Microwave induced three-component synthesis and antimycobacterial activity of benzopyrazolo[3,4-b]quinolindiones.
Three series of novel 4-arylbenzo[h]pyrazolo[3,4-b]quinolin-5,6-diones 4, 7 and 9 have been efficiently obtained in good yields by three-component microwave assisted reaction between aminopyrazoles 1 or 6 (both 1-phenyl and 1-H substituted), 2-hydroxynaphthoquinone 2 and benzaldehydes 3. Compounds 4, 7 and 9 have been evaluated against fifteen Mycobacterium spp strains, and six of them have shown antimycobacterial activity. The highest inhibitory activity with MIC ≤2 μg/mL for three of these compounds (4a, 4b and 4g) was related with their highest lipophilicity and lesser polarity within these series.
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali, Colombia. Electronic address: jairo.quiroga@correounivalle.edu.co.
Jairo
J
Quiroga
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali, Colombia.
Yurina
Y
Diaz
GrupoQ1 Micobacterias, Subdirección Red Nacional de Laboratorios, Instituto Nacional de Salud, Bogotá, Centro Colombiano de Investigación en Tuberculosis CCITB, Bogotá, DC, Colombia.
Juan
J
Bueno
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali, Colombia.
Braulio
B
Insuasty
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali, Colombia.
Rodrigo
R
Abonia
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali, Colombia.
Alejandro
A
Ortiz
Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, Jaén, Spain.
Manuel
M
Nogueras
Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, Jaén, Spain.
Justo
J
Cobo
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D009161:Mycobacterium / Q000145:classification / Q000187:drug effects*; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013045:Species Specificity; D021241:Spectrometry, Mass, Electrospray Ionization
D000995:Antitubercular Agents; D015363:Quinolones
2-Hydroxynaphthoquinone; Aminopyrazoles; Antimycobacterial activity; Microwave irradiation; Pyrazolo[3,4-b]quinolin-5,6-diones; Three-component reactions