1898-06-2Relevant academic research and scientific papers
Cytotoxicity and Antibacterial Evaluation of O-Alkylated/Acylated Quinazolin-4-one Schiff Bases
Manhas, Neha,Singh, Parvesh,Mocktar, Chunderika,Singh, Moganavelli,Koorbanally, Neil
, (2021)
A series of quinazolin-4-one Schiff bases were synthesized and tested in vitro for their cytotoxicity against two cancerous cell lines (MCF-7, Caco-2) and a human embryonic cell line (HEK-293) including their antibacterial evaluation against two Gram-positive and four Gram-negative bacterial strains. Most of the quinazoline-Schiff bases exhibited potent cytotoxicity against Caco-2. 3-[(Z)-({4-[(But-2-yn-1-yl)oxy]phenyl}methylidene)amino]-2-methylquinazolin-4(3H)-one (6f) with the O-butyne functional group displayed three-fold higher cytotoxic activity (IC50=376.8 μM) as compared to 5-fluorouracil (5-FU; IC50=1086.1 μM). However, all compounds were found to be toxic to HEK-293, except for 3-[(Z)-({4-[(2,4-difluorophenyl)methoxy]phenyl}methylidene)amino]-2-methylquinazolin-4(3H)-one (6h) that showed ～three-fold lower toxicity and higher selectivity index than 5-FU. Structure–activity relationship (SAR) analysis revealed that O-alkylation generally increased the anticancer activity and selectivity of quinazoline-4-one Schiff bases toward Caco-2 cells. The fluorinated Schiff-base generally exhibited even more significant cytotoxic activity compared to their chlorine analogs. Surprisingly, none of the quinazoline-4-one Schiff bases displayed encouraging antibacterial activity against the bacterial strains investigated. Most of the compounds were predicted to show compliance with the Lipinski parameters and ADMET profiles, indicating their drug-like properties.
La(III) complex involving the O,N-donor environment of quinazoline-4(3H)- one Schiff's base and their antimicrobial attributes against methicillin-resistant Staphylococcus aureus (MRSA)
Siddappa,Mane, Sunilkumar B.,Manikprabhu, Deene
, p. 634 - 638 (2014)
The incidence of methicillin-resistant Staphylococcus aureus increased during the past few decades, so there is an urgent need of new antimicrobial agents if public health is concerned. Though the Schiff's bases and La(III) complex have enormous biological activity, but less attention was given in their synthesis. In the present investigation, we synthesized a new (E)-3-((2-hydroxynaphthalen-1-yl) methyleneamino)-2-methylquinazoline-4(3H)-one HNMAMQ Schiff's base by the condensation of 3-(2-aminophenyl) quinazolin-2-methyl-4(3H)-one and 2-hydroxy-1-naphthaldehyde. The Schiff's base HNMAMQ and its La(III) complex were characterized by elemental analyses, IR, NMR, mass spectra, and thermal studies. The newly synthesized Schiff's base HNMAMQ and its La(III) complex were evaluated for their antimicrobial activity against methicillin-resistant Staphylococcus aureus isolated from the Gulbarga region in India. The Schiff's base HNMAMQ and its La(III) complex showed good antimicrobial activity and thus represents a potential new drug of choice.
N-amination of 4-pyrimidones by mesitylenesulfonyl hydroxylamine
Ivanov,Tsyrenov,Antonov,Lobanov,Potekhin
, p. 710 - 713 (2002)
The 3-amino derivatives are formed exclusively during the amination of the anions of 6-methyl-4-pyrimidones and 2-methyl-4-quinazolone by mesitylenesulfonyl hydroxylamine.
2-{2"-carbomyl-5"-[3′-amino-2′-methylmono/ dihalosubstituted quinazolin-4′(3'h)-onomethylene]- 1",3",4"-oxadiazol-2"-yl}-4,5-dihydroimidazolines as potential antihypertensive agents
Tyagi, Mirdula
, p. 713 - 721 (2014)
Twelve new 2- {2"-carbomyl - 5" - [3′-amino-2′ - methylmono / dihalosubstituted quinazolin- 4′ (3'H) - onomethylene] - 1",3",4" - oxadiazol-2"-yl} -4, 5- dihydroimidazolines were prepared and evaluated for their cardiovascular activity. The most active compound of this series is 2-{2"- carbomyl-5"-[3′-amino-2′-methyl-6-bromoquinazolin-4′(3'H)-onomethylene]-",3",4"-oxadiazol-2"- yl}-4,5-dihydroimidazolines i.e. compound VIc.
Synthesis of Some Quinazolinone Derivatives Functionalized with N-3 Heterocyclic Side Chain
Youssef, Ahmed S. A.,Hemdan, Magdy M.,El-Mariah, Fatma A.,Hashem, Heba E.
, p. 1626 - 1633 (2018)
A number of quinazolinone derivatives substituted at position-3 are prepared from 3, 1-benzoxazinone. Thus, treatment of 3, 1-benzoxazinon with cyanoacetohydrazide or thionocarbohydrazide gave the quinazolinone derivatives. The quinazolinones have been utilized as synthon for new pyridinone, azete, thiazole, thiazolidinone, thosemicarbazide, and thiosemicarbazone derivatives. The structures of the synthesized compounds were established on the basis of IR, 1HNMR, mass spectral data, and elemental analyses.
Synthesis, biological evaluation, and in silico study of novel library sulfonates containing quinazolin-4(3H)-one derivatives as potential aldose reductase inhibitors
Tokal?, Feyzi Sinan,Demir, Yeliz,Demircio?lu, ?brahim Hakk?,Türke?, Cüneyt,Kalay, Erbay,?endil, K?v?lc?m,Beydemir, ?ükrü
, (2021/10/01)
A series of novel sulfonates containing quinazolin-4(3H)-one ring derivatives was designed to inhibit aldose reductase (ALR2, EC 1.1.1.21). Novel quinazolinone derivatives (1–21) were synthesized from the reaction of sulfonated aldehydes with 3-amino-2-alkylquinazolin-4(3H)-ones in glacial acetic acid with good yields (85%–94%). The structures of the novel molecules were characterized using IR, 1H-NMR, 13C-NMR, and HRMS. All the novel quinazolinones (1–21) demonstrated nanomolar levels of inhibitory activity against ALR2 (KIs are in the range of 101.50–2066.00 nM). Besides, 4-[(2-isopropyl-4-oxoquinazolin-3[4H]-ylimino)methyl]phenyl benzenesulfonate (15) showed higher inhibitor activity inhibited ALR2 up to 7.7-fold compared to epalrestat, a standard inhibitor. Binding interactions between ALR2 and quinazolinones have been investigated using Schr?dinger Small-Molecule Drug Discovery Suite 2021–1, reported possible inhibitor-ALR2 interactions. Both in vitro and in silico study results suggest that these quinazolin-4(3H)-one ring derivatives (1–21) require further molecular modification to improve their drug nominee potency as an ALR2 inhibitor.
Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold
?ztürk, S.,Okay, S.,Y?ld?r?m, A.
, p. 2205 - 2214 (2020/12/09)
For the first time, quinazolin-4(3H)-one-based cationic surfactants were prepared and fully characterized by IR and NMR spectroscopic techniques and elemental analysis. Some of their physicochemical properties, such as density, critical micelle concentrat
Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives
Dai, Zeshu,Li, Dan,Li, Zhiyao,Liu, Heng,Luo, Wen,Shang, Suqin,Tian, Qingqiang,Wang, Shuqi,Wang, Xuetong,Wang, Yin,Wu, Huili,Xiao, Xin,Yuan, Jianyong,Zhou, Shangjun
, (2020/09/10)
Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.
Synthesis and evaluation of anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities of some 3H-quinazolin-4-one derivatives
El-Sayed, Nahed N. E.,Almaneai, Norah M.,Ben Bacha, Abir,Al-Obeed, Omar,Ahmad, Rehan,Abdulla, Maha,Alafeefy, Ahmed M.
, p. 672 - 683 (2019/04/02)
Some new 3H-quinazolin-4-one derivatives were synthesised and screened for anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities. Compound 15d was more potent in reducing the cell viabilities of HT-29 and SW620 cells lines to 38%, 36.7%, compared to 5-FU which demonstrated cell viabilities of 65.9 and 42.7% respectively. The IC50 values of 15d were ～20?μg/ml. Assessment of apoptotic activity revealed that 15d decreased the cell viability by down regulating Bcl2 and BclxL. Moreover, compounds, 8j, 8d/15a/15e, 5b, and 8f displayed lowered IC50 values than oleanolic acid against proinflammatory isoforms of hGV, hG-X, NmPLA2, and AmPLA2. In addition, 8d, 8h, 8j, 15a, 15b, 15e, and 15f showed better anti-α-amylase than quercetin, whereas 8g, 8h, and 8i showed higher anti-α-glucosidase activity than allopurinol. Thus, these compounds can be considered as potential antidiabetic agents. Finally, none of the compounds showed higher antiproteases or xanthine oxidase activities than the used reference drugs.
Quinazolinone platinum metal complexes: In silico design, synthesis and evaluation of anticancer activity
Sawant, Sanjay D.,Sahu, Megha,Nerkar, Amit G.
, p. 2164 - 2170 (2018/09/10)
Dihydrofolate reductase (DHFR) has been explored as a target for the development of agents for wide variety of human diseases, including cancer, autoimmune and infectious diseases. Several metal complexes are being used in management of cancer. The square planar Pt(II) complex, cis PtCl2(NH3)2 turned out to be even more effective at forcing filamentous growth. Cisplatin is an inorganic heavy metal complex that has activity similar to cell-cycle-phase-nonspecific alkylating agents such as cyclophosphamide and some other Ni and Cu metal complexes. It produces intrastrand DNA cross-link and form DNA adducts, thus inhibiting the synthesis of DNA, RNA and proteins preferentially. in silico Screening of platinum metal complexes was performed by Vlife MDS 4.3 software. In this procedure, selection of molecule, selection of PDB, optimization of PDB and docking of molecules was carried out. Synthesis of metal complexes was done by multi component reaction method. Platinum metal complexes of quinazolinone Schiff bases prioritized by in silico studies were characterized by IR, TLC, NMR, XRD, FESEM and some physico-chemical parameters. Prioritized molecules were further evaluated by in vitro anticancer cell line assay on ten cell lines with adriamycin as standard. The results showed that the platinum metal complexes of qunazolinone Schiff bases can be potential anticancer agents through DHFR inhibitory mechanism.
