Antimicrobial Activity of Some Novel Armed Thiophene Derivatives and Petra/Osiris/Molinspiration (POM) Analyses

Molecules

Abdul Wadood¹  Salim Al-Showiman²  Fatima Alatibi²  Yahia Nasser Mabkhot²  Nahed Nasser E. El-Sayed²  Abdur Rauf³  Nabila Abdelshafy Kheder⁴  Saud Bawazeer⁵  Taibi Ben Hadda⁶ 

[1] Department of Biochemistry, UCSS, Abdul Wali Khan University Mardan, Mardan 23250, Pakistan;Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia;Department of Geology, University of Swabi, Khyber Pakhtunkhwa, Anbar 23561, Pakistan;Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Khalid University, Abha 61441, Saudi Arabia;Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, P. O. Box 42, Makkah 21955, Saudi Arabia;LCM Laboratory, Faculty of Sciences, University of Mohamed Premier, Oujda 60000, Morocco;

关键词: armed thiophenes;    antimicrobial activity;    Petra/Osiris/Molinspiration (POM) analyses;   

DOI  :  10.3390/molecules21020222

来源: DOAJ

【 摘 要 】

Tetrasubstituted 2-acetylthiophene derivative 5 was synthesized and then condensed with various nitrogen nucleophiles such as 5-amino-1,2,4-triazole, 2-aminobenzimidazole, aniline or p-chloroaniline to afford the corresponding iminothiophene derivatives 6–8a,b. Condensation of thiophene 5 with malononitrile as carbon nucleophile afforded compound 9, which underwent nucleophilic addition with DMF-DMA to afford compound 10. The newly synthesized products were characterized by elemental analysis, IR, MS, 1H-13C-NMR and CHN analysis and then evaluated for their antimicrobial activity. Results of the in vitro antibacterial activity showed that thiophene derivative 7 was found to be more potent than the standard drug gentamicin against Pseudomonas aeruginosa. Some of these compounds showed potential antimicrobial activities. Molecular docking and Osiris/Molinspiration analyses show the crucial role and impact of substituents on bioactivity and indicate the unfavorable structural parameters in actual drug design: more substitution with electronic donor group doesn’t guarantee more effective bioactivity. This study should greatly help in an intelligent and a controlled pharmacomodulation of antibiotics.

【 授权许可】

Unknown