title: Synthesis and antituberculosis activity of novel unfolded and macrocyclic derivatives of ent-kaurane steviol.
abstract: New derivatives of steviol 1, the aglycone of the glycosides of Stevia rebaudiana, including a novel class of semisynthetic diterpenoids, namely macrocyclic ent-kauranes were synthesized. These compounds possess antituberculosis activity inhibiting the in vitro growth of Mycobacterium Tuberculosis (H37R(V) strain) with MIC 5-20 μg/ml that is close to MIC 1 μg/ml demonstrated by antituberculosis drug isoniazid in control experiment. For the first time it was found that the change of ent-kaurane geometry (as in steviol 1) of tetracyclic diterpenoid skeleton to ent-beyerane one (as in isosteviol 2) influences on antituberculosis activity.
authors.affiliation: A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan 420088, Russia.
authors.forename: Ravil N
authors.initials: RN
authors.lastname: Khaybullin
authors.forename: Irina Yu
authors.initials: IY
authors.lastname: Strobykina
authors.forename: Alexey B
authors.initials: AB
authors.lastname: Dobrynin
authors.forename: Aidar T
authors.initials: AT
authors.lastname: Gubaydullin
authors.forename: Regina V
authors.initials: RV
authors.lastname: Chestnova
authors.forename: Vasiliy M
authors.initials: VM
authors.lastname: Babaev
authors.forename: Vladimir E
authors.initials: VE
authors.lastname: Kataev
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D045786:Diterpenes, Kaurane / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D036625:Stevia / Q000737:chemistry
chemical_list: D000995:Antitubercular Agents; D045786:Diterpenes, Kaurane; D047028:Macrocyclic Compounds; C012042:steviol