唑啉衍生物，其中R.sup.1、R.sup.2和R.sup.3为H、可选卤代烷基、可选卤代烷氧基、OH、卤、NO.sub.2、氨基（可选带有乙酰基或烷基）、COOH、烷氧羰基、CN、烷酰基、2-噁唑基，或R.sup.1和R.sup.2可结合在一起表示--(CH.sub.2).sub.p--或--O(CH.sub.2).sub.q O--（p为3-5，q为1-3）形成环，m和n各自为0或1，R.sup.4和R.sup.5为H或烷基，X为C或N，Y为CH.sub.2 OH、CHO或COOR.sup.6（R.sup.6为烷基、苄基或H），A为烷基、羰基或磺酰基，B为烷基，E为烷基，可用卤素取代或烯基，Z为O或S，除了n为0，m为1且Y为CH.sub.2 OH的化合物外，以及除了n为0，Y为COOR.sup.6（R.sup.6为烷基）的化合物外，其盐，其制备方法，含有该衍生物作为活性成分的抗高脂血症组合物，以及治疗高脂血症的方法，包括给予该衍生物。

  公开号：

  US05480899A1
• 作为产物：
  描述：

  对氨基苯酚 、 5-(羟基甲基)-3-苯基噁唑啉-2-酮 在 偶氮二甲酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 生成 4-(3-phenyl-2-oxooxazolidin-5-yl)methoxyaniline
  参考文献：
  名称：

  3-Aryl-5-phenoxymethyl-1,3-oxazolidin-2-ones as positive allosteric modulators of mGluR2 for the treatment of schizophrenia: Hit-to-lead efforts

  摘要：

  Hit to lead optimization of (5R)-5-hexyl-3-phenyl-1,3-oxazolidin-2-one as a positive allosteric modulator of mGluR2 is described. Improvements in potency and metabolic stability were achieved through SAR on both ends of the oxazolidinone. An optimized lead compound was found to be brain penetrant and active in a rat ketamine-induced hyperlocomotion model for antipsychotic activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.089

文献信息

• OXAZOLIDINE DERIVATIVE AND PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0605729A1

  公开（公告）日：1994-07-13

  An oxazolidine derivative represented by general formula (I), a salt thereof, a process for the production thereof, an antihyperlipidemic containing the same as the active ingredient, and a method of curing hyperlipidemia by administering the same, wherein R¹, R² and R³ represent each H, optionally halogenated alkyl, optionally halogenated alkoxy, OH, halo, NO₂, optionally acetylated or alkylated amino, COOH, alkoxycarbonyl, CN, alkanoyl or 2-oxazolyl, provided that R¹ and R² may be combined with each other to represent -(CH₂)p- or -O-(CH₂)q-O-, wherein p represents 3 to 5 and q represents 1 to 3, thus forming a cyclic structure; m and n represent each 0 or 1; R⁴ and R⁵ represent each H or alkyl; X represents C or N; Y represents CH₂OH, CHO or COOR⁶, R⁶ representing alkyl, benzyl or H; A represents alkylene, carbonyl or sulfonyl; B represents alkylene; E represents optionally halogenated alkylene or alkenylene; and Z represents O or S; provided that the case where n is 0, m is 1 and Y is CH₂OH and the case where n is 0 and Y is COOR⁶, R⁶ being alkyl, are excluded.

  一种由通式(I)代表的噁唑烷衍生物、其盐、其生产工艺、一种以其为有效成分的抗高血脂药物以及一种通过服用其治疗高血脂症的方法，其中R¹、R²和R³分别代表H、任选卤代烷基、OH、卤代、NO₂、任选乙酰化或烷基化氨基、COOH、烷氧基羰基、CN、烷酰基或2-氧代烷基、任选卤代烷氧基、OH、卤代、NO₂、任选乙酰化或烷基化氨基、COOH、烷氧羰基、CN、烷酰基或 2-噁唑基，条件是 R¹ 和 R² 可以相互结合代表-(CH₂)p-或-O-(CH₂)q-O-，其中 p 代表 3 至 5，q 代表 1 至 3，从而形成环状结构；m 和 n 分别代表 0 或 1；R⁴ 和 R⁵ 分别代表 H 或烷基；X 代表 C 或 N；Y 代表 CH₂OH、CHO 或 COOR⁶，R⁶ 代表烷基、苄基或 H；A 代表亚烷基、羰基或磺酰基；B 代表亚烷基；E 代表任选卤代亚烷基或烯基；Z 代表 O 或 S；但不包括 n 为 0、m 为 1 和 Y 为 CH₂OH 的情况，以及 n 为 0 和 Y 为 COOR⁶（R⁶ 为烷基）的情况。
• US5480899A
  申请人：——

  公开号：US5480899A

  公开（公告）日：1996-01-02
• 3-Aryl-5-phenoxymethyl-1,3-oxazolidin-2-ones as positive allosteric modulators of mGluR2 for the treatment of schizophrenia: Hit-to-lead efforts
  作者：Edward J. Brnardic、Mark E. Fraley、Robert M. Garbaccio、Mark E. Layton、John M. Sanders、Chris Culberson、Marlene A. Jacobson、Brian C. Magliaro、Pete H. Hutson、Julie A. O’Brien、Sarah L. Huszar、Jason M. Uslaner、Kerry L. Fillgrove、Cuyue Tang、Yuhsin Kuo、Sylvie M. Sur、George D. Hartman

  DOI：10.1016/j.bmcl.2010.03.089

  日期：2010.5

  Hit to lead optimization of (5R)-5-hexyl-3-phenyl-1,3-oxazolidin-2-one as a positive allosteric modulator of mGluR2 is described. Improvements in potency and metabolic stability were achieved through SAR on both ends of the oxazolidinone. An optimized lead compound was found to be brain penetrant and active in a rat ketamine-induced hyperlocomotion model for antipsychotic activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Oxazolidine derivatives and pharmaceutically acceptable salts thereof
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：US05480899A1

  公开（公告）日：1996-01-02

  An oxazolidine derivative represented by the formula (I) ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H, optionally halogenated alkyl, optionally halogenated alkoxy, OH, halo, NO.sub.2, amino optionally having acetyl or alkyl, COOH, alkoxycarbonyl, CN, alkanoyl, 2-oxazolyl, or R.sup.1 and R.sup.2 may be combined with each other to represent --(CH.sub.2).sub.p -- or --O(CH.sub.2).sub.q O-- (p is 3-5, q is 1-3) to form a ring, m and n are each 0 or 1, R.sup.4 and R.sup.5 are H or alkyl, X is C or N, Y is CH.sub.2 OH, CHO or COOR.sup.6 (R.sup.6 is alkyl, benzyl or H), A is alkylene, carbonyl or sulfonyl, B is alkylene, E is alkylene which may be substituted with halo or is alkenylene, Z is O or S, except for a compound wherein n is 0, m is 1 and Y is CH.sub.2 OH, and except for a compound wherein n is 0, Y is COOR.sup.6 (R.sup.6 is alkyl), a salt thereof, a process for its preparation, anti-hyperlipidemic composition containing the derivative as an active ingredient and a method for treating hyperlipidemia comprising administering the derivative.

  一种由化学式（I）表示的噁唑啉衍生物，其中R.sup.1、R.sup.2和R.sup.3为H、可选卤代烷基、可选卤代烷氧基、OH、卤、NO.sub.2、氨基（可选带有乙酰基或烷基）、COOH、烷氧羰基、CN、烷酰基、2-噁唑基，或R.sup.1和R.sup.2可结合在一起表示--(CH.sub.2).sub.p--或--O(CH.sub.2).sub.q O--（p为3-5，q为1-3）形成环，m和n各自为0或1，R.sup.4和R.sup.5为H或烷基，X为C或N，Y为CH.sub.2 OH、CHO或COOR.sup.6（R.sup.6为烷基、苄基或H），A为烷基、羰基或磺酰基，B为烷基，E为烷基，可用卤素取代或烯基，Z为O或S，除了n为0，m为1且Y为CH.sub.2 OH的化合物外，以及除了n为0，Y为COOR.sup.6（R.sup.6为烷基）的化合物外，其盐，其制备方法，含有该衍生物作为活性成分的抗高脂血症组合物，以及治疗高脂血症的方法，包括给予该衍生物。