A theoretical insight into the reducing properties of bicyclic dithia hydrocarbons and hetero-bicyclic dithiolopyrrolone
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ORIGINAL RESEARCH
A theoretical insight into the reducing properties of bicyclic dithia hydrocarbons and hetero-bicyclic dithiolopyrrolone compounds with rotation-restricted planar disulfide linkage Elambalassery G. Jayasree 1
&
Chinthu Sukumar 1 & Suseeladevi Asha 2
Received: 21 April 2020 / Accepted: 10 August 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract The current study primarily involves the investigation of reducing properties of dithia-substituted bicyclic hydrocarbons. Adiabatic electron affinities (AEA) of the selected dithiabicyclic systems were investigated under gas and aqueous phase conditions. Calculated AEA values suggest the neutral-anion radical of the systems to be a perfect redox couple similar to cystines. Higher affinity to capture an electron is obtained in the aqueous environment. Natural bond orbital and atoms in molecule analyses were performed to obtain insight into the S–S bonding properties. One electron added radicals with elongated disulfide linkage indicates the viability of the systems towards rupturing upon reduction making it more suitable in drug carrier designing. The current investigation is also extended to biologically important dithiolopyrrolone (DTP) class of compounds and compared with dithiabicyclic hydrocarbons. The AEA range for neutral DTPs is found to be higher indicating more tendency of these systems to get reduced. Keywords Adiabatic electron affinity . Bicyclic hydrocarbons . Disulfide . Drug carriers . DTP
Introduction Caged and bridged bicyclic compounds are the frequently found structural motif in many natural products and pharmaceutical compounds [1–3]. These are found in flame retardants, polymers, lubricants, insecticides, and spasmolytics and have further potential applications particularly in the area of therapeutics as antidepressants, antivirals, and anticancer drugs [4–10]. Many bicyclic compounds containing functional groups at the bridge head position are found to be unusually stable which makes them suitable for many practical applications. Mostly polycyclic or caged bicyclic systems containing Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11224-020-01613-w) contains supplementary material, which is available to authorized users. * Elambalassery G. Jayasree [email protected] 1
Department of Chemistry, University of Kerala, Thiruvananthapuram, Kerala 695581, India
2
Analytical and Spectroscopy division, VSSC, Thiruvananthapuram, India
suitably tuned substituents are selected as drug scaffolds which are the core structural unit in drug design [11]. Lenci et al. recently emphasized the significance of bicyclic acetals in several biological interactions thus exploiting the importance of developing molecular scaffolds from such molecular frameworks [12]. Tuning bicyclic compounds with high conformational rigidity for metabolic stability makes them a better candidate in drug targeting by improving the target binding affinity and selectivity [13]. Conformational
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