Novel arylpyridine-based 1,3,4-oxadiazoles: Synthesis, antibacterial, and anti-inflammatory evaluation

被引：8

作者：

Vasantha, Sowmya Padejjar ^{[1
]}

Poojary, Boja ^{[1
]}

Chandrashekarappa, Revanasiddappa Bistuvalli ^{[2
]}

机构：

[1] Mangalore Univ, Dept Chem, Mangalagangothri 574199, Karnataka, India

[2] NGSM Inst Pharmaceut Sci, Dept Pharmaceut Chem, Mangalore, Karnataka, India

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2019年 / 66卷 / 06期

关键词：

bioorganic chemistry; medicinal chemistry; organic chemistry; BIOLOGICAL EVALUATION; PYRIDINE-DERIVATIVES; FUNGICIDAL ACTIVITY; DESIGN; CYCLOOXYGENASE-2; ANTICANCER; INHIBITORS; DISCOVERY; POTENT; SERIES;

D O I：

10.1002/jccs.201800248

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In view of developing novel bioactive compounds, a series of 2-(5-[2-methyl-6-arylpyridin-3-yl]-1,3,4-oxadiazol-2-ylthio)-1-arylethanones (6a-n) were designed and synthesized in good yield. Novel compounds were evaluated for their antibacterial and anti-inflammatory activities. All synthesized compounds were screened for their antibacterial activity against Staphylococcus aureus, Bascillus subtilis, Eschericia coli, and Pseudomonas aeruginosa strains. Compounds 6a, 6b, 6c, 6h, and 6i displayed the highest antibacterial activity with minimal inhibitory concentration (MIC) values ranging from 6.25-12.5 mu g/mL in comparison with the standard Ciprofloxacin. The results of anti-inflammatory activity of carrageenan-induced footpad edema assay indicated that tested compounds exhibited remarkable anti-inflammatory activity with percentage of inhibition of 63.9-70.1% (potency 96.8-106.20% of indomethacin activity) after 3 hr. Particularly, 6c-e and 6j-l were found to be excellent inhibitors of inflammation, with potential higher than that of the standard, Indomethacin.

引用

页码：638 / 650

页数：13

共 38 条

[1] New 1,3,4-oxadiazole/oxime hybrids: Design, synthesis, anti-inflammatory, COX inhibitory activities and ulcerogenic liability [J].

Abd-Ellah, Heba S. ;

Abdel-Aziz, Mohamed ;

Shoman, Mai E. ;

Beshr, Eman A. M. ;

Kaoud, TamerS. ;

Ahmed, Al-Shaimaa F. F. .

BIOORGANIC CHEMISTRY, 2017, 74 :15-29

[2] Synthesis and antitubercular activity of imidazo[2,1-b] thiazoles [J].

Andreani, A ;

Granaiola, M ;

Leoni, A ;

Locatelli, A ;

Morigi, R ;

Rambaldi, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (09) :743-746

[3]

[Anonymous], 2003, CHEM ENG NEWS, P30

[4] Design, synthesis, and evaluation of anti-inflammatory, analgesic, ulcerogenicity, and nitric oxide releasing studies of novel indomethacin analogs as non-ulcerogenic derivatives [J].

Bhandari, Shashikant V. ;

Parikh, Jignesh K. ;

Bothara, Kailash G. ;

Chitre, Trupti S. ;

Lokwani, Deepak K. ;

Devale, Titiksh L. ;

Modhave, Nileema S. ;

Pawar, Vidya S. ;

Panda, Santosh .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (04) :520-530

[5]

Challener C. A., 2001, CHIRAL DRUGS, P175

[6] Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles) [J].

Chen, HS ;

Li, ZM ;

Han, YF .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (11) :5312-5315

[7] Synthesis and Fungicidal Activity of Novel 2,5-Disubstituted-1,3,4-oxadiazole Derivatives [J].

Cui, Zi-Ning ;

Shi, Yan-Xia ;

Zhang, Li ;

Ling, Yun ;

Li, Bao-Ju ;

Nishida, Yoshihiro ;

Yang, Xin-Ling .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (47) :11649-11656

[8] Synthesis and biological evaluation of novel pyridine derivatives as potential anticancer agents and phosphodiesterase-3 inhibitors [J].

Davari, Atieh Sadat ;

Abnous, Khalil ;

Mehri, Soghra ;

Ghandadi, Morteza ;

Hadizadeh, Farzin .

BIOORGANIC CHEMISTRY, 2014, 57 :83-89

[9] Synergistic effect of [1H-[1,2,4]Oxadiazole[4,3-a]quinoxalin-1-one] and antidepressant drugs in the mouse forced swimming test: Possible involvement of serotonergic pathway [J].

Ergun, Yusuf ;

Orhan, Ozlem Fatma ;

Ozer, Ufuk Guney ;

Gisi, Gokce .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2010, 630 (1-3) :74-78

[10] Design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates [J].

Fu, Liqiang ;

Liu, Xin ;

Ling, Chenyu ;

Cheng, Jianjun ;

Guo, Xingsheng ;

He, Huili ;

Ding, Shi ;

Yang, Yushe .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) :814-819

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