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Molecules 2016, 21(2), 222; doi:10.3390/molecules21020222

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

1
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia
2
National Organization for Drug Control and Research, Agouza, Giza 35521, Egypt
3
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Khalid University, Abha 61441, Saudi Arabia
4
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
5
Department of Biochemistry, UCSS, Abdul Wali Khan University Mardan, Mardan 23250, Pakistan
6
Department of Geology, University of Swabi, Khyber Pakhtunkhwa, Anbar 23561, Pakistan
7
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, P. O. Box 42, Makkah 21955, Saudi Arabia
8
LCM Laboratory, Faculty of Sciences, University of Mohamed Premier, Oujda 60000, Morocco
*
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 5 January 2016 / Revised: 28 January 2016 / Accepted: 1 February 2016 / Published: 17 February 2016
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [6830 KB, uploaded 22 February 2016]   |  

Abstract

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. View Full-Text
Keywords: armed thiophenes; antimicrobial activity; Petra/Osiris/Molinspiration (POM) analyses armed thiophenes; antimicrobial activity; Petra/Osiris/Molinspiration (POM) analyses
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MDPI and ACS Style

Mabkhot, Y.N.; Alatibi, F.; El-Sayed, N.N.E.; Al-Showiman, S.; Kheder, N.A.; Wadood, A.; Rauf, A.; Bawazeer, S.; Hadda, T.B. Antimicrobial Activity of Some Novel Armed Thiophene Derivatives and Petra/Osiris/Molinspiration (POM) Analyses. Molecules 2016, 21, 222.

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