WORLD JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES

Vadivelu et al. World Journal of Pharmacy and Pharmaceutical Sciences

SJIF Impact Factor 7.421

Volume 8, Issue 6, 515-540 Review Article ISSN 2278 – 4357

2,5-DISUBSTITUTED -1,3,4 OXADIAZOLE: MOLECULES OF

MULTIFARIOUS APPLICATIONS – A REVIEW

Annapoorna Vadivelu*, A. Nazreen Banu, Y. Nafoura Begam and P. Madhivardhana

MTPG & RIHS, Puducherry.

ABSTRACT
Article Received on
05 April 2019, Oxadiazole or furadiazole are the 5-membered heterocyclic compound
Revised on 26 April 2019,
Accepted on 16 May 2019 containing oxygen and nitrogen. It has become an important
DOI: 10.20959/wjpps20196-13967 construction motif for the development of new drugs. A series of
derivatives of 1, 3, 4-oxadiazole having verities of biological activities
can be Synthesized by various methods. The activities includes anti-
*Corresponding Author
Dr. Annapoorna Vadivelu cancer, anti-microbial, anti-inflammatory, anti-HIV, anti-tubercular,
MTPG & RIHS, Puducherry. anti-diabetic, anti-fungal etc. It also attracted the interest in medicinal
chemistry as surrogates (bioisosteres) for carboxylic acids, esters, and
carbamides. The review presents a brief summary of the chemistry, synthesis and a broad
view on the various pharmacological activities possessed by different compounds substituted
with 1,3,4-oxadiazole nucleus.

KEYWORDS: 2,5-disubstituted -1,3,4 oxadiazole, chemistry, synthesis and biological

activities.

INTRODUCTION
Simple five membered heterocycles possessing one oxygen atom and two nitrogen atoms are
considered as 1, 3, 4-oxadiazole and its derivatives. 1,3,4-oxadiazole can exist in different
isomeric forms, they are 1,2,5-oxadiazole(1), 1,2,4-oxadiazole(2), 1,2,3-oxadiazole(3), 1,3,4-
oxadiazole(4). Oxygen and nitrogen containing 5-membered heterocyclic nucleus is assessed
against various diseases. So they are given importance in medicinal chemistry because of
their diverse medicinal potential. Substituted 1,3,4-oxadiazole is have broad spectrum of
biological activities in pharmaceutical and agrochemical field. 1, 3, 4-oxadiazole shows wide
variety of activities such as virucidal, CNS depressant, genotoxic, anticonvulsant,
insecticidal, anti tubercular, anti HIV, anti inflammatory. It also known to exhibit anti

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malarial, Muscle relaxants, anti tumour, lipid peroxidation inhibitor, anti microbial and
remarkable analgesic, anti convulsant, diuretic, hypnotic and sedative properties.

Oxadiazole is a heterocyclic aromatic chemical compounds having a five member ring

containing one oxygen and two nitrogen atoms and molecular formula of oxadiazole
C2H2N2O. There are four isomers of oxadiazole: (1) 1,2,3-oxadiazole (2) 1,2,4-oxadiazole,
(3) 1,2,5- oxadiazole and (4) 1,3,4-oxadiazole are known, but the 1,2,3-isomer is unbalanced
and reverts to the diazoketone tautomer. Name for oxadiazole ring such as ‘Azoxime’ (1,2,4-
oxadiazole), ‘ urazan’ (1,2,5-oxadiazole , Furazans’ (1,2,5-oxadiazole and Biazole,
oxybiazole’ (1,3,4- oxadiazole).

(1) (2) (3) (4)

SYNTHESIS
Stefano cicchi[1] et al., Reported the synthesis of 2-aryl-1,3,4-oxadiazole derivative using (N-
isocyanoimino)-triphenylphosphorane with benzoic acid derivative.

N S Reddy[2] et al., Reported the synthesis of 2,5-di aryl/alkenyl -1,3,4-oxadiazole by the

Fe(II) / TEMPO catalysed oxidative cyclization of aroylhydrazones in the presence of
oxygen.

G. Zhang[3] et al., Reported the synthesis of 2,5-disubstituted-1,3,4-oxadiazole from the N-

arylidenearoylhydrazide in the presence of Cu(OTf)2.

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S. Guin[4] et al., Reported the synthesis of symmetrical and asymmetrical 2,5-disubstituted-

1,3,4-oxadiazole by the oxidative cyclisation of acylhydrazones in the presence of potassium
carbonate.

W. Yu, G. Huang[5] et al., Reported the synthesis of 2,5-diaryl-1,3,4-oxadiazole via N-

acylation of aryl tetrazoles with aryl aldehydes followed by thermal rearrangement.

L. Wang[6] et al., Reported the synthesis of 2,5-disubstituted-1,3,4-oxadiazole from hydrazine

hydrate and the corresponding 2-acyl-4,5-dichloropyridine-3-ones in polyphosphoric acid
(PPA) or BF3.

Y D Park[7] et al., Reported the synthesis of2,5-disubstituted -1,3,4-oxadiazole by 2-

iodoxybenzoic acid / tetraethylammonium bromide mediated oxidative cyclization of –
hydrazidehydrazones.

D Kumar[8] et al., Reported the synthesis of 5-substituted-2-ethoxy-1,3,4-oxadiazole by N

acylation /dehydrative cyclisation between ethyl carbazate and N-acylbenzotriazole in the
presence of Ph3P-I2 in very good yields.

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S. Wet-Osot[9] et al., Reported the synthesis of 2-amino-substituted -1,3,4-oxadiazole

derivative by the condensation of semicarbazide with aldehydes followed by I2-mediated
oxidative C-O bond formation.

P. Niu, J. Khang[10] et al., Reported the synthesis of 5-substituted-2-amino-1,3,4-oxadiazole

by the heterocyclization of semicarbazones in the presence of CBr4 as bromine source.

R. Kapoor[11] et al., Reported the synthesis of 2-amino-1,3,4-oxadiazole by the reaction of

isocyanide and hydrazides catalysed by palladium.

T. Fang[12] et al., prepared the 2-amino-5-aryl / alkyl-1,3,4-oxadiazole using tosyl chloride /

pyridine mediated cyclisation of thiosemicarbazide.

S.J Dolman[13] et al., Reported the synthesis of 2,5-disubstituted-1,3,4-oxadiazole by

oxidative desulfurization in the presence of iodobenzene and oxone.

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Gudipati R[14] et al., Synthesised 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)

phenylimino}-indolin-2-one derivative.

Ahsan MJ[15] et al., Synthesised a series of 1,5-dimethyl-2-phenyl- 4-{[(5-aryl-1,3,4-

oxadiazol-2yl) methyl]amino}-1,2-dihydro-3H-pyrazol-3-one derivatives.

Kotaiah Y[16] et al., SynthesizedN-substitute phenyl-5-methyl-6-(5-(4-substitutedphenyl)-

1,3,4oxadiazol-2-yl) thieno [2,3-d]pyrimidin-4-amine derivatives and phenylamino-5-
methylthieno[2,3d]pyrimidine-6-carboxylic acid derivatives were subtited on it.

RamazaniA[17] et al., synthesised 1,3,4-oxadiazole derivatives by the reaction between (N-

isocyanimino) triphenylphosphorane, bis-aldehydes (isophthalaldehyde and terphthal
aldehyde) and aromatic (or hetero aromatic) carboxylic acids.

KU WM[18] et al., Designed and synthesised 1,3,4-oxadiazole moiety containing sulfone

groups (scheme: 5) and were Reported to have ability to mycelia growth of
Ralstoniasolanacearum in vitro also having better control effect against tobacco bacterial wilt
so sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential
bactericides for plants.

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Puthiyapurayil P[19] et al., Synthesised S-substituted-1, 3, 4-oxadiazole bearing N-methyl4

(trifluoromethyl)phenyl pyrazole moiety.

Znang XM[20] et al., Synthesised 1, 3, 4-oxadiazole derivative condensed with 1,4-

benzodioxan moiety and some of the derivatives.

Sun J[21] et al. Synthesised quinoline derivatives of 1, 3, 4-oxadiazole.

RaneRA[22] et al. Synthesised 42 novel 4-nitropyrrole-based 1, 3, 4-oxadiazoles.

Valente S[23] et al., Reported 1, 3, 4-oxadiazole containing hydroxamates and 2aminoanilides

as histone deacetylase inhibitors. In this some of them were most potent and selective against
HDAC.

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Lai H[24] et al., Synthesised a series of functionalized 1,2-benzisothiazol-3(2H)-one—1,3,4-

oxadiazole hybrid derivatives.

Khan KM[25] et al., Synthesised, a series of 5-substituted-1,3,4-oxadiazole-2yl-N-(2 methoxy-

5chlorophenyl)-2-sulfanyl acetamide.

El-Din MM[26] et al., Reported the synthesis of a new series of 1,3,4-oxadiazole derivatives
possessing sulfonamide moiety.

Singh AK[27] et al., Synthesised a series of 1, 3, 4- oxadiazole derivatives.

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Tabatabai SA[28] et al., Synthesised some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-

oxadiazole.

Desai NC[29] et al., Synthesised novel series of 2-{5-[4-(1-aza-2-(2-thienyl) vinyl) penyl]

(1,3,4oxa-diazol-2-ylthio)}-N-arylacetamide.

Raval JP[30] et al., Synthesised a series of 2(4-pyridyl)-5[(aryl/heteroarylamino)-1-oxoethyl]

thio-1,3,4oxadiazole.

Ningaiah S[31], et al., Synthesised a novel series of 2-(5-methyl-1,3-diphenyl-1H-pyrazol-4-

yl)-5phenyl-1,3,4-oxadiazole.

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Qi DQ,[32] et al., Designed and synthesised a series of pyrazole-based 1, 3, 4-oxadiazole

derivatives.

Roy PP[33] et al., Synthesised some novel 2, 5- Disubstituted 1, 3, 4-Oxadiazole derivatives.

Ali Ramazani[34] et al., Reported the synthesis of 2,5-disubstituted-1,3,4-oxadiazole

derivative using (N-isocyanimino) triphenylphosphorane, a secondary amine, a carboxylic
acid and an aromatic aldehyde in CH2Cl2 at ambient temperature in high yields without using
any catalyst or activation.

Wenquan Yu[35] et al., Reported the synthesis of 2,5-disubstituted (aryl, alkyl, and/or vinyl)-
1,3,4-oxadiazole by cyclization of acylhydrazone substrates obtained from the condensation
of aldehydes and hydrazides employing by iodine in presence of potassium carbonate.

Fouad Bentiss[36] et al., Reported the synthesis of 2,5-disubstituted -1,3,4-oxadiazole by the

reaction of aromatic acid with hydrazine dihydrochloride in a mixture of
orthophosphoricacid, phosphoruspentoxide.

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Frank T. Coppo Karen[37] et al., Reported the synthesis of 2-amino-1,3,4-oxadiazole from

acylhydrazines and isothiocyanates.

Changkun Li[38] et al., Reported the synthesis of 2,5-disubstituted-1,3,4-oxadiazole from

carboxylic acid and acylhydrazides, diacylhydrazide formation via HATU coupling followed
by the addition of Burgees reagent.

Agnieazka Kudelko[39] et al., Reported the synthesis of 2-styryl-1,3,4-oxadiazole by

cyclocondensation of cinnamic acid hydrazide and triethylorthoesters under microwave
irradiation.

Nida N Farshori[40] et al., Reported the synthesis of 2,5-disubstituted -1,3,4-oxadiazole

derivative by the condensation reaction of hydrazide of undec-10-enoic acid with 2-furoic
acid.

Mohamed S Behalo[41] et al., Reported the synthesis of 2,5-disubstituted-1,3,4-oxadiazole by

the treatment of 2-((4_(pheoxathin-2-yl)phthalazin-1-yl)oxy)acetohydrazide with aromatic
acids or aldehydes in the presence of cerium ammonium nitrate in dichloromethane or in
polyethylene glycol.

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Morteza Rouhani[42] et al., Reported the synthesis of fully substituted 1,3,4-oxadizole by the
reaction of aromatic carboxylic acids, acenaphthoquinone and (N-isocyanimino)triphenyl
phosphorane.

PHARMACOLOGICAL ACTIONS
ANTI BACTERIAL ACTIVITY
N. Bhardwajand K Saraf[43] et al., were Synthesized and evaluated the 2,5-disubstituted -
1,3,4-oxadiazole derivative for the anti- microbial avtivity.

N.B Patel and J.C Patel.[44] Reported the synthesis and evaluation of 3-(1,3,4-oxadiazol-
2yl)quinazolin-4(3H)-ones for anti microbial activity.

Chao Jun- Shu[45] et al., Reported the synthesis and evaluation of 2,5-disubstituted 1,3,4-
oxadizole derivative for anti microbial activity.

Shyma PC[46] et al., Reported the synthesis of 3-acetyl-2-aryl-2H/methyl-5-[3-(6-methyl

pyridinyl)]-2,3-dihydro-[1,3,4]-oxadiazole derivatives and screened for anti-microbial and
anti-oxidant activity.

Keshari K J[47] et al., Reported the synthesis and evaluated the anti-bacterial activity of 2,5-
disubstituted -1,3,4-oxadiazole derivatives against E.coli, S. epidermidis and S. aureus.

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R. Saini[48] et al. Reported the synthesis and evaluation of 2,5disubstituted 1,3,4-oxadiazole

derivative for anti microbial activity.

Aates O Eznur[49] et al., Reported the anti microbial activity of aryl-2-[N, Ndisubstituted
thiocarbamoyl thioacyl amino]-1,3,4-oxadiazole derivative.

N Jain[50] et al., Reported the synthesis and evaluation of 2[5(aryl) [1,3,4]oxadiazole-2-yl

sulfanyl alkanoic acid for anti microbial activity.

S Kumar[51] et al., Reported the synthesis and evaluation of 5-substituted-2-amino-1,3,4-

oxadiazole derivative for anti microbial activity.

S N Channamata[52] et al., Reported the synthesis and evaluation of disubstituted 1,3,4-

oxadiazole carrying 2(aryloxymethyl)phenyl moiety for anti microbial activity.

Aatesh OE[53] et al., Reported the synthesis and evaluation of 5-[substituted-(1,1-biphenyl)-3-

yl]-1,3,4-oxadiazole-2(3H)-thione derivative and screened for anti-microbial activity against
various bacterial strains namely Staphylococcus aureus and Pseudomonas aeruginosa.

NitiBhardwaj[54] et al., Evaluated the anti-bacterial activity of 2-(phenyl substituted)-5-indole-

1,3,4-oxadiazole derivative.

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Chao Jun- Shu[55] et al., Reported the evaluation of 5-[4-(5-phenyl-1,3,4-oxadiazole-2-yl-

sulfonylmethyl)-biphenyl-2-yl]-tetrazole derivative as anti-microbial activity against Bacillus
subtilis and Eschericha coli.

Jain[56] et al., Reported the synthesis and evaluation of 2-(3,4,5-trihydroxyphenyl)-5-aryl-

1,3,4-oxadiazole for anti-microbial activity against E.coli, Pseudomonas aeruginosa,
Klebsiella pneumonia and Staphylococcus aureus.

Farshori[57] et al., Reported the synthesis and evaluation of 5-alkenyl/hydroxyalkenyl-2-

phenylamine -1,3,4-oxadiazoles derivative and tested for their anti -microbial activity.

ANTI-FUNGAL ACTIVITY
Ming-Zhi Z[58] et al., Reported the synthesis and evaluation of three series of indole based
1,3,4-oxadiazole derivatives and designed them as analogues of the anti-fungal product
pimprinine.

RamaprasadGC[59] et al., Reported the synthesis and evaluation of 5-[substituted-(1,10-

biphenyl)-3-yl]-1,3,4-oxadiazole-2(3H)-thiones for anti-fungal, anti-bacterial and analgesic
Activities.

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Shridhar AH[60] et al., discussed the anti-fungal activity of 2,5-disubstituted-1,3,4-oxadiazole

derivatives against the fungus Candida ablicans and Aspergillus niger.

Palak K[61] et al., Reported the anti-fungal activity of 3,5-bis-(5-furan-2-yl)-1,3,4-oxadiazole-

2-yl)-azo dye against the fungal strains of Candida ablicans and Candida parapsilosis.

Arun KW[62] et al., Reported the synthesis and evaluation of 2-[5-(substituted sulfanyl)-1,3,4-
oxadiazol-2-yl] phenol derivatives for the anti-fungal activity against the candida ablicans.

Kumar[63] et al., Reported the synthesis of 2-substituted-5-[isopropylthiazole] clubbed with

1,3,4-oxadiazole and tested of their anti-fungal activity against Candida tropicalis,
Adperagillus niger.

Chen[64] et al., Reported the synthesis and evaluation of 5-(3,4,5-trimethoxyphenyl)-2-

sulfonyl-1,3,4-oxadiazoles and screened for their anti-fungal activity against Gibberllazeae,
Botrytis cinerea, Sclerotianasclerotium.

Karthikeyan[65] et al., evaluated the 2,4-dichloro-5-flourophenyl-1,3,4-oxadiazole derivative

for their anti-fungal activity against the Penicillium marneffei, Aspergillus fumigatus and
Candida ablicans.

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Liu[66] et al., Synthesized sulfoxide derivative containing trimethylphenyl substituted 1,3,4-

oxadiazole derivative and tested for their anti-fungal activity.

ANTI-INFLAMMATORY ACTIVITY
M MBurbuliene[67] et al., Reported the synthesis and evaluation of 5-[2-disubstituted amino-
6-methyl pyrimidine-4-yl)-sufanyl methyl]-3H-1,3,4-oxadiazole-2-thiones for anti-inflamm
atory activity.

A.Husain and A.Mohammed[68] et al., Synthesized and evaluated the novel 1,3,4-oxadiazole
derivatives for their anti-inflammatory properties.

A.Mymoona[69] et al., Synthesized and evaluated Aroylpropionicacid based 2,5-disubstituted-

1,3,4oxadiazoles for anti-inflammatory and analgesic activity.

P. Erhan[70] et al., Synthesized and evaluated acylthiosemicarbazides, 1,3,4- oxadiazoles, -3-

thiones for antiinflammatory activity.

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Kumar H[71] et al., Reported the synthesis and anti-inflammatory activity of disubstituted
1,3,4-oxadiazole derivatives by the carrageenan induced rat paw edema test method.

A Mohammed[72] et al., Reported the synthesis and evaluation of 2-substituted-aryl-5-(2,4,6-

trichloro-phenoxy-methyl)-1,3,4-oxadiazoles derivatives for their anti-inflammatory activity.

Burbuliene MM[73] et al., were evaluated the 5-[(2-disubstituted-amino-6-methylpyrimidine-

4-yl)-sulfonylmethyl]-3H-1,3,4-oxadiazole -2-thione for their anti-inflammatory activity.

A.K. Singh[74] et al., Synthesized and evaluated disubstituted 1,3,4-oxadiazole derivatives for
anti inflammatory activity.

M. Akhter[75] et al., Synthesized and evaluvated Aroylpropionic acid based 2,5disubstituted-

1,3,4-oxadiazoles and evaluated their anti inflammatory activity.

ANALGESIC ACTIVITY
A.Husain[76] etal., Synthesized and evaluvated the novel 1,3,4-oxadiazole derivatives and
evaluated their analgesic properties.

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D. Dhansay[77] et al., Synthesized and evaluvated the novel 2,5-Disubstituted 1,3,4-

Oxadiazole and evaluated their Analgesic, Anti-Inflammatory, Anti-Bacterial and Anti
Tubercular Activity.

B. Jayashankar[78] et al., Synthesized 2, 5-Disubstituted 1, 3, 4-Oxadiazole and evaluated their

analgesic activity.

K. Selvakumar[79] et al., Synthesized, characterized 1,3,4oxadiazole derivatives and evaluated

their analgesic activity.

ANTI CONVULSANT ACTIVITY

Y. Mohammad[80] et al., Synthesized disubstituted oxadiazole derivates and evaluated for
anticonvulsant activity.

Z. Afshin[81] et al., Synthesized new 2-substituted-5{2-[(2-halobenzyl)thio)phenyl}1,3,4-

oxadiazoles evaluated as anticonvulsant agents.

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A Zarghi[82] et al., Synthesized new 2-substituted benzyloxyphenyl -1,3,4oxadiazoles and

evaluated as anticonvulsant agents.

Kikkeri PH[83] et al., Reported the synthesis of novel 1-[5-(4-methoxy-phenyl)-[1,3,4]-

oxadiaol-2-yl] derivatives and screened for anti-convulsant activity.

A.Almasirad[84] et al., Synthesized new 2-substituted-5-[2-(2fluorophenoxy) phenyl]1,3,4-

oxadiazole and 1,2,4-triazoles and evaluate their anticonvulsant activity.

Y Mohammad[85] et al., Reported the synthesis and evaluation of 2-(4-chlorophenyl)-amino-

5-(4-pyridyl)-1,3,4-oxadiazole for their anti-convulsant activity.

A Zarghi[86] et al., Reported the synthesis and evaluation of 2-substituted-5-{2-[(2-

halobenzyl)-thio]-phenyl-1,3,4-oxadiazole derivatives of their anti-convulsantactivity.

ANTI TUBERCULAR ACTIVITY

S. R.Pattan[87] et al., Synthesized and evaluated the disubstituted 1,3,4-oxadiazole derivatives
for anti-tubercular activity.

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Yarshahar[88] et al., Synthesized and evaluated anti-tuberculostatic activity of disubstituted

1,3,4-oxadiazole derivatives.

Rajesh AR[89] et al., Reported the synthesis and anti-microbial evaluation of 2-nitropyrrole
based 1,3,4-oxadiazoles and screened for anti-bacterial, anti-fungal, and anti-tubercular
activities.

Bakal RL[90] et al., Reported the identification and development of 2,5-disubstituted

oxadiazoleand screened for ant-tubercular activity against Mycobacterium bovis.

Fliur Macaev[91] et al., Reported the synthesis of 5-aryl-2-thio-1,3,4-oxadiazole derivatives

and screened for anti-mycobacterial activity.

F Macaev[92] et al., Reported the synthesis of 5-aryl-2-thio-1,3,4-oxadiazole derivatives and

screened for anti-tubercular activity against Mycobacterium tuberculosis.

Pathan S R[93] et al., Reported the synthesis and evaluation of 2,5-disubstituted -1,3,5-
oxadiazole derivatives for anti-tubercular activity.

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R.L. Bakal[94] et al., Synthesized 2,5-disubstituted oxadiazole derivatives and evaluated as

potential candidate for treatment of XDR and MDR tuberculosis.

F. Macaev[95] et al., studied the structure and – anti tuberculosis activity of a series of 5-aryl-
2-thio 1,3,4 oxadiazole derivatives.

ANTI-TUMOUR ACTIVITY
S. Bondock[96] et al., Synthesized 2,5-disubstituted- 1,3,4oxadiazole and evaluated for Anti-
tumor activity.

Desai NC[97] et al., Reported the synthesis, characterization anti-microbial screening and
cytotoxic activities of thiazole clubbed 1,3,4-oxadiazole derivatives.

Bondock S[98] et al., Reported the synthesis of novel series of 2,5-disubstituted – 1,3,4-
oxadiazole derivatives and evaluated for anti-cancer activity.

Aboraia AS[99] et al., Reported the synthesis and anti-cancer activity of 5-(2-hydroxyphenyl)-
3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione.

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PULMONARY VASODILATORY ACTIVITY

P. J. Shirote[100] et al., Synthesized disubstituted-1,3,4oxadiazoles and evaluated for
pulmonary vasodilatory activity.

OTHER ACTIVITIES
Mohammed M EI S[101] et al., Reported the synthesis and evaluation of furanyl-1,3,4-
oxadiazole derivatives and tested on tyrosinase enzyme activity.

RavichandranV[102] et al., Reported the synthesis and QSAR study of disubstituted 1,3,4-
oxadiazole naphthyridines as HIV -1 integrase inhibitors.

Ru Y[103] et al., designed, Synthesized and evaluated for their immunosuppressive activity of
2,5-disubstituted-1,3,4-oxadiazole derivatives.

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