4-[(E)-1-naphthylmethylidene]-2-phenyl-1,3-oxazol-5(4H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(E)-1-naphthylmethylidene]-2-phenyl-1,3-oxazol-5(4H)-one
• 英文别名: (4E)-4-((naphthalene-3-yl)methylene)-2-phenyloxazol-5(4H)-one；4-Naphthalen-2-ylmethylene-2-phenyl-4H-oxazol-5-one；4-(Naphthalen-2-ylmethylene)-2-phenyloxazol-5(4H)-one；(4E)-4-(naphthalen-2-ylmethylidene)-2-phenyl-1,3-oxazol-5-one
• 化学式: C₂₀H₁₃NO₂
• 分子量: 299.329
• InChiKey: VJEQAFKSQWRSLC-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  马尿酸 、 2-萘甲醛 在 N-甲基吗啉 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以89%的产率得到4-[(E)-1-naphthylmethylidene]-2-phenyl-1,3-oxazol-5(4H)-one
  参考文献：
  名称：

  4-Benzylidene-2-phenyl-5(4H)-oxazolones 的实际合成

  摘要：

  摘要 在 2-氯-4,6-二甲氧基-1 存在下，马尿酸与各种醛反应合成 4-苯亚甲基-2-苯基-5(4H)-恶唑酮，已开发出一种简单的替代方法。 ,3,5-三嗪/N-甲基吗啉在 75 °C。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2012.696301

文献信息

• 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。
• 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.
• Practical Synthesis of 4-Benzylidene-2-phenyl-5(4<i>H</i>)-oxazolones
  作者：V. Siddaiah、G. Mahaboob Basha、D. Sudhakar、R. Srinuvasarao、Y. Santosh Kumar

  DOI：10.1080/00397911.2012.696301

  日期：2013.8.18

  Abstract A simple and alternative method has been developed for the synthesis of 4-benzylidene-2-phenyl-5(4H)-oxazolones via reactions of hippuric acid with various aldehydes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine/N-methylmorpholine at 75 °C. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental

  摘要 在 2-氯-4,6-二甲氧基-1 存在下，马尿酸与各种醛反应合成 4-苯亚甲基-2-苯基-5(4H)-恶唑酮，已开发出一种简单的替代方法。 ,3,5-三嗪/N-甲基吗啉在 75 °C。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要