In the research delineate herein, an innovative sequence of new series of multi-functional target mols. (9a-i) having indole-N-phenyltriazole bi-heterocyclic hybrids unified with N-arylated butanamides was synthesized as alk. phosphatase inhibitor.The structural validation of all the formulated compounds was accomplished through IR, EI-MS, 1H NMR, 13C NMR and CHN anal. data.The in vitro enzyme inhibitory investigation revealed the efficacy of these bi-heterocyclic derivatives, 9a-i, as potent inhibitors of alk. phosphatase relative to the standard used.The compound 9h was found to be the most active compound (IC50 = 0.062 ± 0.017 μM), and its inhibitory activity is about 10 times higher than potassium dihydrogen phosphate (KH2PO4) (IC50 = 5.251 ± 0.468 μM).The kinetics mechanism was attributed by evaluating the Lineweaver-Burk plots, which revealed that compound 9h inhibited the alk. phosphatase non-competitively to form an enzyme-inhibitor complex.The inhibition constant Ki determined from Dixon plots for this compound was 0.045 μM.The computational study was in full agreement with the exptl. records and these ligands exhibited good interactions and binding energy values.These mols. also demonstrated mild cytotoxicity toward red blood cell membranes when analyzed through hemolysis.So, based on the presented results, these mols., being the promising inhibitors of alk. phosphatase, might be deliberated as suitable medicinal scaffolds to render normal calcification of bones and teeth.