Synthesis and antimycobacterial evaluation of fluoroquinolones derivatives coupled with isoprenyl moiety at the C-7 position

Authors:Ribeiro, C. A.; Dos Reis, D. B.; Reis, I. F.; De Carvalho, A. N.; Lourenço, M. C. S.; De Souza, M. V. N.; Pinheiro, A. C.; Saraiva, M. F.
Source: Medicinal Chemistry Research, v. 31, p. 949-959, 2022
Publisher: Springer

Abstract

In this work, we report the synthesis and antitubercular activity of sixteen fluoroquinolones analogs of Cipro-, Gati-, Moxi-, and Gemifloxacin coupled with the terpenes, prenol, geraniol, nerol or farnesol, being all new compounds. The reactions were carried in a microwave reactor with short reaction times of 3–10 min, providing compounds in moderated yields. Fourteen of sixteen assessed fluoroquinolone derivatives were active against the M. tuberculosis, being the best result observed to a compound two times more active than the starting fluoroquinolone Gemifloxacin. These results confirm the potential of fluoroquinolone derivatives as lead compounds in antimycobacterial drug discovery.

Keywords: tuberculosis, fluoroquinolone derivatives, terpenoid, gemifloxacin
Document Type: Research Article
DOI: 10.1007/s00044-022-02891-1
Publication date: 29 de abril de 2022