3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one | 40691-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one
• 英文别名: ox-glycine；Ox-Gly；(2-oxo-4,5-diphenyl-oxazol-3-yl)-acetic acid；4,5-diphenyl-2-oxo-4-oxazolin-3-ylacetic acid；3(2H)-Oxazoleacetic acid, 2-oxo-4,5-diphenyl-；2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)acetic acid
• CAS: 40691-13-2
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: ANUZNUZVUXSPIF-UHFFFAOYSA-N

物化性质

• 熔点：
  184 °C
• 沸点：
  496.9±55.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one 在 氧气 作用下， 生成 马尿酸
  参考文献：
  名称：

  Guziec, Frank S.; Tewes, Edwin T., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1807 - 1808

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-(4,5-diphenyl-2-oxo-3H-1,3-oxazol-3-yl)ethanoate 在 氢氧化钾 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以85%的产率得到3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors

  摘要：

  A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3H-1,3-oxazole derivatives were prepared as selective cyclooxygenase-2 (COX-2) inhibitors. Among the synthesized compounds, 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzensulfonamide (compound 6) showed selective COX-2 inhibition with a selectivity index of >50 (IC50COX-1 = >100 mu M, IC50COX-2 = 2 mu m) in purified enzyme (PE) assay. Compound 6 also exhibited selective COX-2 inhibition in human whole blood assay. Molecular docking studies showed that 6 can be docked into the COX-2 binding site thus providing the molecular basis for its activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.039

文献信息

• 8-Oxo-4-thia-1-azabicyclo (4.2.0)-oct-2-ene derivatives
  申请人：SmithKline Corporation

  公开号：US04103086A1

  公开（公告）日：1978-07-25

  Novel bicyclic .beta.-lactams and intermediates useful in their preparation are disclosed. In particular, 7.beta.-acyl-amino- and 7.beta.-amino-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids are prepared. The acylated compounds are antibacterial agents.

  披露了新型的双环β-内酰胺和其在制备中有用的中间体。特别是，制备了7β-酰氨基-和7β-氨基-8-氧代-4-噻-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸。这些酰化化合物是抗菌剂。
• Methods and intermediates for preparing cis-4-oxoazetidine intermediates
  申请人：SmithKline Corporation

  公开号：US04166816A1

  公开（公告）日：1979-09-04

  The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

  含有氮的醋酸卤化物或酐与在次甲基碳原子上带有羧烷氧基团的希夫碱进行立体特异性环加成反应，为合成具有抗菌活性的头孢菌素同类物提供了新的中间体和方法。
• Cis-4-oxoazetidine intermediates and methods of preparing them
  申请人：SmithKline Corporation

  公开号：US04072674A1

  公开（公告）日：1978-02-07

  The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

  含氮的醋酸卤化物或酐与在次甲基碳原子上带有羧烷氧基团的希夫碱进行立体特异性环加成，提供了新的中间体和方法，用于制备具有抗菌活性的合成头孢菌素同类物。
• Substituted azetidinones
  申请人：SmithKline Corporation

  公开号：US04200572A1

  公开（公告）日：1980-04-29

  Substituted azetidine intermediates for preparing novel bicyclic .beta.-lactam penicillin analogs which have antibacterial activity are disclosed.

  公开了用于制备具有抗菌活性的新型双环β-内酰胺青霉素类似物的替代氮杂环丙烷中间体。
• 7-Acylamino-8-oxo-3-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid
  申请人：SmithKline Corporation

  公开号：US04089956A1

  公开（公告）日：1978-05-16

  A new series of 7-acylamino-8-oxo-3-oxa-1-azabicyclo-[4.2.0]octane-2-carboxylic acid derivatives is described which compounds have antibacterial activity especially against certain Gram negative organisms.

  描述了一系列新的7-酰胺基-8-酮基-3-氧杂-1-氮杂双环[4.2.0]辛烷-2-羧酸衍生物，这些化合物具有抗细菌活性，特别针对某些革兰氏阴性微生物。