37029-30-4Relevant academic research and scientific papers
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)
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 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 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
Molecular modeling studies and synthesis of novel methyl 2-(2-(4-Oxo-3-aryl-3,4-dihydroquinazolin-2-ylthio)acetamido)alkanoates with potential anti-cancer activity as inhibitors for methionine synthase
Elfekki, Ismail Mahmoud,Hassan, Walid Fathalla Mohamed,Elshihawy, Hosam Eldin Abd Elhamed,Ali, Ibrahim Ahmed Ibrahim,Eltamany, Elsayed Hussein Mostafa
, p. 675 - 694 (2014/08/05)
Cobalamin-dependant cytosolic enzyme methionine synthase (MetS) catalyses the transfer of a methyl group from the methyltetrahydrofolate (MTHF) to homocysteine (Hcy) to produce methionine and tetrahydrofolate (THF). MetS is over-expressed in the cytosol of certain breast and prostate tumour cells. Methionine used as a source of one carbon atom for the building of the DNA of the tumour cells, structural protein and enzymes. In this study, we designed, synthesized and evaluated the cytotoxic activity of a series of substituted methyl 2-(2-(4-oxo-3-aryl-3,4-dihydroquinazolin-2-ylthio)acetamido)acetate and dipeptide that mimic the substructure of MTHF. These inhibitors were docked in to the MTHF binding domain in such the same way as MTHF in its binding domain. The free energies of the binding were calculated and compared to the IC 50 values. This series has been developed by dicyclohexylcarbodiimide (DCC) and azide coupling methods of amino acid esters with carboxylic acid derivatives, respectively. Compound methyl 3-hydroxy-2-(2-(3-(4-methoxyphenyl)- 4-oxo-3,4-dihydroquinazolin-2-ylthio)acetamido)propanoate exhibited the highest IC50 value 20 μg/mL against PC-3 cell line and scored the lowest free energy of the binding (-07.19 kJ/mol).
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 89; 90; sheet 4, (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
SYNTHESIS AND CHEMISTRY OF 2-(5-MERCAPTO-4-PHENYL-1,2,4-TRIAZOL-3-YL)-3-PHENYL-4(3H)-QUINAZOLONE
El-Deen, I. M.,Mohamed, S. M.,Ismail, M. M.,Abdel-Megid, M.
, p. 621 - 624 (2007/10/02)
Several 4-phenyl-1-(3-phenyl-4(3H)-oxo-2-quinazolinylthioacetyl) thiosemicarbazide (4) and 2-(5-Mercapto-4-phenyl-1,2,4-triazol-3-yl)-3-phenyl-4(3H)-quinazolone (5) have been synthesized by condensation of 3-Phenyl-4(3H)-oxo-2-quinazolinyl-thioacetyl hydr
