Volume 56, Issue 9 pp. 2411-2418

Article

Synthesis, antimicrobial activity, and molecular docking study of formylnaphthalenyloxymethyl-triazolyl-N-phenylacetamides

Mahesh B. Muluk,

Mahesh B. Muluk

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Sambhaji T. Dhumal,

Sambhaji T. Dhumal

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004 Maharashtra, India

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Pramod S. Phatak,

Pramod S. Phatak

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Naziya N. M. A. Rehman,

Naziya N. M. A. Rehman

Department of Microbiology, Dr. Babasaheb Ambedkar Marathwada University, Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Prashant P. Dixit,

Prashant P. Dixit

Department of Microbiology, Dr. Babasaheb Ambedkar Marathwada University, Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Prafulla B. Choudhari,

Prafulla B. Choudhari

Department of Pharmaceutical Chemistry, Bharati Vidhyapeeth College of Pharmacy, Kolhapur, 416013 Maharashtra, India

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Ramrao A. Mane,

Ramrao A. Mane

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004 Maharashtra, India

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Kishan P. Haval,

Corresponding Author

Kishan P. Haval

[email protected]

orcid.org/0000-0002-2526-8738

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub-Campus, Osmanabad, 413501 Maharashtra, India

E-mail: [email protected]Search for more papers by this author

Mahesh B. Muluk,

Mahesh B. Muluk

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Sambhaji T. Dhumal,

Sambhaji T. Dhumal

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004 Maharashtra, India

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Pramod S. Phatak,

Pramod S. Phatak

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Naziya N. M. A. Rehman,

Naziya N. M. A. Rehman

Department of Microbiology, Dr. Babasaheb Ambedkar Marathwada University, Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Prashant P. Dixit,

Prashant P. Dixit

Department of Microbiology, Dr. Babasaheb Ambedkar Marathwada University, Sub-Campus, Osmanabad, 413501 Maharashtra, India

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Prafulla B. Choudhari,

Prafulla B. Choudhari

Department of Pharmaceutical Chemistry, Bharati Vidhyapeeth College of Pharmacy, Kolhapur, 416013 Maharashtra, India

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Ramrao A. Mane,

Ramrao A. Mane

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004 Maharashtra, India

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Kishan P. Haval,

Corresponding Author

Kishan P. Haval

[email protected]

orcid.org/0000-0002-2526-8738

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub-Campus, Osmanabad, 413501 Maharashtra, India

E-mail: [email protected]Search for more papers by this author

First published: 17 July 2019

https://doi.org/10.1002/jhet.3628

Citations: 19

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Abstract

In the present study, substituted formylnaphthalenyloxymethyl-triazolyl-N-phenylacetamide derivatives (6a–k) have been designed and synthesized employing click chemistry approach and evaluated for their in vitro antifungal and antibacterial activities. All the newly synthesized compounds were thoroughly characterized by ¹H NMR, ¹³C NMR, and HRMS spectral techniques. Among the screened compounds, 6d, 6e, 6j, and 6k have shown good antifungal and antibacterial activities. Compound 6k has shown very effective antimicrobial activity. We further performed exploratory docking studies on microbial DNA gyrase to rationalize the in vitro biological data and to demonstrate the mechanism of antimicrobial activity. This is the first report to demonstrate the formylnaphthalenyloxymethyl, triazole, and N-phenylacetamide hybrids as potential antimicrobial agents.

Supporting Information

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Description

jhet3628-supp-0001-supp info.docxWord 2007 document , 5.4 MB

Scheme S1. Synthesis of substituted formylnaphthalenyloxymethyl-triazolyl-N-phenylacetamides (6a-k).

Figure S1. ¹H NMR spectrum of compound 6a

Figure S2. ¹³C NMR spectrum of compound 6a

Figure S3. HRMS of compound 6a

Figure S4. ¹H NMR spectrum of compound 6b

Figure S5. ¹³C NMR spectrum of compound 6b

Figure S6. HRMS of compound 6b

Figure S7. ¹H NMR spectrum of compound 6c

Figure S8. HRMS of compound 6c

Figure S9. ¹³C NMR spectrum of compound 6c

Figure S10. ¹H NMR spectrum of compound 6d

Figure S11. HRMS of compound 6d

Figure S12. ¹H NMR spectrum of compound 6e

Figure S13. ¹³C NMR spectrum of compound 6e

Figure S14. HRMS of compound 6e

Figure S15. ¹H NMR spectrum of compound 6f

Figure S16. ¹³C NMR spectrum of compound 6f

Figure S17. HRMS of compound 6f

Figure S18. ¹H NMR spectrum of compound 6g

Figure S19. ¹³C NMR spectrum of compound 6g

Figure S20. HRMS of compound 6g

Figure S21. ¹H NMR spectrum of compound 6h

Figure S22. HRMS of compound 6h

Figure S23. ¹H NMR spectrum of compound 6i

Figure S24. ¹³C NMR spectrum of compound 6i

Figure S25. HRMS of compound 6i

Figure S26. ¹H NMR spectrum of compound 6j

Figure S27. ¹³C NMR spectrum of compound 6j

Figure S28. HRMS of compound 6j

Figure S29. ¹H NMR spectrum of compound 6k

Figure S30. HRMS of compound 6k

Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

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Volume56, Issue9

September 2019

Pages 2411-2418

Synthesis, antimicrobial activity, and molecular docking study of formylnaphthalenyloxymethyl-triazolyl-N-phenylacetamides

Abstract

Supporting Information

REFERENCES AND NOTES

Citing Literature

References

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Synthesis, antimicrobial activity, and molecular docking study of formylnaphthalenyloxymethyl-triazolyl-N-phenylacetamides

Abstract

Supporting Information

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Citing Literature

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