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Synthesis,Urease Inhibition and Molecular Modelling Studies of Novel derivatives of the Naturally Occurring b-Amyrenone

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Natural Products and Bioprospecting 2019年第1期9卷 49-59页

作者： Jean J.K.Bankeu Hira Sattar Yannick S.F.Fongang Syeda W.Muhammadi Conrad V.Simoben Fidele Ntie-Kang Guy R.T.Feuya Marthe A.T.Tchuenmogne Mehreen Lateef Bruno N.Lenta Muhammad S.Ali Augustin S.Ngouela Department of Chemistry Faculty of ScienceThe University of BamendaP.O.Box 39BambiliCameroon International Center for Chemical and Biological Sciences University of KarachiKarachi 75270Pakistan Department of Chemistry Higher Teacher Training CollegeUniversity of MarouaP.O.Box 55MarouaCameroon Department of Pharmaceutical Chemistry Martin-Luther University of Halle-WittenbergWolfgang-Langenbeck-Str.406120 Halle(Saale)Germany Department of Chemistry Faculty of ScienceUniversity of BueaP.O.Box 63BueaCameroon Department of Chemistry Faculty of ScienceScientific and Technical University of MasukuBox 943FrancevilleGabon Department of Chemistry Faculty of ScienceUniversity of Yaounde´IP.O.Box 812Yaounde´Cameroon Multi-Disciplinary Research Laboratory(MDRL) Bahria University Medical and Dental CollegeBahria UniversityKarachiPakistan Department of Chemistry Higher Teacher Training CollegeUniversity of Yaounde´IP.O.Box 47Yaounde´Cameroon

Urease enzyme(UE)has been reported to be a potent virulence factor for Helicobacter pylori(HP)bacteria indicated to be responsible for various gastrointestinal diseases.Therefore,the spread of HP,currently regarded by the World Health Organization as a class 1 carcinogen,could be better controlled by targeting UE.It is in this line that we have synthesized three new derivatives(2–4)of the naturally occurring olean-12-en-3-one(1),which was previously isolated from the figs of Ficus vallis-choudae Delile(Moraceae).Among the synthesized compounds,3 and 4 contain an indole moiety.Their structures were unambiguously assigned by spectroscopic and spectrometric techniques(1D-NMR,2D-NMR and MS).The starting material and the synthesized compounds were screened for UE inhibition activity,and showed significant activities with IC50 values ranging from 14.5 to 24.6 lM,with compound(1)being the most potent as compared to the positive control thiourea(IC50=21.6 lM).Amongst the synthetic derivatives,compound 4 was the most potent(IC50-=17.9 lM),while the others showed activities close to that of the control.In addition,molecular docking study of target compounds 2–4 was performed in an attempt to explore their binding mode for the design of more potent UE inhibitors.

关键词： Helicobacter pylori Urease inhibition Docking olean-12-en-3-one derivatives

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