Synthesis and Antiviral Bioactivities of 2-Aryl- or 2-Methyl-3-(substituted- Benzalamino)-4(3H)-quinazolinone Derivatives

Gao, Xingwen; Cai, Xueli; Yan, Kai; Song, Baoan; Gao, Lili; Chen, Zhuo

doi:10.3390/12122621

Cited by 54 publications

(36 citation statements)

References 17 publications

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“…The compound solution was smeared on the left side and the solvent was on the right side for control. The local lesion numbers were then recorded 3-4 days after inoculation [23]. For each compound, three repetitions were conducted to ensure the reliability of the results, which were measured according to the following formula:…”

Section: Antiviral Activity Bioassaymentioning

confidence: 99%

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Shi

Chen

et al. 2012

Molecules

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Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1 H-NMR, 13 C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.

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Section: Antiviral Activity Bioassaymentioning

confidence: 99%

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Shi

Chen

et al. 2012

Molecules

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“…The electronic spectrum of green colored C2 complex exhibits an absorption at 638 nm attributed to 4 A 2 (F)→ 4 T 1 (P) transition indicating a tetrahedral geometry.…”

Section: Resultsmentioning

confidence: 99%

“…Magentic susceptibility measurements were made at room temperature on Gouy balance using Hg[Co(SCN) 4 ] as the calibrant. Diamagnetic corrections were made using Pascal's constants.…”

Section: A Study Of Antimentioning

confidence: 99%

“…They exhibit diverse biological properties like, antimicrobial, [1][2][3] antiviral, 4) anticancer, 5) anticonvulsant, 6) CNS depressant 7) and antihypertensive activity. 8) Amongst these, C-2 and N-3 disubstituted quinazolines with aryl and heteroaryl groups at N-3 position have shown enhanced anti-inflammatory activity as a result of their nitric oxide inhibitory activities.…”

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confidence: 99%

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A Study of Anti-inflammatory and Analgesic Activity of New 2,3-Disubstituted 1,2-Dihydroquinazolin-4(3H)-one Derivative and Its Transition Metal Complexes

Hunoor

Patil

Badiger

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Quinazolinones and their derivatives have drawn much attention owing to their various pharmacological properties. They exhibit diverse biological properties like, antimicrobial, [1][2][3] antiviral, 4) anticancer, 5) anticonvulsant, 6) CNS depressant 7) and antihypertensive activity. 8) Amongst these, C-2 and N-3 disubstituted quinazolines with aryl and heteroaryl groups at N-3 position have shown enhanced anti-inflammatory activity as a result of their nitric oxide inhibitory activities. 9)A good deal of research has been carried out on the coordinating behavior of 2,3-disubstituted quinazolin-4(3H)-ones which offer various potential donor sites. [10][11][12][13][14][15] In comparison, 2,3-disubstituted 1,2-dihydroquinazolinones and their metal complexes are not much explored. We have recently reported the synthesis of 1,2-dihydroquinazolinones by the condensation of 2-aminobenzoylhydrazide with aryl and heteroaryl aldehydes and their chelating behavior towards transition and inner transition metal ions. [16][17][18][19][20][21][22] Their antimicrobial potency is also tested against different bacterial and fungal strains. Our continued research in this perspective resulted in a new approach, in which 2-aminobenzoylhydrazide is converted to hydrazone in the first step. The reaction of this hydrazone with aromatic aldehydes results in the formation of biologically active 1,2-dihydroquinazolinones, with different substituent at C-2 and N-3 positions.Aroylhydrazones of salicylaldehyde, which typically act as tridentate planar chelate coordinating through phenolic oxygen, amide oxygen and imine nitrogen (Chart 1a) are known for their interesting biological activities.23) Keeping the framework of coordinating sites of aroylhydrazones intact, we have designed quinazoline analogue (Chart 1b) of aroylhydrazone of o-hydroxyacetophenone which is structurally similar with aroylhydrazones of salicylaldehyde. Recent investigation show that coordination of organic molecules and anti-inflammatory drugs with Co(II), Ni(II), Cu(II), Fe(II) and Zn(II) metal ions resulted in the enhancement of their activity. [24][25][26] Thus, the present article charts the progress of our methodology in the synthesis of new 1,2-dihydroquinazolin-4(3H)-one derivative viz., 2-hydroxy-2-ethyl-(3-carboxylideneamino)-3-(2-(4-methyl-phenyl))-1,2-dihydroquinazolin-4(3H)-one (HECMDQ) (C1) with different substituent at C-2 and N-3 positions and its coordinating behavior towards Co(II), Ni(II), Cu(II) and Zn(II) ions. The results of analgesic activity are impressive and perhaps suggestive of future success. ExperimentalMaterials Methylanthranilate (S.D. Fine Chemicals, India), hydrazinehydrate (Spectrochem, India) o-hydroxyacetophenone (Himedia, India), pmethylbenzaldehyde (Spectrochem, India) and metal(II) chlorides used in the present study were of AR grade and used as supplied. All the solvents were distilled before use. o-Aminobenzoylhydrazide 27) and o-hydroxyacetophenone-o-aminobenzoylhydrazone 28) were prepared following the literature procedures.P...

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“…Several studies on the acute toxic effects of BAS in insects and bacteria have been published [4][5][6][7][8]. Quinazolinone alkaloids possess a diverse range of biological activities including cytotoxicity [9], anti-inflammatory [10], anticancer, antimicrobial, anticonvulsant [11][12][13][14][15] and cardiovascular activity [16,17]. These compounds also act as cardiotonic, antihistaminic, antifungal, antiviral, antimycobacterial and antimalarial agents [18][19][20][21][22][23][24] and they have demonstrated psychotropic, hypnotic and a range of other central nervous system (CNS) effects [25][26][27].…”

Section: Introductionmentioning

confidence: 99%