2,5-bis(4-nitrophenyl)oxazole | 54814-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,5-bis(4-nitrophenyl)oxazole
• 英文别名: 2,5-bis-(4-nitro-phenyl)-oxazole；2,5-Bis-(4-nitro-phenyl)-oxazol；2,5-Bis(4-nitrophenyl)-1,3-oxazole
• CAS: 54814-29-8
• 化学式: C₁₅H₉N₃O₅
• 分子量: 311.254
• InChiKey: NTZWKGGAODIHMS-UHFFFAOYSA-N

物化性质

• 熔点：
  228-232 °C
• 沸点：
  537.0±60.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 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：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-nitrophenyl)oxazole 在 20 % Pd(OH)2/C 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 (2S,2'S)-tert-butyl 2,2'-N,N′-(4,4'-(oxazole-2,5-diyl)bis(4,1-phenylene))bis(azanediyl)bis(oxomethylene)dipyrrolidine-1-carboxylate
  参考文献：
  名称：

  [EN] HEPATITIS C VIRUS INHIBITORS
  [FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物，包括这些化合物的组合物，以及抑制NS5A蛋白功能的方法。

  公开号：

  WO2011082077A1
• 作为产物：
  描述：

  2,5-二苯基恶唑 在 硫酸 、 硝酸 作用下， 反应 2.67h， 以72%的产率得到2,5-bis(4-nitrophenyl)oxazole
  参考文献：
  名称：

  [EN] HEPATITIS C VIRUS INHIBITORS
  [FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物，包括这些化合物的组合物，以及抑制NS5A蛋白功能的方法。

  公开号：

  WO2011082077A1

文献信息

• Reaction of Pyrylium Salts with Nucleophiles. Part 24.New Mono- and Bispyridinium Salts with a Central 2,5-Diaryloxazole Group
  作者：Iosif Schiketanz、Daniela Istrati、Calin Deleanu、Constantin Draghici、Alexandru T. Balaban

  DOI：10.1135/cccc19970769

  日期：——

  Reduction of nitro substituted 2,5-diaryloxazoles with hydrazine hydrate and Raney nickel affords in good yield 2,5-diaryloxazoles having amino group(s) on the aryl ring(s) . The reaction of 2,4,6-trisubstituted pyrylium perchlorates with mono- and diamino-2,5-diaryloxazoles yields new mono- and bispyridinium perchlorates with a central 2,5-diaryloxazole group. Their electronic, ¹³C NMR and ¹H NMR spectra are presented and discussed.

  用水合肼和Raney镍还原硝基取代的2,5-二芳基噁唑醇，可以得到含有氨基的2,5-二芳基噁唑醇，收率较高。2,4,6-三取代吡啶盐酸盐与单氨基和二氨基-2,5-二芳基噁唑醇的反应产生新的中央含有2,5-二芳基噁唑醇基团的单和双吡啶盐酸盐。它们的电子、¹³C NMR和¹H NMR光谱已经被提出并讨论。
• Hepatitis C Virus Inhibitors
  申请人：Lopez Omar D.

  公开号：US20110294819A1

  公开（公告）日：2011-12-01

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物，包括这些化合物的组合物以及抑制NS5A蛋白功能的方法。
• HCV NS5A Replication Complex Inhibitors. Part 4.1 Optimization for Genotype 1a Replicon Inhibitory Activity
  作者：Denis R. St. Laurent、Michael H. Serrano-Wu、Makonen Belema、Min Ding、Hua Fang、Min Gao、Jason T. Goodrich、Rudolph G. Krause、Julie A. Lemm、Mengping Liu、Omar D. Lopez、Van N. Nguyen、Peter T. Nower、Donald R. O’Boyle、Bradley C. Pearce、Jeffrey L. Romine、Lourdes Valera、Jin-Hua Sun、Ying-Kai Wang、Fukang Yang、Xuejie Yang、Nicholas A. Meanwell、Lawrence B. Snyder

  DOI：10.1021/jm301796k

  日期：2014.3.13

  A series of symmetrical E-stilbene prolinamides that originated from the library-synthesized lead 3 was studied with respect to HCV genotype 1a (G-1a) and genotype 1b (G-1b) replicon inhibition and selectivity against BVDV and cytotoxicity. SAR emerging from an examination of the prolinamide cap region revealed 11 to be a selective HCV NS5A inhibitor exhibiting submicromolar potency against both G-1a and G-1b replicons. Additional structural refinements resulted in the identification of 30 as a potent, dual G-1a/1b HCV NS5A inhibitor.
• Hepatitis C Virus NS5A Replication Complex Inhibitors. Part 6: Discovery of a Novel and Highly Potent Biarylimidazole Chemotype with Inhibitory Activity Toward Genotypes 1a and 1b Replicons
  作者：Makonen Belema、Van N. Nguyen、Jeffrey L. Romine、Denis R. St. Laurent、Omar D. Lopez、Jason T. Goodrich、Peter T. Nower、Donald R. O’Boyle、Julie A. Lemm、Robert A. Fridell、Min Gao、Hua Fang、Rudolph G. Krause、Ying-Kai Wang、A. Jayne Oliver、Andrew C. Good、Jay O. Knipe、Nicholas A. Meanwell、Lawrence B. Snyder

  DOI：10.1021/jm4016203

  日期：2014.3.13

  A medicinal chemistry campaign that was conducted to address a potential genotoric liability associated with an aniline-derived scaffold in a series of HCV NS5A inhibitors with dual GT-1a/-1b inhibitory activity is described. Anilides 3b and 3c were used as vehicles to explore structural modifications that retained antiviral potency while removing the potential for metabolism-based unmasking of the embedded aniline. This effort resulted in the discovery of a highly potent biarylimidazole chemotype that established a potency benchmark in replicon assays, particularly toward HCV GT-1a, a strain with significant clinical importance. Securing potent GT-1a activity in a chemotype class lacking overt structural liabilities was a critical Milestone in the effort to realize the full clinical potential of targeting the HCV NS5A protein.
• Ingham, Journal of the Chemical Society, 1927, p. 698
  作者：Ingham

  DOI：——

  日期：——