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1-(苯并呋喃-2-基)-4-硝基-3-芳基丁-1-酮和3-(苯并呋喃-2-基)-4,5-二氢-5-芳基-1-[4-(芳基)-1,3-噻唑-2-基]-1H-吡唑的合成与抗菌活性评价

Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl]-1H-pyrazoles.

作者信息

Abdel-Wahab Bakr F, Abdel-Aziz Hatem A, Ahmed Essam M

机构信息

Applied Organic Chemistry Department, National Research Center, Dokki, Giza, Egypt.

出版信息

Eur J Med Chem. 2009 Jun;44(6):2632-5. doi: 10.1016/j.ejmech.2008.09.029. Epub 2008 Oct 2.

Abstract

2-Acetylbenzofuran 1 on treatment with substituted aldehydes affords the corresponding chalcones 2a-c. Treatment of the chalcones with nitromethane under Michael addition condition furnished the corresponding Michael adducts 3a-c. Cyclocondensation of the chalcones 2a and 2b with thiosemicarbazide under basic refluxing conditions gave 3-(benzofuran-2-yl)-5-(4-aryl)-4,5-dihydropyrazole-1-carbothioamides 4a,b. The pyrazolines 7a-d were synthesized by treating 4a,b with phenacyl bromides in refluxing ethanol. All the synthesized compounds were screened for their antibacterial and antifungal activities at 100 microg concentration. Some of our compounds showed excellent antimicrobial activities than control drugs.

摘要

2-乙酰基苯并呋喃1与取代醛反应可得到相应的查耳酮2a - c。在迈克尔加成条件下,查耳酮与硝基甲烷反应得到相应的迈克尔加成产物3a - c。在碱性回流条件下,查耳酮2a和2b与硫代氨基脲进行环缩合反应,得到3-(苯并呋喃-2-基)-5-(4-芳基)-4,5-二氢吡唑-1-碳硫酰胺4a,b。通过在回流乙醇中用苯甲酰溴处理4a,b合成了吡唑啉7a - d。所有合成的化合物均在100微克浓度下进行了抗菌和抗真菌活性筛选。我们的一些化合物显示出比对照药物更好 的抗菌活性。

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