2-(3-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester | 942232-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester
• 英文别名: methyl 2-(3-nitrophenyl)-1,3-oxazole-4-carboxylate；Methyl 2-(3-nitrophenyl)-1,3-oxazole-4-carboxylate
• CAS: 942232-57-7
• 化学式: C₁₁H₈N₂O₅
• 分子量: 248.195
• InChiKey: BDXKOGGQMJHUMK-UHFFFAOYSA-N

物化性质

• 沸点：
  405.0±51.0 °C(predicted)
• 密度：
  1.375±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2-(3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-phenyl)-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion

  摘要：

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.

  DOI：

  10.1021/jm070139l
• 作为产物：
  描述：

  间硝基苯甲酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 三苯基膦 作用下， 以 四氯化碳 、 氯仿 、 乙腈 为溶剂， 反应 145.33h， 生成 2-(3-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion

  摘要：

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.

  DOI：

  10.1021/jm070139l

文献信息

• A Direct Synthesis of Oxazoles from Aldehydes
  作者：Thomas H. Graham

  DOI：10.1021/ol101346w

  日期：2010.8.20

  An expedient method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles is presented. The method relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification and affords the oxazoles under relatively mild conditions.
• Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion
  作者：Iain M. McDonald、James W. Black、Ildiko M. Buck、David J. Dunstone、Eric P. Griffin、Elaine A. Harper、Robert A. D. Hull、S. Barret Kalindjian、Elliot J. Lilley、Ian D. Linney、Michael J. Pether、Sonia P. Roberts、Mark E. Shaxted、John Spencer、Katherine I. M. Steel、David A. Sykes、Martin K. Walker、Gillian F. Watt、Laurence Wright、Paul T. Wright、Wei Xun

  DOI：10.1021/jm070139l

  日期：2007.6.1

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.