- Benzo[α]phenoxazines and benzo[α]phenothiazine from vitamin K3: Synthesis, molecular structures, DFT studies and cytotoxic activity
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Synthesis and characterization of fluorescent benzo[α]phenoxazines viz., M-1B (10-chloro-6-methyl-7a,11a-dihydro-5H-benzo[α]phenoxazin-5-one), M-2B 6,10-dimethyl-7a,11a-dihydro-5H-benzo[α]phenoxazin-5-one), M-3B (6-methyl-7a,11a-dihydro-5H-benzo[α]phenoxazin-5-one) and benzo[α]phenthiazine, M-4B (6-methyl-5H-benzo[α]phenothiazin-5-one) were carried out. 1H and 13C chemical shifts were assigned from the 2DgHSQCAD NMR experiments. Compound M-1B crystallizes in the orthorhombic space group P212121, while M-2B and M-4B crystallize in the monoclinic space group P21/c. The crystal network of M-1B showed slipped π-π stacking and Cl...Cl interactions, while M-2B facilitated ladder like π-π stacked polymeric chains. The C...S contacts were observed in the crystal environment of M-4B. All these structures possess C-H...O interactions. Electronic structure and charge distribution in terms of molecular electrostatic potential and frontier orbital analyses based on the MO6-2X based density functional theory further showed that monomer and dimer structures are in keeping with the single crystal X-ray data and provide insights for the growth of the crystal network. Antiproliferative activity of M-1B-M-4B was determined from the MTT assay against a human breast adenocarcinoma cell line (MCF-7), human carcinoma cell line (HeLa) and normal skin cell line. All these compounds showed significant cytotoxic activity against MCF-7 and HeLa by inducing apoptosis and thus can be viewed as potential candidates for antitumor therapy. Compounds M-2B and M-4B were further found to be topoisomerase II inhibitors.
- Chadar, Dattatray,Rao, Soniya S.,Khan, Ayesha,Gejji, Shridhar P.,Bhat, Kiesar Sideeq,Weyhermüller, Thomas,Salunke-Gawali, Sunita
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- Phenothiazone derivatives and analogs
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Phenothiazone derivatives and analogs thereof, pharmaceutical compositions and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders and inflammation.
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