title: Synthesis and evaluation of new fluorinated anti-tubercular compounds.
abstract: Treatment of tuberculosis (TB) and the discovery of effective new anti-tubercular drugs are among the most urgent priorities in health organizations all over the world. In the present study, fluorinated analogs of some of the most important anti-TB agents such as p-aminosalicylic acid (PAS), thiacetazone and pyrazinamide were synthesized and tested against TB. The fluorinated analog of thiacetazone was 20 times more potent than the parent compound against M.tuberculosis H37-RV, while the fluorinated p-aminosalicylic acid (PAS) was almost three times less potent than PAS. A few other halogenated analogs of thioacetazone were also synthesized and subjected to anti-M.tuberculosis screening tests. The best halogen substituent was found to be fluorine which has the smallest size from one hand and the strongest electronegativity from the other hand among the halogen atoms. Fluorine therefore could be considered as a golden substituent to improve the anti-M.tuberculosis activity of thioacetazone.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran. ; Central Research Laboratories, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
authors.forename: Marjan
authors.initials: M
authors.lastname: Esfahanizadeh
authors.affiliation: Central Research Laboratories, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
authors.forename: Koroush
authors.initials: K
authors.lastname: Omidi
authors.affiliation: Department of Chemistry and Biochemistry, University of the Sciences in Philadelphia, Philadelphia, PA, USA.
authors.forename: Joel
authors.initials: J
authors.lastname: Kauffman
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
authors.forename: Ali
authors.initials: A
authors.lastname: Gudarzi
authors.affiliation: Department of Microbiology, School of Medicine, Zahedan University of Medical Sciences, Zahedan, Iran.
authors.forename: Shahram
authors.initials: S
authors.lastname: Shahraki Zahedani
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
authors.forename: Salimeh
authors.initials: S
authors.lastname: Amidi
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran. ; Central Research Laboratories, Shahid Beheshti University of Medical Sciences, Tehran, Iran. ; Phytochemistry Research Center, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
authors.forename: Farzad
authors.initials: F
authors.lastname: Kobarfard
keywords: Anti-tuberculosis drugs; Fluorinated analogs; PAS; Pyrazinamide; Thiacetazone
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