Bismuth-Catalyzed Synthesis of Macrocyle Bisguanidines

Bismuth-Catalyzed Synthesis of Macrocyle Bisguanidines

Gomes, Amenson; Cunha, Silvio

Abstract:

The bisguanidines are a class of substances characterized by the presence of two guanidine groups separated by a carbon chain, Figure 1. The strong basicity of bisguanidines is due to stabilization of its conjugate acid by resonance effect, which occurs in each of the guanidine groups. The bisguanidines have a broad pharmacological potential, with antiseptic, antihypertensive, anti-inflammatory, antitrypanosomiasis, antidepressant, antitumor and antiviral activities. The presence of nitrogen atoms and the planar geometry of guanidinium group allows for bisguanidines act as ligand for different metals, an important feature for the bioinorganic chemistry, as well as for organocatalises. Due to large spectrum of activity of the bisguanidines, we developed a synthetic route to synthesize macrocycle bisguanidines through the reaction of bisthiourea and amines, promoted by a mixture of NaBIO3/BiI3.

The bisguanidines are a class of substances characterized by the presence of two guanidine groups separated by a carbon chain, Figure 1. The strong basicity of bisguanidines is due to stabilization of its conjugate acid by resonance effect, which occurs in each of the guanidine groups. The bisguanidines have a broad pharmacological potential, with antiseptic, antihypertensive, anti-inflammatory, antitrypanosomiasis, antidepressant, antitumor and antiviral activities. The presence of nitrogen atoms and the planar geometry of guanidinium group allows for bisguanidines act as ligand for different metals, an important feature for the bioinorganic chemistry, as well as for organocatalises. Due to large spectrum of activity of the bisguanidines, we developed a synthetic route to synthesize macrocycle bisguanidines through the reaction of bisthiourea and amines, promoted by a mixture of NaBIO3/BiI3.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0333-2

Referências bibliográficas

• [1] 1Wang, Y; Sauer, D. R.; Djuric, S. W. Tetrahedron Lett. 2009, 50, 5149.
• [2] 2Greenhill, J. V.; Lee, L. In Ellis, G. P.; Luscombe, D. K., Eds.; Progress in Medicinal Chemistry; Elsevier Science: New York 1993; Vol. 30; Chaper 5.
• [3] 3Herres-Pawlis, S.; Ulrich, F.; Henkel, G. Acta Cryst. 2006, E62, 2138.
• [4] 4Tanaka, Shinji; Nagasawa, K. Synlett 2009, 4, 667.

Como citar:

Gomes, Amenson; Cunha, Silvio; "Bismuth-Catalyzed Synthesis of Macrocyle Bisguanidines", p-333-333. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0333-2