Twenty-seven 1, 5-disubstituted-pyridin-2 (1H)-one derivatives were synthesized and evaluated for their anti-cancer and anti-fibrosis activity by A549 and NIH3T3 cell viability assays, respectively. To study the selectivity between the cancer and fibrosis cell lines, pharmacophore models (F1–F4) were built in advance for compounds with pyridin-2 (1H)- one scaffold, which revealed the relationship between the occupation of the aromatic sub- ...