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Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs.

Rajput CS, Singhal S - J Pharm (Cairo) (2013)

Bottom Line: A series of 3-[2'-(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5-10), 3-[2'-(3(″)-chloro-2(″)-oxo-4(″)-substitutedphenylazetidin-1(″)-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11-16), and 3-[2'-(2(″)-substitutedphenyl-4(″)-oxo-1(″),3(″)-thiazolidin-3(″)-yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17-22) have been synthesized in the present study.The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, (1)H NMR, and mass spectral data.All the newly synthesized compounds were screened for anti-inflammatory and analgesic activities.

View Article: PubMed Central - PubMed

Affiliation: Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India ; Jubilant Chemsys Ltd. R & D B-34, Sector 58, Noida 201301, India.

ABSTRACT
A series of 3-[2'-(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5-10), 3-[2'-(3(″)-chloro-2(″)-oxo-4(″)-substitutedphenylazetidin-1(″)-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11-16), and 3-[2'-(2(″)-substitutedphenyl-4(″)-oxo-1(″),3(″)-thiazolidin-3(″)-yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17-22) have been synthesized in the present study. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, (1)H NMR, and mass spectral data. All the newly synthesized compounds were screened for anti-inflammatory and analgesic activities.

No MeSH data available.


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Mentions: The synthetic routes of compounds are outlined in Scheme 1. As shown in Scheme 1, compounds 2-methylsubstitued-4H-3,1-benzoxazin-4-ones (1,2) were synthesized by the known procedure of Bogert [28]. Substituted anthranilic acid reacted with acetic anhydride to give 2-methylsubstituted-4H-3,1-benzoxazin-4-ones (1,2), which further reacted with 2-amino phenyl amine in acetic acid to yield 3-(2′-aminophenyl)-2-methyl-6-substituted quinazolin-4-ones (3,4). Compounds (3,4) when treated with different substituted aromatic aldehydes formed various substituted arylidene derivatives (5–10). These arylidene derivatives on treatment with chloroacetylchloride in presence of triethylamine yielded 3-[2′-(3′′-chloro-2′′-oxo-4′′-substituted phenylazetidin-1′′-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11–16). On the other hand, these arylidene derivatives on reaction with thioglycolic acid and anhydrous ZnCl2 furnished 3-[2′-(2′′-substitutedphenyl-4′′-oxo-1′′,3′′-thiazolidin-3′′-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones. (17–22). The structures of the compounds synthesized were assigned on the basis of elemental analysis, IR, 1H NMR, and Mass spectral data.


Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs.

Rajput CS, Singhal S - J Pharm (Cairo) (2013)

© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4590821&req=5

Mentions: The synthetic routes of compounds are outlined in Scheme 1. As shown in Scheme 1, compounds 2-methylsubstitued-4H-3,1-benzoxazin-4-ones (1,2) were synthesized by the known procedure of Bogert [28]. Substituted anthranilic acid reacted with acetic anhydride to give 2-methylsubstituted-4H-3,1-benzoxazin-4-ones (1,2), which further reacted with 2-amino phenyl amine in acetic acid to yield 3-(2′-aminophenyl)-2-methyl-6-substituted quinazolin-4-ones (3,4). Compounds (3,4) when treated with different substituted aromatic aldehydes formed various substituted arylidene derivatives (5–10). These arylidene derivatives on treatment with chloroacetylchloride in presence of triethylamine yielded 3-[2′-(3′′-chloro-2′′-oxo-4′′-substituted phenylazetidin-1′′-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11–16). On the other hand, these arylidene derivatives on reaction with thioglycolic acid and anhydrous ZnCl2 furnished 3-[2′-(2′′-substitutedphenyl-4′′-oxo-1′′,3′′-thiazolidin-3′′-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones. (17–22). The structures of the compounds synthesized were assigned on the basis of elemental analysis, IR, 1H NMR, and Mass spectral data.

Bottom Line: A series of 3-[2'-(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5-10), 3-[2'-(3(″)-chloro-2(″)-oxo-4(″)-substitutedphenylazetidin-1(″)-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11-16), and 3-[2'-(2(″)-substitutedphenyl-4(″)-oxo-1(″),3(″)-thiazolidin-3(″)-yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17-22) have been synthesized in the present study.The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, (1)H NMR, and mass spectral data.All the newly synthesized compounds were screened for anti-inflammatory and analgesic activities.

View Article: PubMed Central - PubMed

Affiliation: Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India ; Jubilant Chemsys Ltd. R & D B-34, Sector 58, Noida 201301, India.

ABSTRACT
A series of 3-[2'-(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5-10), 3-[2'-(3(″)-chloro-2(″)-oxo-4(″)-substitutedphenylazetidin-1(″)-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11-16), and 3-[2'-(2(″)-substitutedphenyl-4(″)-oxo-1(″),3(″)-thiazolidin-3(″)-yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17-22) have been synthesized in the present study. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, (1)H NMR, and mass spectral data. All the newly synthesized compounds were screened for anti-inflammatory and analgesic activities.

No MeSH data available.