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Abstract

The present work reports the synthesis of 4-(1-(substituted phenyl)-1H-naphtho[1,2-e][1,3]oxazin-2(3H)-yl)-1-thia-4-azaspiro-[4.5]-decan-3-one IV(a-h) by 4-(((substituted phenyl)(2-hydroxynaphthalen- 1-yl)ethyl)amino)-1-thia-4-azaspiro[4.5]decan-3-one with formaldehyde in acetonitrile, containing a spiro ring obtained from the reaction of cyclohexylidene hydrazine and thioglycollic acid in DMF (cyclohexanone reacts with hydrazine hydrate in pyridine). The structures of the synthesized compounds have been established on the basis of elemental analysis, UV-vis absorption spectroscopy, IR, 1H NMR and mass spectral studies. The in vitro antimicrobial screening of all novel compounds was done against S. aureus, E. coli, P. aeruginosa and B. subtilis. The activity of compounds IVb, IVc, IVe and IVf compounds showed moderate to good activity against the tested microbes.

Keywords

Thioglycolic acid β-Naphthol Aromatic aldehyde Hydrazine hydrates Antimicrobial activity Cyclohexone.

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Bahadur Singh, R., Srivastava, K., Prakash Tiwari, R., & Srivastava, J. (2021). Synthesis of Novel Oxazin Analogs of Thio-4-azaspiro[4.5]decan-3-one for their Antimicrobial Activity. Asian Journal of Organic & Medicinal Chemistry, 6(2), 116–120. https://doi.org/10.14233/ajomc.2021.AJOMC-P323
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References

  1. E. Flefel, W. El-Sayed, A. Mohamed, W. El-Sofany and H. Awad, Synthesis and Anticancer Activity of New 1-Thia-4-azaspiro[4.5]decane, Their Derived Thiazolopyrimidine and 1,3,4-Thiadiazole Thioglycosides, Molecules, 22, 170 (2017); https://doi.org/10.3390/molecules22010170
  2. K. Stein, J. Farmer, S. Singhal, F. Marra, S. Sutherland and C. Quiñonez, The Use and Misuse of Antibiotics in Dentistry, J. Am. Dent. Assoc., 149, 869 (2018); https://doi.org/10.1016/j.adaj.2018.05.034
  3. S.C. Jain, J. Sinha, S. Bhagat, W. Errington and C.E. Olsen, A Facile Synthesis of Novel Spiro[Indole-pyrazolinyl-thiazolidine]-2,4¢-dione, Synth. Commun., 33, 563 (2003); https://doi.org/10.1081/SCC-120015810
  4. P.K. Gadekar, A. Roychowdhury, P.S. Kharkar, V.M. Khedkar, M. Arkile, H. Manek, D. Sarkar, R. Sharma, V. Vijayakumar and S. Sarveswari, Design, Synthesis and Biological Evaluation of Novel Azaspiro Analogs of Linezolid as Antibacterial and Antitubercular Agents, Eur. J. Med. Chem., 122, 475 (2016); https://doi.org/10.1016/j.ejmech.2016.07.001
  5. E.M. Hussein, G.S. Masaret and K.S. Khairou, Efficient Synthesis and Antimicrobial Evaluation of Some Mannich Bases from 2-Arylidine-1-thia-4-azaspiro[4.5]decan-3-ones, Chem. Cent. J., 9, 25 (2015); https://doi.org/10.1186/s13065-015-0101-8
  6. A. Kashyap, N. Adhikari, A. Das, A. Shakya, S.K. Ghosh, U.P. Singh and H.R. Bhat, Review on Synthetic Chemistry and Antibacterial Importance of Thiazole Derivatives, Curr. Drug Discov. Technol., 15, 214 (2018); https://doi.org/10.2174/1570163814666170911144036
  7. R. Mishra, N. Sachan, N. Kumar, I. Mishra and P. Chand, Thiophene Scaffold as Prospective Antimicrobial Agent: A Review, J. Heterocycl. Chem., 55, 2019 (2018); https://doi.org/10.1002/jhet.3249
  8. E.M.H. Ali, M.S. Abdel-Maksoud and C.H. Oh, Thieno[2,3-d]-pyrimidine as a Promising Scaffold in Medicinal Chemistry: Recent Advances, Bioorg. Med. Chem., 27, 1159 (2019); https://doi.org/10.1016/j.bmc.2019.02.044
  9. V. Chaskar, V. Vyavhare, K. Padalkar, K. Phatangare and H. Deokar, An Environmentally Benign One-Pot Synthesis of 1,2-Dihydro-1-aryl-naphtho[1,2-e][1,3]oxazine-3-one Derivatives Catalyzed by phospho-molybdic acid, J. Serb. Chem. Soc., 76, 21 (2011); https://doi.org/10.2298/JSC100410016C
  10. S.S. Didwagh and P.B. Piste, Novel Synthesis and Antimicrobial Activity of Bis-oxazine Derivatives, J. Chem. Pharm. Res., 5, 271 (2013).
  11. K. Hajela, A.K. Jha and J. Pandey, Non Steroidal Estrogen Antagonists: Current Status and Future Perspectives, Curr. Med. Chem. Immunol. Endocr. Metab. Agents, 1, 235 (2001); https://doi.org/10.2174/1568013013359023
  12. M. Krasavin, A. Lukin, T. Vedekhina, O. Manicheva, M. Dogonadze, T. Vinogradova, N. Zabolotnykh, E. Rogacheva, L. Kraeva, V. Sharoyko, T.B. Tennikova, D. Darin and E. Sokolovich, Attachment of a 5-nitro-furoyl Moiety to Spirocyclic Piperidines Produces Non-Toxic Nitrofurans that are Efficacious in vitro Against Multidrug-Resistant Mycobacterium tuberculosis, Eur. J. Med. Chem., 166, 125 (2019); https://doi.org/10.1016/j.ejmech.2019.01.050
  13. V. Francesconi, L. Giovannini, M. Santucci, E. Cichero, M.P. Costi, L. Naesens, F. Giordanetto and M. Tonelli, Synthesis, Biological Evaluation and Molecular Modeling of Novel Azaspiro Dihydrotriazines as Influenza Virus Inhibitors Targeting the Host Factor Dihydrofolate Reductase (DHFR), Eur. J. Med. Chem., 155, 229 (2018); https://doi.org/10.1016/j.ejmech.2018.05.059
  14. H.E.A. Ahmed, H.A. Abdel-Salam and M.A. Shaker, Synthesis, Characterization, Molecular Modeling, and Potential Antimicrobial and Anticancer Activities of Novel 2-aminoisoindoline-1,3-dione Derivatives, Bioorg. Chem., 66, 1 (2016); https://doi.org/10.1016/j.bioorg.2016.03.003