Following the principles of bioisosterism we envisioned to synthesize novel analogs of lead compound α- cyclohexyl-α-hydroxy-benzeneacetic acid-4-(diethylamino)-2-butynyl ester with planned structural modifications. Compounds synthesized were characterized by spectroscopic techniques to establish their structures and evaluated for their anti-spasmodic, anti-cholinergic and antimicrobial potency. The antispasmodic and anti-cholinergic testing was carried out by muscle relaxation studies on isolated Wistar rat’s ileum, contracted with acetylcholine and acetylcholine antagonist property on frog rectus abdominal muscle preparation respectively. The sedative potency of the compounds was evaluated following one-way ANOVA followed by Scheffe’s post hoc analysis to find out the significance. The compounds were evaluated in vitro, for their antibacterial activity using acetone as a solvent and MIC was done by broth dilution method. The fungal susceptibility testing on different fungi was done by cupdiffusion method using Clotrimazole (100mcg/mL) as standard using acetone as a solvent. The compounds have shown promising results and definite structure-activity relationship could be established.