ChemInform Abstract: Synthesis and Pharmacological Evaluation of Some Novel 5‐Aryl‐6‐arylamino‐1‐phenylpyrazolo[3,4‐d]pyrimidin‐4(5H)‐ones as Analgesic and Antiinflammatory Agents.

Shishoo, C. J.; Pathak, U. S.; Rathod, Ishwarsinh S.; Jain, Kishore S.; Nargund, Laxmivenkatesh G.; Taranalli, Ashok D; Patel, Harish M.; Kumar, Virendra; Shirsath, Vikas S.

doi:10.1002/chin.199947167

Cited by 4 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Unfortunately, some cardiovascular side effects such as myocardial infarction and increased incidences of high blood pressure caused by the highly selective COX-2 inhibitors led to the withdrawal of rofecoxib and valdecoxib from the market 10,11 . Pyrazolo [3,4-d]pyrimidine represents one of the most frequently found scaffold in a wide variety of anti-inflammatory agents 12,13 . The 5-benzamido-1H-pyrazolo [3,4-d]pyrimidin-4-one derivative (7) showed superior inhibitory profile against COX-2 when compared to that of reference standards N-[2-(cyclohexyloxy) 4-nitrophenyl]methane sulfonamide (NS398) and indomethacin 14 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Bakr

Azouz

Abdellatif

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

A new group of 1-phenylpyrazolo [3,4-d]pyrimidine derivatives 14a-d-21 were synthesized from 2-(6-methyl-1-phenyl-1H-pyrazolo [3,4-d]pyrimidin-4-yloxy)acetohydrazide (12). All the synthesized compounds were evaluated for their cyclooxygenase (COX) inhibition, antiinflammatory activity and ulcerogenic liability. All the target compounds were more potential in inhibiting COX-2 than COX-1. Compounds having pyrazolyl moiety in a hybrid structure with pyrazolo[3,4-d]pyrimidine scaffold (14a-d, 16 and 17) showed higher edema inhibition percentage activities (34-68%) and the 5-aminopyrazole derivative (14c, ED 50 ¼ 87.9 mmol/kg) was the most potent one4celecoxib (ED 50 ¼ 91.9 mmol/kg). While, the in vivo potent compounds (14a-d, 16, 17 and 21) caused variable ulceration effect (ulcer index ¼ 0.33-4.0) comparable to that of celecoxib (ulcer index ¼ 0.33), the pyrazol-3-one derivative (16) and the acetohydrazide (21) were the least ulcerogenic derivatives showing the same ulcerogenic potential of celecoxib.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Bakr

Azouz

Abdellatif

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…These are exemplified by the variously substituted bicyclic pyrazolo[3,4- d ]pyrimidine Ia,b [6, 7] and II [8] derivatives and the tricyclic pyrazolo[3,4- d ]-[1,2,4]triazolo[1,5- a ]pyrimidin-4-one III [6], pyrazolo[3,4- d ][1,3]thiazolo[3,2- a ]pyrimidin-4-one IVa,b [9], and pyrazolo[3,4- e ][1,2,4]triazolo[4,3- a ]pyrimidin-5-one Va,b [10, 11] derivatives (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anti-Inflammatory, and Ulcerogenicity Studies of Novel Substituted and Fused Pyrazolo[3,4-d]pyrimidin-4-ones

El-Tombary

2013

Sci. Pharm.

View full text Add to dashboard Cite

In the present investigation, some new pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives (7–12) as well as fused pyrazolo[3′,4′:4,5]pyrimido[1,2-b]pyridazin-4(1H)-one (14–16) and 7,8,9,10-tetrahydropyrazolo[3′,4′:4,5]pyrimido[1,2-b]-cinnolin-4(1H)-one (17) ring systems were synthesized using the starting compound 5-amino-6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (5). The structures of the newly synthesized compounds were elucidated by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The theoretical calculation of their lipophilicity as C log P was performed. The anti-inflammatory activity of all newly synthesized compounds was evaluated using the carrageenan-induced paw edema test in rats using indomethacin as the reference drug. Ulcer indices for the most active compounds were calculated. Seven compounds (10b, 11a–f) showed consistently good anti-inflammatory activity. In particular, 5-{[4-(4-bromophenyl)-3-(4-chlorophenyl)-1,3-thiazol-2(3H)-ylidene]amino}-6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (11e) and its 3,4-bis(4-chlorophenyl) analog (11f) were found to be the most effective among the other derivatives, showing activity comparable to that of indomethacin with minimal ulcerogenic effects. Correlation of the biological data of the active compounds with their theoretically calculated C log P values revealed that lipophilicity influences the biological response.

show abstract

Design, Synthesis and Evaluation of Novel Thiopyrimidine-Glucuronide Compounds with Promising Biological Activities

Wanare¹

2022

Asian J. Org. Med. Chem.

View full text Add to dashboard Cite

3-Methyl-5-acetyl-7-[(2-sulfanylidene-6-aryl-1,2-dihydropyrimidin-4-yl)amino]-1,2-benzisoxazoles (2a-n) were obtained from N-(5-acetyl-3-methyl-1,2-benzoxazol-7-yl)-3-arylprop-2-enamides (1a-n) and thiourea. Products (2a-n) oxidized with KMnO4 to afford 5-acetyl-7-[(2-sulfanylidene-6-aryl-1,2- dihydropyrimidin-4-yl)amino]-1,2-benzisoxazole-3-carboxylic acids (3a-n). Reaction of 3a-n with D-gluconic acid and pyridine yielded β-D-glucuronosyl-5-acetyl-7-[(2-sulfanylidene-6-aryl-1,2- dihydropyrimidin-4-yl)amino]-1,2-benzisoxazol-3-carboxylates (4a-n). The present synthesis featured the formation of dihydropyrimidine skeleton through ring closure of key intermediates and installation of pyrimidine ring with amino group. The structures of all the newly synthesized compounds were characterized by analytical data, IR, 1 H NMR and mass spectrometry.

show abstract

ChemInform Abstract: Synthesis and Pharmacological Evaluation of Some Novel 5‐Aryl‐6‐arylamino‐1‐phenylpyrazolo[3,4‐d]pyrimidin‐4(5H)‐ones as Analgesic and Antiinflammatory Agents.

Cited by 4 publications

References 0 publications

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Synthesis, Anti-Inflammatory, and Ulcerogenicity Studies of Novel Substituted and Fused Pyrazolo[3,4-d]pyrimidin-4-ones

Design, Synthesis and Evaluation of Novel Thiopyrimidine-Glucuronide Compounds with Promising Biological Activities

Contact Info

Product

Resources

About