985-28-4Relevant academic research and scientific papers
2,4-DIARYL-2,3-DIHYDROBENZOTHIAZEPINES
Orlov, V. D.,Kolos, N. N.,Ruzhitskaya, N. N.
, p. 1293 - 1297 (1983)
2,4-Diaryl-2,3-dihydrobenzothiazepines are obtained in a single stage from chalcones and ortho-aminothiophenol in the presence of triethylamine.The nature of the electronic transitions in their UV absorption spectra is discussed with the use of quantum-chemical methods.It was shown that the seven-membered ring does not invert in the range of temperatures between -80 and +140 deg C and is in the boat form.The main initial event in the fragmentation of the molecules of the obtained compounds under electron impact is the formation of benzothiazole-containing radicalions.In an acidic medium 2,4-diphenyl-2,3-dihydrobenzothiazepine is hydrolyzed to 3-(2-aminophenylthio)-1,3-diphenyl-1-propanone, and in its reaction with 2,4-dinitrophenylhydrazine chalcone hydrazone and o-aminothiophenol are formed.
Design, synthesis, and biological evaluation of 1,3,5-trisubstituted pyrazoles as tyrosine kinase inhibitors
Gawandi, Sinthiya J.,Desai, Vidya G.,Shingade, Sunil G.
, p. 267 - 278 (2019/01/16)
We report herein, silica supported molybdic acid mediated oxidative C–N bond formation for the regioselective synthesis of new 1,3,5-trisubstituted pyrazole derivatives. This transformation furnishes a novel synthetic approach with solvent-free neat heat conditions, which was found to be flexible with wide substrate scope and better efficiency towards rapid synthesis of new 1,3,5-trisubstituted pyrazoles. Selected series of the synthesized derivatives were screened for their liability against carcinogenesis. A molecular docking study of the synthesized derivatives was performed in the active site of the tyrosine kinase enzymes. Based on the molecular docking study specific compounds were screened in vitro for their anticancer activity, which showed potent micro molar activity against human MDA-MB-231 breast cancer line and human leukemia cell line K-562 using 3-(4,5-dimethylthiazol-2-yl)–2, 5-diphenyltetrazolium bromide (MTT) assay. Compound 3l possesses higher inhibitory activity with IC50 0.58 ± 0.02 μM against the MDA-MB-231 cell line. Whereas compound 3k showed higher inhibitory activity with IC50 value 0.78 ± 0.03 μM against the K-562 cell line. Fluorescence microscopic studies revealed that the compounds showed late apoptotic mode of cell death. These results can lead to further exploitation of tested pyrazole compounds to the highly active drug molecule. [Figure not available: see fulltext.].
Regioselective synthesis of 1,3,5-trisubstituted pyrazoles
Desai, Vidya G.,Satardekar, Pooja C.,Polo, Sampada,Dhumaskar, Kashinath
experimental part, p. 836 - 842 (2012/01/15)
A new and a simple approach toward synthesis of 1,3,5-trisubstituted pyrazoles from chalcone arylhydrazones via oxidative cyclization has been achieved. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone was successfully used as an oxidizing agent to give excellen
Larvicidal studies of chalcones and their derivatives
Das,Begum,Choudhury,Banerji
, p. 161 - 164 (2007/10/03)
Chalcone (1,3-diphenyl-2-propen-1-one) is considered as the lead compound among all the chalcone type compounds used for the larvicidal studies, as it has the highest toxicity against the larvae of Culex quinquefasciatus. 4-Phenylbut-3-en-2-one, where a methyl group replaces the phenyl group of chalcone, is less active than chalcone; but still has higher activity than other derived compounds except the oxime of the same compound, while 1,5-diphenylpenta-1,4-dien-3-one (in which the lengthening of the acyclic conjugated portion occurs) has almost no activity at 100 ppm at an interval of 24 h. ANOVA and CD values of the compounds show that larvicidal activity of 4-phenylbut-3-en-2-one and its oxime is greater than its phenylhydrazone, which has, however, higher activity than that of semicarbazone of 4-phenylbut-3-en-2- one. On the other hand the activities of 1,5-diphenylpenta-1,4-dien-3-one itself and 2,4-dinitrophenylhydrazone of chalcone and chalcone type compounds are almost nil at 100 ppm concentration at an interval of 24 h at 30 ± 2°C. The probable explanation of the fall of larvicidal activities of these compounds has been presented.
Chemical transformations of 2,4-diaryl-2,3-dihydro-1H,1,5-benzodiazepines
Orlov,Kolos,Desenko,Lavrushin
, p. 631 - 636 (2007/10/02)
The behavior of 2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine in acylation, alkylation, nitrosation, oxidation, reduction, salt formation, and opening of the diazepine ring under the influence of various dinucleophiles and acids was studied. It is shown that the dihydrodiazepine ring is extremely sensitive to acidic reagents and undergoes rearrangement to an imidazole ring under their influence. The structure of the cis- and trans-tetrahydroazepines were analyzed thoroughly.
