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
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. EKB Journal Management System, 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". EKB Journal Management System, 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', EKB Journal Management System, 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. EKB Journal Management System, 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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