Molecules 2016, 21(2), 222; doi:10.3390/molecules21020222
Antimicrobial Activity of Some Novel Armed Thiophene Derivatives and Petra/Osiris/Molinspiration (POM) Analyses
Yahia Nasser Mabkhot 1,*
, Fatima Alatibi 1, Nahed Nasser E. El-Sayed 1,2, Salim Al-Showiman 1, Nabila Abdelshafy Kheder 3,4, Abdul Wadood 5, Abdur Rauf 6, Saud Bawazeer 7 and Taibi Ben Hadda 8
, Fatima Alatibi 1, Nahed Nasser E. El-Sayed 1,2, Salim Al-Showiman 1, Nabila Abdelshafy Kheder 3,4, Abdul Wadood 5, Abdur Rauf 6, Saud Bawazeer 7 and Taibi Ben Hadda 81
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)
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
Figure 1
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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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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