Synthesis and Anti-inflammatory Activity of New 2,3-Dihydro-4(1H)-quinazolinone Derivatives

Sakr, Samy

doi:10.21608/zjps.2003.178067

Cited by 3 publications

(3 citation statements)

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“…The benzamide intermediate 4 was identified by matching its M.p. with the reported one [22] and incorporation in the formation of the 2,3-dihydroquinazolin-4(1H)-one derivatives 5a-c. Cyclization of benzamide 4 with three aldehydes resulted in formation of 2,3dihydroquinazolin-4(1H)-one derivatives 5a-c. The difference in aliphatic and aromatic aldehydes reactivity investigates the using of different solvents where acidified ethanol was used either with formaldehyde or acetaldehyde while glacial acetic acid was used in case of benzaldehyde.…”

Section: Chemistrymentioning

confidence: 53%

“…A mixture of 1-methyl-2Hbenzo[d] [1,3]oxazine-2,4(1H)-dione (3, 5 gm, 0.0028 mole) and p-aminoacetophenone (3.8 gm, 0.028 mole) in glacial acetic acid (50 ml) was refluxed for 4 hrs. The solution was cooled then poured into distilled water and the yellowish green solid formed was filtered and washed with water then dried to obtain the desired product 4, which has yellowish green color, yield= 83%, M.p.175-176°C as reported [21][22][23] .…”

Section: Preparation Of N-(4-acetylphenyl)-2-(methylamino)benzamide 4...mentioning

confidence: 99%

“…Our targeted compounds 5a,c and 6a-c were prepared according to the defined scheme 1. Using a reported procedure, N-methyl isatoic anhydride 3; the starting material; was refluxed for 4 hrs with paminoacetophenone in glacial acetic acid to produce the benzamide intermediate 4 [21][22][23]. Benzamide 4 is a versatile intermediate for the synthesis of different quinazolinones derivatives [26][27][28].…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Antibacterial Evaluation of New developed 2,3-Dihydroquinazolin-4(1H)-ones

Emam

Kothayer²,

Ibrahim³

et al. 2022

Egypt. J. Chem.

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Antibacterial agents structurally based on quinazolin-4-one pharmacophore, have been designed and synthesized. Where the targeted compounds 5a, c and 6a-c were in vitro screened against three gram positive and three gram negative bacteria strains compared to ciprofloxacin as reference drug. Most of compounds had moderate antibacterial activity while compound 5c showed the most significant activity and could be considered as a new lead compound for antibacterial drug design.

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Section: Chemistrymentioning

confidence: 53%

Section: Preparation Of N-(4-acetylphenyl)-2-(methylamino)benzamide 4...mentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Antibacterial Evaluation of New developed 2,3-Dihydroquinazolin-4(1H)-ones

Emam

Kothayer²,

Ibrahim³

et al. 2022

Egypt. J. Chem.

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Synthesis of New 2,3‐Dihydroquinazolin‐4(1H)‐one Derivatives for Analgesic and Anti‐inflammatory Evaluation

El‐Sabbagh

Ibrahim

Baraka

et al. 2010

Archiv der Pharmazie

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Starting from isatoic anhydrides, several new 2,3-dihydroquinazolin-4(1H)-one derivatives bearing chalcone or pyrazole or thiazole moieties at the third position were synthesized. The analgesic and anti-inflammatory activities for most compounds were studied at a dose level of 50 mg/kg via the acetic-acid-induced writhing-response method and carrageenan-induced edema method, respectively. The study showed that the chalcones bearing a 4-chlorophenyl group 4c or 4-nitrophenyl group 4b were the most active ones as analgesics. Both chalcone 4c and N-phenyl pyrazole bearing 4-methoxy phenyl group 5b showed a higher anti-inflammatory activity than celecoxib but still lower than that of diclofenac sodium. Moreover, the chalcone 4c has nearly the same ulcerogenic index as the selective cyclooxygenase-2 inhibitor celecoxib.

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Quinazoline‐tethered hydrazone: A versatile scaffold toward dual anti‐TB and EGFR inhibition activities in NSCLC

Emam

Dahal

Singh

et al. 2021

Archiv der Pharmazie

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Globally, lung cancer and tuberculosis are considered to be very serious and complex diseases. Evidence suggests that chronic infection with tuberculosis (TB) can often lead to lung tumors; therefore, developing drugs that target both diseases is of great clinical significance. In our study, we designed and synthesized a suite of 14 new quinazolinones (5a-n) and performed biological investigations of these compounds in Mycobacterium tuberculosis (MTB) and cancer cell lines. In addition, we conducted a molecular modeling study to determine the mechanism of action of these compounds at the molecular level. Compounds that showed anticancer activity in the preliminary screening were further evaluated in three cancer cell lines (A549, Calu-3, and BT-474 cells) and characterized in an epidermal growth factor receptor (EGFR) binding assay. Cytotoxicity in noncancerous lung fibroblast cells was also evaluated to obtain safety data. Our theoretical and experimental studies indicated that our compounds showed a mechanism of action similar to that of erlotinib by inhibiting the EGFR tyrosine kinase. In turn, the antituberculosis activity of these compounds would be produced by the inhibition of enoyl-ACP-reductase. From our findings, we were able to identify two potential lead compounds (5i and 5l) with dual activity and elevated safety toward noncancerous lung fibroblast cells. In addition, our data identified three compounds with excellent anti-TB activities (compounds 5i, 5l, and 5n).

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Synthesis and Anti-inflammatory Activity of New 2,3-Dihydro-4(1H)-quinazolinone Derivatives

Cited by 3 publications

References 0 publications

Synthesis and Antibacterial Evaluation of New developed 2,3-Dihydroquinazolin-4(1H)-ones

Synthesis and Antibacterial Evaluation of New developed 2,3-Dihydroquinazolin-4(1H)-ones

Synthesis of New 2,3‐Dihydroquinazolin‐4(1H)‐one Derivatives for Analgesic and Anti‐inflammatory Evaluation

Quinazoline‐tethered hydrazone: A versatile scaffold toward dual anti‐TB and EGFR inhibition activities in NSCLC

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