Affiliation:
1. Laboratorio de Química Supramolecular y Nanociencias, Instituto Politécnico Nacional UPIBI, Av. Acueducto s/n,
Barrio la Laguna Ticomán, Ciudad de México, 07340, Mexico
2. Laboratorio de Biofísica y Biocatálisis, Sección de
Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y
Salvador Díaz Mirón s/n, Casco de Santo Tomás, Distrito Federal 11340, México
Abstract
Abstract:
Benzimidazole (BI) and its derivatives are interesting molecules in medicinal
chemistry because several of these compounds have a diversity of biological activities and some
of them are even used in clinical applications. In view of the importance of these compounds,
synthetic chemists are still interested in finding new procedures for the synthesis of these classes
of compounds. Astemizole (antihistaminic), Omeprazole (antiulcerative), and Rabendazole
(fungicide) are important examples of compounds used in medicinal chemistry containing BI
nuclei. It is interesting to observe that several of these compounds contain 2-aminobenzimidazole
(2ABI) as the base nucleus. The structures of 2ABI derivatives are interesting because they have
a planar delocalized structure with a cyclic guanidine group, which have three nitrogen atoms
with free lone pairs and labile hydrogen atoms. The 10-π electron system of the aromatic BI ring
conjugated with the nitrogen lone pair of the hexocyclic amino group, making these heterocycles
to have an amphoteric character. Synthetic chemists have used 2ABI as a building block to
produce BI derivatives as medicinally important molecules. In view of the importance of the BIs,
and because no review was found in the literature about this topic, we reviewed and summarized
the procedures related to the recent methodologies used in the N-substitution reactions of 2ABIs
by using aliphatic and aromatic halogenides, dihalogenides, acid chlorides, alkylsulfonic
chlorides, carboxylic acids, esters, ethyl chloroformates, anhydrides, SMe-isothioureas, alcohols,
alkyl cyanates, thiocyanates, carbon disulfide and aldehydes or ketones to form Schiff bases. The
use of diazotized 2ABI as intermediate to obtain 2-diazoBIs was included to produce Nsubstituted
2ABIs of pharmacological interest. Some commentaries about their biological activity
were included.
Funder
Secretaría de Investigación y Posgrado del Instituto Politécnico Nacional
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry
Reference176 articles.
1. Enumula S.; Pangal A.; Gazge M.; Javed A.; Shaikh J.A.; Ahmed K.; Diverse pharmacological aspects of benzimidazole derivatives: A review. Res J Chem Sci 2014,4,78-88
2. Srestha N.; Banerjee J.; Srivastava S.; A review on chemistry and biological significance of benzimidazole nucleus. IOSR J Pharm 2014,4(12),28-41
3. Yerragunta V.; Patil P.; Srujana S.; Devi R.; Srujana G.R.; Divya A.; Benzimidazole derivatives and its biological importance: A review. PharmaTutor 2014,2,109-113
4. Hamiduzzaman M.; Mannan S.J.; Dey A.; Rahman S.M.A.; Evaluation of analgesic, antipyretic, hypoglycemic and CNS depressant activity of 2-bromopopylamine hydrobromide, 3-bromopopyl ammonium bromide, ortho-amino aniline and benzimidazole-2-thiol in animal model. Der Pharm Lett 2014,6,47-53
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献