In the recent years, there has been a significant tendency in organic chemistry to imitate chemical phenomena occurring in the nature.  The so-called biomimetic reactions consist in transformation of simple substrates into complex products, usually at mild conditions [1]. One of such reactions is the aminomethylation reaction, discovered and described by Carl Mannich [2]. This reaction makes it possible to introduce amine fragment into the different chemical scaffolds which can increase the affinity of the obtained molecule towards appropriate molecular target. 1,2,4-Triazole-3-thione derivatives known for their antibacterial activity [3,4] were used by many researchers as substrates for the Mannich reaction.

Our research proved that chemical character of the C-5 substituent significantly determines the antibacterial activity of the Mannich bases derived from 4,5-disubstituted 1,2,4-triazole-3-thiones. This activity was considerably increased by an introduction of a chlorine atom to the phenyl ring. Furthermore, the disparities in the activity of appropriate ortho-, meta-, and para- derivatives were analysed. The obtained compounds were particularly active against opportunistic bacteria (Bacillus subtilis, Bacillus cereus). The antibacterial activity of some Mannich bases was similar or higher than the activity of commonly used antibiotics such as ampicillin and cefuroxime.

References

[1] Lindsley, C.W.; Chan, L.K.; Goess, B.C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423.

[2] Mannich, C.; Krosche, W. Arch. Pharm., 1912, 250, 647-667.

[3] Turan-Zitouni, G.; Kaplancıklı, Z.A.; Yıldız, M.T.; Chevallet, P.; Kaya, D. Eur. J. Med. Chem. 2005, 40, 607-613.

[4] Eswaran, S.; Adhikari, A. V.; Shetty, N. S. Eur. J. Med. Chem. 2009, 44, 4637-4647.

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