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Abstract
A new series of 1,2,3-triazole linked mercaptobenzoxazole/oxazolo[4,5-b]pyridine-2-thiol derivatives (6a-j) were synthesized starting from 2-aminophenol/2-aminopyridin-3-ol in three steps via cyclization, alkylation followed by reaction with various aromatic azides using click chemistry approach. All the synthesized compounds were evaluated for their antimicrobial activity viz. E. coli, P. aeruginosa, S. aureus and S. pyogenus and three pathogenic fungi viz. C. albicans, A. niger and A. clavatus and promising compounds were identified.
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References
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- E.A. Sheremet, R.I. Tomanov, E.V. Trukhin and V.M. Berestovitskaya, Synthesis of 4-Aryl-5-nitro-1,2,3-triazoles, Russ. J. Org. Chem., 40, 594 (2004); https://doi.org/10.1023/B:RUJO.0000036090.61432.18
- A. Allais and J. Meier, (Roussel-UCLAF) Ger. Offen., 1815467 (1969).
- K.M. Banu, A. Dinakar and C. Ananthanarayanan, Synthesis, Charact-erization, Antimicrobial Screening and Pharmacological Screening of Some Substituted 1,2,3-Triazoles, Indian J. Pharm. Sci., 4, 202 (1999).
- G. Cirrincione, A. Passannanti, P. Diana, P. Barraja, F. Mingoia and A. Lauria, Pyrrolo[2,3-d][1,2,3]triazoles as Potential Antineoplastic Agents, Heterocycles, 48, 1229 (1998); https://doi.org/10.3987/COM-98-8130
- R. Meier, Aralkyltriazole Compounds, US Patent 4789680A (1986).
- G.N. Raju, T.S.K.T. Prasanna, M.K.L. Surekha, M. Suneetha and R.R. Nadendla, Synthesis, Characterization and Antimicrobial Evaluation of Novel 2-Cyclic Amine Benzoxazole Derivatives, World J. Pharm. Pharm. Sci., 4, 1082 (2015).
- S. Haider, M.S. Alam, H. Hamid, S. Shafi, A. Dhulap, F. Hussain, P. Alam, S. Umar, M.A.Q. Pasha, S. Bano, S. Nazreen, Y. Ali and C. Kharbanda, Synthesis of Novel 2-Mercaptobenzoxazole Based 1,2,3-Triazoles as Inhibitors of Proinflammatory Cytokines and Suppressors of COX-2 Gene Expression, Eur. J. Med. Chem., 81, 204 (2014); https://doi.org/10.1016/j.ejmech.2014.05.012
- R.M. Kumbhare, T.L. Dadmal, M.J. Ramaiah, K.S.V. Kishore, S.N.C.V.L. Pushpa Valli, S.K. Tiwari, K. Appalanaidu, Y.K. Rao and M.P. Bhadra, Synthesis and Anticancer Evaluation of Novel Triazole Linked N-(Pyrimidin-2-yl)benzo[d]thiazol-2-amine Derivatives as Inhibitors of Cell Survival Proteins and Inducers of Apoptosis in MCF-7 Breast Cancer Cells, Bioorg. Med. Chem. Lett., 25, 654 (2015); https://doi.org/10.1016/j.bmcl.2014.11.083
- R.M. Kumbhare, T.L. Dadmal, R. Pamanji, U.B. Kosurkar, L.R. Velatooru, K. Appalanaidu, Y.K. Rao and J.V. Rao, Med. Chem. Res., 23, 4404 (2014); https://doi.org/10.1007/s00044-014-1006-0
References
A.D. Rodríguez, C. Ramírez, I.I. Rodríguez and E. González, Novel Antimycobacterial Benzoxazole Alkaloids, from the West Indian Sea Whip Pseudopterogorgia elisabethae, Org. Lett., 1, 527 (1999); https://doi.org/10.1021/ol9907116
J. Kobayashi, T. Madono and H. Shigemori, Nakijinol, A Novel Sesquiterpenoid Containing a Benzoxazole Ring from an Okinawan Sponge, Tetrahedron Lett., 36, 5589 (1995); https://doi.org/10.1016/00404-0399(50)1068-S
C. Huo, D. An, B. Wang, Y. Zhao and W. Lin, Structure Elucidation and Complete NMR Spectral Assignments of a New Benzoxazolinone Glucoside from Acanthus ilicifolius, Magn. Reson. Chem., 43, 343 (2005); https://doi.org/10.1002/mrc.1529
I.I. Rodriguez and A.D. Rodriguez, Homopseudopteroxazole, a New Antimycobacterial Diterpene Alkaloid from Pseudopterogorgia elisabethae, J. Nat. Prod., 66, 855 (2003); https://doi.org/10.1021/np030052c
J.P. Haansuu, K.D. Klika, P.P. Soderholm, V.V. Ovcharenko, K. Pihlaja, K.K. Haahtela and P.M. Vuorela, Isolation and Biological Activity of Frankiamide, J. Ind. Microbiol. Biotechnol., 27, 62 (2001); https://doi.org/10.1038/sj.jim.7000164
L.Q. Sun, J. Chen, M. Bruce, J.A. Deskus, J.R. Epperson, K. Takaki, G. Johnson, L. Iben, C.D. Mahle, E. Ryan and C. Xu, Synthesis and Structure-Activity Relationship of Novel Benzoxazole Derivatives as Melatonin Receptor Agonists, Bioorg. Med. Chem. Lett., 14, 3799 (2004); https://doi.org/10.1016/j.bmcl.2004.04.082
R. Paramashivappa, P. Phani Kumar, P.V. Subba Rao and A. Srinivasa Rao, Design, synthesis and Biological Evaluation of Benzimidazole/Benzothiazole and Benzoxazole Derivatives as Cyclooxygenase Inhibitors, Bioorg. Med. Chem. Lett., 13, 657 (2003); https://doi.org/10.1016/S0960-894X(02)01006-5
D. Kumar, M.R. Jacob, M.B. Reynolds and S.M. Kerwin, Synthesis and Evaluation of Anticancer Benzoxazoles and Benzimidazoles Related to UK-1, Bioorg. Med. Chem., 10, 3997 (2002); https://doi.org/10.1016/S0968-0896(02)00327-9
P.L. Lopez-Tudanca, L. Labeaga, A. Innerarity, L. Alonso-Cires, I. Tapia, R. Mosquera and A. Orjales, Synthesis and Pharmacological Characteri-zation of a New Benzoxazole Derivative as a Potent 5-HT3 Receptor Agonist, Bioorg. Med. Chem., 11, 2709 (2003); https://doi.org/10.1016/S0968-0896(03)00243-8
D.B. Olsen, S.S. Carroll, J.C. Culberson, J.A. Shafer and L.C. Kuo, Effect of Template Secondary Structure on the Inhibition of HIV-1 Reverse Transcriptase by a Pyridinone Non-nucleoside Inhibitor, Nucleic Acids Res., 22, 1437 (1996); https://doi.org/10.1093/nar/22.8.1437
S. Staszewski, F.E. Massari, A. Kober, R. Gohler, S. Durr, K.W. Anderson, C.L. Schneider, J.A. Waterbury, K.K. Bakshi, V.I. Taylor, C.S. Hildebrand, C. Kreisl, B. Hoffstedt, W.A. Schleif, H. von Briesen, H. Rubsamen-Waigmann, G.B. Calandra, J.L. Ryan, W. Stille, E.A. Emini and V.W. Byrnes, Combination Therapy with Zidovudine Prevents Selection of Human Immunodeficiency Virus Type 1 Variants Expressing High-Level Resistance to L-697,661, a Nonnucleoside Reverse Transcriptase Inhibitor, J. Infect. Dis., 171, 1159 (1995); https://doi.org/10.1093/infdis/171.5.1159
J. Susperregui, M. Bayle, J.M. Léger and G. Déléris, Synthesis, Structure and Trypanocidal Activity of Dibutyltin Derivatives of 2-Mercaptoben-zoxazole and 5-Chloro-2-mercaptobenzothiazole, J. Organomet. Chem., 556, 105 (1998); https://doi.org/10.1016/S0022-328X(97)00782-1
P. Kohli, S.D. Srivastava and S.K. Srivastava, Synthesis and Biological Activity of Mercaptobenzoxazole Based Thiazolidinones and their Arylidenes, J. Chin. Chem. Soc. (Taipei), 54, 1003 (2007); https://doi.org/10.1002/jccs.200700144
J.H. Cho, D.L. Bernard, R.W. Sidwell, E.R. Kern and C.K. Chu, Synthesis of Cyclopentenyl Carbocyclic Nucleosides as Potential Antiviral Agents Against Orthopoxviruses and SARS, J. Med. Chem., 49, 1140 (2006); https://doi.org/10.1021/jm0509750
A. Brik, J. Alexandratos, Y.-C. Lin, J.H. Elder, A.J. Olson, A. Wlodawer, D.S. Goodsell and C.-H. Wong, 1,2,3-Triazole as a Peptide Surrogate in the Rapid Synthesis of HIV-1 Protease Inhibitors, ChemBioChem, 6, 1167 (2005); https://doi.org/10.1002/cbic.200500101
A. Brik, J. Muldoon, Y.-C. Lin, J.H. Elder, D.S. Goodsell, A.J. Olson, V.V. Fokin, K.B. Sharpless and C.-H. Wong, Rapid Diversity-Oriented Synthesis in Microtiter Plates for in situ Screening of HIV Protease Inhibitors, ChemBioChem, 4, 1246 (2003); https://doi.org/10.1002/cbic.200300724
F. Pagliai, T. Pirali, E. Del Grosso, R. Di Brisco, G.C. Tron, G. Sorba and A.A. Genazzani, Rapid Synthesis of Triazole-Modified Resveratrol Analogues via Click Chemistry, J. Med. Chem., 49, 467 (2006); https://doi.org/10.1021/jm051118z
A. Romero, C.-H. Liang, Y.-H. Chiu, S. Yao, J. Duffield, S.J. Sucheck, K. Marby, D. Rabuka, P.Y. Leung, Y.-K. Shue, Y. Ichikawa and C.-K. Hwang, An Efficient Entry to New Sugar Modified Ketolide Antibiotics, Tetrahedron Lett., 46, 1483 (2005); https://doi.org/10.1016/j.tetlet.2005.01.023
M. Chen, S. Lu, G. Yuan, S. Yang and X. Du, Synthesis and Antibacterial Activity of Some Heterocyclic b-Enamino Ester Derivatives with 1,2,3-triazole: Synthesis and Antibacterial Activity of Some Heterocyclic b-Enamino Ester Derivatives with 1,2,3-Triazole, Heterocycl. Commun., 6, 421 (2000); https://doi.org/10.1515/HC.2000.6.5.421
E.A. Sheremet, R.I. Tomanov, E.V. Trukhin and V.M. Berestovitskaya, Synthesis of 4-Aryl-5-nitro-1,2,3-triazoles, Russ. J. Org. Chem., 40, 594 (2004); https://doi.org/10.1023/B:RUJO.0000036090.61432.18
A. Allais and J. Meier, (Roussel-UCLAF) Ger. Offen., 1815467 (1969).
K.M. Banu, A. Dinakar and C. Ananthanarayanan, Synthesis, Charact-erization, Antimicrobial Screening and Pharmacological Screening of Some Substituted 1,2,3-Triazoles, Indian J. Pharm. Sci., 4, 202 (1999).
G. Cirrincione, A. Passannanti, P. Diana, P. Barraja, F. Mingoia and A. Lauria, Pyrrolo[2,3-d][1,2,3]triazoles as Potential Antineoplastic Agents, Heterocycles, 48, 1229 (1998); https://doi.org/10.3987/COM-98-8130
R. Meier, Aralkyltriazole Compounds, US Patent 4789680A (1986).
G.N. Raju, T.S.K.T. Prasanna, M.K.L. Surekha, M. Suneetha and R.R. Nadendla, Synthesis, Characterization and Antimicrobial Evaluation of Novel 2-Cyclic Amine Benzoxazole Derivatives, World J. Pharm. Pharm. Sci., 4, 1082 (2015).
S. Haider, M.S. Alam, H. Hamid, S. Shafi, A. Dhulap, F. Hussain, P. Alam, S. Umar, M.A.Q. Pasha, S. Bano, S. Nazreen, Y. Ali and C. Kharbanda, Synthesis of Novel 2-Mercaptobenzoxazole Based 1,2,3-Triazoles as Inhibitors of Proinflammatory Cytokines and Suppressors of COX-2 Gene Expression, Eur. J. Med. Chem., 81, 204 (2014); https://doi.org/10.1016/j.ejmech.2014.05.012
R.M. Kumbhare, T.L. Dadmal, M.J. Ramaiah, K.S.V. Kishore, S.N.C.V.L. Pushpa Valli, S.K. Tiwari, K. Appalanaidu, Y.K. Rao and M.P. Bhadra, Synthesis and Anticancer Evaluation of Novel Triazole Linked N-(Pyrimidin-2-yl)benzo[d]thiazol-2-amine Derivatives as Inhibitors of Cell Survival Proteins and Inducers of Apoptosis in MCF-7 Breast Cancer Cells, Bioorg. Med. Chem. Lett., 25, 654 (2015); https://doi.org/10.1016/j.bmcl.2014.11.083
R.M. Kumbhare, T.L. Dadmal, R. Pamanji, U.B. Kosurkar, L.R. Velatooru, K. Appalanaidu, Y.K. Rao and J.V. Rao, Med. Chem. Res., 23, 4404 (2014); https://doi.org/10.1007/s00044-014-1006-0