59395-13-0Relevant articles and documents
Organic selenocyanates as strong and directional chalcogen bond donors for crystal engineering
Huynh, Huu-Tri,Jeannin, Olivier,Fourmigué, Marc
, p. 8467 - 8469 (2017)
Organic bis(selenocyanate) derivatives act as powerful chalcogen bond donors for the elaboration of 1D extended structures upon co-crystallization with 4,4′-bipyridine as a ditopic chalcogen bond acceptor.
Potent anti-proliferative activities of organochalcogenocyanates towards breast cancer
Banerjee, Kaustav,Padmavathi, Ganesan,Bhattacherjee, Debojit,Saha, Suchismita,Kunnumakkara, Ajaikumar B.,Bhabak, Krishna P.
, p. 8769 - 8782 (2018/11/30)
The pharmacological importance, particularly the anti-cancer and chemopreventive potentials, of organochalcogen compounds has attracted wide research attention recently. Herein we describe the synthesis of a series of organochalcogenocyanates that have one or more selenocyanate or thiocyanate units in a single molecule. The anti-proliferative activity of these organochalcogenocyanates in different breast cancer cells shows that selenocyanates exhibit much higher anti-proliferative activities than thiocyanates in general. Our study reveals that the activity of benzyl selenocyanate (1, BSC) could be significantly enhanced by 4-nitro substitution (12), which was more selective towards triple-negative breast cancer cells (MDA-MB-231) over other ER+ breast cancer cells (MCF-7 and T-47D). Furthermore, to the best of our knowledge, this is the first report on the synthesis of compounds having more than two selenocyanate units with promising anti-proliferative activities. Our studies further indicate that the apoptotic activities of selenocyanates are associated with modulation of cellular morphology and cell cycle arrest at S-phase. Selenocyanates also inhibited cellular migration and exhibited weak antioxidant activities. An effective binding interaction of compound 12 with serum albumin indicates its feasible transport in the bloodstream for its enhanced anti-cancer properties. Mechanistic studies by western blot analysis demonstrate that benzylic selenocyanates exhibit anti-proliferative activities by modulating key cellular proteins such as Survivin, Bcl-2 and COX-2; this was further supported by molecular docking studies. The results of this study would be helpful in designing suitable chemotherapeutic and chemopreventive drugs in the future.
Synthesis and Multinuclear NMR Characterizations of Some Diselena- and Tetraselenacyclophanes.
Hojjatie, Massoud,Muralidharan, Subramaniam,Freiser, Henry
, p. 1611 - 1622 (2007/10/02)
Several symmetrical and unsymmetrical bis-selenacyclophanes were prepared and characterized by multinuclear (1H, 13C and 77Se) NMR.The symmetrical cyclophanes of phenyl, furyl, pyridyl and thiophenyl appear to exist in predominantly syn conformation in solution at room temperature.VT-1H NMR of some cyclophanes indicate that the equilibrium between the syn conformers which differ in the disposition of the bridge seleniums (symmetric about mirror plane symmetric about inversion center) can be slowed at low temperatures.Interesting 13C shifts are observed in unsymmetrical cyclophanes containing 2,2'-biphenyl, pyridine and furan.The 77Se chemical shifts appear to be related to the size of the cavity of the cyclophanes.
