JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 65 No 3 (2020): Journal of the Chilean Chemical Society
Original Research Papers

CHROMIUM (III) COMPLEX OF 2-AMINO-3-CARBOMETHOXY-4,5,6,7-TETRAHYDROBENZO[B] THIOPHENE: SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY

PDF
  • EMMANUEL SOPBUÉ FONDJO,
  • DÉSIRE ANDRÉ SIÉWÉ,
  • JEAN DE DIEU TAMOKOU,
  • STEVE ENDEGUELE EKOM,
  • KAMAL SOREL DJEUKOUA DIMO,
  • GISCARD DOUNGMO,
  • MALLORY E. WALTERS,
  • APPOLINNAIRE TSOPMO,
  • PETER F. W. SIMON,
  • JULES-ROGER KUIATE
EMMANUEL SOPBUÉ FONDJO
Laboratory of Applied Synthetic Organic Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67 Dschang, Republic of Cameroon
DÉSIRE ANDRÉ SIÉWÉ
Laboratory of Applied Synthetic Organic Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67 Dschang, Republic of Cameroon
JEAN DE DIEU TAMOKOU
Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, PO Box 067 Dschang, Republic of Cameroon
STEVE ENDEGUELE EKOM
Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, PO Box 067 Dschang, Republic of Cameroon
KAMAL SOREL DJEUKOUA DIMO
Laboratory of Applied Synthetic Organic Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67 Dschang, Republic of Cameroon
GISCARD DOUNGMO
Institut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth-Str. 2, 24118 Kiel, Germany
MALLORY E. WALTERS
Department of Chemistry, Carleton University, 1125 Colonel By Drive K1S 5B6, Ottawa, Canada +1-613-520-260 Ext 3122
APPOLINNAIRE TSOPMO
Department of Chemistry, Carleton University, 1125 Colonel By Drive K1S 5B6, Ottawa, Canada +1-613-520-260 Ext 3122
PETER F. W. SIMON
Polymer Chemistry Laboratory, Faculty of Live Sciences, Rhine-Waal University of Applied Sciences, Campus Kleve, Marie-Curie Strasse 1, D-47533 Kleve, Germany
JULES-ROGER KUIATE
Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, PO Box 067 Dschang, Republic of Cameroon
Published September 13, 2020
Keywords
  • Antimicrobial, Complexation reaction, 4,5,6,7-tetrahydrobenzo[b]- thiophene, Chromium complex
How to Cite
SOPBUÉ FONDJO, E., SIÉWÉ, D. A., TAMOKOU, J. D. D., ENDEGUELE EKOM, S., DJEUKOUA DIMO, K. S., DOUNGMO, G., E. WALTERS, M., TSOPMO, A., F. W. SIMON, P., & KUIATE, J.-R. (2020). CHROMIUM (III) COMPLEX OF 2-AMINO-3-CARBOMETHOXY-4,5,6,7-TETRAHYDROBENZO[B] THIOPHENE: SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY. Journal of the Chilean Chemical Society, 65(3), 4908-4913. Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/1496

Copyright (c) 2020 SChQ

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

Abstract

A new chromium (III) coordination compound of 2-amino-3-carbomethoxy-4,5,6,7-tetrahydrobenzo[b]thiophene (ACTT) (3)  with Cr(NO3)3.9H2O in methanol at room temperature for 48 hours has been prepared. The composition of the new complex compound (4) has been confirmed by a number of instrumental methods including IR, NMR, MS and elemental analysis. It was found  that  the ACTT ligand behaves as bidentate  chelating  agent  and  coordinates to  the  central metal ion  through  the nitrogen atom of the amino-group and the oxygen atom of the  carbonyl function of the ester group. The results showed that in the coordination sphere of the complex, the metal ion is coordinated by three chelating ACTT ligands. In the structure of the cation core [Cr(ACTT)3]3+, the three ACTT ligands are linked to the chromium ion through three Cr-N and three Cr-O bonds forming a square bipyramidal geometry. The metal complex and the ACTT ligand were screened for their antimicrobial activities against several strains of bacteria (Staphylococcus aureus ATCC25923, Escherichia coli S2 (1), Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa ATCC27853, Shigella flexneri SDINT) and fungi (Candida albicans ATCC10231, Candida tropicalis PK233, Cryptococcus neoformans H99). The chromium complex showed promising antimicrobial activity against the microorganisms with minimum inhibitory values between 4 and 16 μg/mL.

1496.png

PDF

References

  1. K. Aruna, S. Z. Bootwala, M. Tariq, C. Fernandes, Int. J. Pharm. Biological Sci. 5, 440, (2014)
  2. S. Kumar, N. Kumar, Int. Curr. Pharm. J. 2, 91, (2013)
  3. M. Bouachrine, O. Benaqqa, H. Toufik, M. Hamidi, J. - P. Lère-Porte, F. Serein-Spirau, A. Amine, Analele Universităţii din Bucur. 19, 44, (2010)
  4. R. R. Zaky, A. M. Abdelghay, Res. J. Pharm. Biological Chem. Sci. 2, 764, (2011)
  5. R. M. Mohareb, A. A. Fahmy, Eur. Chem. Bull. 2, 553, (2013)
  6. A. Singh, S. P. Singh, A. Amalraj, P. D. Gokulan, P. Porwal, Int. J. Pharm. Biological Arch. 2, 540, (2011)
  7. W. W. Wardakhana, N. A. Loucab, M. M. Kamel, Acta Chim. Slov. 54, 241, (2007)
  8. V. Alagarsamy, D. Shankar, V. R. Solomon, Arkivoc xvi, 159, (2006)
  9. B. Narayana, B. V. Ashalatha, K. K. V. Raj, N. S. Kumari, Indian J. Chem. 45B, 2703, (2006)
  10. M. A. Gouda, H. F. Eldien, M. M. Girges, M. A. Berghot, Med. Chem. 3, 232, (2013)
  11. S. Turk, M. Hrast, I. Sosi, H. Barreteau, D. Mengin-Lecreulx, D. Blanot, S. Gobec, Acta Chim. Slov. 60, 299, (2013)
  12. K. - T. Wong, R. - T. Chen, Tetrahedron Lett. 43, 3317, (2002)
  13. S. A. Khan, A. Y. Obaid, L. M. Al-Harb, M. N. Arshad, A. M. Asiri, M. B. Hursthouse, Int. J. Electrochem. Sci. 10, 2323, (2015)
  14. N. R. Patil, R. M. Melavanki, H. D. Patil, D. Nagaraja, F. M. Sanningannavar, Int. J. Life Sci. Pharm. Res. 3, 76, (2013)
  15. T. V. Dubinina, D. V. Dyumaeva, S. A. Trashin, M. V. Sedova, A. B. Karpo, V. I. Krasovskii, L. G. Tomilova, Macroheterocycles 5, 156, (2012)
  16. F. A. Mohamed, A. E. El-Alfy, J. Appl. Sci. Res. 9, 183, (2013)
  17. H. R. Maradiya, Turk. J. Chem. 25, 450, (2001)
  18. Md. A. Hossain, Md. C. Sheikh, S. K. A. Z. Mahmud, Md. A. Alam, Int. J. Sci. Tech. Res. 2, 237, (2013)
  19. R. M. S. Pereira, N. E. D. Andrades, N. Paulino, A. C. H. F. Sawaya, M. N. Eberlin, M. C. Marcucci, G. M. Favero, E. M. Novak, S. P. Bydlowski, Molecules 12, 1366, (2007)
  20. A. D. Bansod, R. G. Mahale, A. S. Aswar, J. Indian Chem. Soc. 83, 781, (2006)
  21. R. A. Yaul, V. V. Dhande, B. G. Pethe, A. S. Aswar, Bull. Chem. Soc. Ethiop. 28, 264, (2014)
  22. V. B. Devi, P. Arulmozhichelvan, P. Murugakoothan, Int. J. ChemTech Res. 6, 2140, (2014)
  23. A. A. Alemi, B. Shaabani, Acta Chim. Slov. 47, 369, (2000)
  24. C. - C. Ko, W. - W. V. Yam, J. Mater. Chem. 20, 2070, (2010)
  25. T. Yutaka, I. Mori, M. Kurihara, J. Mizutani, K. Kubo, S. Furusho, K. Matsumura, N. Tamai, H. Nishihara, Inorg. Chem. 40, 4995, (2001)
  26. A. Samadi-Maybodi, S. K. H. Nejad-Darzi, R. Akhoondi, Int. Nano Lett. 1, 58, (2011)
  27. M. Rizzotto in Search for Antibacterial Agents, A. V. Bobbarala ed. InTech, Croatia, 2012; pp. 80-81.
  28. H. Al-Talib, A. Al-Khateeb, H. Hassan, Int. Med. J. 22, 3, (2015)
  29. T. J. Foster, Fed. Eur. Microbiol. Soc. 41, 449, (2017)
  30. M. Goncuoglu, F. S. B. Ormancı, N. D. Ayaz, I. Erol Ann. Microbiol. 60, 494, (2010)
  31. C. Kim, M. Fulke, A. Rahemi, T. Taghavi, A. Asmare, P. Kaseloo, E. Ndegwa, E. Sismour, EC Nutrition 13, 52, (2018)
  32. A. - M. Guérout-Fleury, K. Shazand, N. Frandsen, P. Stragier, Gene 167, 336, (1995)
  33. R. E. W. Hancock, D. P. Speert, Drug Resist. Updates 3, 255, (2000)
  34. P. A. Lambert, J. R. Soc. Med. 95, 26, (2002)
  35. S. Mehata, G. Duan, W. Zhang, Int. J. Infect. Microbiol. 1, 48, (2012)
  36. A. A. M. Lima, J. J. C. Sidrim, N. L. Lima, W. Titlow, M. E. Evans, R. N. Greenberg, J. Clin. Microbiol. 35, 1065, (1997)
  37. M. Sanguinetti, B. Posteraro, C. Lass-Flörl, Mycoses 58, 13, (2015)
  38. M. Maroszyńska, A. Kunicka-Styczyńska, K. Rajkowska, I. Maroszyńska, Acta Biochim. Pol. 60, 724, (2013)
  39. R. J. Kothavade, M. M. Kura, A. G. Valand, M. H. Panthak, J. Med. Microbiol. 59, 880, (2010)
  40. J. Santhanam, A. Fairuz, F. K. Ooi, A. H. Muhamad, J. Kesihat. Masy. Isu Khas 15, 53, (2002)
  41. M. A. Maligie, C. P. Selitrennikoff, Agents Chemother. 49, 2856, (2005)
  42. M. Lozano-Chiu, V. L. Paetznick, M. A. Ghannoum, J. H. Rex, J. Clin. Microbiol. 36, 2822, (1998)
  43. E. S. Fondjo, D. A. Siéwé, J. - D. - D. Tamokou, S. E. Ekom, S. K. D. Djeukoua, G. Doungmo, M. E. Walters, A. Tsopmo, P. F. W. Simon, J. R. Kuiate, Acta Chim. Slov. 67, 211, (2020)
  44. M. G. Reinecke, T. A. Woodrow, E. S. Brown, J. Org. Chem. 57, 1021, (1992)
  45. J. D. Tamokou, M. F. Tala, H. K. Wabo, J. - R. Kuiate, P. Tane, J. Ethnopharmacol. 124, 575, (2009)
  46. S. S. Patil, M. M. Shaikh, Acta Pol. Pharm. Drug Res. 69, 686, (2012)
  47. K. Nakamoto, Infrared and Raman spectra of inorganic and coordination compounds; Part B: Applications in coordination, organometallic, and bioinorganic chemistry, John Wiley & Sons, New Jersey, 2009.
  48. E. J. House, Inorganic Chemistry, Elsevier, San Diego, 2008.
  49. K. K. Ilavenil, M. Dhamodharan, J. Chem. Pharm. Sci. 9, 1462, (2016)
  50. C. Zhu, Y. Wang, Q. Mao, F. Li, Y. Li, C. Chen, Materials 313, 13, (2017)
  51. A. Debnath, F. Hussain, D. T. Masram, Bioinorg. Chem. Appl. 2014, 8, (2014)
  52. V. Balamurugan, S. Sankar, Int. J. Res. Dev. Pharm. Life Sci. 4, 1327, (2015)
  53. R. Al-Hassany, A. T. Mahmood, E. Z. Mohamed, A. A. Baqimaryoosh, A. A. R. Hussein, Acta Chim. Pharm. Indica 6, 25, (2016)
  54. P. Jain, V. Singh, Der Pharm. Chem. 8, 180, (2016)
  55. M. G. Djouossi, J. - D. Tamokou, D. Ngnokam, J. - R. Kuiate, L. A. Tapondjou, D. Harakat, L. Voutquenne-Nazabadioko, BMC Complementary Altern. Med. 15, 8, (2015)
  56. J. S. Chandra, Y. A. S. J. P. Kumaria, P. N. V. V. L. P. Rania, Y. Sunandamma, Indian J. Adv. Chem. Sci. 2, 37, (2013)
  57. M. Thankamony, K. Mohanan, J. Serb. Chem. Soc. 46A, 251, (2007)

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP