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Research Article

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

Rania B. BakrDepartment of Pharmaceutical Organic Chemistry, Beni-Suef University, Beni-Suef, Egypt, and

Amany A. AzouzDepartment of Pharmacology and Toxicology, Beni-Suef University, Beni-Suef, Egypt

Khaled R. A. AbdellatifDepartment of Pharmaceutical Organic Chemistry, Beni-Suef University, Beni-Suef, Egypt, and Correspondence[email protected]

Figures & data

Figure 1. Chemical structures of traditional NSAIDs; aspirin (1), indomethacin (2) and ibuprofen (3), selective COX-2 inhibitors; celecoxib (4), rofecoxib (5), and valdecoxib (6) and reported pyrazolo[3,4-d]pyrimidine derivatives (7–9) with anti-inflammatory activity.

Scheme 1. Reagents and conditions: (a) ethyl chloroacetate, acetone, K₂CO₃, reflux, 6 h; (b) hydrazine hydrate, ethanol, reflux, 5 h; (c) CR(OC₂H₅)=C(CN)X, ethanol, 10 h; (d) chloroacetyl chloride, DMF, K₂CO₃, RT, overnight; (e) ethyl acetoacetate, ethanol, reflux, 12 h; (f) acetylacetone, CH₃COOH, reflux, 6 h; (g) 4-COOC₂H₅-C₆H₄-NHCOCH₂Cl, ethanol, reflux, 8 h; (h) benzoyl chloride, ethanol, reflux, 6 h; (i) 4-chlorophenylisocyanate, dioxane, reflux, 4 h.

Scheme 1. Reagents and conditions: (a) ethyl chloroacetate, acetone, K2CO3, reflux, 6 h; (b) hydrazine hydrate, ethanol, reflux, 5 h; (c) CR(OC2H5)=C(CN)X, ethanol, 10 h; (d) chloroacetyl chloride, DMF, K2CO3, RT, overnight; (e) ethyl acetoacetate, ethanol, reflux, 12 h; (f) acetylacetone, CH3COOH, reflux, 6 h; (g) 4-COOC2H5-C6H4-NHCOCH2Cl, ethanol, reflux, 8 h; (h) benzoyl chloride, ethanol, reflux, 6 h; (i) 4-chlorophenylisocyanate, dioxane, reflux, 4 h.

**Table 1. In vitro COX-1 and COX-2 inhibition of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21) and celecoxib.**

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Table 2. Anti-inflammatory activities for 50 mg/kg dose of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21), (ED₅₀, μmol/kg) of most potent derivatives (14a–d, 16, 17 and 21) and celecoxib.

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Table 3. Ulcerogenic effect for most potent 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d, 16, 17 and 21) and celecoxib.

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

**Table 1. In vitro COX-1 and COX-2 inhibition of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21) and celecoxib.**

Table 2. Anti-inflammatory activities for 50 mg/kg dose of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21), (ED₅₀, μmol/kg) of most potent derivatives (14a–d, 16, 17 and 21) and celecoxib.

Table 3. Ulcerogenic effect for most potent 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d, 16, 17 and 21) and celecoxib.

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

Figures & data

Table 1. In vitro COX-1 and COX-2 inhibition of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21) and celecoxib.

Table 2. Anti-inflammatory activities for 50 mg/kg dose of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21), (ED50, μmol/kg) of most potent derivatives (14a–d, 16, 17 and 21) and celecoxib.

Table 3. Ulcerogenic effect for most potent 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d, 16, 17 and 21) and celecoxib.

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**Table 1. In vitro COX-1 and COX-2 inhibition of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21) and celecoxib.**

Table 2. Anti-inflammatory activities for 50 mg/kg dose of 1-phenylpyrazolo[3,4-d]pyrimidine derivatives (14a–d–21), (ED₅₀, μmol/kg) of most potent derivatives (14a–d, 16, 17 and 21) and celecoxib.