Synthesis of a number of highly oxygenated furo [3,2-c]pyran/chromen-4-one has been accomplished by one-pot reaction from easily available dehydroacetic acid/3-acetyl-4-hydroxycoumarin or their chalcones and α-bromoketones. All the synthesized molecules were characterized utilizing various spectroscopic techniques and screened for anticancer activity (in vitro) against three colon (HCT-116, SW-620, HT-24), lung (A-549), prostate-(PC-3), breast (MCF-7) cell lines. Compounds 5a, 9d, 9f showed good activity against breast MCF-7 cancer cell line having IC 50 values 6.9, 2.8, 5.3 μM, respectively. Of these compounds, 9d showed better activity against prostate PC-3 cell line with IC 50 value 3.8 μM. The synthesized compounds were also studied for antibacterial activity (in vitro) using different strains of bacteria (Bacillus subtilis and Staphylococcus aureus -Gram-positive and Escherichia coli, Pseudomonas aeruginosa -Gram negative) as well as fungal strains (Aspergillus niger and Candida albicans) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. The antimicrobial screening study showed that compound 9f exhibited promising activity against S. aureus and B. subtilis, while 5h showed excellent and 5i and 9b showed better activity against E. coli. Compounds 5d and 5e showed promising activity against P. aeruginosa. The compounds 5c-5e displayed excellent activity against C. albicans and A. niger than Fluconazole.

A series of twenty 2‐(2‐((1‐aryl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl) benzoxazoles were synthesized from different aryl azides by copper catalyzed [3+2] cycloaddition reaction in 78–88 % yield. The structure of products was elucidated using spectroscopic techniques. These compounds were tested for cytotoxicity against five cancer cell lines [MCF‐7 (Breast), HT‐29 (Colon), Hep‐G2 (Liver), A549 (Lung) and PC‐3 (Prostate)] using the standard drug Adriamycin. It was found that 2‐(2‐((1‐(3,4‐dichlorophenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)benzoxazole (6 g) was active against all the above cancer cell lines with good activity against PC‐3 cancer cell line (GI50 value 60 μM) comparative to Adriamycin (GI50 value 0.3 μM). Compound 6 g also displayed significant antioxidant activity (IC50 value 4.56 μM) as compared to standard ascorbic acid (IC50 value 9.10 μM).

Synthesis of a number of highly oxygenated furo[3,2-c]pyran-4-one (4, 5) and furo[3,2-c]chromen-4-one (8, 9) has been accomplished by a simple one pot reaction from easily available versatile starting materials - dehydroacetic acid and 3-acetyl-4-hydroxycoumarin. All the synthesized molecules were characterized utilizing various spectroscopic techniques and screened for anticancer activity (in vitro) against three Colon (HCT-116, SW-620, HT-24), Lung (A-549), Prostate-(PC-3), Breast-(MCF-7) cell lines. Compounds 5a, 9d, 9f showed good activity against breast MCF-7 cancer cell line having IC50 values 6.9, 2.8, 5.3 µM, respectively. Out of these compound 9d showed better activity against prostate PC-3 cell line with IC50 value 3.8 µM. The synthesized compounds were also studied for potential antibacterial activity (in vitro) using different strains of bacteria (Bacillus subtilis and Staphylococcus aureus -Gram-positive, and Escherichia coli- Gram negative) as well as fungal strains (Aspergillus niger and Candida albicans) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. The outcome of the antimicrobial screening study showed that compound 9f exhibited promising activity against S. aureus and B. subtilis while 5h showed excellent and 5i and 9b showed better activity against E. coli. The compounds 5c-5e displayed excellent activity against C. albicans and A. niger than Fluconazole.

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2-Halogenatedphenyl benzoxazole-5-carboxylic acids with mono-halogen (chloro, bromo and fluoro) substituted at ortho-, meta-and para-positions on the phenyl ring were designed and synthesized based on significance of presence of halogen in increasing number of marketed halogenated drugs and importance of benzoxazoles. These 2-alogenatedphenylbenzoxazole-5-carboxylic acids and their methyl esters were screened for anti-inflammatory activity, and cytotoxicity. 2-(3-Chlorophenyl)benzoxaole-5-carboxylic acid (6b) exhibited significant anti-inflammatory activity with IC 50 values of 0.103 mM almost equivalent to the standard drug ibuprofen (0.101 mM). 2-(4-Chlorophenyl)benzoxaole-5-carboxylic acid (6c) showed excellent cytotoxic activity against 22Rv1 cells (human prostate carcinoma epithelial cell lines) with IC 50 value of 1.54 μM better than that of standard drug doxorubicin having IC 50 value of 2.32 μM. More importantly, the selectivity index of this potential molecule was found to be 57.74. Molecular docking analysis resulted in good binding interactions of these compounds with their respective biochemical targets viz. Cyclooxygenase-2 and aldo-keto reductase IC3.