Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
An Efficient Synthesis of Thiophene Conjugated Benzothiazepines: in vitro Screening for their Antimicrobial Activity
Corresponding Author(s) : H.P. Jayadevappa
Asian Journal of Chemistry,
Vol. 32 No. 10 (2020): Vol 32 Issue 10
Abstract
A series of novel thiophene conjugated benzothiazepines were synthesized by the reaction of chalcones with 2-aminobenzenethiol in citrus juice medium. The new compounds were characterized by spectroscopic studies. Results of in vitro antimicrobial evaluation of newly synthesized compounds 5a-j shows that the compounds 5a and 5c have excellent antimicrobial inhibition in the range of 12.5-25.0 μg/mL against bacteria S. aureus, E. coli, P. aeruginosa and fungi A. niger, A. flavus organisms comparable to ciprofloxacin and nystatin and therefore these compounds might acts as lead molecules as antimicrobial agents.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- C.B.W. Phippen and C.S.P. McErlean, Tetrahedron Lett., 52, 1490 (2011); https://doi.org/10.1016/j.tetlet.2011.01.098
- J.B. Bariwal, K.D. Upadhyay, A.T. Manvar, J.C. Trivedi, J.S. Singh, K.S. Jain and A.K. Shah, Eur. J. Med. Chem., 43, 2279 (2008); https://doi.org/10.1016/j.ejmech.2008.05.035
- F.M.A. Altalbawy, Int. J. Mol. Sci., 14, 2967 (2013); https://doi.org/10.3390/ijms14022967
- N.S. Medran, A. La-Venia and S.A. Testero, RSC Adv., 9, 6804 (2019); https://doi.org/10.1039/C8RA10247C
- J. Tian, R. Zhou, H. Sun, H. Song and Z. He, J. Org. Chem., 76, 2374 (2011); https://doi.org/10.1021/jo200164v
- Y.H. Zaki, M.S. Al-Gendey and A.O. Abdelhamid, Chem. Central J.,12, 70 (2018); https://doi.org/10.1186/s13065-018-0439-9
- A. Voskiene and V. Mickevicius, Chem. Heterocycl. Comp., 45, 1485 (2009); https://doi.org/10.1007/s10593-010-0455-8
- M. Shailaja, A. Manjula, C.V. Rao, B. Praseeda and B.M. Reddy, Indian J. Chem., 50B, 214 (2011)
- C.P. Pandhurnekar, E.M. Meshram, H.N. Chopde and R.J. Batra, Org. Chem. Int., 2013, 582079 (2013); https://doi.org/10.1155/2013/582079
- D.C.M. Albanese, N. Gaggero and M. Fei, Green Chem., 19, 5703 (2017); https://doi.org/10.1039/C7GC02097J
- M. Parthasarathy, C. Sureshkumar, S. Dhivya and S. Narasimhan, J. Pharm. Res., 6, 84 (2013); https://doi.org/10.1016/j.jopr.2012.11.018
- S. Preet and D.S. Cannoo, J. Chin. Chem. Soc., 64, 296 (2017); https://doi.org/10.1002/jccs.201600778
- C. Spitz, V. Reboul and P. Metzner, Tetrahedron Lett., 52, 6321 (2011); https://doi.org/10.1016/j.tetlet.2011.07.148
- P. Zhang, L.Z. Wang, H.S. Wu, J.M. Lan, Y. Li and Y.X. Wang, Chin. Chem. Lett., 20, 660 (2009); https://doi.org/10.1016/j.cclet.2009.01.003
- Shyam, D.M. Lokeshwari, K. Ajay Kumar, H.P. Jayadevappa, Int. J. ChemTech. Res., 10, 09 (2017).
- B.C. Manjunath, M. Manjula, K.R. Raghavendra, K.A. Kumar and N.K. Lokanath, Acta Crystallogr. Sect. E Struct. Rep. Online, 70, o261 (2014); https://doi.org/10.1107/S1600536814002529
- V.M. Berestovitskaya, R.I. Baichurin, N.I. Aboskalova and V.V. Gurzhiy, Mend. Commun., 24, 380 (2014); https://doi.org/10.1016/j.mencom.2014.11.025
- B.C. Manjunath, M. Manjula, K.R. Raghavendra, S. Shashikanth, K. Ajay Kumar and N.K. Lokanath, Acta Crystallogr. Sect. E Struct. Rep. Online, 70, o121 (2014); https://doi.org/10.1107/S1600536813034612
- K. Purandhar, M.A. Chari, P.P. Reddy, K. Mukkanti and G.M. Reddy, Lett. Org. Chem., 11, 81 (2014); https://doi.org/10.2174/1570178610999131231123427
- L. Fodor, P. Csomos, T. Holczbauer, A. Kalman, A. Csampai and P.Sohar, Tetrahedron Lett., 52, 224 (2011); https://doi.org/10.1016/j.tetlet.2010.10.160
- M. Mostofi, G.M. Ziarani and N. Lashgari, Bioorg. Med. Chem., 26,3076 (2018); https://doi.org/10.1016/j.bmc.2018.02.049
- L. Wang, P. Zhang, X. Zhang, Y. Zhang, Y. Li and Y. Wang, Eur. J.Med. Chem., 44, 2815 (2009);https://doi.org/10.1016/j.ejmech.2008.12.021
- S. Mor, P. Pahal and B. Narasimhan, Eur. J. Med. Chem., 57, 196 (2012); https://doi.org/10.1016/j.ejmech.2012.09.003
- N. Renuka, G. Pavithra and K.A. Kumar, Der Pharma Chem., 6, 482 (2014).
- F.L. Ansari, F. Iftikhar, Ihsan-ul-Haq, B. Mirza, M. Baseer and U. Rashid, Bioorg. Med. Chem., 16, 7691 (2008); https://doi.org/10.1016/j.bmc.2008.07.009
- M. Kidwai, R. Poddar, A. Jain, R. Kumar and P. Luthra, Mini Rev. Org. Chem., 12, 24 (2014); https://doi.org/10.2174/1570193X11666141029004602
- A.K. Keshar, A. Tewari, S.S. Verma and S.K. Saraf, Cent. Nerv. Syst. Agents Med. Chem., 17, 219 (2017); https://doi.org/10.2174/1871524917666170717113524
- D.M. Lokeshwari, N.D. Rekha, B. Srinivasan, H.K. Vivek and A.K. Kariyappa, Bioorg. Med. Chem. Lett., 27, 3048 (2017); https://doi.org/10.1016/j.bmcl.2017.05.059
- V. Ambrogi, G. Grandolini, L. Perioli, L. Giusti, A. Lucacchini and C. Martini, J. Med. Chem., 30, 429 (1995); https://doi.org/10.1016/0223-5234(96)88253-5
- S.K. Naveen, M.G. Prabhudeva, K.A. Kumar, N.K. Lokanath and I.Warad, IUCrData, 2, x170038 (2017);https://doi.org/10.1107/S2414314617000384
- S. Naveen, M.G. Prabhudeva, K. Ajay Kumar, N.K. Lokanath and M.Abdoh, IUCrData, 1, x161974 (2016);https://doi.org/10.1107/S241431461601974X
- M.G. Prabhudeva, S. Bharath, A.D. Kumar, S. Naveen, N.K. Lokanath, B.N. Mylarappa and K.A. Kumar, Bioorg. Chem., 73, 109 (2017); https://doi.org/10.1016/j.bioorg.2017.06.004
- D.M. Lokeshwari, V.H. Kameshwar and A.K. Kariyappa, Biointerface Res. Appl. Chem., 7, 2158 (2017).
References
C.B.W. Phippen and C.S.P. McErlean, Tetrahedron Lett., 52, 1490 (2011); https://doi.org/10.1016/j.tetlet.2011.01.098
J.B. Bariwal, K.D. Upadhyay, A.T. Manvar, J.C. Trivedi, J.S. Singh, K.S. Jain and A.K. Shah, Eur. J. Med. Chem., 43, 2279 (2008); https://doi.org/10.1016/j.ejmech.2008.05.035
F.M.A. Altalbawy, Int. J. Mol. Sci., 14, 2967 (2013); https://doi.org/10.3390/ijms14022967
N.S. Medran, A. La-Venia and S.A. Testero, RSC Adv., 9, 6804 (2019); https://doi.org/10.1039/C8RA10247C
J. Tian, R. Zhou, H. Sun, H. Song and Z. He, J. Org. Chem., 76, 2374 (2011); https://doi.org/10.1021/jo200164v
Y.H. Zaki, M.S. Al-Gendey and A.O. Abdelhamid, Chem. Central J.,12, 70 (2018); https://doi.org/10.1186/s13065-018-0439-9
A. Voskiene and V. Mickevicius, Chem. Heterocycl. Comp., 45, 1485 (2009); https://doi.org/10.1007/s10593-010-0455-8
M. Shailaja, A. Manjula, C.V. Rao, B. Praseeda and B.M. Reddy, Indian J. Chem., 50B, 214 (2011)
C.P. Pandhurnekar, E.M. Meshram, H.N. Chopde and R.J. Batra, Org. Chem. Int., 2013, 582079 (2013); https://doi.org/10.1155/2013/582079
D.C.M. Albanese, N. Gaggero and M. Fei, Green Chem., 19, 5703 (2017); https://doi.org/10.1039/C7GC02097J
M. Parthasarathy, C. Sureshkumar, S. Dhivya and S. Narasimhan, J. Pharm. Res., 6, 84 (2013); https://doi.org/10.1016/j.jopr.2012.11.018
S. Preet and D.S. Cannoo, J. Chin. Chem. Soc., 64, 296 (2017); https://doi.org/10.1002/jccs.201600778
C. Spitz, V. Reboul and P. Metzner, Tetrahedron Lett., 52, 6321 (2011); https://doi.org/10.1016/j.tetlet.2011.07.148
P. Zhang, L.Z. Wang, H.S. Wu, J.M. Lan, Y. Li and Y.X. Wang, Chin. Chem. Lett., 20, 660 (2009); https://doi.org/10.1016/j.cclet.2009.01.003
Shyam, D.M. Lokeshwari, K. Ajay Kumar, H.P. Jayadevappa, Int. J. ChemTech. Res., 10, 09 (2017).
B.C. Manjunath, M. Manjula, K.R. Raghavendra, K.A. Kumar and N.K. Lokanath, Acta Crystallogr. Sect. E Struct. Rep. Online, 70, o261 (2014); https://doi.org/10.1107/S1600536814002529
V.M. Berestovitskaya, R.I. Baichurin, N.I. Aboskalova and V.V. Gurzhiy, Mend. Commun., 24, 380 (2014); https://doi.org/10.1016/j.mencom.2014.11.025
B.C. Manjunath, M. Manjula, K.R. Raghavendra, S. Shashikanth, K. Ajay Kumar and N.K. Lokanath, Acta Crystallogr. Sect. E Struct. Rep. Online, 70, o121 (2014); https://doi.org/10.1107/S1600536813034612
K. Purandhar, M.A. Chari, P.P. Reddy, K. Mukkanti and G.M. Reddy, Lett. Org. Chem., 11, 81 (2014); https://doi.org/10.2174/1570178610999131231123427
L. Fodor, P. Csomos, T. Holczbauer, A. Kalman, A. Csampai and P.Sohar, Tetrahedron Lett., 52, 224 (2011); https://doi.org/10.1016/j.tetlet.2010.10.160
M. Mostofi, G.M. Ziarani and N. Lashgari, Bioorg. Med. Chem., 26,3076 (2018); https://doi.org/10.1016/j.bmc.2018.02.049
L. Wang, P. Zhang, X. Zhang, Y. Zhang, Y. Li and Y. Wang, Eur. J.Med. Chem., 44, 2815 (2009);https://doi.org/10.1016/j.ejmech.2008.12.021
S. Mor, P. Pahal and B. Narasimhan, Eur. J. Med. Chem., 57, 196 (2012); https://doi.org/10.1016/j.ejmech.2012.09.003
N. Renuka, G. Pavithra and K.A. Kumar, Der Pharma Chem., 6, 482 (2014).
F.L. Ansari, F. Iftikhar, Ihsan-ul-Haq, B. Mirza, M. Baseer and U. Rashid, Bioorg. Med. Chem., 16, 7691 (2008); https://doi.org/10.1016/j.bmc.2008.07.009
M. Kidwai, R. Poddar, A. Jain, R. Kumar and P. Luthra, Mini Rev. Org. Chem., 12, 24 (2014); https://doi.org/10.2174/1570193X11666141029004602
A.K. Keshar, A. Tewari, S.S. Verma and S.K. Saraf, Cent. Nerv. Syst. Agents Med. Chem., 17, 219 (2017); https://doi.org/10.2174/1871524917666170717113524
D.M. Lokeshwari, N.D. Rekha, B. Srinivasan, H.K. Vivek and A.K. Kariyappa, Bioorg. Med. Chem. Lett., 27, 3048 (2017); https://doi.org/10.1016/j.bmcl.2017.05.059
V. Ambrogi, G. Grandolini, L. Perioli, L. Giusti, A. Lucacchini and C. Martini, J. Med. Chem., 30, 429 (1995); https://doi.org/10.1016/0223-5234(96)88253-5
S.K. Naveen, M.G. Prabhudeva, K.A. Kumar, N.K. Lokanath and I.Warad, IUCrData, 2, x170038 (2017);https://doi.org/10.1107/S2414314617000384
S. Naveen, M.G. Prabhudeva, K. Ajay Kumar, N.K. Lokanath and M.Abdoh, IUCrData, 1, x161974 (2016);https://doi.org/10.1107/S241431461601974X
M.G. Prabhudeva, S. Bharath, A.D. Kumar, S. Naveen, N.K. Lokanath, B.N. Mylarappa and K.A. Kumar, Bioorg. Chem., 73, 109 (2017); https://doi.org/10.1016/j.bioorg.2017.06.004
D.M. Lokeshwari, V.H. Kameshwar and A.K. Kariyappa, Biointerface Res. Appl. Chem., 7, 2158 (2017).