7-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-4H-benz[1,4]oxazin-3-one | 253687-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-4H-benz[1,4]oxazin-3-one
• 英文别名: (3-oxo-4H-1,4-benzoxazin-7-yl)methyl 4-methylbenzenesulfonate
• CAS: 253687-19-3
• 化学式: C₁₆H₁₅NO₅S
• 分子量: 333.365
• InChiKey: YGCVIKDHWKBJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 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：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)哌嗪 、 7-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-4H-benz[1,4]oxazin-3-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以50%的产率得到7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  A Series of 6- and 7-Piperazinyl- and -Piperidinylmethylbenzoxazinones with Dopamine D4 Antagonist Activity:  Discovery of a Potential Atypical Antipsychotic Agent

  摘要：

  As part of a program to develop dopamine D4 antagonists for the treatment of schizophrenia, we discovered a series of 6- and 7-(phenylpiperazinyl)- and -(phenylpiperidinyl)methylbenzoxazinones through mass screening of our compound library. A structure-activity relationship SAR study was carried out involving substituents on the phenyl ring, and several selective D4 antagonists were identified. The 7-substituted benzoxazinones showed more activity in neurochemical and behavioral tests than the 6-substituted series. One of the most potent and selective compounds (26) was found to have potent activity in animal tests predictive of antipsychotic activity in humans after oral administration. This paper describes the SAR of the benzoxazinone series and the preclinical characterization of 26.

  DOI：

  10.1021/jm990277d
• 作为产物：
  描述：

  3-氧代-3,4-二氢-2H-苯并[1,4]噁嗪-7-甲醛 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 7-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-4H-benz[1,4]oxazin-3-one
  参考文献：
  名称：

  A Series of 6- and 7-Piperazinyl- and -Piperidinylmethylbenzoxazinones with Dopamine D4 Antagonist Activity:  Discovery of a Potential Atypical Antipsychotic Agent

  摘要：

  As part of a program to develop dopamine D4 antagonists for the treatment of schizophrenia, we discovered a series of 6- and 7-(phenylpiperazinyl)- and -(phenylpiperidinyl)methylbenzoxazinones through mass screening of our compound library. A structure-activity relationship SAR study was carried out involving substituents on the phenyl ring, and several selective D4 antagonists were identified. The 7-substituted benzoxazinones showed more activity in neurochemical and behavioral tests than the 6-substituted series. One of the most potent and selective compounds (26) was found to have potent activity in animal tests predictive of antipsychotic activity in humans after oral administration. This paper describes the SAR of the benzoxazinone series and the preclinical characterization of 26.

  DOI：

  10.1021/jm990277d

文献信息

• J. Med. Chem. 1999, 42, 5181-5187
  作者：

  DOI：——

  日期：——
• A Series of 6- and 7-Piperazinyl- and -Piperidinylmethylbenzoxazinones with Dopamine D4 Antagonist Activity:  Discovery of a Potential Atypical Antipsychotic Agent
  作者：Thomas R. Belliotti、David J. Wustrow、Wouter A. Brink、Kim T. Zoski、Yu-Hsin Shih、Steven Z. Whetzel、Lynn M. Georgic、Ann E. Corbin、Hyacinth C. Akunne、Thomas G. Heffner、Thomas A. Pugsley、Lawrence D. Wise

  DOI：10.1021/jm990277d

  日期：1999.12.1

  As part of a program to develop dopamine D4 antagonists for the treatment of schizophrenia, we discovered a series of 6- and 7-(phenylpiperazinyl)- and -(phenylpiperidinyl)methylbenzoxazinones through mass screening of our compound library. A structure-activity relationship SAR study was carried out involving substituents on the phenyl ring, and several selective D4 antagonists were identified. The 7-substituted benzoxazinones showed more activity in neurochemical and behavioral tests than the 6-substituted series. One of the most potent and selective compounds (26) was found to have potent activity in animal tests predictive of antipsychotic activity in humans after oral administration. This paper describes the SAR of the benzoxazinone series and the preclinical characterization of 26.