TY - JOUR
T1 - Synthetic Procedures to Access 2-Guanidinobenzazoles of Biological Interest
AU - Rosales-Hernández, Martha C.
AU - Mendieta-Wejebe, Jessica E.
AU - Tamay-Cach, Feliciano
AU - Cruz, Alejandro
N1 - Publisher Copyright:
© 2023 Bentham Science Publishers.
PY - 2023
Y1 - 2023
N2 - Benzazoles (Bz) and derivatives are interesting molecules in medicinal chemistry. Several of these compounds display diverse biological activities; some are still used in clinical applications. In this way, synthetic chemists are interested in developing new procedures to access compounds with the guanidine moiety as 2-aminobenzimidazole (2ABI), Astemi-zole (antihistaminic), Albendazole (anthelmintic) and Carbendazim (fungicide). The guani-dine group, considered a super base bonded to a benzoxazole ring, results in the 2-guanidino-benzazoles (2GBZs), which could modify the biological activity of these heterocycles. On these bases, we prepared this review article, which covers chemical aspects of 2-guanidino-benzoazoles as potential therapeutic agents and summarizes the current knowledge on the mechanism of pharmacological activities such as cytotoxic, inhibition of cell proliferation via angiogenesis and apoptosis. Specifically, it highlights the most recent results of synthetic approaches to 2GBZs with variety of modifications and functionalization with aromatic, carbo-hydrate, and amino-acid moieties as illustrated on 28 schemes and is concluded with 141 references. Additionally, the format of this interesting review is exclusively designed on specifically classified category of chemical reactions with primary precursors such as o-substi-tuted anilines and 2-aminobenzazoles (2ABZs). This will constitute the important goals and novelty of this paper to facilitate synthetic chemists in the investigation about development of new pharmacophores.
AB - Benzazoles (Bz) and derivatives are interesting molecules in medicinal chemistry. Several of these compounds display diverse biological activities; some are still used in clinical applications. In this way, synthetic chemists are interested in developing new procedures to access compounds with the guanidine moiety as 2-aminobenzimidazole (2ABI), Astemi-zole (antihistaminic), Albendazole (anthelmintic) and Carbendazim (fungicide). The guani-dine group, considered a super base bonded to a benzoxazole ring, results in the 2-guanidino-benzazoles (2GBZs), which could modify the biological activity of these heterocycles. On these bases, we prepared this review article, which covers chemical aspects of 2-guanidino-benzoazoles as potential therapeutic agents and summarizes the current knowledge on the mechanism of pharmacological activities such as cytotoxic, inhibition of cell proliferation via angiogenesis and apoptosis. Specifically, it highlights the most recent results of synthetic approaches to 2GBZs with variety of modifications and functionalization with aromatic, carbo-hydrate, and amino-acid moieties as illustrated on 28 schemes and is concluded with 141 references. Additionally, the format of this interesting review is exclusively designed on specifically classified category of chemical reactions with primary precursors such as o-substi-tuted anilines and 2-aminobenzazoles (2ABZs). This will constitute the important goals and novelty of this paper to facilitate synthetic chemists in the investigation about development of new pharmacophores.
KW - 2-aminobenzazoles
KW - Cyanoguanidine
KW - alkylthiocyanates
KW - benzozazolilthioureas
KW - carbon disulfide
KW - guanidinobenzazoles
KW - o-substituted anilines
KW - s-methylisothioureas
UR - http://www.scopus.com/inward/record.url?scp=85150028521&partnerID=8YFLogxK
U2 - 10.2174/1570179419666220615143529
DO - 10.2174/1570179419666220615143529
M3 - Artículo de revisión
C2 - 35708075
AN - SCOPUS:85150028521
SN - 1570-1794
VL - 20
SP - 504
EP - 522
JO - Current Organic Synthesis
JF - Current Organic Synthesis
IS - 5
ER -