Hassan, E., Elkerdawy, M., Abzeid, A., Zayed, S. (2023). Microwave and Conventional Synthesis of Some New Mercapto Pyrazolaldehyde Bonded to Indolyldihydropyrimidine Thione Derivatives as In Vivo Anti-inflammatory, and Analgesic, and In Vitro Antimicrobial Agents. test, 66(3), 439-448. doi: 10.21608/ejchem.2022.142051.6213
Entesar Hassan; Mohamed Elkerdawy; Asmaa Abzeid; Salem Zayed. "Microwave and Conventional Synthesis of Some New Mercapto Pyrazolaldehyde Bonded to Indolyldihydropyrimidine Thione Derivatives as In Vivo Anti-inflammatory, and Analgesic, and In Vitro Antimicrobial Agents". test, 66, 3, 2023, 439-448. doi: 10.21608/ejchem.2022.142051.6213
Hassan, E., Elkerdawy, M., Abzeid, A., Zayed, S. (2023). 'Microwave and Conventional Synthesis of Some New Mercapto Pyrazolaldehyde Bonded to Indolyldihydropyrimidine Thione Derivatives as In Vivo Anti-inflammatory, and Analgesic, and In Vitro Antimicrobial Agents', test, 66(3), pp. 439-448. doi: 10.21608/ejchem.2022.142051.6213
Hassan, E., Elkerdawy, M., Abzeid, A., Zayed, S. Microwave and Conventional Synthesis of Some New Mercapto Pyrazolaldehyde Bonded to Indolyldihydropyrimidine Thione Derivatives as In Vivo Anti-inflammatory, and Analgesic, and In Vitro Antimicrobial Agents. test, 2023; 66(3): 439-448. doi: 10.21608/ejchem.2022.142051.6213

Microwave and Conventional Synthesis of Some New Mercapto Pyrazolaldehyde Bonded to Indolyldihydropyrimidine Thione Derivatives as In Vivo Anti-inflammatory, and Analgesic, and In Vitro Antimicrobial Agents

Egyptian Journal of Chemistry
Volume 66, Issue 3, March 2023, Pages 439-448    PDF (1.23 M)
Document Type: Original Article
DOI: 10.21608/ejchem.2022.142051.6213
Authors
Entesar Hassan* 1; Mohamed Elkerdawy2; Asmaa Abzeid1; Salem Zayed1
1Chemistry Department, Faculty of Science, South Valley University, Qena
2Pharmaceutical chemistry department,Faculty of pharmacy, Mansoura University, Mansoura
Abstract
The five-membered heterocyclic group of pyrazoles/pyrazolines plays an important role in drug discovery besides to their wide range of the biological, agrochemical and pharmacological properties. The synthesis of the pyrazole derivative 2 was achieved via the reaction between oxoketene gem-dithiol 1 and phenylhydrazine. Subsequently, the key synthon mercaptopyrazole derivative 2 was qualified to react with some reagents e.g. DMF/POCl3 and/or sulfanilic acid to afford pyrazolecarbaldehyde 3 and/or pyrazolyl aminobenzenesulfonic acid derivative 4. The Schiff bases 5a-c and/or the cyclic adducts 7, 8a,b and/or 9 resulted from the condensation of the formylated adduct 3 with the appropriate substituted amines such as p-nitroaniline, p-chloroaniline, sulfanilic acid, guanidine sulfate, thiourea and/or acetophenone. The celecoxib analog 6 was obtained by the condensation of the terminal sulfonic acid group in the adduct 4 with 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one. The previously prepared compounds 2, 4-9 were obtained in both conventional and/or microwave conditions and they were screened for their in vivo and in vitro activities. The structures of the newly prepared compounds have been confirmed by means of elemental analyses, FT-IR, MS, 1H-NMR and/or 13C-NMR.
Keywords
Pyrazoles; oxoketene gem-dithiol; celecoxib analog; Vilsmeier-Haack formylation; Schiff bases; carrageenan paw edema
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