Importance of Fluorine in Benzazole Compounds

Abstract

Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed.

δ-Lactones—A New Class of Compounds That Are Toxic to E. coli K12 and R2–R4 Strains

“…The next step in our research was the use of δ-lactones as a function of commonly used antibiotics: ciprofloxacin, bleomycin, and cloxacillin a component of the general drug product Syntarpen. Cloxacillin is a beta-lactam antibiotic used to treat bacterial infections, recommended mainly in skin and soft tissue infections, lower respiratory tract infections and osteomyelitis [ 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 ]. Ciprofloxacin is an organic chemical compound, a chemotherapeutic agent from the second-generation quinolone group, with a bactericidal effect, showing its activity by disrupting bacterial DNA replication, inhibiting bacterial DNA topoisomerase and DNA gyrase.…”

“…It is the most potent drug among fluoroquinolones. Ciprofloxacin is particularly active against Gram-negative bacteria such as Hemophilus influenzae , Neisseria gonorrhoeae , Salmonella, Shigella , Pseudomonas aeruginosa , Escherichia coli , Staphylococcus aureus , Mycobacterium tuberculosis , Enterobacteriaceae , Bartonella quintana ,), it shows variable activity towards others [ 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 ].…”

“…The synthesis of unsaturated secondary alcohols 3 ( Figure 2 ) was carried out following the procedure described by others and Gaylord and Becker [ 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 ]. A solution of aryl bromide 1 (0.08 mol) in diethyl ether ( Figure 2 ) was added dropwise to magnesium turnings (0.08 mol) and heated under reflux for 4 h. The mixture was cooled on ice and a solution of 3-methyl crotonaldehyde 2 in diethyl ether ( Figure 2 ) was added dropwise and stirred for 24 h. The mixture was dissolved in diethyl ether and added to ice and water.…”

“…The analysis of the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was performed on the basis of the original method described in detail others and by Prost [ 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 ] with its individual modifications for specific compounds analyzed and described in the works [ 5 , 6 , 7 , 8 , 9 ].…”

The First Insight Into the Supramolecular System of D,L-α-Difluoromethylornithine: A New Antiviral Perspective

“…Fluorine-based agents have better pharmacological and biological sequelae ( Wang et al, 2014 ; Al.-Harthy et al, 2020 ). They significantly increase biological activity , aqueous solubility, dipole moment, pKa ( Hagmann, 2008 ; Klebe, 2013 ; Pollock et al, 2015 ), enhance membrane permeability, metabolic stability, biological half-life, bio-absorption, safety ( Al.-Harthy et al, 2000 ; Barnes-Seeman et al, 2014 ; Nenajdenko, 2014 ; Gillis et al, 2015 ; Westwell, 2015 ), biological potency ( Ferreira de Freitas and Schapira, 2017 ), and binding affinity to target proteins ( Al.-Harthy et al, 2000 ; Kim et al, 2000 ; Kirk, 2006 ; Tressaud and Haufe, 2008 ; Zhou et al, 2009 ; Persch et al, 2015 ).…”