title: Synthesis and photophysical characterization of quasi push-pull dicyanodibenzodioxins and their anti-tumor activity against glioma cell line C6.
abstract: Dibenzodioxins bearing multiple electron withdrawing groups were synthesized using a simple one-step methodology including examples of molecules possessing electron acceptor groups in both ends. As a consequence internal charge delocalization occurs and the optical spectra are found to be bathochromically shifted compared to similar examples known thus far. A theoretical analysis of the molecular orbitals reveals the origin of the peaks in the dibenzodioxin optical spectra. Select examples exhibit in vitro neuro-cytotoxicity against glioma cell line C6, a finding which enhances existing knowledge about the pharmacologically relevant structural motifs in dibenzodioxins.
authors.affiliation: Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India. Electronic address: subhadeepb@goa.bits-pilani.ac.in.
authors.forename: Subhadeep
authors.initials: S
authors.lastname: Banerjee
authors.affiliation: Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India.
authors.forename: Anjan
authors.initials: A
authors.lastname: Chattopadhyay
authors.affiliation: Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India.
authors.forename: Arnab
authors.initials: A
authors.lastname: Banerjee
authors.affiliation: Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India.
authors.forename: Meera
authors.initials: M
authors.lastname: Haridas
authors.affiliation: Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India.
authors.forename: Praveen
authors.initials: P
authors.lastname: Saini
authors.affiliation: Indian Institute of Chemical Biology, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata 700032, India.
authors.forename: Moitreyi
authors.initials: M
authors.lastname: Das
authors.affiliation: Department of Chemistry, Goa University, Taleigao Plateau, Goa 403206, India.
authors.forename: Mahesh S
authors.initials: MS
authors.lastname: Majik
authors.affiliation: National Institute of Science Education and Research, Bhubaneswar, Gajapati Nagar, Orissa 751005, India.
authors.forename: Yogesh Kr
authors.initials: YK
authors.lastname: Maurya
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004147:Dioxins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005910:Glioma / Q000188:drug therapy* / Q000473:pathology; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D055668:Photochemical Processes; D011412:Propanolamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D051381:Rats
chemical_list: D000970:Antineoplastic Agents; D004147:Dioxins; D009570:Nitriles; D011412:Propanolamines; C006708:benzoral
keywords: Cell viability; Dibenzodioxins; Internal charge transfer; Quasi push–pull; Solvatochromism