(Z)-2-Methyl-5-oxo-4-(2-thienylmethylene)-4,5-dihydro-1,3-oxazole | 83396-71-8

• 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: (Z)-2-Methyl-5-oxo-4-(2-thienylmethylene)-4,5-dihydro-1,3-oxazole
• 英文别名: 2-methyl-4-(2-thienyl)-5(4H)-oxazolone；2-methyl-4-(Z)-thiophen-2-ylmethylene-4H-oxazol-5-one；4(6)-hydroxypyrimidine；(4Z)-2-Methyl-4-(2-thienylmethylene)-1,3-oxazol-5(4H)-one；(4Z)-2-methyl-4-(thiophen-2-ylmethylidene)-1,3-oxazol-5-one
• CAS: 83396-71-8
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: FNIJNQKPASQIFL-YVMONPNESA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  302.2±52.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-Methyl-5-oxo-4-(2-thienylmethylene)-4,5-dihydro-1,3-oxazole 在 盐酸 、 (+)-(S)-PROPRAPHOS rhodium 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 3-(2-噻吩基)-D-丙氨酸
  参考文献：
  名称：

  Unusual amino acids IV. Asymmetric synthesis of thienylalanines

  摘要：

  (Z)-2-N-Acylamino-3-thienyl-acrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active 2-N-acetyl(or benzoyl)-3-(2- or 3-thienyl)-alanines with optical yields up to 90 % using the rhodium complexes of ''PROPRAPHOS'' 6a,b and O,N-bis(diphenylphosphino)-2-exo-hydroxy,3-endo-methylamino-norbornane 6c as chiral catalysts, Recrystallization and deacylation of the obtained amino acid derivatives yields the optically pure hydrochlorides of the thienylalanines and the free amino acids.

  DOI：

  10.1016/s0957-4166(00)80424-3
• 作为产物：
  描述：

  2-噻吩甲醛 、 N-乙酰甘氨酸 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 反应 1.0h， 以79%的产率得到(Z)-2-Methyl-5-oxo-4-(2-thienylmethylene)-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis

  摘要：

  三个变种的苯丙氨酸脱氢酶作为生物催化剂，用于将一系列与苯丙酮酸结构相关的2-氧酸转化为相应的α-氨基酸，即苯丙氨酸的非天然类似物，其底物范围已被研究。这些变种酶比野生型酶更能容忍非天然底物，特别是那些在苯环的4-位有取代基的底物。在所有情况下，都表现出了优秀的对映选择性。

  DOI：

  10.1039/b406364c

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。
• Functionalized 1,3‐Diaminotruxillic Acids by Pd‐Mediated C–H Activation and [2+2]‐Photocycloaddition of 5(4 <i>H</i> )‐Oxazolones
  作者：Clara Carrera、Antonio Denisi、Carlos Cativiela、Esteban P. Urriolabeitia

  DOI：10.1002/ejic.201900548

  日期：2019.8.15

  C. C. and E. P. U. thank the Gobierno de Aragon–Fondo Social Europeo (Spain, reference group Aminoacidos y Peptidos E19_17R) for financial support and the Servicio General de Apoyo a la Investigacion–SAI, Universidad de Zaragoza. E. P. U. thanks the COST program under the CA15106 (CHAOS, C–H Activation in Organic Synthesis) grant.

  CC 和 EPU 感谢 Gobierno de Aragon–Fondo Social Europeo（西班牙，参考组 AminoacidOS y PeptidOS E19_17R）提供资金支持，感谢 Servicio General de Apoyo a la Investigacion–SAI，萨拉戈萨大学。EPU 感谢 CA15106（CHAOS，有机合成中的 C–H 激活）资助下的 COST 计划。
• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。
• 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.
• Synthesis and Stereospecific Ring Opening of the (<i>Z</i>/<i>E</i>)-Isomers of 2-Methyl(Phenyl)-4-(thienylmethylene)-5(4<i>H</i>)-oxazolones
  作者：C. Cativiela、M. D. Diaz De Villegas、J. A. Mayoral、E. Melendez

  DOI：10.1055/s-1983-30556

  日期：——