A Review of Modern Methods of Synthesis 1, 3, 4-Oxadiazole as a Bioactive Compounds

Authors

  • hajar adeeb College of Education Ibn al-Haitham for pure sciences

DOI:

https://doi.org/10.31185/wjps.262

Abstract

ABSTRACT: Oxadiazole ring is a heterocyclic molecule with an oxygen and two nitrogen atoms spread throughout its five-membered structure. There are four different isomers that have been discovered, Because of their wide applications in a range of sectors, including medications . Some of these biological activity are; anticonvulsant capacity, anticancer as well, antibacterial, antiviral, antifungal,  antimalarial, antitubercular, anti-asthmatic, antidepressant, antidiabetic, antioxidant, antiparkinsonian, analgesic and  anti-inflammatory, are just some of the therapeutic uses that have drawn attention to drug candidates containing an oxadiazole moiety. This review, we will examine the various methods of oxadiazole synthesis. The molecular docking of some oxadiazole compounds has been studied to investigate the active derivatives and to evaluate their activity. The synthesis of the oxadiazole ring has sparked a lot of attention since then. A large number of oxadiazole derivatives, as well and methods, were reported New antimicrobial drugs have been developed from a number of different areas in recent years in an effort to reduce the prevalence of drug-resistant bacteria. Furthermore, this review touches upon the importance of structural modification in fine-tuning the biological activities of 1,3,4-oxadiazole derivatives. By altering the substituents and the position of functional groups, researchers can tailor the pharmacological properties to target specific diseases or conditions, making them highly versatile and attractive in drug discovery.

References

REFERENCES

Z. M. Abbas, D. F. Hussain, and R. M. Shakir, “Synthesis of Some New Heterocyclic Fused Rings Compounds Based on 5-Aryl-1, 3, 4-Oxadiazole,” Ibn AL-Haitham J. Pure Appl. Sci., vol. 30, no. 2, pp. 161–176, 2017.

H. I. Omar–Eldeen, “Synthesis and Antimicrobial Evaluation of Some Bis-1, 3, 4-Butane-1-3, 4-Oxadiazole Derivatives,” Ibn Al-Haitham J. Pure Appl. Sci., vol. 22, no. 3, 2009.

I. Y. Majeed, S. A. Saoud, A. A. Ahmed, and E. F. Mustafa, “Synthesis, Characterization and Antibacterial Activity of Some New Five-Seven Membered Rings Attached to Sulfonamide Compounds,” Ibn AL-Haitham J. Pure Appl. Sci., vol. 27, no. 2, pp. 170–177, 2017.

S. Bhatia and M. Gupta, “1, 3, 4-Oxadiazole as antimicrobial agents: An overview,” J. Chem. Pharm. Res, vol. 3, no. 3, pp. 137–147, 2011.

A. L. Jarallah, K. F. Ali, R. M. Shakir, and S. A. Saoud, “Synthesis, Antibacterial and Antifungal Activities for Novel Derivatives of 2, 2’-(((1-benzylbenzoimidazol-2-yl) methyl) azanediyl) bis (ethan-1-ol),” Ibn AL-Haitham J. Pure Appl. Sci., vol. 32, no. 1, pp. 57–79, 2019.

S. Vardan, H. Smulyan, S. Mookherjee, and R. Eich, “Effects of tiodazosin, a new antihypertensive, hemodynamics and clinical variables,” Clin. Pharmacol. Ther., vol. 34, no. 3, pp. 290–296, 1983.

S. R. PATTAO, P. A. Rabara, J. S. PATTAN, A. A. Bukitagar, V. S. WAKALC, and D. S. MUSMADE, “Synthesis and evaluation of some novel substituted 1, 3, 4-oxadiazole and pyrazole derivatives for antitubercular activity,” Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem., vol. 48, no. 10, pp. 1453–1456, 2009.

H. P. Shah, B. R. Shah, J. J. Bhatt, N. C. Desai, P. B. Trivedi, and N. K. Undavia, “Synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles as potential antimicrobial, anticancer and anti-HIV agents,” 1998.

G. A. Pinna et al., “Synthesis, Modelling, and Antimitotic Properties of Tricyclic Systems Characterised by a 2‐(5‐Phenyl‐1H‐pyrrol‐3‐yl)‐1, 3, 4‐oxadiazole Moiety,” ChemMedChem Chem. Enabling Drug Discov., vol. 4, no. 6, pp. 998–1009, 2009.

X. Qian and R. Zhang, “Syntheses and insecticidal activities of novel 2, 5‐disubstituted‐1, 3, 4‐oxadiazoles,” J. Chem. Technol. Biotechnol. Int. Res. Process. Environ. Clean Technol., vol. 67, no. 2, pp. 124–130, 1996.

W. Wang et al., “Synthesis and insecticidal evaluation of novel N‐pyridylpyrazole derivatives containing diacylhydrazine/1, 3, 4‐oxadiazole moieties,” J. Heterocycl. Chem., vol. 56, no. 4, pp. 1330–1336, 2019.

H. Rajak, M. D. Kharya, and P. Mishra, “Synthesis and Local Anesthetic Activity of Some Novel N‐[5‐(4‐Substituted) phenyl‐1, 3, 4‐oxadiazol‐2‐yl]‐2‐(Substituted)‐Acetamides,” Arch. der Pharm. An Int. J. Pharm. Med. Chem., vol. 341, no. 4, pp. 247–261, 2008.

H. S. Jasim, S. A. Saoud, and H. A. J. Almuslamawy, “Study of Acute and Chronic Sinusitis–Symptoms, Diagnosis and Treatment: A Review Article,” Ibn AL-Haitham J. Pure Appl. Sci., vol. 35, no. 3, pp. 83–90, 2022.

D. Dewangan et al., “Synthesis and Molecular Docking Study of Novel Hybrids of 1, 3, 4‐Oxadiazoles and Quinoxaline as a Potential Analgesic and Anti‐Inflammatory Agents,” J. Heterocycl. Chem., vol. 55, no. 12, pp. 2901–2910, 2018.

R. Maheshwari, P. Chawla, and S. A. Saraf, “Comparison between antioxidant activity of 2, 5-disubstituted 1, 3, 4-oxadiazoles containing heteroaromatic ring and aromatic ring at 2nd position,” Med. Chem. Res., vol. 20, pp. 1650–1655, 2011.

M. Shaban, A. E. Nasar, and S. M. EL-Badary, “Synthesis of some 1, 3, 4-oxadiazole and bis 1, 3, 4-oxadiazole that possess nematicidal insecticidal and herbicidal activity,” J. Islam. Acad. Sci., vol. 4, no. 3, pp. 184–191, 1991.

X.-L. Wang, J. Li, H.-Y. Lin, H.-L. Hu, B.-K. Chen, and B. Mu, “Synthesis, structures and electrochemical properties of two novel metal–organic coordination complexes based on trimesic acid (H3BTC) and 2, 5-bis (3-pyridyl)-1, 3, 4-oxadiazole (BPO),” Solid State Sci., vol. 11, no. 12, pp. 2118–2124, 2009.

J. H. Kim, “Synthesis and electro-optical properties of poly (p-phenylenevinylene) derivative with conjugated 1, 3, 4-oxadiazole pendant and its AC electroluminescence,” Synth. Met., vol. 158, no. 21–24, pp. 1028–1036, 2008.

M. K. Huda and S. K. Dolui, “Luminescence property of poly (1, 3-bis (phenyl-1, 3, 4-oxadiazole)) s containing polar groups in the main chain,” J. Lumin., vol. 130, no. 11, pp. 2242–2246, 2010.

X. Song et al., “Synthesis and investigation of the antibacterial activity and action mechanism of 1, 3, 4-oxadiazole thioether derivatives,” Pestic. Biochem. Physiol., vol. 147, pp. 11–19, 2018.

A. N. Ambhore et al., “Design, synthesis and in silico study of pyridine based 1, 3, 4-oxadiazole embedded hydrazinecarbothioamide derivatives as potent anti-tubercular agent,” Comput. Biol. Chem., vol. 80, pp. 54–65, 2019.

P. Li et al., “Novel bisthioether derivatives containing a 1, 3, 4‐oxadiazole moiety: design, synthesis, antibacterial and nematocidal activities,” Pest Manag. Sci., vol. 74, no. 4, pp. 844–852, 2018.

C. Ainsworth and R. E. Hackler, “Alkyl-1, 3, 4-oxadiazoles,” J. Org. Chem., vol. 31, no. 10, pp. 3442–3444, 1966.

V. K. Tandon and R. B. Chhor, “An efficient one pot synthesis of 1, 3, 4-oxadiazoles,” Synth. Commun., vol. 31, no. 11, pp. 1727–1732, 2001.

F. Bentiss, M. Lagrenee, and D. Barbry, “Rapid synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles under microwave irradiation,” Synth. Commun., vol. 31, no. 6, pp. 935–938, 2001.

S. H. Mashraqui, S. G. Ghadigaonkar, and R. S. Kenny, “An expeditious and convenient one pot synthesis of 2, 5-disubstituted-1, 3, 4-oxadiazoles,” Synth. Commun., vol. 33, no. 14, pp. 2541–2545, 2003.

G. V. M. Sharma, A. Begum, Rakesh, and P. R. Krishna, “Zirconium (IV) Chloride Mediated Cyclodehydration of 1, 2‐Diacylhydrazines: A Convenient Synthesis of 2, 5‐Diaryl 1, 3, 4‐Oxadiazoles,” Synth. Commun., vol. 34, no. 13, pp. 2387–2391, 2004.

Z. Shang, “Oxidative Cyclization of Aromatic Aldehyde N‐Acylhydrazones by bis (Trifluoroacetoxy) iodobenzene,” Synth. Commun., vol. 36, no. 20, pp. 2927–2937, 2006.

M. Dabiri, P. Salehi, M. Baghbanzadeh, M. A. Zolfigol, and M. Bahramnejad, “Silica Sulfuric Acid: An Efficient and Versatile Acidic Catalyst for the Rapid and Ecofriendly Synthesis of 1, 3, 4‐Oxadiazoles at Ambient Temperature,” Synth. Commun., vol. 37, no. 7, pp. 1201–1209, 2007.

D. M. Pore, S. M. Mahadik, and U. V Desai, “Trichloroisocyanuric acid–mediated one-pot synthesis of unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles at ambient temperature,” Synth. Commun., vol. 38, no. 18, pp. 3121–3128, 2008.

Y. A. Efimova, T. V Artamonova, and G. I. Koldobskii, “Tetrazoles: LIII. Microwave-activated acylation of 5-substituted tetrazoles,” Russ. J. Org. Chem., vol. 44, pp. 1345–1347, 2008.

R. Badri and M. Gorjizadeh, “A novel, one-pot synthesis of 2, 5-disubstituted-1, 3, 4-oxadiazoles using 1, 4-bis (triphenylphosphonium)-2-butene peroxodisulfate,” Phosphorus, Sulfur, and Silicon, vol. 185, no. 3, pp. 544–549, 2010.

I. Y. Majeed, D. Al-Saady, and S. A. Saoud, “Synthesis and characterization of some new compounds derivatives from para-amino benzoic acid,” Int. J. Sci. Technol., vol. 8, no. 3, 2013.

S. P. Pardeshi, S. S. Patil, and V. D. Bobade, “N-Chlorosuccinimide/1, 8-Diazabicyclo [5.4. 0] undec-7-ene (DBU)–Mediated Synthesis of 2, 5-Disubstituted 1, 3, 4-Oxadiazoles,” Synth. Commun., vol. 40, no. 11, pp. 1601–1606, 2010.

M. Kidwai and R. Mohan, “Synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles using dry media,” Org. Prep. Proced. Int., vol. 35, no. 4, pp. 426–429, 2003.

M. Kidwai, D. Bhatnagar, and N. K. Mishra, “Polyethylene glycol (PEG) mediated green synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles catalyzed by ceric ammonium nitrate (CAN),” Green Chem. Lett. Rev., vol. 3, no. 1, pp. 55–59, 2010.

I. Ali, “Chloramine-T mediated synthesis of 1, 3, 4-Oxadiazole as antibacterial agents,” Der Pharm. Sin., 2011.

M. Dabiri, P. Salehi, M. Baghbanzadeh, and M. Bahramnejad, “Alum (KAl (SO 4) 2· 12H 2 O): an efficient and inexpensive catalyst for the one-pot synthesis of 1, 3, 4-oxadiazoles under solvent-free conditions,” Monatshefte für Chemie-Chemical Mon., vol. 138, pp. 1253–1255, 2007.

A. Pace, S. Buscemi, and N. Vivona, “Heterocyclic rearrangements in constrained media. A zeolite-directed photorearrangement of 1, 2, 4-oxadiazoles,” J. Org. Chem., vol. 70, no. 6, pp. 2322–2324, 2005.

S. Guin, T. Ghosh, S. K. Rout, A. Banerjee, and B. K. Patel, “Cu (II) catalyzed imine C–H functionalization leading to synthesis of 2, 5-substituted 1, 3, 4-oxadiazoles,” Org. Lett., vol. 13, no. 22, pp. 5976–5979, 2011.

T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, and M. Miura, “Copper-mediated direct arylation of 1, 3, 4-oxadiazoles and 1, 2, 4-triazoles with aryl iodides,” Org. Lett., vol. 11, no. 14, pp. 3072–3075, 2009.

S. Rostamizadeh and S. Ghamkhar, “A mild and facile method for one pot synthesis of 2, 5-di-substituted 1, 3, 4-oxadiazoles at room temperature,” Chinese Chem. Lett., vol. 19, no. 6, pp. 639–642, 2008.

C. Dobrotă, C. C. Paraschivescu, I. Dumitru, M. Matache, I. Baciu, and L. L. Ruţă, “Convenient preparation of unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles promoted by Dess–Martin reagent,” Tetrahedron Lett., vol. 50, no. 17, pp. 1886–1888, 2009.

A. E.-G. E. Amr, S. F. Mohamed, N. A. Abdel-Hafez, and M. M. Abdalla, “Antianexiety activity of pyridine derivatives synthesized from 2-chloro-6-hydrazino-isonicotinic acid hydrazide,” Monatshefte für Chemie-Chemical Mon., vol. 139, pp. 1491–1498, 2008.

M. Akhter, A. Husain, B. Azad, and M. Ajmal, “Aroylpropionic acid based 2, 5-disubstituted-1, 3, 4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities,” Eur. J. Med. Chem., vol. 44, no. 6, pp. 2372–2378, 2009.

R. M. Shakir, A. Ariffin, and M. A. Abdulla, “Synthesis of new 2, 5-di-substituted 1, 3, 4-oxadiazoles bearing 2, 6-di-tert-butylphenol moieties and evaluation of their antioxidant activity,” molecules, vol. 19, no. 3, pp. 3436–3449, 2014.

S. A. Saoud, K. F. Ali, and R. M. Shakir, “Relationship Between the structure of Newly Synthesized derivatives of 1, 3, 4-oxadiazole Containing 2-Methylphenol and their Antioxidant and Antibacterial Activities,” Orient. J. Chem., vol. 33, no. 4, p. 1781, 2017.

M. Luczynski and A. Kudelko, “Synthesis and biological activity of 1, 3, 4-oxadiazoles used in medicine and agriculture,” Appl. Sci., vol. 12, no. 8, p. 3756, 2022.

B. K. Banik et al., “Green synthetic approach: An efficient eco-friendly tool for synthesis of biologically active oxadiazole derivatives,” Molecules, vol. 26, no. 4, p. 1163, 2021.

W. Yu, L. P. Cheng, W. Pang, and L. L. Guo, “Design, synthesis and biological evaluation of novel 1, 3, 4-oxadiazole derivatives as potent neuraminidase inhibitors,” Bioorg. Med. Chem., vol. 57, p. 116647, 2022.

I. K. Jóźwik, D. O. Passos, and D. Lyumkis, “Structural biology of HIV integrase strand transfer inhibitors,” Trends Pharmacol. Sci., vol. 41, no. 9, pp. 611–626, 2020.

J. Crispim-Neto and M. C. S. de Mattos, “Tribromoisocyanuric acid as an alternative oxidant in the synthesis of 2-amino-1, 3, 4-oxadiazoles from 1-acylthiosemicarbazides,” Tetrahedron Lett., vol. 121, p. 154494, 2023.

W.-G. Duan et al., “Synthesis and herbicidal activity of 5-dehydroabietyl-1, 3, 4-oxadiazole derivatives,” 2011.

L. G. Maciel et al., “Inhibition of 3-Hydroxykynurenine Transaminase from Aedes aegypti and Anopheles gambiae: A Mosquito-Specific Target to Combat the Transmission of Arboviruses,” ACS bio med Chem Au, vol. 3, no. 2, pp. 211–222, 2023.

Y. Yang, Q. Zhang, Y. Yu, G. Li, S. Xiao, and Z. Ma, “Improving crop health: Understanding the interaction mechanisms between crops and their pathogens,” Front. Plant Sci., vol. 14, p. 1161154, 2023.

A. B. Syeda, M. Ferazoddin, M. Rajeswari, J. P. Paul, and B. Juluru, “Design, Synthesis and Anticancer Evaluation of Benzoxazole Resemble Substituted Arylamide Derivatives of Bis-1, 3, 4-Oxadiazole-oxazolo [4, 5-b] pyridin-2-yl) as Anticancer Agents,” Chem. Data Collect., vol. 43, p. 100971, 2023.

Poonam, G. Bhasin, R. Srivastava, and R. Singh, “Oxadiazoles: moiety to synthesis and utilize,” J. Iran. Chem. Soc., pp. 1–13, 2022.

B. D. Mohammad et al., “Heterocyclic Compounds as Dipeptidyl Peptidase-IV Inhibitors with Special Emphasis on Oxadiazoles as Potent Anti-Diabetic Agents,” Molecules, vol. 27, no. 18, p. 6001, 2022.

A. M. Abdelfattah, A. E. M. Mekky, and S. M. H. Sanad, “Synthesis, antibacterial activity and in silico study of new bis (1, 3, 4-oxadiazoles),” Synth. Commun., vol. 52, no. 11–12, pp. 1421–1440, 2022.

R. F. Muslim, I. Y. Majeed, S. E. Saleh, M. M. Saleh, M. N. Owaid, and J. A. Abbas, “Preparation, Characterization and Antibacterial Activity of some New Oxazolidin-5-one Derivatives Derived from Imine Compounds,” J. Chem. Heal. Risks, vol. 12, no. 4, pp. 725–732, 2022, doi: 10.22034/jchr.2022.688557.

J. Shi et al., “Design, synthesis and antifungal evaluation of phenylthiazole‐1, 3, 4‐oxadiazole thione (ketone) derivatives inspired by natural thiasporine A,” Pest Manag. Sci., 2023.

T. Glomb and P. Świątek, “Antimicrobial activity of 1, 3, 4-oxadiazole derivatives,” Int. J. Mol. Sci., vol. 22, no. 13, p. 6979, 2021.

V. Adimule, A. H. Jagadeesha Gowda, S. S. Nandi, and D. Bowmik, “Antimalarial activity of novel class of 1, 3‐benzoxaborole derivatives containing 1, 3, 4‐oxadiazole moiety,” Drug Dev. Malar. Nov. Approaches Prev. Treat., pp. 285–302, 2022.

N. J. ABDULRADA, D. F. HUSSAIN, and S. SAOUD, “Synthesis, Characterization and Antibacterial of Some New 4, 4’-(pyridine-2, 6-diylbis (1, 3, 4-oxadiazole-5, 2-diyl)) bisphenolPolymer.,” Int. J. Pharm. Res., vol. 11, no. 3, 2019.

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Published

2023-12-30

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Chemistry

How to Cite

adeeb, hajar. (2023). A Review of Modern Methods of Synthesis 1, 3, 4-Oxadiazole as a Bioactive Compounds. Wasit Journal for Pure Sciences, 2(4), 237-253. https://doi.org/10.31185/wjps.262