Vol.:(0123456789) 1 3 Chemical Papers https://doi.org/10.1007/s11696-019-01047-7 ORIGINAL PAPER Spectroscopic, quantum mechanical studies, ligand protein interactions and photovoltaic eﬃciency modeling of some bioactive benzothiazolinone acetamide analogs Y. Sheena Mary 1 · Gözde Yalcin 2,3 · Y. Shyma Mary 1 · K. S. Resmi 1 · Renjith Thomas 4 · Tijen Önkol 5 · Esin Nagihan Kasap 6 · Ilkay Yildiz 7 Received: 5 August 2019 / Accepted: 27 December 2019 © Institute of Chemistry, Slovak Academy of Sciences 2020 Abstract In the present work, the molecules, N-(4-chlorophenyl)-2-[6-(benzoyl)-2-benzothiazolinone-3-yl]acetamide (CBBA), N- (6-methyl-2-pyridyl)-2-[6-(2-chlorobenzoyl)-2-benzothiazolinone-3-yl]acetamide (MCBA), N-(3-Chlorophenyl)-2-[6- (2-ﬂuorobenzoyl)-2-benzothiazolinone-3-yl]acetamide (CFBA) and N-(6-methyl-2-pyridyl)-2-[6-(2-ﬂuorobenzoyl)-2-ben- zothiazolinone-3-yl]acetamide (MFBA) have been synthesized followed by the study of vibrational spectra and electronic properties. Photochemical and thermochemical modeling of the title compounds is also performed to analyze its ability to be used as phtosensitizers in dye-sensitized solar cells (DSSCs) and the compounds are found to show good light harvest- ing eﬃciency (LHE) and good free energy of electron injection to be used in the photo-voltaic cells. The non-linear opti- cal (NLO) activity of the compounds has been investigated and second-order hyperpolarizability values vary in the order CFBA > CBBA > MCBA > MFBA. Natural bond orbital analysis provided insights into the various possible intramolecular interactions. Molecular docking has been accomplished by the Schrodinger suite to understand the binding interactions of the analyzed ligands with Cyclooxygenase 1 (COX1). Molecular docking studies indicated that compound MFBA had the best binding aﬃnity. Keywords DFT · Docking · Benzothiazolinone · MEP · NLO Introduction Currently used nonsteroidal anti-inflammatory drugs (NSAIDs) act through the COX-1 and COX-2 and show side eﬀects, gastrointestinal toxicity, which is due to a result of the inhibition of COX-1 isoenzyme (Meyer-Kirchrath and Schror 2000). Moreover, COX inhibition results in upregulation of the 5-LOX pathway, causing various side eﬀects (Charlier and Michaux 2003). Therefore, developing potential drugs with high analgesic and anti-inﬂammatory activities and low side eﬀects is very important. In 2010, some 2-benzothiazolinon derivatives were synthesized for investigating their analgesic and anti-inﬂammatory activi- ties (Onkol et al. 2010). Additionally, the compounds had been tested for inhibitory activities against cyclooxygenase. CFBA was found to show analgesic and anti-inﬂammatory activities to the reference compounds aspirin and indometha- cin, respectively. Khamees et al. (2020) reported the eﬀect of o-diﬂuoro and p-methyl substituents on the structure, opti- cal properties and anti-inﬂammatory activity of phenoxy Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-019-01047-7) contains supplementary material, which is available to authorized users. * Y. Sheena Mary marysheena2018@rediﬀmail.com 1 Department of Physics, Fatima Mata National College (Autonomous), Kollam, Kerala, India 2 Biotechnology Institute, Ankara University, 06560 Yenimahalle, Ankara, Turkey 3 Bioengineering Department, Faculty of Engineering, Recep Tayyip Erdogan University, 53100 Rize, Turkey 4 Department of Chemistry, St. Berchmans College (Autonomous), Changanassery, Kerala, India 5 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey 6 Department of Basic Sciences, Faculty of Pharmacy, Gazi University, Ankara, Turkey 7 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, Yenimahalle 06560, Ankara, Turkey