2-phenyl-4-salicyliden-4H-oxazol-5-one

• 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-phenyl-4-salicyliden-4H-oxazol-5-one
• 英文别名: 4-(2-hydroxybenzylidene)-2-phenyloxazol-5-one；2-Phenyl-4-salicyliden-4H-oxazol-5-on；4-[(2-Hydroxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: RYCRLHLKROXZRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 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：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-salicyliden-4H-oxazol-5-one 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以60%的产率得到2-(5-phenyl-3,3a-dihydro-[1,3]oxazolo[5,4-c][1,2]oxazol-3-yl)phenol
  参考文献：
  名称：

  El-Maghraby; El Ela Hassan, Journal of the Indian Chemical Society, 1982, vol. 59, # 7, p. 867 - 868

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 在 potassium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 生成 2-phenyl-4-salicyliden-4H-oxazol-5-one
  参考文献：
  名称：

  新型非核苷HIV-1逆转录酶抑制剂咪唑-5-酮的合成，生物学活性和对接研究

  摘要：

  设计，合成了一系列新的取代的咪唑-5-酮，并使用逆转录酶测定试剂盒（Roche，Colorimetric）评估了其在体外的逆转录酶（RT）抑制活性。从体外筛选观察到，新合成的化合物具有RT抑制活性。进行对接研究以研究合成化合物对RT酶的结合方向和亲和力。

  DOI：

  10.1016/j.bmc.2012.02.037

文献信息

• Design, Synthesis, and Antimicrobial Activity of Novel Fluorine-Containing Imidazolones
  作者：N. C. Desai、K. R. Wadekar、H. K. Mehta、U. P. Pandit

  DOI：10.1134/s1070428021060142

  日期：2021.6

  Abstract A simple synthetic protocol have been developed for the preparation of novel N-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N′-phenylthiourea derivatives by the reaction of 4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones with N-(3-chloro-4-fluorophenyl)- and N-[3-(trifluoromethyl)phenyl)hydrazinecarbothioamides. The synthesized imidazolones have been characterized by using

  摘要 一个简单的合成方案已被开发用于新颖的制备ñ - （4-苯亚甲基-5-氧代-2-苯基-4,5-二氢-1- ħ -咪唑-1-基）ñ由'-phenylthiourea衍生物4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones 与N- (3-chloro-4-fluorophenyl)- 和N- [3-(trifluoromethyl)phenyl)hydrazinecarbothioamides 的反应. 合成的咪唑酮已通过使用不同的光谱技术进行表征，并评估了它们对某些细菌和真菌菌株的抗菌活性。发现含有 2-硝基亚苄基和 4-甲氧基亚苄基取代基的咪唑酮衍生物对真菌菌株白色念珠菌和棒状曲霉..
• An ionic liquid gel: a heterogeneous catalyst for Erlenmeyer–Plochl and Henry reactions
  作者：Megha Jagadale、Altafhusen Naikwade、Rajashri Salunkhe、Mohan Rajmane、Gajanan Rashinkar

  DOI：10.1039/c8nj00367j

  日期：——

  ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully

  通过将1-丁基-3-甲基咪唑鎓氢氧化物（[Bmim] OH）截留在琼脂水溶液中来制备离子液体凝胶。离子液体凝胶的特征在于傅立叶变换红外（FT-IR），傅立叶变换拉曼（FT-Raman）光谱，扫描电子显微镜（SEM），热重分析（TGA）和能量色散X射线分析（EDX）。离子液体凝胶已成功地用作涉及醛，马尿酸和乙酸酐的Erlenmeyer-Plochl反应的多相催化剂，以及室温下醛与硝基甲烷在乙醇中的亨利反应。离子液体凝胶的异质性已通过进行热过滤测试和浸出研究得到证实。此外，
• Synthesis, Characterization and Biological Activity of 5-Arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4<i>H</i>-imidazol-4-ones
  作者：B. B. Baldaniya

  DOI：10.1155/2010/264036

  日期：——

  Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q)have been synthesized and characterized by elemental analyses, IR, NMR, and mass spectra. The products have been evaluated for antibacterial and antifungal activities against different strains of bacteria and fungi.

  一些新型的5-芳基亚醛基-3-(6,7-二氯-1,3-苯并噻唑-2-基)-2-苯基-3,5-二氢-4H-咪唑-4-酮 (6a-q)已经合成并通过元素分析、红外光谱、核磁共振和质谱进行了表征。这些产物已经针对不同菌株的细菌和真菌进行了抗菌和抗真菌活性评价。
• Benzothiazol Clubbed Imidazol-4-ones as Anti-fungal, Anti-tubercular and Anti-HIV-1 Agents: Their Synthesis and Molecular Docking Study
  作者：Navin B. Patel、Asif R. Shaikh、Vatsal M. Patel、Edgar E. Lara-Ramirez、Gildardo Rivera

  DOI：10.2174/1570180815666180712150050

  日期：2019.3.8

  The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol- 2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities.

  The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1.

  The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells.

  Compound 4i (50 &#181;M) showed better antifungal activity against A. clavatus. Compound 4g (50 &#181;M) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 &#181;M) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 &#181;M concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol).

  The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).

  背景：本研究描述了新合成的5-(4-取代苯甲醛基)-3-[4-(5-甲基苯并噻唑-2-基)-苯基]-2-苯基-3,5-二氢咪唑-4-酮（4a-o）的抗菌、抗分枝杆菌和抗HIV-1评估。进行了对接研究以预测潜在的结合亲和力。 目标：本研究的主要目的是开发新的苯甲醛候选类，结合苯并噻唑，具有更低毒性和改善的抗菌、抗结核和抗HIV-1活性。 方法：通过光谱研究（红外、1H核磁共振、13C核磁共振和质谱）对所述化合物进行表征。使用Lowenstein-Jensen培养基法进行体外抗分枝杆菌活性评估，使用微量稀释法进行抗菌活性评估。通过比色法MTT确定抗HIV-1逆转录酶活性，以及在MT-4细胞中抑制病毒诱导细胞病变活性。 结果：化合物4i（50 μM）对A. clavatus表现出更好的抗真菌活性。化合物4g（50 μM）具有95%的抑制活性，对M. tuberculosis H37Rv表现出良好活性。化合物4k对MT-4细胞（含有整合HTLV-1基因的CD4+人类T细胞）表现出50%的CC50（50 μM），而对HIV-1诱导的细胞病变的EC50浓度值为16 μM。分子对接研究表明，4k与靶标结合的结合能量为Vina评分（-10.3 Kcal/mol）。 结论：初步的体外评估结果显示，一些化合物具有有前途的抗菌活性和抗结核活性。在苯甲醛基上的各种取代基中，硝基基团对改善抗HIV-1活性最有益。对接结果表明，4k化合物可能作为逆转录酶的非竞争性或弱抑制剂起作用。
• A new, efficient and chemoselective one-pot protocol for synthesis of 4-arylidene-2-phenyl-5(4<i>H</i>)-oxazolones from aryl aldehyde bisulfite adducts promoted by POCL₃
  作者：Ahmad R. Khosropour、Mohammad M. Khodaei、Seyed J. Hoseini Jomor

  DOI：10.1002/jhet.5570450308

  日期：2008.5

  A one-pot procedure for the synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones directly from aryl aldehyde bisulfite adducts in the absence of Ac2O in good to excellent yields using phosphoryl chloride is reported. In addition, the observed chemoselectivity can be considered as a noteworthy advantage of this method.

  据报道，在不存在Ac 2 O的情况下，使用磷酰氯可以一锅法直接从芳基醛亚硫酸氢盐加合物合成4-亚芳基-2-苯基-5（4 H）恶唑酮。另外，观察到的化学选择性可以认为是该方法的显着优点。