(+)-4-(S)-(3,4-difluorophenyl)-5-(S)-methyl-2-oxo-oxazolidine-3-carboxylic acid-4-nitrophenyl ester | 218450-15-8

• 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: (+)-4-(S)-(3,4-difluorophenyl)-5-(S)-methyl-2-oxo-oxazolidine-3-carboxylic acid-4-nitrophenyl ester
• 英文别名: 4-(3,4-difluorophenyl)-5-methyl-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester；3-Oxazolidinecarboxylicacid,4-(3,4-difluorophenyl)-5-methyl-2-oxo-,4-nitrophenylester,(4R,5R)-rel-；(4-nitrophenyl) (4S,5S)-4-(3,4-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 218450-15-8
• 化学式: C₁₇H₁₂F₂N₂O₆
• 分子量: 378.289
• InChiKey: DARRWSODOOEPJH-BJOHPYRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-propylamine 、 (+)-4-(S)-(3,4-difluorophenyl)-5-(S)-methyl-2-oxo-oxazolidine-3-carboxylic acid-4-nitrophenyl ester 以 四氢呋喃 为溶剂， 反应 10.0h， 以89%的产率得到SNAP 7915
  参考文献：
  名称：

  De Novo Design of a Novel Oxazolidinone Analogue as a Potent and Selective α_1A Adrenergic Receptor Antagonist with High Oral Bioavailability

  摘要：

  DOI：

  10.1021/jm000085e
• 作为产物：
  描述：

  benzhydrylidene-(3,4-difluoro-benzyl)-amine 在 叔丁基锂 、 甲氧基胺盐酸盐 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 生成 (+)-4-(S)-(3,4-difluorophenyl)-5-(S)-methyl-2-oxo-oxazolidine-3-carboxylic acid-4-nitrophenyl ester
  参考文献：
  名称：

  Determination of the relative and absolute stereochemistry of a potent and α1A-selective adrenoceptor antagonist

  摘要：

  The binding affinities and selectivities of antagonists 1-4 for the alpha (1A)-adrenoceptor are dependent on the stereochemical orientation of the groups at the C-4 and C-5 positions of the oxazolidinone ring. The unambiguous assignment of the relative and absolute configurations of the diastereomers of SNAP 7915 (1) is reported. (C) 2000 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0960-894x(00)00524-2

文献信息

• [EN] OXAZOLIDINONES USEFUL AS ALPHA 1A ADRENOCEPTOR ANTAGONISTS<br/>[FR] OXAZOLIDINONES UTILES EN TANT QU'ANTAGONISTES DU RECEPTEUR ALPHA 1A ADRENERGIQUE
  申请人：MERCK & CO INC

  公开号：WO2000027816A1

  公开（公告）日：2000-05-18

  (4-Aryl-4-hydroxypiperidinyl) alkylcarbamoyl oxazolidinone compounds and pharmaceutically acceptable salts thereof are disclosed. The synthesis of these compounds and their use as alpha 1a adrenergic receptor antagonists is also described. One application of these compounds is in the treatment of benign prostatic hyperplasia. These compounds are selective in their ability to relax smooth muscle tissue enriched in the alpha 1a receptor subtype without at the same time inducing hypotension. One such tissue is found surrounding the urethral lining. Therefore, one utility of the instant compounds is to provide acute relief to males suffering from benign prostatic hyperplasia, by permitting less hindered urine flow. Another utility of the instant compounds is provided by combination with a human 5-alpha reductase inhibitory compound, such that both acute and chronic relief from the effects of benign prostatic hyperplasia can be achieved.

  本发明公开了(4-芳基-4-羟基哌啶基)烷基氨基恶唑烷酮化合物及其药学上可接受的盐。还描述了这些化合物的合成及其作为α1A肾上腺素受体拮抗剂的用途。这些化合物的一个应用是用于治疗良性前列腺增生。这些化合物具有选择性，能够放松富含α1A受体亚型的平滑肌组织，而不会同时引起低血压。例如，这种组织在尿道周围存在。因此，本发明化合物的一种用途是帮助患有良性前列腺增生的男性获得急性缓解，使尿流受阻程度降低。本发明化合物的另一种用途是通过与人5α-还原酶抑制剂化合物的组合使用，从而实现对良性前列腺增生影响的急性和慢性缓解。
• Determination of the relative and absolute stereochemistry of a potent and α1A-selective adrenoceptor antagonist
  作者：Bharat Lagu、John M. Wetzel、Carlos Forray、Michael A. Patane、Mark G. Bock

  DOI：10.1016/s0960-894x(00)00524-2

  日期：2000.12

  The binding affinities and selectivities of antagonists 1-4 for the alpha (1A)-adrenoceptor are dependent on the stereochemical orientation of the groups at the C-4 and C-5 positions of the oxazolidinone ring. The unambiguous assignment of the relative and absolute configurations of the diastereomers of SNAP 7915 (1) is reported. (C) 2000 Elsevier Science Ltd. AII rights reserved.
• De Novo Design of a Novel Oxazolidinone Analogue as a Potent and Selective α_1A Adrenergic Receptor Antagonist with High Oral Bioavailability
  作者：Bharat Lagu、Dake Tian、Yoon Jeon、Chao Li、John M. Wetzel、Dhanapalan Nagarathnam、Quanrong Shen、Carlos Forray、Raymond S. L. Chang、Theodore P. Broten、Richard W. Ransom、Tsing-Bao Chan、Stacey S. O'Malley、Terry W. Schorn、A. David Rodrigues、Kelem Kassahun、Douglas J. Pettibone、Roger Freidinger、Charles Gluchowski

  DOI：10.1021/jm000085e

  日期：2000.7.1