Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety.
Treatment of 2-cyano-N-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetamide (1) with phenyl isothiocyanate/dimethylsulphate afforded the corresponding ketene N,S-acetal 2 which upon treatment with hydrazine hydrate and 4-aminoantipyrine afforded the pyrazolo derivatives 3 and 4, respectively. 3-aminopyrazole derivative 3 was utilized as key intermediate for the synthesis of pyrazolo[3,4-d]pyrimidine 5, pentaaza-as-indacene 6, triaza-cyclopenta[c]phenanthrene 7, pyrazolo[1,5-a]pyrimidine 8, 9 and (dimethyl-pyrrol-1-yl)pyrazole 10 derivatives. Furthermore, treatment of 1 with DMF/DMA gave the corresponding acrylamide derivative 11 which upon treatment with hydrazine hydrate afforded the corresponding 3-aminopyrazole derivative 12. Moreover, coupling of 1 with 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-diazonium chloride gave the hydrazone derivative 13 which upon cyclization with acetic acid afforded the corresponding pentaaza-fluorene derivative 14. Representative compounds of the synthesized products were evaluated as antimicrobial agents. Some of these compounds exhibited promising activities.
Chemistry Department, Faculty of Science, Mansoura University, El-Gomhoria Street, Mansoura 35516, Egypt. dr_mostafa_chem@yahoo.com
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D000528:Alternaria / Q000187:drug effects; D000880:Anthraquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003500:Cyclization; D005670:Fusarium / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011720:Pyrazoles / Q000737:chemistry*; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D011720:Pyrazoles; C031280:pyrazole