Recent Advances of Quinazolinone Derivatives as Marker for Various Biological Activities

Chawla, Anshul; Batra, Chesta

doi:10.7897/2230-8407.04309

Cited by 28 publications

(13 citation statements)

References 33 publications

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“…From these preliminary in vitro cytotoxicity results and SAR, it is observed that a bulky group at the 9-position of the 5-styryltetrazolo[1,5- c ]quinazoline moiety generally leads to loss of cytotoxicity. The observed cytotoxicity of 3a and 3b is due to the presence of a halide or small hydrophobic substituents at position 9 in analogy with the literature observation for the analogous styrylquinazolinones [ 7 , 13 , 14 ]. The 6-substituted 2-styrylquinazoline derivatives have been found to exhibit antimitotic properties and to inhibit tubulin polymerization [ 13 ].…”

Section: Resultssupporting

confidence: 83%

Synthesis, Cytotoxicity and Molecular Docking Studies of the 9-Substituted 5-Styryltetrazolo[1,5-c]quinazoline Derivatives

2017

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In this paper, we describe the synthesis of the 5-styryltetrazolo[1,5-c]quinazolines substituted at the 9-position with a 4-fluorophenyl ring directly or via a conjugated π-spacer (C=C or C≡C bond) based on the 6-bromo-4-chloro-2-styrylquinazoline scaffold. The structures of the synthesized compounds were characterized based on a combination of 1H-NMR, 13C-NMR, IR and high resolution mass spectral data as well as microanalyses. The tetrazoloquinazolines were evaluated for potential in vitro cytotoxicity against the human breast adenocarcinoma (MCF-7) and cervical cancer (HeLa) cells. The anti-proliferative assays demonstrated that the 9-bromo-5-styryltetrazolo[1,5-c]quinazoline 3a and 9-bromo-5-(4-fluorostyryl)tetrazolo[1,5-c]quinazoline 3b exhibit significant cytotoxicity against both cell lines. A carbon-based substituent at the 9-position resulted in complete loss of cytotoxicity against both cell lines except for the 5,9-bis((E)-4-fluorostyryl)tetrazolo[1,5-c]quinazoline 4e, which was found to exhibit comparable cytotoxicity to that of Melphalan (IC50 = 61 μM) against the MCF-7 cell line with IC50 value of 62 μM. Molecular docking against tubulin (PDB:1TUB) showed that compounds 3a, 3b and 4e bind to the tubulin heterodimer. Binding involves hydrogen bonding for 3a and 3b and halogen interactions for 4e.

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Section: Resultssupporting

confidence: 83%

Synthesis, Cytotoxicity and Molecular Docking Studies of the 9-Substituted 5-Styryltetrazolo[1,5-c]quinazoline Derivatives

2017

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“…The analogous ( E )-3-(3-carboxyphenyl)-2-(4-cyanostyryl)quinazolin-4(3 H )-one ( 2 ) is an effective antibiotic in vivo against methicillin-resistant Staphylococcus aureus (MRSA) and it inhibits cell wall biosynthesis by binding to DD-transpeptidases involved in cross-linking of the cell wall [9]. Extensive structure activity relationship studies on the 3-substituted 2-styrylquinazolin-4(3 H )-ones revealed that the entire styrylquinazolin-4(3 H )-one scaffold was required for inhibition of tubulin polymerization [7] and for antimicrobial activity [6,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

et al. 2015

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Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also evaluated against six Gram-positive and four Gram-negative bacteria, as well as two strains of fungi. Molecular docking studies (in silico) were conducted on compounds 5a, b, d and 6a, b, d-f to recognize the hypothetical binding motif of the title compounds within the active site of the dihydrofolate reductase and thymidylate synthase enzymes.

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“…Although many attractive procedures have been developed for rapid access to quinazolinones,2a,b, 3, 5 the related synthesis of pyridoquinazolones is still very limited. So far, known procedures require a high temperature (210 °C), multistep synthesis, or specific ortho ‐halogen‐substituted benzoyl derivatives as the substrates 6.…”

Section: Model Synthesis Of Pyridoquinazolones: Optimization Of the Rmentioning

confidence: 99%

Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

et al. 2014

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A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium-catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et 3 N promotes the preferential formation of angular products. Interestingly, a light-induced 4+4 reaction of the product was also observed.

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Recent Advances of Quinazolinone Derivatives as Marker for Various Biological Activities

Cited by 28 publications

References 33 publications

Synthesis, Cytotoxicity and Molecular Docking Studies of the 9-Substituted 5-Styryltetrazolo[1,5-c]quinazoline Derivatives

Synthesis, Cytotoxicity and Molecular Docking Studies of the 9-Substituted 5-Styryltetrazolo[1,5-c]quinazoline Derivatives

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

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