21323-40-0Relevant academic research and scientific papers
Synthesis and in vitro cytotoxicity evaluation of new 2-thioxo-benzo[g]quinazolin-4(3h)-one derivatives
Al-Salahi, Rashad,El Dib, Rabab A.,Marzouk, Mohamed
, p. 1735 - 1751 (2015)
Preparation of the titled 2-thioxo-benzo[g]quinazolin-4(3H)-ones (1-4) has been previously reported. In the present study, compounds (1-4) were elaborated in high and quantitative yields by simple modification on the reported synthetic route. Treatment of 2-thioxo-benzo[g]quinazolin-4(3H)-ones (1-4) with hydrazine hydrate or with different alkyl(heteroalkyl) halides afforded smoothly the target products 5, 6 or 7-28 in good and high yields. The in vitro cytotoxicity of compounds 1-28 was evaluated against colon HCT-116, hepatocellular Hep-G2, and breast MCF-7, prostate PC-3 and lung A-549 cancer cell lines, using MTT assay. The IC50-values of the target compounds are recorded in μg/mL and doxorubicin used as a reference drug. The results revealed that compounds 1, 3, 7, 10, 13, 14, 15, 16, 20, 21 and 22 had significant cytotoxic effects in relation to the reference drug. The structures of compounds 1-28 were elucidated by means of 1H- and 13C-NMR and HREI mass spectrometry.
Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones and Their Reactions with Alkyl Halides and α-Glycopyranosyl Bromides
Khodair, Ahmed I.,Elsafi, Mona A.,Al-Issa, Siham A.
, p. 2358 - 2368 (2019)
A series of 3-substituted 2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones 4a–e were synthesized from the reaction of 3-aminonaphthalene-2-carboxylic acid 1 with isothiocyanate derivatives 2a–e. The alkylation of 4a–e with alkyl halides gave 3-substituted 2-alkylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin-4-ones 5a–o. S-Glycosylation was carried out via the reaction of 4a–e with glycopyranosyl bromides 7a and 7b under anhydrous alkaline conditions. The structure of the compounds was established as S-nucleoside and not N-nucleoside. Conformational analysis has been studied by homonuclear and heteronuclear two-dimensional NMR methods (2D DFQ-COSY, heteronuclear multiple quantum coherence, and heteronuclear multiple bond correlation). The S site of alkylation and glycosylation was determined from the 1H and?13C heteronuclear multiple quantum coherence experiments.
