SINTEZ, FLUORESTSENTNYE I ANTIBAKTERIAL'NYE SVOISTVA N-(2’-AMINOARIL)ZAMESHCHENNYKH 1,2,4-OKSADIAZOL-5(4N)-ONOV
Abstract and keywords
Abstract:
Sintezirovan ryad iz vos'mi novykh 2’-aminoariloksadiazol-5(4N)-onov po reaktsii vosstanovleniya sootvetstvuyushchikh nitroproizvodnykh khloridom olova (II). Izucheny antibakterial'nye i fluorestsentnye svoistva proizvodnykh. Naideno soedinenie s umerennoi antibakterial'noi aktivnost'yu v otnoshenii chuvstvitel'nogo shtamma grampolozhitel'noi bakterii Staphylococcus aureus ATCC-25923 (3-amino-4-(3-(3,4-dikhlorfenil)-5-okso-1,2,4-oksadiazol-4(5H)-il)-benzonitril, MIK 64 mkg/ml). Soedineniya prodemonstrirovali slabye fluorestsentnye svoistva pri obluchenii svetom λ = 355 nm.

Keywords:
Oksadiazol-5(4N)-on, Vosstanovlenie, Khlorid olova(II), Antibakterial'naya aktivnost', fluorestsentsiya
References

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

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