Synthesis, antibacterial properties and 2D-QSAR studies of quinolone-triazole conjugates

Hassan M Faidallah; Adel S Girgis; Anand D Tiwari; Hitesh H Honkanadavar; Sean J Thomas; Ahmed Samir; Atef Kalmouch; Khalid A Alamry; Khalid A Khan; Tarek S Ibrahim; Amany M M Al-Mahmoudy; Abdullah M Asiri; Siva S Panda

doi:10.1016/j.ejmech.2017.10.042

Synthesis, antibacterial properties and 2D-QSAR studies of quinolone-triazole conjugates

Eur J Med Chem. 2018 Jan 1:143:1524-1534. doi: 10.1016/j.ejmech.2017.10.042. Epub 2017 Oct 16.

Authors

Affiliations

¹ Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
² Pesticide Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt.
³ Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
⁴ Department of Chemistry & Physics, Augusta University, Augusta, GA 30912, USA.
⁵ Microbiology Department, Faculty of Veterinary Medicine, Cairo University, Cairo, Egypt.
⁶ Peptide Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt.
⁷ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulaziz University, Jeddah, 21589, Saudi Arabia; Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt.
⁸ Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt.
⁹ Department of Chemistry & Physics, Augusta University, Augusta, GA 30912, USA. Electronic address: sspanda12@gmail.com.

PMID: 29126731
DOI: 10.1016/j.ejmech.2017.10.042

Abstract

A set of 1,2,3-triazole incorporated quinolone antibiotic conjugates 10-15, 17-19 were synthesized via microwave assisted click chemistry technique. Some of the aryl-substituted conjugates 17-19 show promising antibacterial properties against the tested Gram-positive (S. aureus and S. pyogenes) and Gram-negative bacteria (S. typhi) with potency higher than that of the parent antibiotics 1-3. 2D-QSAR modeling supports the observed biological properties.

Keywords: 1,2,3-Triazole; Antibacterial; Conjugate; QSAR; Quinolone.

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Anti-Bacterial Agents / toxicity
Bacteria / drug effects*
Chemistry Techniques, Synthetic
Microbial Sensitivity Tests
Quantitative Structure-Activity Relationship*
Quinolones / chemistry*
Triazoles / chemical synthesis*
Triazoles / chemistry
Triazoles / pharmacology*
Triazoles / toxicity

Substances

Anti-Bacterial Agents
Quinolones
Triazoles