Utility of 2-Methyl-quinazolin-4(3H)-one in the Synthesis of Heterocyclic Compounds with Anticancer Activity

Helali, Aisha Youssif Hassan; Sarg, Marwa T.; Koraa, M. M.; El‐Zoghbi, Mona S.

doi:10.4236/ojmc.2014.41002

Cited by 16 publications

(11 citation statements)

References 43 publications

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“…Many nitrogen containing macrocyclic compounds are found as fragments of many natural products, fine chemicals and several biologically active compounds [ 7 ]. Various nitrogen-containing macrocyclic ligands have been reportedly used as antifungal [ 8 , 9 , 10 , 11 ], antibacterial [ 5 , 10 , 11 ], hypolipidemic [ 12 ], anticancer [ 13 ], antihistaminic [ 14 ], analgesic [ 15 , 16 ], antitubercular [ 17 , 18 ], anticonvulsant [ 19 ], anti-inflammatory [ 15 , 16 , 20 ] anti-tumor [ 8 ] and anti-HIV agents [ 21 ]. Their potential applications as corrosion inhibitors cannot be ruled out because compounds with N, S, O and P heteroatoms are generally known to possess anticorrosion properties and the corrosion inhibition potentials of a number of macrocycles have been reported [ 22 , 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial Studies and Corrosion Inhibition Potential of 1,8-dimethyl-1,3,6,8,10,13-hexaazacyclotetradecane: Experimental and Quantum Chemical Studies

et al. 2016

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The macrocylic ligand, 1,8-dimethyl-1,3,6,8,10,13-hexaazacyclotetradecane (MHACD) was synthesized by the demetallation of its freshly synthesized Ni(II) complex (NiMHACD). Successful synthesis of NiMHACD and the free ligand (MHACD) was confirmed by various characterization techniques, including Fourier transform infra-red (FT-IR), proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), ultraviolet-visible (UV-vis), and energy dispersive X-ray (EDX) spectroscopic techniques. The anti-bacteria activities of MHACD were investigated against Staphylococcus aureus and Enterococcus species and the results showed that MHACD possesses a spectrum of activity against the two bacteria. The electrochemical cyclic voltammetry study on MHACD revealed that it is a redox active compound with promising catalytic properties in electrochemical applications. The inhibition potential of MHACD for mild steel corrosion in 1 M HCl was investigated using potentiodynamic polarization method. The results showed that MHACD inhibits steel corrosion as a mixed-type inhibitor, and the inhibition efficiency increases with increasing concentration of MHACD. The adsorption of MHACD obeys the Langmuir adsorption isotherm; it is spontaneous and involves competitive physisorption and chemisorption mechanisms. Quantum chemical calculations revealed that the energy of the highest occupied molecular orbital (HOMO) of MHACD is high enough to favor forward donation of charges to the metal during adsorption and corrosion inhibition. Natural bond orbital (NBO) analysis revealed the presence of various orbitals in the MHACD that are capable of donating or accepting electrons under favorable conditions.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial Studies and Corrosion Inhibition Potential of 1,8-dimethyl-1,3,6,8,10,13-hexaazacyclotetradecane: Experimental and Quantum Chemical Studies

et al. 2016

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“…To date, orthoesters have received minimal use for the preparation of these systems. Syntheses that did employ these building blocks focused almost exclusively on the use of triethyl orthoformate to prepare derivatives without C2 substitution [ 5 , 10 ]. Although the current method is somewhat limited by the sparse number of available orthoesters, the simplicity of our approach and its ability to provide a wide range of targets makes it a valuable addition to the field.…”

Section: Introductionmentioning

confidence: 99%

Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from β-Aminoamides and Orthoesters

2018

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Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110 °C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.

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“…Quinazolinones are an interesting class of heterocyclic compounds that have great importance in medicinal chemistry and reported to possess a diverse range of pharmacological activities such as antimicrobial [ 1 – 5 ], anti-inflammatory [ 6 ], antioxidant [ 7 ], anticonvulsant [ 8 ], antihypertensive [ 9 ], bronchodilator [ 10 ], and anticancer activities [ 11 ]. The quinazoline-4-one moiety has shown versatile pharmacodynamic action in many of its synthetic analogues as well as in many isolated derivatives of naturally occurring alkaloids [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of 3-(Substituted)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one

Appani

Bhukya

Gangarapu³

2016

Scientifica

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A series of novel 3-(substituted)-2-(substituted quinazolinylamino)quinazolin-4(3H)-ones were synthesized by the reaction of 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. The starting materials 3-(substituted)-2-hydrazino-quinazolin-4(3H)-ones were synthesized from various primary amines by a multistep synthesis. All the title compounds were tested for their antibacterial activity using ciprofloxacin as reference standard. Compounds 3-(4-fluorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (9a) and 3-(4-chlorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (9h) emerged as the most active compounds of the series. These compounds have shown most potent antibacterial activity against the tested organisms of Proteus vulgaris and Bacillus subtilis having zone of inhibition values of 1.1 cm and 1.4 cm for compound 9a 1.2 cm and 1.0 cm for compound 9h, respectively.

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Utility of 2-Methyl-quinazolin-4(3H)-one in the Synthesis of Heterocyclic Compounds with Anticancer Activity

Cited by 16 publications

References 43 publications

Synthesis, Characterization, Antimicrobial Studies and Corrosion Inhibition Potential of 1,8-dimethyl-1,3,6,8,10,13-hexaazacyclotetradecane: Experimental and Quantum Chemical Studies

Synthesis, Characterization, Antimicrobial Studies and Corrosion Inhibition Potential of 1,8-dimethyl-1,3,6,8,10,13-hexaazacyclotetradecane: Experimental and Quantum Chemical Studies

Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from β-Aminoamides and Orthoesters

Synthesis and Antibacterial Activity of 3-(Substituted)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one

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