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Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024

Copyright (c) 2024 Udayabhaskar Jekkoju

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Synthesis, Characterization and Antibacterial Screening of Some Novel Compounds containing Multi N-Fused Heterocycles

https://doi.org/10.14233/ajchem.2024.32265
J. Udaya Bhaskar
School of Science, GITAM (Deemed to be University), Visakhapatnam-530045, India; Dr. Reddy’s Laboratories Ltd., Srikakulam-532409, India
https://orcid.org/0009-0007-6963-8706
G. Srinivasa Rao
School of Science, GITAM (Deemed to be University), Visakhapatnam-530045, India
https://orcid.org/0000-0001-9647-7206
Pranab Chatterjee
Dr. Reddy’s Laboratories Ltd., Srikakulam-532409, India
https://orcid.org/0009-0002-3848-6432
D.K. Sahoo
Dr. Reddy’s Laboratories Ltd., Srikakulam-532409, India
https://orcid.org/0009-0006-8697-7550
S. Srinivasa Rao
Dr. Reddy’s Laboratories Ltd., Srikakulam-532409, India
https://orcid.org/0009-0001-1530-5072
B. Pulla Rao
Department of Chemistry, Acharya Nagarjuna University Nagarjuna Nagar, Guntur-522510, India
https://orcid.org/0009-0005-5965-0002

Corresponding Author(s) : J. Udaya Bhaskar

judayabhaskar22@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024

Abstract

An attempt has been made to synthesize novel multi N-fused heterocyclic compounds containing four divergent heterocyclic compounds such as imidazole, pyrimidine, morpholine and indole. A series of N-(4-(1H-benzo[d]imidazol-2-yl)-6-phenylpyrimidin-2-yl)-2-(4-((E)-3-(2-morpholino-9H-pyrido[2,3-b]indol-3-yl)acryloyl)phenylamino)acetamide (6a-c) was accomplished in good yields with 1-(1H-benzo-[d]imidazol-2-yl)ethanone (1) as starting compound and through the formation of (E)-1-(1H-benzo[d]imidazol-2-yl)-3-phenylprop-2-ne-1-ones (2a-c), 4-(1H-benzo[d]imidazol-2-yl)-6-phenylpyrimidin-2-amines (3a-c) and N-(4-(1H-benzo[d]imidazol-2-yl)-6-phenylpyrimidin-2-yl)-2-chloroacetamides (4a-c) as intermediates on extension of the reaction. The structural elucidation of all the synthesized compounds were characterized by IR, 1H NMR, mass spectral data and elemental analysis. Further, the title compounds were also used to evaluate their antibacterial activity.

Keywords

Pyrimidine derivatives Fused heterocyclic compounds Antibacterial activity
Bhaskar, J. U., Rao, G. S., Chatterjee, P., Sahoo, D., Rao, S. S., & Rao, B. P. (2024). Synthesis, Characterization and Antibacterial Screening of Some Novel Compounds containing Multi N-Fused Heterocycles. Asian Journal of Chemistry, 36(9), 2185–2190. https://doi.org/10.14233/ajchem.2024.32265
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References
  1. E.M. Boyd and J. Sperry, Org. Lett., 16, 5056 (2014); https://doi.org/10.1021/ol5024097
  2. W. Wang, L. Lei, Z. Liu, H. Wang and Q. Meng, Molecules, 24, 877 (2019); https://doi.org/10.3390/molecules24050877
  3. A. Ramirez-Villalva, D. Gonzalez-Calderon, C. Gonzalez-Romero, M. Morales-Rodriguez, B. Jauregui-Rodríguez, E. Cuevas-Yáñez and A. Fuentes-Benítes, Eur. J. Med. Chem., 97, 275 (2015); https://doi.org/10.1016/j.ejmech.2015.04.047
  4. P. Zhan, X. Chen, D. Li, Z. Fang, E. de Clercq and X. Liu, Med. Res. Rev., 33(S1), 1 (2013); https://doi.org/10.1002/med.20241
  5. K. El-mahdy and R. Abdel-Rahman, Heterocycles, 85, 2391 (2012); https://doi.org/10.3987/REV-12-745
  6. A.H. Bacelar, M.A. Carvalho and M.F. Proenca, Eur. J. Med. Chem., 45, 3234 (2010); https://doi.org/10.1016/j.ejmech.2010.03.047
  7. J.P. De la Cruz, T. Carrasco, G. Ortega and F.S. De la Cuesta, Lipids, 27, 192 (1992); https://doi.org/10.1007/BF02536177
  8. Y. Fang, J. Xu, Z. Li, Z. Yang, L. Xiong, Y. Jin, Q. Wang, S. Xie, W. Zhu and S. Chang, Bioorg. Med. Chem., 26, 4080 (2018); https://doi.org/10.1016/j.bmc.2018.06.035
  9. A.A. Abu-Hashem, M.M. Youssef and H.A.R. Hussein, J. Chin. Chem. Soc., 58, 41 (2011); https://doi.org/10.1002/jccs.201190056
  10. S.A. Rahaman, Y. Rajendra Pasad, P. Kumar and B. Kumar, Saudi Pharm. J., 17, 255 (2009); https://doi.org/10.1016/j.jsps.2009.08.001
  11. Z. Machon and J. Cieplik, Pol. J. Pharmacol., 40, 201 (1988).
  12. A. Agarwal, K. Srivastava, S.K. Puri and P.M.S. Chauhan, Bioorg. Med. Chem., 13, 4645 (2005); https://doi.org/10.1016/j.bmc.2005.04.061
  13. N.R. Mohamed, M.M. El-Saidi, Y.M. Ali and M.H. Elnagdi, Bioorg. Med. Chem., 15, 6227 (2007); https://doi.org/10.1016/j.bmc.2007.06.023
  14. P.A. Stocks, K.J. Raynes, P.G. Bray, B.K. Park, P.M. O’Neill and S.A. Ward, J. Med. Chem., 45, 4975 (2002); https://doi.org/10.1021/jm0108707
  15. A.A. Abu-Hashem, M.F. El-Shehry and F.A. Badria, Acta Pharm., 60, 311 (2010); https://doi.org/10.2478/v10007-010-0027-6
  16. A. Gangjee, F. Mavandadi and S.F. Queener, J. Med. Chem., 40, 1173 (1997); https://doi.org/10.1021/jm960717q
  17. P.F. Torrence, X. Fan, X. Zhang and P.M. Loiseau, Bioorg. Med. Chem. Lett., 16, 5047 (2006); https://doi.org/10.1016/j.bmcl.2006.07.042
  18. Q. Ren, Z. Cui, H. He and Y.J. Gu, J. Fluor. Chem., 128, 1369 (2007); https://doi.org/10.1016/j.jfluchem.2007.06.007
  19. M.N.S. Saudi, M.R. Gaafar, M.Z. El-Azzouni, M.A. Ibrahim and M.M. Eissa, Med. Chem. Res., 17, 541 (2008); https://doi.org/10.1007/s00044-008-9097-0
  20. A. Ali, G.E. Taylor, K. Ellsworth, G. Harris, R. Painter, L.L. Silver and K. Young, J. Med. Chem., 46, 1824 (2003); https://doi.org/10.1021/jm020483c
  21. S.A. Patil, R. Patil, L.M. Pfeffer and D.D. Miller, Future Med. Chem., 5, 1647 (2013); https://doi.org/10.4155/fmc.13.126
  22. S. Sridhar, P.Y. Rajendra and S.C. Dinda, Int. J. Pharm. Sci. Res., 2, 2562 (2011); https://doi.org/10.13040/IJPSR.0975-8232.2(10).2562-65
  23. E. Szarvasi, D. Festal, M. Grand, J.C. Depin and T.N. Luong, Eur. J. Med. Chem. Ther., 16, 327 (1981).
  24. H. Wahe, P.F. Asobo, R.A. Cherkasov, A.E. Nkengfack, G.N. Folefoc, Z.T. Fomum and D. Doepp, ARKIVOC, 170 (2003); https://doi.org/10.3998/ark.5550190.0004.e16
  25. L. Kang-Chien, L. Liang-Chu and C. Ji-Wang, Taiwan Yao Hsueh Tsa Chih., 31, 91 (1979).
  26. R.P. Srivastava, S.S. Singh, S. Abuzar, S. Sharma, S. Gupta, J.C. Katiyar and R.K. Chatterjee, Indian J. Chem., 32B, 1035 (1993).
  27. V.L. Rusinov, V.N. Charushin and O.N. Chupakhin, Russ. Chem. Bull., 67, 573 (2018); https://doi.org/10.1007/s11172-018-2113-8
  28. K. Oukoloff, B. Lucero, K.R. Francisco, K.R. Brunden and C. Ballatore, Eur. J. Med. Chem., 165, 332 (2019); https://doi.org/10.1016/j.ejmech.2019.01.027
  29. K.V. Savateev, V.V. Fedotov, E.N. Ulomskiy and V.L. Rusinov, Chem. Heterocycl. Compd., 54, 197 (2018); https://doi.org/10.1007/s10593-018-2254-6
  30. P. Forche Asobo, H. Wahe, J.T. Mbafor, A.E. Nkengfack, Z.T. Fomum, E.F. Sopbue and D. Döpp, J. Chem. Soc., Perkin Trans. 1, 457 (2001); https://doi.org/10.1039/b005511p
  31. A. Kreutzberger and M. Leger, Arch. Pharm., 315, 438 (1982); https://doi.org/10.1002/ardp.19823150509
  32. N. Zhang, S. Ayral-Kaloustian, T. Nguyen, J. Afragola, R. Hernandez, J. Lucas, J. Gibbons and C. Beyer, J. Med. Chem., 50, 319 (2007); https://doi.org/10.1021/jm060717i
  33. K. Savateev, V. Fedotov, I. Butorin, O. Eltsov, P. Slepukhin, E. Ulomsky, V. Rusinov, R. Litvinov, D. Babkov, E. Khokhlacheva, P. Radaev, P. Vassiliev and A. Spasov, Eur. J. Med. Chem., 185, 111808 (2020); https://doi.org/10.1016/j.ejmech.2019.111808
  34. F. Goli-Garmroodi, M. Omidi, M. Saeedi, F. Sarrafzadeh, A. Rafinejad, M. Mahdavi, G.R. Bardajee, T. Akbarzadeh, L. Firoozpour, A. Shafiee and A. Foroumadi, Tetrahedron Lett., 56, 743 (2015); https://doi.org/10.1016/j.tetlet.2014.12.099
  35. E.M. Grivsky, S.C. Lee, W. Sigel, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); https://doi.org/10.1021/jm00177a025
  36. J. Matsumoto and S. Minami, J. Med. Chem., 18, 74 (1975); https://doi.org/10.1021/jm00235a017
  37. A.D. Broom, J.L. Shim and G.L. Anderson, J. Org. Chem., 41, 1095 (1976); https://doi.org/10.1021/jo00869a003
  38. G. Singh, A.K. Yadav and K. Mishraa, Indian J. Chem., 41, 430 (2002).
  39. L.R. Bennett, C.J. Blankley, R.W. Fleming, R.D. Smith and D.K. Tessman, J. Med. Chem., 24, 382 (1981); https://doi.org/10.1021/jm00136a006
  40. A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Rezazadeh and M. Behnam, J. Comb. Chem., 11, 375 (2009); https://doi.org/10.1021/cc800189j
  41. Z. Liu, Y. Tian, J. Liu, B. Huang, D. Kang, E. De Clercq, D. Daelemans, C. Pannecouque, P. Zhan and X. Liu, Eur. J. Med. Chem., 140, 383 (2017); https://doi.org/10.1016/j.ejmech.2017.07.012
  42. M. Wolf and A.A. Mascitti, US Patent 3395156 (1968); Chem. Abstr., 69, 96504 (1968).
  43. G. Winters and N.D. Mola, Ger. Patent 2442667 (1975); Chem. Abstr., 83, 28096 (1975).
  44. M.Y. Chang, C.L. Pai and Y.H. Kung, Tetrahedron Lett., 46, 8463 (2005); https://doi.org/10.1016/j.tetlet.2005.10.015
  45. A.I. Barry, The antimicrobial Susceptibility Test, Principles and Practices, EBLS, edn. 4, p. 80 (1976).
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