28831-35-8Relevant academic research and scientific papers
2-thioquinazolinone compound and preparation method and application thereof
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Paragraph 0053; 0105-0110, (2021/09/08)
The invention provides a 2-thioquinazolinone compound and a preparation method and application thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: mixing an anthranilamide compound, an isothiocyanate compound, a bromide and a polar organic solvent, and carrying out a series cyclization reaction in an air atmosphere to obtain the 2-thioquinazolinone compound. According to the preparation method, the 2-thioquinazolinone compound can be prepared by one-step reaction without adding a catalyst, the yield and the purity of the product are high, the reaction route is simple, the operation is simple, and the preparation method is suitable for industrial production.
Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N -(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds
Nguyen, Cong T.,Nguyen, Quang T.,Dao, Phuc H.,Nguyen, Thuan L.,Nguyen, Phuong T.,Nguyen, Hung H.
, (2019/10/03)
Ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4) with thiocarbonyl-bis-thioglycolic acid gave a new compound name N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide (5). Knoevenagel condensation of (5) with appropriate aldehydes gave fourteen (Z)-N-(5-arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide compounds (6a-o) with moderate yield. The chemical structure of the compounds was elucidated on the basis of IR, 1H-NMR, 13C-NMR, and HR-MS spectral data. The 5-arylidene-2-thioxothiazolidinone compounds exhibited mild-to-moderate cytotoxic activity against both K562 (chronic myelogenous leukemia) cells and MCF7 (breast cancer) cells.
Synthesis, molecular modeling and anti-cancer evaluation of a series of quinazoline derivatives
Khodair, Ahmed I.,Alsafi, Mona A.,Nafie, Mohamed S.
, (2019/10/16)
Quinazolines were surveyed as biologically relevant moieties against different cancer cell lines, so in the present study, we analyzed novel derivatives as target-oriented chemotherapeutic anti-cancer drugs. A series of 3-substituted 2-thioxo-2,3-dihydro-1H-quinazolin-4-ones 4a-e were synthesized via the reaction of 2-aminobenzoic acid (1) with isothiocyanate derivatives 2a-e. S-alkylation and S-glycosylation were carried via the reaction of 4a-e with alkyl halides and α-glycopyranosyl bromides 7a,b under anhydrous alkaline and glycoside conditions, respectively. The S-alkylated and S-glycosylated structures, and not that of the N-alkylated and N-glycosylated isomers, have been selected for the products. Conformational analysis has been studied by homo- and heteronuclear two-dimensional NMR methods (DQF-COSY, HMQC, and HMBC). The S site of alkylation and glycosylation were determined from the 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments. All derivatives were subjected to molecular docking calculations, which selected some derivatives (5n, 8c, 8g, 9c, and 9a) as promising ones based on their excellent binding affinities towards the EGFR tyrosine kinase molecular target. The in vitro cytotoxic activity against MCF-7 and HepG2 cell lines showed effective anti-proliferative activity of the analyzed derivatives with lower IC50 values especially 9a with IC50 = 2.09 and 2.08 μM against MCF-7 and HepG2, respectively, and their treatments were safe against the normal cell line Gingival mesenchymal stem cells (GMSC). Moreover, RT-PCR reaction investigated the apoptotic pathway for the compound 9a, which activated the P53 genes and its related genes. So, further work is recommended for developing it as a chemotherapeutic drug.
Synthesis, anticancer and apoptosis-inducing activities of quinazoline–isatin conjugates: epidermal growth factor receptor-tyrosine kinase assay and molecular docking studies
El-Azab, Adel S.,Al-Dhfyan, Abdullah,Abdel-Aziz, Alaa A.-M.,Abou-Zeid, Laila A.,Alkahtani, Hamad M.,Al-Obaid, Abdulrahman M.,Al-Gendy, Manal A.
, p. 935 - 944 (2017/07/24)
A new series of quinazolinone compounds 16–34 incorporating isatin moieties was synthesized. The antitumor efficacy of the compounds against MDA-MB-231, a breast cancer cell line, and LOVO, a colon cancer cell line, was assessed. Compounds 20, 21, 22, 23, 25, 27, 28, 29, 30, 31, 32, 33, and 34 displayed potent antitumor activity against MDA-MB-231 and LOVO cells (IC50: 10.38–38.67 μM and 9.91–15.77 μM, respectively); the comparative IC50 values for 5-fluorouracil and erlotinib in these cells lines were 70.28 μM, 22.24 μM and 15.23 μM, 25.31 μM respectively. The EGFR-TK assay and induction of apoptosis for compound 31 were investigated to assess its potential cytotoxic activity as a representative example of the novel synthesized compounds. At a concentration of 10 μM, compound 31 exhibited efficient inhibitory effect against EGFR-TK and induced apoptosis in MDA-MB-231 cells. Furthermore, a molecular docking study for compound 31 and erlotinib was performed to verify the binding mode toward the EGFR kinase enzyme, and showed a similar interaction as that with erlotinib alone. Graphical Abstract: Compound 31 showed potent antitumor activity and efficient inhibitory effect against EGFR-TK and induced apoptosis of MDA-MB-231 cells at a concentration of 10 μM.
Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate
Ismail, El Fekki,Ali, Ibrahim A.I.,Fathalla, Walid,Alsheikh, Amer A.,Tamney, El Said El
, p. 104 - 120 (2017/06/19)
A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4- dihydroquinazolin-2-ylthio) acetohydrazide 6. {figure presented}.
Synthesis, molecular structure and spectroscopic studies of some new quinazolin-4(3H)-one derivatives; An account on the N- versus S-Alkylation
Hagar, Mohamed,Soliman, Saied M.,Ibid, Farahate,El Ashry, El Sayed H.
, p. 667 - 679 (2016/01/09)
A new series of N- and S-alkylated products of 3-aryl-1H,3H-quinazolin-2,4-dione and 3-aryl-2-mercapto-3H-quinazolin-4-one, respectively, were prepared in good yields via efficient nucleophilic substitution reaction of the SH and NH substrates with methyl
Synthesis and spectral characterisation of novel 2,3-disubstituted quinazolin-4(3H)-one derivatives
Mahmoud, Mahmoud R.,Abou-Elmagd, Wael S.I.,Abdelwahab, Salwa S.,Soliman, El-Sayed A.
experimental part, p. 66 - 71 (2012/05/04)
A new series of 2,3-disubstituted quinazolinones was synthesised via the reaction of readily obtainable 2-thioxo-3-phenylquinazolin-4(3H)-one 1 with ethyl chloroacetate followed by hydrazinolysis to afford the hydrazide 3. This was allowed to react with d
1-Aryl substituted-3-(2′-chlorophenyl)-5-(3″-phenyl-4″- oxo-(3″H)-quinazolin-2″-mercaptoacetyl)formazans as insecticidal agents
Sah, Pramilla,Kachhawaha, Vanita,Singhvi
experimental part, p. 431 - 435 (2011/08/09)
Synthesis of some novel formazans have been carried out by the reaction of 2-mercapto-2-(methylamido-2′-chloro-N-benzylidene)-3-phenyl-4-oxo-(3H) -quinazoline with diazotised solution of aromatic amines in pyridine and screened for their insecticidal acti
SUBSTITUED 3,4-DIHYDROTHIENO [2,3-D] PYRMIDINES AS TISSUE TRANSGLUTAMINASE INHIBITORS
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Page/Page column 72-73, (2010/11/08)
The present invention provides novel compounds and methods useful for treating transglutaminase associated disorders such as celiac spru, Alzheimer's disease and Huntington's disease. Certain compounds of the invention are tissue transglutaminase inhibito
Structure-activity relationship study of novel tissue transglutaminase inhibitors
Duval, Eric,Case, April,Stein, Ross L.,Cuny, Gregory D.
, p. 1885 - 1889 (2007/10/03)
Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative
