4-(3'-pyridylmethylidene)-2-phenyl-5(4H)-oxazolone | 102913-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3'-pyridylmethylidene)-2-phenyl-5(4H)-oxazolone
• 英文别名: 2-phenyl-4-(3-pyridinylmethylene)-5(4H)-oxazolone；2-phenyl-4-(pyridin-3-ylmethylene)oxazol-5(4H)-one；(4Z)-2-phenyl-4-(pyridin-3-ylmethylidene)-1,3-oxazol-5-one
• CAS: 102913-29-1
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: VLVHAYVBYFGEEF-LCYFTJDESA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  402.8±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3'-pyridylmethylidene)-2-phenyl-5(4H)-oxazolone 在 氢氧化钾 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 4-(3-吡啶)-1H-吡唑-3-羧酸
  参考文献：
  名称：

  Cativiela, Carlos; Villegas, Maria D. Diaz de; Mayoral, Jose A., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 851 - 855

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吡啶甲醛 、 马尿酸 在 sodium acetate 、 乙酸酐 作用下， 以56%的产率得到4-(3'-pyridylmethylidene)-2-phenyl-5(4H)-oxazolone
  参考文献：
  名称：

  Structure-Activity Design, Synthesis and Biological Activity of Newer Imidazole- Triazine Clubbed Derivatives as Antimicrobial and Antitubercular Agents

  摘要：

  方法：应用PLSR方法对（Z）-5-乙烯基-3-（4-甲氧基-6-甲基-1,3,5-三唑-2-基）-2-苯基-3,5-二氢-4H-咪唑-4-酮（B1-B10）的二维定量构效关系（2D-QSAR）进行确定。设计的化合物经合成，并通过红外光谱、1H核磁共振、13C核磁共振和质谱数据进行光谱验证，同时对其进行了不同抗结核和抗微生物物种的生物筛选。

  DOI：

  10.2174/1570178618666210521150011

文献信息

• Novel Peptide Mimetic Inhibitors of Hepatitis C Serine Protease Derived from Isomannide
  作者：Estela Muri、Thalita Barros、Sergio Pinheiro、John Williamson、Amílcar Tanuri、Helena Pereira、Rodrigo Brindeiro、José Neto、Octávio Antunes

  DOI：10.1055/s-0028-1083332

  日期：2009.2

  Hepatitis C (HCV) infection is a cause of chronic liver disease such as cirrhosis, carcinoma, or liver failure, and the current therapy is effective in only 50% of patients. Serine proteases, which are present in HCV, are the most studied class of proteolytic enzymes­, and are a primary target in the drug development field. In this paper, we describe the synthesis and biological studies of a novel­ class of peptide mimetic compounds as potential HCV serine protease inhibitors.

  丙型肝炎病毒感染是导致肝硬化、肝癌或肝功能衰竭等慢性肝病的原因之一，而目前的治疗方法仅对50%的患者有效。HCV中的丝氨酸蛋白酶是最受研究的蛋白酶类别，也是药物开发领域的主要靶点。本文描述了一类新型肽模拟化合物作为潜在HCV丝氨酸蛋白酶抑制剂的合成和生物学研究。
• Oxazolone analogs as amyloid aggregation inhibitors and for the treatment of alzheimer's disease and disorders related to amyloidosis
  申请人：——

  公开号：US20040180943A1

  公开（公告）日：2004-09-16

  Disclosed are compounds of the Formula I 1 and their use in a method of inhibiting the aggregation of amyloid proteins and in a method of imaging amyloid deposits.

  揭示了Formula I1的化合物及其在抑制淀粉样蛋白聚集的方法和成像淀粉样沉积的方法中的应用。
• Novel synthesis of (S)-1-[5-(benzoylamino)-1,4-dioxo-6-phenylhexyl]-L-proline and analogs: potent angiotensin converting enzyme inhibitors
  作者：Robert F. Meyer、Ernest D. Nicolaides、Francis G. Tinney、Elizabeth A. Lunney、Ann Holmes、Milton L. Hoefle、Ronald D. Smith、Arnold D. Essenburg、Harvey R. Kaplan、Ronald G. Almquist

  DOI：10.1021/jm00140a010

  日期：1981.8

  in vitro angiotensin converting enzyme (ACE) inhibitory activity of 1 was confirmed. Some of the novel analogues (6, 11, 13, and 17) were also found to be potent inhibitors of ACE in vitro with an IC50 of 1.4-8.8 x 10(-9) M (IC50 for captopril = 0.9 x 10(-8) M). In vivo these compounds (6, 11, 17, and 18) were much less active than captopril, especially by the oral route. Against angiotensin I (AI) challenge

  开发了一种新的合成（S）-1- [5-（苯甲酰氨基）-1,4-二氧代-6-苯基己基] -L-脯氨酸（1）和23种类似物的方法。δ-（酰基氨基）-γ-酮酸中间体是使用3-羰基甲氧基丙酰氯通过改良的Dakin-West反应获得的。L-脯氨酸的酰化和非对映异构体混合物的重结晶在三个反应步骤中得到光学纯的标题化合物。证实了体外血管紧张素转化酶（ACE）的抑制活性为1。还发现一些新型类似物（6、11、13和17）是体外有效的ACE抑制剂，IC50为1.4-8.8 x 10（-9）M（卡托普利的IC50 = 0.9 x 10（- 8）M）。在体内，这些化合物（6、11、17和18）的活性比卡托普利低得多，尤其是通过口服途径。针对血压正常的大鼠的血管紧张素I（AI）攻击，1和6在30 mg / kg口服时产生小于50％的抑制，但是在3 mg / kg iv下产生57至82％的抑制。两种途径的抑制持续不到
• Pseudo-peptides derived from isomannide: inhibitors of serine proteases
  作者：Thalita G. Barros、Sergio Pinheiro、J. S. Williamson、Amílcar Tanuri、M. Gomes、Helena S. Pereira、R. M. Brindeiro、José B. A. Neto、O. A. C. Antunes、Estela M. F. Muri

  DOI：10.1007/s00726-009-0273-4

  日期：2010.3

  In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.
• Cycloaddition of 2-acylmethyl-1H-benzimidazoles to 4-arylidene-1,3-oxazol-5-ones
  作者：I. B. Dzvinchuk、M. O. Lozinskii

  DOI：10.1007/s10593-007-0135-5

  日期：2007.7