Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety

• Published in: European journal of medicinal chemistry Vol. 45; no. 5; pp. 1843 - 1848
• Main Authors: Gouda, M.A., Berghot, M.A., Shoeib, A.I., Khalil, A.M.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Masson SAS 01-05-2010; Elsevier
• Subjects: Alternaria - drug effects; Aminopyrazole; Anthraquinone; Anthraquinones - chemical synthesis; Anthraquinones - chemistry; Anthraquinones - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antimicrobial agent; Biological and medical sciences; Chemical control; Control; Cyclization; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; Fusarium - drug effects; General aspects; Ketene N, S-acetal; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Pharmacology. Drug treatments; Phenanthrene; Phytopathology. Animal pests. Plant and forest protection; Pseudomonas aeruginosa - drug effects; Pyrazoles - chemistry; Pyrimidine; Staphylococcus epidermidis - drug effects; Stereoisomerism; Structure-Activity Relationship; Phenanthrene; Aminopyrazole; Anthraquinone; Ketene N, S-acetal; Antimicrobial agent; Pyrimidine; Five membered ring; Nitrile; Angular nitrogen heterocycle; Nitrogen heterocycle; Antifungal agent; Malonic acid derivatives; Pyrazolopyrimidine derivatives; Structure activity relation; Vinylic compound; Bicyclic compound; Pyrazole derivatives; Aromatic compound; Chemical synthesis; Anthraquinone derivatives; Quinone; Pesticides; Tetracyclic compound; Tricyclic compound; Condensed benzenic compound; In vitro; Fungicide; Ketene N,S-acetal; Carboxamide; Antibacterial agent
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.01.021

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-1
H-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.
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