Synthesis of novel triazolyl pyranochromen-2(1H)-ones and their antibacterial activity evaluation

• Published in: Medicinal chemistry research 2016-06, Vol.25 (6), p.1057-1073
• Main Authors: Kumar, Shiv, Prasad, Suchita, Kumar, Bipul, Gautam, Hemant K., Sharma, Sunil K.
• Format: Article
• Language: English
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Cell Biology; Original Research; Pharmacology/Toxicology
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-016-1549-3

A series of thirty-three novel triazolyl pyranochromen-2(1 H )-one derivatives have been synthesized via Cu (I) catalysed Huisgen 1,3-dipolar cycloaddition reaction. All of the synthesized compounds have been fully characterized from their spectral data and evaluated for antibacterial activity against both gram-positive and gram-negative bacteria. The activity results revealed that amongst all the compounds screened, six compounds, i.e. 2-[4-(((7-ethyl-2,2,6-trimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2- g ]chromen-10-yl)oxy)methyl)-1 H -1,2,3-triazol-1-yl]acetic acid ( 41 ), 10-[(1-(1,3-dihydroxypropan-2-yl)-1 H -1,2,3-triazol-4-yl)methoxy]-3-ethyl-4,8,8-trimethyl-7,8-dihydropyrano[3,2- g ]chromen-2(6 H )-one ( 44 ), 3-ethyl-4,8,8-trimethyl-10-[(1-((2 R ,3 R ,4 S ,5 S ,6 R )-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2 H -pyran-2-yl)-1 H -1,2,3-triazol-4-yl)methoxy]-7,8-dihydropyrano[3,2- g ]chromen-2(6 H )-one ( 46 ), 2-[4-(((7-hexyl-2,2,6-trimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2- g ]chromen-10-yl)oxy)methyl)-1 H -1,2,3-triazol-1-yl]acetic acid ( 52 ), 10-[(1-(1,3-dihydroxypropan-2-yl)-1 H -1,2,3-triazol-4-yl)methoxy]-3-hexyl-4,8,8-trimethyl-7,8-dihydropyrano[3,2- g ]chromen-2(6 H )-one ( 55 ) and 3-hexyl-4,8,8-trimethyl-10-[(1-((2 R ,3 R ,4 S ,5 S ,6 R )-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2 H -pyran-2-yl)-1 H -1,2,3-triazol-4-yl)methoxy]-7,8-dihydropyrano[3,2- g ]chromen-2(6 H )-one ( 57 ), exhibited moderate activity against all the strains studied with zone of inhibition between 10 and 16 mm and MIC values in the range of 75–170 µg/mL as compared to the standard used. The information obtained from structure–activity relationship can be used to design and develop the next generation of compounds with higher antibacterial efficacy.