2-methyl-4-[(E)-(3-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one | 57731-07-4

• 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: 2-methyl-4-[(E)-(3-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one
• 英文别名: 2-methyl-4-(3-nitro-benzyliden)-4H-oxazol-5-one；2-Methyl-4-(3-nitro-benzyliden)-4H-oxazol-5-on；2-methyl-4-(3-nitrobenzylidene)oxazol-5(4H)-one；(4E)-2-methyl-4-[(3-nitrophenyl)methylidene]-1,3-oxazol-5-one
• CAS: 57731-07-4
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: ABNNCLKVUMXLSZ-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-4-[(E)-(3-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one 在 盐酸 、 乙酰氯 作用下， 生成 methyl 2-hydroxy-3-(3-nitrophenyl)prop-2-enoate
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8
• 作为产物：
  描述：

  间硝基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 以72%的产率得到2-methyl-4-[(E)-(3-nitrophenyl)methylidene]-1,3-oxazol-5(4H)-one
  参考文献：
  名称：

  Husain, M Imtiaz; Kumar, Vinay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 4, p. 285 - 288

  摘要：

  DOI：

文献信息

• Compounds and Their Salts Specific to the PPAR Receptors and the EGF Receptors and Their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20090048343A1

  公开（公告）日：2009-02-19

  The present invention relates to compounds comprising the general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR 3 , —CH(OR 3 )COOH, in which R 3 is selected from H, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及具有一般式（I）的化合物，其中R1和R2，可以相同也可以不同，选自包括-H或具有1至6个碳原子的直链或支链烷基基团，或者共同形成具有5或6个原子的芳香或脂肪环的群；Y和Z，可以相同也可以不同，选自包括-H，-OH，-COOH，-OR3，-CH(OR3)COOH的群，其中R3选自H，苯基，苄基，-CF3或-CF2CF3，乙烯基，烯丙基和具有1至6个碳原子的直链或支链烷基基团。
• Compounds and their Salts Specific to the PPAR Receptors and the EGF Receptors and their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20130005813A1

  公开（公告）日：2013-01-03

  The present invention relates to compounds comprising the general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR 3 , —CH(OR 3 )COOH, in which R 3 is selected from H, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及通式（I）的化合物，其中R1和R2可以相同或不同，选自包括-H或具有1到6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环的群体；Y和Z可以相同或不同，选自包括-H、-OH、-COOH、-OR3、-CH（OR3）COOH的群体，其中R3选自H、苯基、苄基、-CF3或-CF2CF3、乙烯基、丙烯基和具有1到6个碳原子的线性或支链烷基。
• Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field
  申请人：Nogra Pharma Limited

  公开号：US10016381B2

  公开（公告）日：2018-07-10

  The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR3, —CH(OR3)COOH, in which R3 is selected from H, phenyl, benzyl, —CF3 or —CF2CF3, vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及包含通式(I)的化合物，其中 R1 和 R2（可以相同或不同）选自-H 或具有 1 至 6 个碳原子的直链或支链烷基，或共同形成具有 5 或 6 个原子的芳香族或脂肪族环；Y 和 Z（可以相同或不同）选自-H、-OH、-COOH、-OR3、-CH(OR3)COOH 组，其中 R3 选自 H、苯基、苄基、-CF3 或-CF2CF3、乙烯基、烯丙基和具有 1 至 6 个碳原子的直链或支链烷基。
• Oxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships
  作者：Khalid Mohammed Khan、Uzma Rasool Mughal、Mahmud Tareq Hassan Khan、Zia-Ullah、Shahnaz Perveen、Muhammad Iqbal Choudhary

  DOI：10.1016/j.bmc.2006.05.014

  日期：2006.9

  The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosinase inhibitory properties having IC50 values in the range of 1.23 +/- 0.37-17.73 +/- 2.69 mu M, whereas standard inhibitors L-mimosine and kojic acid have IC50 values 3.68 +/- 0.02 and 16.67 +/- 0.52 mu M,, respectively. Compounds 4-8 having IC50 values 3.11 +/- 0.95, 3.51 +/- 0.25, 3.23 +/- 0.66, 1.23 +/- 0.37, and 2.15 +/- 0.75, respectively, were found to be very active members of the series, even better than both the standard inhibitors. However, compounds 3, 9-11, 13, 14, 16, 17, and 19 were found to be better than kojic acid but not L-mimosine. (2-Methyl-4-[E,2Z)-3-phenyl-2-propenyliden]-1,3-oxazol-5(4H)-one (7) bearing a cinnamyol residue at C-4 of oxazolone moiety and an IC50 = 1.23 +/- 0.37 mu M was found to be the most active one among all tested compounds. These studies reveal that the substitution of functional group (s) at C-4 and C-2 positions plays a vital role in the activity of this series of compounds. It is concluded that compound 7 may act as a potential lead molecule to develop new drugs for the treatment of tyrosinase based disorders. (c) 2006 Elsevier Ltd. All rights reserved.
• Sen; Shanker, Bollettino Chimico Farmaceutico, 1996, vol. 135, # 8, p. 465 - 467
  作者：Sen、Shanker

  DOI：——

  日期：——