employee from 01.01.2025 to 01.01.2026
Saint Petersburg, Russian Federation
Yaroslavl, Russian Federation
Saint Petersburg, Russian Federation
Saint Petersburg, Russian Federation
Yaroslavl, Russian Federation
student
Yaroslavl, Russian Federation
Saint Petersburg, Russian Federation
A series of eight new 2'-aminoaryloxadiazol-5(4H)-ones has been synthesized via the reduction of the corresponding nitro derivatives with tin(II) chloride. The antibacterial and fluorescent properties of the derivatives have been studied. We obtain the compound with moderate antibacterial activity against a sensitive strain of the Gram-positive bacterium Staphylococcus aureus ATCC-25923 (3-amino-4-(3-(3,4-dichlorophenyl)-5-oxo-1,2,4-oxadiazol-4(5H)-yl)benzonitrile, MIC 64 µg/mL. It demonstrates weak fluorescent properties upon irradiation with light at λ = 355 nm.
oxadiazol-5(4H)-one, reduction, tin(II) chloride, antibacterial activity, fluorescence
1. Pace A., Pierro P. The new era of 1,2,4-oxadiazoles. Org. Biomol. Chem., 2009, 7(21), 4337. DOI:https://doi.org/10.1039/b908937c
2. Mao T., Meng Q., Zhang H., Zhang J.J., Shi S., Guan Z., Jiang X., Zhang F., Lei H., Lin X. 760-P: Discovery of GSBR-1290, a Highly Potent, Orally Available, Novel Small Molecule GLP-1 Receptor Agonist. Diabetes, 2023, 72, 760-P. DOI:https://doi.org/10.2337/db23-760-P
3. Ohmoto K., Okuma M., Yamamoto T., Kijima H., Sekioka T., Kitagawa K., Yamamoto S., Tanaka K., Kawabata K., Sakata A., Imawaka H., Nakai H., Toda M. Design and Synthesis of New Orally Active Inhibitors of Human Neutrophil Elastase. Bioorg. Med. Chem., 2001, 9, 1307–1323. DOI:https://doi.org/10.1016/s0968-0896(01)00007-4
4. Semenov A. V., Baykov S. V., Soldatova N. S., Geyl K. K., Shetnev A. A., Boyarskiy V. P., Postnikov P. S. Expanding the antiviral arsenal: N-arylated 1, 2, 4-oxadiazol-5 (4H)-ones show high activity against orthopoxviruses. Europ. J. Med. Chem., 2025, 118124. DOI:https://doi.org/10.1016/j.ejmech.2025.118124
5. Kumar R., Yadav R. K., Mazumder A., Salahuddin, Kukreti N., Singh H., Khan F., Singh S. K. Insights into adopted synthetic approaches for 1,2,4-oxadiazoles: A review. Synth. Commun., 2023, 53(21), 1761–1783. DOI:https://doi.org/10.1080/00397911.2023.2256008
6. Deegan T. L., Nitz T. J., Cebzanov D., Pufko D. E., Porco J. A. Jr. Parallel synthesis of 1,2,4-oxadiazoles using CDI activation. Bioorg. Med. Chem. Lett., 1999, 9(2), 209–212. DOI:https://doi.org/10.1016/s0960-894x(98)00712-4
7. Ispikoudi M., Litinas K.E., Fylaktakidou K.C. A Convenient Synthesis of 5-Amino-Substituted 1,2,4 Oxadiazole Derivatives via Reactions of Amidoximes with Carbodiimides. Heterocycles, 2008, 75(6), 1321–1328. DOI:https://doi.org/10.3987/com-08-11340
8. Neves Filho R. A. W., Bezerra N. M. M., Guedes J. M., Srivastava R. M. An easy synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids and arylamidoximes mediated by ethyl chloroformate. J. Braz. Chem. Soc., 2009, 20(7), 1365–1369. DOI:https://doi.org/10.1590/s0103-50532009000700023
9. Phakhodee W., Duangkamol C., Wiriya, N., Pattarawarapan M. A convenient one-pot synthesis of N substituted amidoximes and their application toward 1,2,4-oxadiazol-5-ones. RSC Adv., 2018, 8(67), 38281–38288. DOI:https://doi.org/10.1039/c8ra08207c
10. Porcheddu A., Cadoni R., De Luca L. A fast and efficient one-pot microwave assisted synthesis of variously di-substituted 1,2,4-oxadiazoles. Org. Biomol. Chem., 2011, 9(21), 7539. DOI:https://doi.org/10.1039/c1ob06055d
11. Baykov S.V., Sharonova T., Osipyan A. T., Rozhkov S.S., Shetnev A.A., Smirnov A. V. A convenient and mild method for 1,2,4-oxadiazole preparation: cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO. Tetrahedron Lett., 2016, 57(26), 2898–2900. DOI:https://doi.org/10.1016/j.tetlet.2016.05.071
12. Soldatova N., Semenov A., Geyl K., Baykov S., Shetnev A., Konstantinova A., Korsakov M., Yusubov M., Postnikov P. Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts. Adv. Synth. Catal., 2021, 363, 1–12. DOI:https://doi.org/10.1002/adsc.202100426
13. Konstantinova A.S., Shetnev A.A., Volobueva A.S., Korsakov M.K. N-Arylation of 1,2,4- and 1,3,4 Oxadiazolones under Activated Aromatic Nucleophilic Substitution Conditions. Russ. J. Org. Chem., 2023, 59, 1874–1883. DOI:https://doi.org/10.1134/S1070428023110052
14. Shinichi Y., Yamazaki S. A DFT Study of Reduction of Nitrobenzene to Aniline with SnCl2 and Hydrochloric Acid. J. Phys Org Chem., 2016, 29(7), 361–367. DOI:https://doi.org/10.1002/poc.3543
15. Bellamy F.D., Ou K. Selective Reduction of Aromatic Nitro Compounds with Stannous Chloride in Non Acidic and Non Aqueous Medium. Tetrahedron Lett, 1984, 25(8), 839–842. DOI:https://doi.org/10.1016/s0040-4039(01)80041-1.
16. Gasilina, O.A., Romanycheva, A.A., Shetnev, A.A. Korsakov M.K. Synthesis, Antibacterial, and Antimonooxidase Activity of 4-(2-Methyl-1,3-oxazol-5-yl)benzenesulfonamide. Russ. J. Gen. Chem., 2023, 93, 2749–2755. DOI:https://doi.org/10.1134/S1070363223110038



