Synthesis of new dithiolethione and methanethiosulfonate systems endowed with pharmaceutical interest

Elena Gabriele; Federica Porta; Giorgio Facchetti; Corinna Galli; Arianna Gelain; Fiorella Meneghetti; Isabella Rimoldi; Sergio Romeo; Stefania Villa; Chiara Ricci; Nicola Ferri; Akira Asai; Daniela Barlocco; Anna Sparatore

doi:10.3998/ark.5550190.p009.805

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Synthesis of new dithiolethione and methanethiosulfonate systems endowed with pharmaceutical interest

Elena Gabriele; Federica Porta; Giorgio Facchetti; Corinna Galli; Arianna Gelain; Fiorella Meneghetti; Isabella Rimoldi; Sergio Romeo; Stefania Villa; Chiara Ricci; Nicola Ferri; Akira Asai; Daniela Barlocco; Anna Sparatore

Volume 2017, Issue 2, Commemorative Issue in Honor of Prof. Jacek Młochowski on the occasion of his 80th anniversary, pp. 235-250

DOI: http://dx.doi.org/10.3998/ark.5550190.p009.805

Paper ID: MJ-9805UP

Received on 2016-07-19; Accepted on 2016-09-09; Published on 2016-09-20

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The Free Internet Journal for Organic Chemistry Archive for Organic Chemistry Paper Arkivoc 2017, part ii, 235-250 Synthesis of new dithiolethione and methanethiosulfonate systems endowed with pharmaceutical interest Elena Gabriele,a§ Federica Porta,a§ Giorgio Facchetti,a Corinna Galli,a Arianna Gelain,a Fiorella Meneghetti,a Isabella Rimoldi,a Sergio Romeo,a Stefania Villa,a Chiara Ricci,b Nicola Ferri,c Akira Asai,d Daniela Barlocco,a and Anna Sparatore*a a b c Dept. Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milano, Italy Dept. Pharmacological and Biomolecular Sciences, Università di Milano, Via Balzaretti 9, 20133 Milano, Italy Dept. Pharmaceutical and Pharmacological Sciences, Università di Padova, Via Marzolo 5, 35131 Padova, Italy d Center for Drug Discovery, Graduate School of Pharmaceutical Sciences, University of Shizuoka 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan § These authors equally contributed to this work Email: [email protected] Dedicated to Prof. Jacek Młochowski on the occasion of his 80th anniversary Received 07-19-2016 Accepted 09-09-2016 Published on line 09-20-2016 Abstract Here we report synthetic methodology affording in the most efficient way the rapid preparation of new dithiolethiones (DTTs) and methanethiosulfonates (MTSs). These were evaluated as STAT3 inhibitors since these electrophilic systems could react with thiol groups of STAT3-SH2 domain. The results showed that MTSs strongly interacted with the SH2 domain, whereas the corresponding DTTs possessed lower affinity, independently from the nature of the linked heterocyclic scaffold. Keywords: 1,2,5-Oxadiazole, N-Methylimidazole, STAT3-SH2 domain, Coupling reactions DOI: http://dx.doi.org/10.3998/ark.5550190.p009.805 Page 235 © ARKAT USA, Inc