4-[(Z)-(2-Eth­oxy-4-oxochroman-3-yl­idene)methyl­amino]benzene­sulfonamide monohydrate

In the mol­ecule of the title compound, C18H18N2O5S·H2O, the heterocyclic ring adopts a twisted conformation, while the aromatic rings are oriented at a dihedral angle of 45.46 (3)°. Intra­molecular C—H⋯O and N—H⋯O inter­actions result in the formations of planar five- and six-membered rings. In the crystal structure, N—H⋯O hydrogen bonds link the NH2 and SO2 groups through R 2 2(8) ring motifs, while C—H⋯O and N—H⋯O hydrogen bonds result in the formation of R 2 1(7) ring motifs. N—H⋯O and O—H⋯O hydrogen bonds link the uncoordinated water mol­ecules, forming a polymeric network. A weak C—H⋯π inter­action is also present

3-(6-Bromo-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothia­diazine-1,1-dione

The mol­ecular structure of the title compound, C16H11BrN2O4S, is very similar to that of the previously reported fluoro analogue [al-Rashida et al. (2010 ▶). Acta Cryst. E66, o2707]. The mean planes of the bicyclic chromone system and the benzene ring of the benzothia­diazine derivative make a dihedral angle of 58.23 (8)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules are linked into layers by N—H⋯O and C—H⋯O hydrogen bonds, generating an infinite two-dimensional network

3-(6-Fluoro-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothia­diazine-1,1-dione

In the title compound, C16H11FN2O4S, the mean planes of the bicyclic chromone system and of the benzene ring of the benzothia­diazine derivative make a dihedral angle of 54.28 (5)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules are linked into layers by N—H⋯O and C—H⋯O hydrogen bonds, generating an infinite two-dimensional network

Novel acridine-based thiosemicarbazones as ‘turn-on' chemosensors for selective recognition of fluoride anion: a spectroscopic and theoretical study

New thiosemicarbazide-linked acridines 3a–c were prepared and investigated as chemosensors for the detection of biologically and environmentally important anions. The compounds 3a–c were found selective for fluoride (F−) with no affinity for other anions, i.e. −OAc, Br−, I−, HSO4−, SO42−, PO43−, ClO3−, ClO4−, CN− and SCN−. Further, upon the gradual addition of a fluoride anion (F−) source (tetrabutylammonium fluoride), a well-defined change in colour of the solution of probes 3a–c was observed. The anion-sensing process was studied in detail via UV–visible absorption, fluorescence and 1H-NMR experiments. Moreover, during the synthesis of acridine probes 3a–c nickel fluoride (NiF2), a rarely explored transition metal fluoride salt, was used as the catalyst. Theoretical studies via density functional theory were also carried out to further investigate the sensing and anion (F−) selectivity pattern of these probes

Pyrazole derivatives of pyridine and naphthyridine as proapoptotic agents in cervical and breast cancer cells

Cancer is one of the leading causes of death worldwide. The increasing prevalence and resistance to chemotherapy is responsible for driving the search of novel molecules to combat this disease. In search of novel compounds with pro-apoptotic potential, pyrazolo-pyridine and pyrazolo-naphthyridine derivatives were investigated against cervical cancer (HeLa) and breast cancer (MCF-7) cells. The anti-proliferative activity was determined through the MTT assay. Potent compounds were then analyzed for their cytotoxic and apoptotic activity through a lactate dehydrogenase assay and fluorescence microscopy after propidium iodide and DAPI staining. Flow cytometry was used to determine cell cycle arrest in treated cells and pro-apoptotic effect was verified through measurement of mitochondrial membrane potential and activation of caspases. Compounds 5j and 5k were found to be most active against HeLa and MCF-7 cells, respectively. G0/G1 cell cycle arrest was observed in treated cancer cells. Morphological features of apoptosis were also confirmed, and an increased oxidative stress indicated the involvement of reactive oxygen species in apoptosis. The compound-DNA interaction studies demonstrated an intercalative mode of binding and the comet assay confirmed the DNA damaging effects. Finally, potent compounds demonstrated a decrease in mitochondrial membrane potential and increased levels of activated caspase-9 and -3/7 confirmed the induction of apoptosis in treated HeLa and MCF-7 cells. The present work concludes that the active compounds 5j and 5k may be used as lead candidates for the development of lead drug molecules against cervical and breast cancer

Sulfa Drugs as Inhibitors of Carbonic Anhydrase: New Targets for the Old Drugs

Sulfa drugs are well-known antibacterial agents containing N-substituted sulfonamide group on para position of aniline ring (NH2RSO2NHR′). In this study 2,4-dichloro-1,3,5-triazine derivatives of sulfa drugs, sulfamerazine (1b), sulfaquinoxaline (2b), sulfadiazine (3b), sulfadimidine (4b), and sulfachloropyrazine (5b) (1a–5a) were synthesized and characterized. Their carbonic anhydrase inhibition activity was evaluated against bovine cytosolic carbonic anhydrase isozyme II (bCA II). For the sake of comparison the CA inhibition activity of the parent sulfa drugs (1b–5b) was also evaluated. A significant increase in CA inhibition activity of sulfa drugs was observed upon substitution with 2,4-dichloro-1,3,5-triazine moiety. Molecular docking studies were carried out to highlight binding site interactions. ADME properties were calculated to evaluate drug likeness of the compounds

Chromone containing sulfonamides as potent carbonic anhydrase inhibitors

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Pyrazole derivatives of pyridine and naphthyridine as proapoptotic agents in cervical and breast cancer cells

Abstract Cancer is one of the leading causes of death worldwide. The increasing prevalence and resistance to chemotherapy is responsible for driving the search of novel molecules to combat this disease. In search of novel compounds with pro-apoptotic potential, pyrazolo-pyridine and pyrazolo-naphthyridine derivatives were investigated against cervical cancer (HeLa) and breast cancer (MCF-7) cells. The anti-proliferative activity was determined through the MTT assay. Potent compounds were then analyzed for their cytotoxic and apoptotic activity through a lactate dehydrogenase assay and fluorescence microscopy after propidium iodide and DAPI staining. Flow cytometry was used to determine cell cycle arrest in treated cells and pro-apoptotic effect was verified through measurement of mitochondrial membrane potential and activation of caspases. Compounds 5j and 5k were found to be most active against HeLa and MCF-7 cells, respectively. G0/G1 cell cycle arrest was observed in treated cancer cells. Morphological features of apoptosis were also confirmed, and an increased oxidative stress indicated the involvement of reactive oxygen species in apoptosis. The compound-DNA interaction studies demonstrated an intercalative mode of binding and the comet assay confirmed the DNA damaging effects. Finally, potent compounds demonstrated a decrease in mitochondrial membrane potential and increased levels of activated caspase-9 and -3/7 confirmed the induction of apoptosis in treated HeLa and MCF-7 cells. The present work concludes that the active compounds 5j and 5k may be used as lead candidates for the development of lead drug molecules against cervical and breast cancer