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Synthesis Of Novel 2,5-Disubstitue 1,3,4-Oxadiazol Compounds

Year 2020, , 330 - 338, 15.04.2020
https://doi.org/10.17714/gumusfenbil.612725

Abstract

Compounds containing
1,3,4-oxadiazole ring in the structure have a broad spectrum of biological activity.
Generally; antibacterial, antifungal, analgesic, anti-inflammatory, antiviral,
anticancer, antidiabetic, antihelmintic, anticonvulsant effect has been
demonstrated by recent studies. Therefore, in this study, the reaction of
hydrazine hydrate and pirocaine have been investigated and synthesis of
benzohydrazide derivative molecules has been carried out.

Then, by the ring closure of these compounds in the
presence of acetic anhydride and acetic acid, the synthesis of 1,3,4-oxadiazole
compounds which were not previously mentioned in the literature and containing
different groups at 2,5 positions was carried out. Investigation of
antibacterial and antifungal properties of synthesized compounds were performed
with Escherichia coli ATCC 36218, Staphylococcus aureus ATCC 25923 and Candida
albicans ATCC 10231 microorganisms. It was observed that those compounds containing lipophilic acetate group bound
to phenyl ring had antibacterial and antifungal properties.

References

  • Ahsan, M.J., Samy, J.G., Khalilullah, H., Nomani, M.S., Saraswat, P., Gaur, R. ve Singh, A., 2011. Molecular properties prediction and synthesis of novel 1, 3, 4-oxadiazole analogues as potent antimicrobial and antitubercular agents. Bioorganic and Medicinal Chemistry Letters, 21(24), 7246-7250.
  • Akhtar, T., Hameed, S., Al-Masoudi, N.A., Loddo, R. ve Colla, P.L., 2010. In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2- thione derivatives. Acta Pharmazie, 58, 135-149.
  • Akhter, M., Husain, A., Azad, B. ve Ajmal, M., 2009. Aroylpropionic acid based 2,5- disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities. European Journal of Medicinal Chemistry, 44, 2372–2378.
  • Bishayee, A., Karmakar, R., Mandal, A., Kundu, S.N. ve Chatterjee, M., 1997. Vanadium-mediated chemoprotection against chemical hepatocarcinogenesis in rats: haematological and histological characteristics. European Journal of Cancer Prevention, 6(1), 58-70.
  • Buslov, I. ve Hu, X., 2014. Transition Metal-Free Intermolecular α-C-H Amination of Ethers at Room Temperature. Advanced Synthesis and Catalysis, 356, 3325-3330.
  • De Oliveira, C.S., Lira, B.F., Barbosa-Filho, J.M., Lorenzo, J.G.F. ve De Athayde-Filho, P.F., 2012. Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012. Molecules,17, 10192-10231.
  • Dilmaghani, K.A., Jazani, N.H., Pur, F.N., Shokoufeh, N., Ghadiri, F. ve Fakhraee, F.M., 2012. Synthesis of 5-(4-aminophenyl)-2-(arylamino)-1,3,4-thiadiazoles and their schiff base derivatives as antimycobacterial agents. Chemistry of Heterocyclic Compounds, 48, 362-367.
  • Gao, P. ve Wei, Y., 2013. Efficient oxidative cyclization of N-acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions. Heterocyclic Communications, 19(2), 113-119.
  • Hirao, I., Yashuhiko, K. ve Toshiyuki, H., 1971. Studies of the synthesis of furan compound XXIV. The synthesis of 5-[2-(5-nitro-2-furyl)-l-(2-furyl)-vinyl] l,3,4-oxadiazole and its related compounds. Bulletin of Chemical Society of Japan, 44, 1923-1927.
  • Husain, A., Ahmad, F.J., Ajmal, M. ve Ahuja, P., 2008. Synthesis of 1-(4-phenoxyphenyl)-3-[5-(substituted aryl)-1, 3, 4-oxadiazol-2-yl] propan-1-ones as safer anti-inflammatory and analgesic agents. Journal of the Serbian Chemical Society, 73(8-9), 781-791.
  • Ibrahim, E.S.A., Soliman, R. ve Gabr, M., 1979. Synthesis of 4-Substituted Aminobenzoate Quaternary Salts as Potent Antispasmodic Agents. Journal of Pharmaceutical Sciences, 68(3), 332-335.
  • James, N.D. ve Growcott J.W., 2009. Zibotentan endothelin ETA receptor antagonist oncolytic. Drugs of the Future, 34, 624-633.
  • Jayashankar, B., Rai K.M.L., Baskaran, N. ve Sathish, H.S., 2009. Synthesis and pharmacological evaluation of 1,3,4- oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry, 44, 3898-3902.
  • Kalyoncuoğlu, N., Rollas, S., Sür-Altiner, D., Yeğenoğlu, Y. ve Anğ, O., 1992. 1-[p-(Benzoylamino) benzoyl]-4-substituted thiosemicarbazides: synthesis and antibacterial and antifungal activities. Die Pharmazie, 47(10), 796-797.
  • Kanthiah, S., Kalusalingam, A., Velayutham, R., Vimala, A.T. ve Beyatricks, J., 2011. 5-(2-aminophenyl)-1, 3, 4-oxadiazole-2 (3H)-thione derivatives: synthesis, characterization and antimicrobial evaluation, International Journal of Pharmaceutical Sciences Review and Research, 6(1), 64-67.
  • Mamolo, M.G., Zampieri, D., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Scialino, G. ve Banfi, E., 2005. Antimycobacterial activity of new 3-substituted 5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives. Preliminary molecular modeling investigations. Bioorganic and Medicinal Chemistry, 13(11), 3797-3809.
  • Naveena, C.S., Boja, P. ve Kumari, N.S., 2010. Synthesis, characterization and antimicrobial activity of some disubstituted 1,3,4-oxadiazoles carrying 2-(aryloxymethyl)phenyl moiety. European Journal of Medicinal Chemistry, 45, 4708-4719.
  • Offe, H.A., Siefken, W. ve Domagk, G., 1952. Hydrazinderivate und ihre Wirksamkeit gegenüber Mycobacterium tuberculosis. Zeitschrift für Naturforschung B, 7(8), 446-462.
  • Ogata, M., Atobe, H., Kushida, H. ve Yamamoto, K., 1971. In vitro sensitivity of mycoplasma isolated from various animals and sewage to antibiotics and nitrofurans. The Journal of Antibiotics, 24, 443-451.
  • Parmar, S.S., Gupta, A.K., Gupta, T.K. ve Stenberg, V.I., 1975. Synthesis of substituted benzylidinohydrazines and their monoamine oxidase inhibitory and anticonvulsant properties. Journal of Pharmaceutical Sciences, 64(1), 154-157.
  • Partyka, R.A. ve Crenshaw, R.R., 1977. 1, 3, 4-oxadiazole amides. U.S. Patent 4001-238.
  • Rostom, S.A.F., Shalaby, M.A. ve El-Demellawy, M.A., 2003. Synthesis of new 1-(4- chlorophenyl)-4-hydroxy-1H-pyrazole- 3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. European Journal of Medicinal Chemistry, 38, 959-974.
  • Savarino, A., 2006. A historical sketch of the discovery and development of HIV-1 integrase inhibitors. Expert Opinion on Investigational Drugs,15, 1507–1522.
  • Schlecker, R. ve Thieme, P.C., 1988. The synthesis of antihypertensive 3-(1,3,4-oxadiazol-2-yl) phenoxypropanolahines. Tetrahedron, 44, 3289-3294.
  • Seki, H., Kawaguchi, T. ve Higuchi, T., 1988. Specificity of esterases and structure of prodrug esters: Reactivity of various acylated acetaminophen compounds and acetylaminobenzoated compounds. Journal of Pharmaceutical Sciences, 77(10), 855-860.
  • Sengupta, P., Mal, M., Mandal, S., Singh, J. ve Maity, T. K., 2008. Evaluation of antibacterial and antifungal activity of some 1,3,4-oxadiazoles. Iranian Journal of Pharmacology and Therapeutics, 7(2), 165-167.
  • Shyma, P.C., Balakrishna, K., Peethambar, S.K.ve Vijesh, A.M., 2015. Synthesis, characterization, antidiabetic and antioxidant activity of 1,3,4-oxadiazole derivatives bearing 6-methyl pyridine moiety. Der Pharma Chemica, 7(12), 137-145.
  • Sridhara, A.M., Reddy, K.R.V., Keshavayya, J., Goud, P.S.K., Somashekar, B.C., Bose, P., Peethambar, S.K. ve Gaddam, S.K., 2010. Synthesis and antimicrobial activity of 2-substituted [4-(1,3,4-oxadiazol-2-yl methyl)] phthalazin-1(2H)-one derivatives. European Journal of Medicinal Chemistry, 45, 4983-4989.
  • Thakkar, S.S., Thakor, P., Doshi, H. ve Ray, A., 2017. 1, 2, 4-Triazole and 1, 3, 4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities. Bioorganic and Medicinal Chemistry, 25(15), 4064-4075.
  • Vardan, S., Smulyan, H., Mookherjee, S. ve Eich, R., 1983. Effects of tiodazosin, a new antihypertensive, hemodynamics and clinical variables. Clinical Pharmacology and Therapeutics, 34(3), 290-296.
  • Yan, R., Zhang, Z.M., Fang, X.Y., Hu, Y. ve Zhu, H.L., 2012. Synthesis, molecular docking and biological evaluation of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents. Bioorganic and Medicinal Chemistry, 20(4), 1373-1379.

Yeni 2,5-Disubstitüe 1,3,4-Oksadiazol Bileşiklerinin Sentezi

Year 2020, , 330 - 338, 15.04.2020
https://doi.org/10.17714/gumusfenbil.612725

Abstract

Yapısında
1,3,4- oksadiazol halkası içeren bileşikler geniş bir biyolojik aktivite
spektrumuna sahiptir. Genel olarak; antibakteriyel, antifungal, analjezik,
antiinflamatuar, antiviral, antikanser, antidiabetik, antihelmintik,
antikonvülsan etki gösterdikleri son yıllarda yapılan çalışmalarla ortaya
konulmuştur. Bu nedenle bu çalışmada öncelikle prokain bileşiğinden yola
çıkılarak hidrazin hidrat ile reaksiyonları incelendi ve benzohidrazit türevi moleküllerin
sentezi yapıldı. Sonrasında bu bileşiklerin asetik anhidrit ve asetik asit
varlığında halka kapanma reaksiyonları ile daha önce literatürde yer almayan ve
2,5 konumlarında farklı gruplar içeren 1,3,4-oksadiazol bileşiklerinin sentezi
gerçekleştirildi. Sentezlenen bileşiklerin antibakteriyel ve antifungal
özelliklerinin araştırılması
Escherichia
coli
ATCC 36218, Staphylococcus
aureus
ATCC 25923 ve Candida albicans
ATCC 10231 mikroorganizmaları ile yapıldı. Bileşikler içinde fenil
halkasına bağlı lipofilik asetat grubu bulunduranların antibakteriyel ve
antifungal özelliklere sahip olduğu gözlendi.

References

  • Ahsan, M.J., Samy, J.G., Khalilullah, H., Nomani, M.S., Saraswat, P., Gaur, R. ve Singh, A., 2011. Molecular properties prediction and synthesis of novel 1, 3, 4-oxadiazole analogues as potent antimicrobial and antitubercular agents. Bioorganic and Medicinal Chemistry Letters, 21(24), 7246-7250.
  • Akhtar, T., Hameed, S., Al-Masoudi, N.A., Loddo, R. ve Colla, P.L., 2010. In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2- thione derivatives. Acta Pharmazie, 58, 135-149.
  • Akhter, M., Husain, A., Azad, B. ve Ajmal, M., 2009. Aroylpropionic acid based 2,5- disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities. European Journal of Medicinal Chemistry, 44, 2372–2378.
  • Bishayee, A., Karmakar, R., Mandal, A., Kundu, S.N. ve Chatterjee, M., 1997. Vanadium-mediated chemoprotection against chemical hepatocarcinogenesis in rats: haematological and histological characteristics. European Journal of Cancer Prevention, 6(1), 58-70.
  • Buslov, I. ve Hu, X., 2014. Transition Metal-Free Intermolecular α-C-H Amination of Ethers at Room Temperature. Advanced Synthesis and Catalysis, 356, 3325-3330.
  • De Oliveira, C.S., Lira, B.F., Barbosa-Filho, J.M., Lorenzo, J.G.F. ve De Athayde-Filho, P.F., 2012. Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012. Molecules,17, 10192-10231.
  • Dilmaghani, K.A., Jazani, N.H., Pur, F.N., Shokoufeh, N., Ghadiri, F. ve Fakhraee, F.M., 2012. Synthesis of 5-(4-aminophenyl)-2-(arylamino)-1,3,4-thiadiazoles and their schiff base derivatives as antimycobacterial agents. Chemistry of Heterocyclic Compounds, 48, 362-367.
  • Gao, P. ve Wei, Y., 2013. Efficient oxidative cyclization of N-acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions. Heterocyclic Communications, 19(2), 113-119.
  • Hirao, I., Yashuhiko, K. ve Toshiyuki, H., 1971. Studies of the synthesis of furan compound XXIV. The synthesis of 5-[2-(5-nitro-2-furyl)-l-(2-furyl)-vinyl] l,3,4-oxadiazole and its related compounds. Bulletin of Chemical Society of Japan, 44, 1923-1927.
  • Husain, A., Ahmad, F.J., Ajmal, M. ve Ahuja, P., 2008. Synthesis of 1-(4-phenoxyphenyl)-3-[5-(substituted aryl)-1, 3, 4-oxadiazol-2-yl] propan-1-ones as safer anti-inflammatory and analgesic agents. Journal of the Serbian Chemical Society, 73(8-9), 781-791.
  • Ibrahim, E.S.A., Soliman, R. ve Gabr, M., 1979. Synthesis of 4-Substituted Aminobenzoate Quaternary Salts as Potent Antispasmodic Agents. Journal of Pharmaceutical Sciences, 68(3), 332-335.
  • James, N.D. ve Growcott J.W., 2009. Zibotentan endothelin ETA receptor antagonist oncolytic. Drugs of the Future, 34, 624-633.
  • Jayashankar, B., Rai K.M.L., Baskaran, N. ve Sathish, H.S., 2009. Synthesis and pharmacological evaluation of 1,3,4- oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry, 44, 3898-3902.
  • Kalyoncuoğlu, N., Rollas, S., Sür-Altiner, D., Yeğenoğlu, Y. ve Anğ, O., 1992. 1-[p-(Benzoylamino) benzoyl]-4-substituted thiosemicarbazides: synthesis and antibacterial and antifungal activities. Die Pharmazie, 47(10), 796-797.
  • Kanthiah, S., Kalusalingam, A., Velayutham, R., Vimala, A.T. ve Beyatricks, J., 2011. 5-(2-aminophenyl)-1, 3, 4-oxadiazole-2 (3H)-thione derivatives: synthesis, characterization and antimicrobial evaluation, International Journal of Pharmaceutical Sciences Review and Research, 6(1), 64-67.
  • Mamolo, M.G., Zampieri, D., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Scialino, G. ve Banfi, E., 2005. Antimycobacterial activity of new 3-substituted 5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives. Preliminary molecular modeling investigations. Bioorganic and Medicinal Chemistry, 13(11), 3797-3809.
  • Naveena, C.S., Boja, P. ve Kumari, N.S., 2010. Synthesis, characterization and antimicrobial activity of some disubstituted 1,3,4-oxadiazoles carrying 2-(aryloxymethyl)phenyl moiety. European Journal of Medicinal Chemistry, 45, 4708-4719.
  • Offe, H.A., Siefken, W. ve Domagk, G., 1952. Hydrazinderivate und ihre Wirksamkeit gegenüber Mycobacterium tuberculosis. Zeitschrift für Naturforschung B, 7(8), 446-462.
  • Ogata, M., Atobe, H., Kushida, H. ve Yamamoto, K., 1971. In vitro sensitivity of mycoplasma isolated from various animals and sewage to antibiotics and nitrofurans. The Journal of Antibiotics, 24, 443-451.
  • Parmar, S.S., Gupta, A.K., Gupta, T.K. ve Stenberg, V.I., 1975. Synthesis of substituted benzylidinohydrazines and their monoamine oxidase inhibitory and anticonvulsant properties. Journal of Pharmaceutical Sciences, 64(1), 154-157.
  • Partyka, R.A. ve Crenshaw, R.R., 1977. 1, 3, 4-oxadiazole amides. U.S. Patent 4001-238.
  • Rostom, S.A.F., Shalaby, M.A. ve El-Demellawy, M.A., 2003. Synthesis of new 1-(4- chlorophenyl)-4-hydroxy-1H-pyrazole- 3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. European Journal of Medicinal Chemistry, 38, 959-974.
  • Savarino, A., 2006. A historical sketch of the discovery and development of HIV-1 integrase inhibitors. Expert Opinion on Investigational Drugs,15, 1507–1522.
  • Schlecker, R. ve Thieme, P.C., 1988. The synthesis of antihypertensive 3-(1,3,4-oxadiazol-2-yl) phenoxypropanolahines. Tetrahedron, 44, 3289-3294.
  • Seki, H., Kawaguchi, T. ve Higuchi, T., 1988. Specificity of esterases and structure of prodrug esters: Reactivity of various acylated acetaminophen compounds and acetylaminobenzoated compounds. Journal of Pharmaceutical Sciences, 77(10), 855-860.
  • Sengupta, P., Mal, M., Mandal, S., Singh, J. ve Maity, T. K., 2008. Evaluation of antibacterial and antifungal activity of some 1,3,4-oxadiazoles. Iranian Journal of Pharmacology and Therapeutics, 7(2), 165-167.
  • Shyma, P.C., Balakrishna, K., Peethambar, S.K.ve Vijesh, A.M., 2015. Synthesis, characterization, antidiabetic and antioxidant activity of 1,3,4-oxadiazole derivatives bearing 6-methyl pyridine moiety. Der Pharma Chemica, 7(12), 137-145.
  • Sridhara, A.M., Reddy, K.R.V., Keshavayya, J., Goud, P.S.K., Somashekar, B.C., Bose, P., Peethambar, S.K. ve Gaddam, S.K., 2010. Synthesis and antimicrobial activity of 2-substituted [4-(1,3,4-oxadiazol-2-yl methyl)] phthalazin-1(2H)-one derivatives. European Journal of Medicinal Chemistry, 45, 4983-4989.
  • Thakkar, S.S., Thakor, P., Doshi, H. ve Ray, A., 2017. 1, 2, 4-Triazole and 1, 3, 4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities. Bioorganic and Medicinal Chemistry, 25(15), 4064-4075.
  • Vardan, S., Smulyan, H., Mookherjee, S. ve Eich, R., 1983. Effects of tiodazosin, a new antihypertensive, hemodynamics and clinical variables. Clinical Pharmacology and Therapeutics, 34(3), 290-296.
  • Yan, R., Zhang, Z.M., Fang, X.Y., Hu, Y. ve Zhu, H.L., 2012. Synthesis, molecular docking and biological evaluation of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents. Bioorganic and Medicinal Chemistry, 20(4), 1373-1379.
There are 31 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Meltem Tan 0000-0003-4190-6047

Publication Date April 15, 2020
Submission Date August 29, 2019
Acceptance Date January 24, 2020
Published in Issue Year 2020

Cite

APA Tan, M. (2020). Yeni 2,5-Disubstitüe 1,3,4-Oksadiazol Bileşiklerinin Sentezi. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 10(2), 330-338. https://doi.org/10.17714/gumusfenbil.612725