New drug candidates remained under consideration by the pharmaceutical industries to cure new arising diseases. To fulfill the requirement of new drug candidates, synthetic chemistry has added much in this regard. A large number of bioactive compounds have been synthesized by different fields of chemistry which emphasize the significance of synthetic chemistry in the field of pharmacy. The significant potentency of tyrosinase, urease, alkaline phosphate and α-glucosidase inhibitors based on indole and oxadiazole scaffold has been reported in literature previously. The presented work is also about the synthesis of some new bioactive molecules by coupling different bioactive functionalities. The valuable biological activities of derivatives of indole, amide, and 1,3,4-oxadiazole prompted us to synthesize some new compounds comprising amalgamation of these functionalities; and to demonstrate their % hemolytic activities and enzyme inhibitory potentials supported by the computational docking simulations. The presented work has been extended into different seven (7) schemes. In the first scheme the starting compound, 4-(1H-indol-3-yl)butanoic acid (1) was converted to alkyl/aralkyl substituted (6a-m) and un/substituted benzyl derivatives (6n-r) in four steps through formation of ethyl 4-(1H-indol-3-yl)butanoate (2). First step includes refluxing of 1 with concentrated H2SO4 in ethanol for 8 hours and second step includes stirring of 2 with hydrazine and methanol at room temperature for 14 hours. The compound 3 was also refluxed with CS2 in ethanol having dissolved KOH for 16 hours to synthesize 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazole-2-thiol (4) which was further reacted with various alkyl/aralkyl halides (5a-r) in N,Ndimethylformamide (DMF) and lithium hydride (LiH) to synthesize eighteen alkyl/aralkyl-5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazol-2-yl-sufide (6a-m, Scheme- 1) and un/substituted benzyl-5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazol-2-yl-sufide (6a-r, Scheme-1). Different aryl amines (7a,c,e,h-j,n-q) were reacted with 2-bromoacetyl bromide (8) to synthesize 2-bromo-N-(un/substituted)acetamides (9a-j, Scheme-2), aryl amines (7c-m,p) with 3-bromopropanoyl chloride (11) to synthesize 3-bromo-N- (substituted)propanamides (12a-l, Scheme-3), aryl/aralkyl amines (7c-g,i,k,m,p,q) with 4-chlorobutanoyl chloride (14) to synthesize 4-chloro-N-(substitutedphenyl)butanamides (15a-j, Scheme-4), un/substituted anilines (7a-m) with 3- (chloromethyl)benzoylchloride (17) to synthesize 3-(chloromethyl)-N-(un/substitutedphenyl)bezamides (18a-m, Scheme-5), substituted anilines (7b-i,k-m) with 4- (chloromethyl)benzoylchloride (20) to synthesize 4-(chloromethyl)-N-(substitutedphenyl)bezamides (21a-k, Scheme-6) and morpholine (23a) & un/substitutedpiperidines (23b-d) with 4-(bromomethyl)benzenesulfonyl chloride (24) to synthesize 1-{[4-(bromomethyl)phenyl]sulfonyl}morpholine (25a, Scheme-7) and 1-{[4- (bromomethyl)phenyl]sulfonyl}un/substituted-piperidines (25b-d, Scheme-7) as electrophiles. The compound 4, in DMF and LiH, was stirred with 2-bromo-N- (un/substituted)acetamides (9a-j) to synthesize twenty ten of 2-({5-[3-(1H-indol-3- yl)propyl]-1,3,4-oxadiazol-2-yl}sulfanyl)-N-(un/substituted)acetamides derivatives (10a-j, Scheme-2). Twelve compounds were synthesized as 3-({5-[3-(1H-indol-3-yl)propyl]- 1,3,4-oxadiazol-2-yl}sulfanyl)-N-(substituted-phenyl)propanamides derivatives (13al, Scheme-3), by reaction of 3-bromo-N-(substituted-phenyl)propanamides (12a-l) with 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazol-2-thiol (4) in DMF and LiH. Ten compounds were synthesized as 4-({5-[3-(1H-indol-3-yl)Propyl]-1,3,4- oxadiazol-2-yl}sulfanyl)-N-(substituted)butanamides derivatives (16a-j, Scheme-4), by reaction of 4-chloro-N-(substituted-phenyl)butanamides (15a-j) with 5-[3-(1Hindol-3-yl)propyl]-1,3,4-oxadiazol-2-thiol (4) in DMF and LiH. Thirteen compounds were synthesized as 3-[({5-[3-(1H-indol-3-yl)propyl]- 1,3,4-oxadiazol-2-yl}sulfanyl)methyl]-N-(un/substituted-phenyl)benzamides (19a-m, Scheme-5), by reaction of 3-(chloromethyl)-N-(un/substituted-phenyl)bezamides (18a-m) with 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazol-2-thiol (4) in DMF and LiH. Eleven compounds were synthesized as 4-[({5-[3-(1H-indol-3-yl)propyl]- 1,3,4-oxadiazol-2-yl}sulfanyl)methyl]-N-(substituted-phenyl)benzamides (22a-k, Scheme-6), by reaction of 4-(chloromethyl)-N-(substituted-phenyl)bezamides (21a-k) with 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazol-2-thiol (4) in DMF and LiH. Four compounds were synthesized as 5-[3-(1H-indol-3-yl)propyl]-1,3,4- oxadiazol-2-thiol derivatives (26a-d, Scheme-7), by reaction of 1-{[4- (bromomethyl)phenyl]sulfonyl}morpholine (25a) and 1-{[4- (bromomethyl)phenyl]sulfonyl}un/substituted-piperidines (25b-d) with 5-[3-(1Hindol-3-yl)propyl]-1,3,4-oxadiazol-2-thiol (4) in DMF and LiH. The structural characterization has been well supported by spectral data of IR (Infra Red), 1H-NMR (Proton Nuclear Magnetic Resonance), 13C-NMR (Carbon-13 Nuclear Magnetic Resonance), 2D-NMR HMBC (Heteronuclear Multiple Bond Correlation) and EIMS (Electron Impact Mass Spectrometry). Some of the 1 H-NMR, 13 C-NMR EIMS and IR spectra of synthesized compounds are also presented for the obvious perceptive of signals. The physical data of all the compounds is also provided which included color, state, yield, melting points (in case of solids), molecular formula and molecular mass. The biological evaluation of these compounds included enzyme inhibitory activity against four enzymes including tyrosinase, α-glucosidase, Jack bean urease and alkaline phosphate and finally evaluation of % hemolytic activity. The enzyme inhibition data is also explicated in detail through molecular docking studies. The reference standards used were kojic acid for tyrosinase, acarbose for α-glucosidase, thiourea for Jack bean urease, KH2PO4 (potassium dihydrogen phosphate) for alkaline phosphate, Triton X-100 and PBS (phosphate buffer saline) for % hemolytic evaluation. All the compounds were found active and showed excellent results in various studies mentioned above. The biological activity data in comparison of each scheme with the reference standard drugs is presented in results and discussion section.