1,3,4- Oxadiazole, A Complete Review on Biological Activities of Newly Synthesized Derivatives
Amisha Bhopatrao*, Pooja Chavan, Hritisha Chavan, Pravin Chaudhari, Zahra Dadan, Ajay Kharche
Konkan Gyanpeeth Rahul Dharkar College of Pharmacy and Research Institute, Karjat, 4020, India.
*Corresponding Author E-mail: amishabhopatrao@gmail.com
ABSTRACT:
The heterocyclic molecules known as oxadiazoles, which include one oxygen and two nitrogen atoms in a five-membered ring, have a variety of beneficial biological effects1. The 1,3,4-oxadiazole nucleus is a crucial biological scaffold with a wide range of biological functions. 1,3,4-oxadiazole and its derivatives have become significant pharmacological scaffolds, particularly in the treatment of cancer disease, because to their extensive and powerful activity. Numerous 1,3,4-oxadiazole compounds with di-, tri-, aromatic-, and heterocyclic substitutions have been found to have strong anticancer properties2.
ANTICANCER ACTIVITY:
Camelia ES et. al developed a number of new 2,5-diaryl/heteroaryl-1,3,4-oxadiazoles and synthesised (1) in an effort to create novel chemotherapeutic drugs with powerful anticancer properties. HT29 (colon adenocarcinoma) and MDA-MB-231, two standardised human cell lines, were used to test the compounds' anticancer potential (breast adenocarcinoma)3.
Various derivatives of 1,3,4- oxadiazole such as (E)-5-[(5-(2-arylvinyl)-1,3,4-oxadiazol-2- yl)]-4-chloro-2-R1 -benzenesulfonamides, (E)-4-[5-styryl1,3,4-oxadiazol-2- yl]benzenesulfonamides and (E)-2-(2,4-dichlorophenyl)-5-(2-arylvinyl)-1,3,4-oxadiazols were prepared by Krzysztof S et. al and found to be effective against HeLa, HCT-116, and MCF-7 cell lines of tumor in in-vitro cytotoxic activity studies. The compound bearing 5-nitrothiophene moiety i. e. (E)-2,4-Dichloro-5-(5-(2-(5-nitrothiophen-2-yl)vinyl)-1,3,4-oxadiazol-2-yl) benzenesulfonamide (2) showed potential antitumor activity4.
Abdulraheem SA et. al prepared derivatives of 1,2,3-triazole-incorporated thymol-1,3,4-oxadiazole and tested them for antitumor activity by thymidylate synthase inhibitory activity. The compound named, 2-(4-((5-((2- isopropyl-5-methylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)phenol (3) was showing best results on three cell lines MCF-7, HCT-116, and HepG2. This compound showed better results than the standard anticancer drugs 5- fluorouracil and doxorubicin5.
Xu Han et. al synthesized 66 derivatives of 2-phenyl-4H-chromone containing amide and 1,3,4-oxadiazole moieties and evaluated them against 5 cancer cell lines of human. They found that substituents on phenyl ring are contributing in potential telomerase inhibitor activity. Amongst these compounds (E)-2–(5,7-dimethoxy-4-oxo-2–(3,4,5-trimethoxyphenyl)-4H-chromen-3-yloxy)-N-(5-styryl-1,3,4-oxadiazol-2-yl acetamide (4) was arresting MGC-803 cell cycle at G2/M phase, inducing apoptosis and also reducing the expression of dyskerin (a fragment of telomerase). With these results they concluded that it can be used as an efficient telomerase inhibitor6.
Kaseem et al developed New sugar hydrazones incorporating furan and/or 1,3,4-thiadiazole ring systems and tested their anticancer activities against human liver carcinoma cell (HepG-2) and at human normal retina pigmented epithelium cells (RPE-1). High activity was shown by ethyl 2-((5-(4-(2-(furan-2-carbonyl)hydrazinyl)-4-oxobutanamido)-1,3,4-thiadiazol-2-yl)thio)acetate (5).7
The anticancer activity of a number of quinoxaline-1,3,4-oxadiazole hybrid derivatives was tested against human leukaemia HL-60 cells by Ono et al. These substances significantly slow down the multiplication of HL-60 cells, yet they are extremely hazardous to healthy human cells. When compared to the positive control XK469, (6) compound can considerably limit cell proliferation8.
A549, MDA-MB-231, and MCF-7 cells were utilised to test the anticancer activity of a series of new 1,3,4-oxadiazole fused tetrazol amide derivative (7) developed and synthesised by Kotla et al. When compared to the common medication Doxorubicin, the majority of the compounds showed good anticancer activity and safety 9.
ANTI-INFLAMMATORY ACTIVITY:
Palaska et. al synthesized Sixteen 1-(2-naphthyloxyacetyl)-4-substituted-3-thiosemicarbazide, 2-(2-naphthyloxymethyl)-5-substitutedamino-1,3,4-oxadiazole, 2-(2-naphthyloxymethyl)-5-substitutedamino -1,3,4-thiadiazole and 5-(2-naphthyloxymethyl)-4-substituted-1,2,4-triazole-3-thione derivatives and evaluated them for their anti- inflammatory activity using carrageenan-induced foot pad edema assay. 2-(2-naphthyloxymethyl)-5-methylamino-1,3,4-oxadiazole, 5-(2-naphthyloxymethyl)-4-methyl-1,2,4- triazole-3-thione and 5-(2-naphthyloxymethyl)-4-ethyl-1,2,4-triazole-3-thione (8) was showing good effects10.
Nargund et. al developed 5-[ [(acetamMophen-4-yl)oxy]methyl]-2-substituted phenyiamino)-l,3,4-oxadiazoles (9) and tested them by using the Carrageenan-induced edema test in rat paw, the activity ranged from 44 to 63 % for a-d, with indomethacin which is used as the standard reference drug, showing 88.5% protection11.
Singh AK et.al synthesized various derivatives of 1,3,4- oxadiazole and evaluated them using rat-paw-edema method and compounds namely [3-Chloro-N-[5-(3-Chloro-phenyl)-[1,3,4] oxadiazole-2yl] benzamide, and [4-Nitro-N-[5-(4-Nitro-phenyl)-[1,3,4] oxadiazole-2yl] (10) benzamide showed good inflammatory activity12.
Burbuliene MM et al synthesized 5-[(2-disubstitutedamino-6-methyl-pyrimidin-4-yl)-sulfanylmethyl]-3H1,3,4-oxadiazole-2-thiones and their S-alkyl-, N3-acyl- and N3-aminomethyl derivatives and found 5-[(6-methyl-2-piperidin-1-yl-pyrimidin-4-yl)- sulfanylmethyl]-3H-1,3,4-oxadiazole-2-thione (11) derivatives more effective in anti-inflammatory potential13.
Zheng XJ et al synthesized benzothiazole derivatives bearing a 1,3,4- oxadiazole moiety and they found that one compound (12) containing R1 = 3-CH3, R2= H possess anti-inflammatory activity through cox-2 inhibition14.
Koksal M et al developed a novel group of 5-(3,4- dichlorophenyl)-1,3,4-oxadiazole-2(3H)-one Mannich bases and tested them using in vitro lipopolysaccharide (LPS)- induced NO production and in vivo carrageenan footpad edema. Among these compounds (13), with (R= 4-Phenyl), (R= 3-Carboxylic acid), (R= 2-Ethyloxycarbonyl) showed better activity15.
Kumar H synthesized new derivatives of 1,3,4-Oxadiazole/ thiadiazole and after evaluation compound (14) (R=CH3CH2CH2CH2-) showed good anti-inflammatory potential16.
Abd-Ellah HS designed novel 1,3,4-Oxadiazole/Oxime hybrids and evaluated them for anti-inflammatory potential. Among these derivatives compound (15) (R= 4-OCH3 and X= Cl) was having ability inhibit both cox-1 and cox-2 enzymes 17
Shaikh A et al designed new derivatives of 5-(5-(aryl)-1,3,4-oxadiazol-2-yl)-3,4- dihydro-6-methyl-4-styrylpyrimidin-2(1H)-one and evaluated them using carrageenan-induced rat paw edema method. They found that the compound (16) with Ar= 2NO2C6H4 and another compound with Ar= 3NO2C6H4 were more effective 18.
Adnan AK et al developed various derivatives by the reaction of 1-adamantanecarbonyl chloride with certain carboxylic acid hydrazides in pyridine yielded the corresponding N-acyl adamantane-1-carbohydrazide derivatives, which were cyclized to the corresponding 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles via heating with phosphorus oxychloride. Among which 4 derivatives (17) showed good response with anti-inflammatory activity19.
ANTIMICROBIAL ACTIVITY:
Khalilullah H et al synthesized novel derivatives of 1,3,4-oxadizole derivatives containing 1,4-benzodioxane ring and evaluated for antibacterial activity against Staphylococcus aureus, Escherichia coli and Bacillus subtilis and antifungal activity against Aspergillus niger, Aspergillus flavus and Candida albicans by twofold serial dilution technique. Some compounds (18) were showing more potential against microbes in comparison with standard/reference drugs 20.
Rasras AJ designed new derivatives by hybridization of cholic acid with the heterocyclic moiety and tested for antimicrobial activity against gram positive, gram negative and fungi. They found that 4 compounds (19) were active against S. aureus and 2 exerted selective activity against gram positive bacteria21.
Peraman et al. developed new derivatives of 1,3,4- oxadiazole with nalidixic acid as a pharmacophore. One compound (20) was showing good activity against Pseudomonas aeruginosa and Staphylococcus aureus than the reference drugs ciprofloxacin and amoxicillin 22.
Sekhar MM et al developed novel derivatives of pyrimidinyl 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. They evaluated the synthesized compounds for their antimicrobial activity and found 2 compounds (21) with (R= 4-Cl) and (R= 4-NO2) effective against P. aeruginosa 23
Gupta V et al synthesized a series of 3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-one and tested for antibacterial activity against Staphylococcus aureus , Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli. They found that presence of stearyl moiety at second position of 4(3H) quinazolinone, (22) increased the biological activity and showed better antibacterial activity 24.
Farshori NN et al developed 1,3,4-oxadiazole derivatives and screened them for antibacterial activity. Compounds (23) with R= C25H39O2N3, R= C25H39O2N3, R= C25H39OSN3, R=C25H39OSN3 were showing better antibacterial activity 25.
Song X et al designed 1,3,4-oxadiazole thioether derivatives containing 2-chloro-5-methylene pyridine, 2-chloro-5-methylene thiazole, 3,4-dimethoxy-2-methylene pyridine, and N, N-dimethyl-2-ethylamino moieties and assessed for their antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) via the turbidimeter test in vitro. Compound (24) with R1= 4-ClC6H4, R2= 3,4-diOCH3 pyridine-2-yl- showed good activity 26.
Musad EA et al synthesized two novel two of five membered heterocyclic bis(1,3,4-oxadiazole) derivatives and 3,5-bis(substituted)pyrazoles, isoxazoles and 4 compounds (25) were showing good antibacterial effects27
Salahuddin et al synthesized 1,3,4-oxadiazole bearing 1H-benzimidazole derivatives (25) and evaluated them for antimicrobial potential and found that some compounds were active against Escherichia coli, Staphylococcus aureus, Candida albicans and Aspergillus flavus28
Desai NC et al synthesized 2-{5-[4-(1-aza-2-(2-thienyl)vinyl)phenyl](1,3,4-oxadiazol-2-ylthio)}-N-arylacetamides, tested for their antimicrobial activity on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogenes, Candida albicans, Aspergillus niger and Aspergillus clavatus. Compounds (26) with R= 2,4 (CH3)2, R= 3,4-(Cl)2, R= –3-OCH3 were more active in their antibacterial activity29
ANALGESIC ACTIVITY:
Almasirad A et al synthesized a series of new 1,3,4-oxadiazoles and 1,2,4- triazoles. Compounds were created. The formalin-induced nociception test was used to assess their analgesic activity. In the early phase of the formalin test, mefenamic acid (as the reference drug) had no activity whereas compound (27) a (X=SO, R =H) and b(X= SO2, R=H) significantly reduced nociception 30.
Bala S et al developed novel derivatives 1,3,4 -oxadiazole. They evaluated the synthesized compound for their analgesic activity by using tail immersion method and found 2 compounds (28) that show good analgesic activity 31.
Dewangan D et al studied the compounds 4-(5-(4-(3-methylquinoxalin-2-yl)phenyl)-1,3,4-oxadiazol2-yl)benzenamine and 2-(5-(4-(3-methylquinoxalin-2-yl)phenyl)-1,3,4-oxadiazol2-yl)benzenamine were studied in animals. The analgesic effects of 1,3,4-oxadiazol-2-ylbenzenamine, (29) were excellent 32
Zadorozhnii PV et al have predicted the analgesic activity and acute toxicity of 2-amino-5-aryl-1,3,4- oxadiazole derivatives (30). These substances were showing analgesic effects and are related to their ability to inhibit the COX-1 and COX-2 enzymes 33
Ingale N etal developed new 3-[(5-substituted-1,3,4-oxa-diazol-2-yl-thio)acetyl] series has been developed. The structure of the synthesised compounds (31) was determined using physicochemical, elemental analysis, and spectral data. At a dose of 200mg/kg bw, the title compounds were tested in vivo for analgesic activity 34
Kalsi R et al developed various new formazans of substituted oxadiazole 2(3H)-thiones (32) and tested them for analgesic activity against carrageenin-induced paw oedema in albino rats using cotton pellet implantation methods in albino rats of either sex. The toxicity of the compounds was determined by calculating their LD50 value in albino mice 35.
Bhargavi VM et al developed novel 1,2,4-oxadiazolo sulfonamides Discovery Studio v3.5, molecular docking with COX-2 enzyme, is used to investigate the molecular interactions of the obtained compounds. Compounds with a high LibDock score are tested for analgesic and anti-inflammatory activity in vivo. The compound (33) 4-Methoxy-N-[(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]benzenesulfonamide has the greatest analgesic activity36
Husain A et al developed a novel drug derivatives of 1-(4-phenoxyphenyl)-3- [5-(substituted aryl)-1,3,4- oxadiazol-2-yl]propan-1-one. They evaluated the synthesised compounds (34) for their analgesic activity by performing the acetic acid-induced writhing test. Fair number of Compounds show better analegic activity37
Ramaprasad GC et al developed novel derivatives of 5-(50-fluoro-20-methoxybiphenyl-3-yl)-1,3,4-oxadiazol-2(3H)-one. They evaluated the synthesised compounds by using elemental and spectral analysis. Compounds (36) methyl4-[5-(5'-fluoro-2'-methoxybiphenyl-3-yl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]butanoate and 4-[5-(5'-Fluoro-2'-methoxybiphenyl-3-yl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]butanenitrile show good analgesic activities 38.
Chawla G et al developed a novel derivative of 1,3,4-Oxadiazole. They evaluated and synthesised the compound as the literature survey indicates that many 1,3,4-oxadiazoles have been synthesized with the aim to get compounds (37) of significant analgesic activities with reduced adverse effects 39.
ANTI-CONVULSANT ACTIVITY:
Wang S et al developed novel derivative of 1,3,4-oxadiazole. They evaluated the synthesised compound for their anticonvulsant activity by using maximal elctroshock and subcutaneous pentylenetetrazole. 6- ((5-(pentylthio)-1,3,4-oxadiazol-2-yl) methoxy)-3,4-dihydroquinolin-2(1H)-one (38) exhibits the best anticonvulsant activity 40.
Tabatabai AS. Et al designed the novel derivative of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole. They evaluated the synthesised compound using pentylenetetrazole induced lethal convulsion test for their anticonvulsant activity. Amino substitution on position 5 of 1,3,4-oxadiazole ring produces the compound (39), 2-Amino-5-(2-phenoxy) phenyl-1,3,4-oxadiazole which shows respectable anticonvulsant activity 41
Bhat AM. et al discovered new 1,3,4oxadiazole derivative of phthalimide. They evaluated the synthesised compound for their anticonvulsant activity by using maximal elctroshock seizure test. Compound (40), 1-{5-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)amino]-1,3,4-oxadiazol-2-yl}-3-(4- methoxyphenyl) thiourea having methoxy substitution at para position of distal aryl ring shows promising anticonvulsant activity42
Jain N. Et al developed Two novel series 2a–2d (2Z)-N-[5-(4-substituted)phenyl-1,3,4-oxadiazol-2-yl]-2- [(2Z)-
3,7-dimethyl-Octa-2,6-dien-1-ylidene]hydrazinecarboxamide and 1a–1d5-(4-substituted)phenyl-N- [(1Z,2Z)-3,7-dimethylocta-2,6-Dien-1-ylidene]-1,3,4-oxadiazol-2-amine.They evaluated the synthesised compounds (41) for their anticonvulsant activity by using maximal Electroshock induced seizures (MES) and subcutaneous Metrazole (ScMET) induced seizure models in mice. Compound b (R= - Cl) shows good anticonvulsant activity 43
Kashaw K S Et al designed a novel derivative of 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2-yl]-2- styrylquinazoline-4(3H)-ones. They evaluated the synthesised compound for their anticonvulsant activity by using maximal electroshock-induced seizures method. Compounds (42) [R1-Cl,R2-CH3] ,and o [R1- N(CH3)2, R2-Cl] showed better anticonvulsant activity44
Almasirad A et al developed a new derivative of 5-[2-(phenylthio) phenyl]-1,3,4-oxadiazole. They evaluated the synthesised compound for their anticonvulsant activity using PTZ and rotarod tests, respectively. The compound (43), 5-[2-(phenylthio)phenyl]-1,3,4-oxadiazole-2(3H)-one was observed exhibiting better anticonvulsant activity 45
Gupta A et al discovered a novel derivative of 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2. They evaluated the synthesised compound for their anticonvulsant activity by using maximal electroshock induced seizures (MES). Compound (44) with (R=F) was found to be exhibit better anticonvulsant activity 46
Zarghi A Et al developed a novel drug derivative of 5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles. They evaluated the synthesised compounds (45), for their anticonvulsant activity by using PTZ and MES models. compound b (R1-F, R2-NH2) shows better anticonvulsant activity 47.
Siddiqui N et al developed novel derivatives of 3-(4-substitutedphenyl)-N-(5-(4-substitutedphenyl-1,3,4- oxadiazol-2-yl)but-2-enamide. They evaluated the synthesised compounds for their anticonvulsant activity by using MES and subcutaneous pentylenetetrazole test. Compounds (46), (2E)-3-(4-Bromophenyl)-N- (5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)but-2-enamide and (2E)-3-(4-Chlorophenyl)-N-(5-(3,4- dimethoxyphenyl)-1,3,4-oxadiazol-2-yl)but-2-enamide exhibit better anticonvulsant activity 48.
Kumar P et al developed a novel derivative of 2,5-disubstituted-1,3,4-oxadiazole. They evaluated the synthesised compounds for the anticonvulsant activity using (MES) seizure method. Compound (47), N-[{5-(3-Chlorophenyl)-1,3,4-oxadiazole-2-yl}methyl]-4-methoxyaniline exhibit better anticonvulsant activity 49.
Table. 1. Pharmacological activity of 1,3,4-oxadiazole Derivatives and their structures.
CONCLUSION:
New derivatives of 1,3,4-oxadiazole have been synthesized over the past years by using various routes of synthesis. These derivatives can be a better option for treating deadliest diseases by using their preferred biological activity. Hence these derivatives can be an alternative to the drugs with more side effects.
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Received on 06.08.2023 Modified on 15.11.2023
Accepted on 17.01.2024 ©AJRC All right reserved
Asian J. Research Chem. 2024; 17(4):243-249.