Mini-review
Recent advances of tetrazole derivatives as potential anti-tubercular and anti-malarial agents

https://doi.org/10.1016/j.ejmech.2018.12.001Get rights and content

Highlights

  • Tetrazole, a bioisostere of the carboxylic acid group, can replace the carboxyl group in drugs to increase the lipophilicity, bioavailability and reduce side effects.

  • This review covers the recent advances of tetrazoles as potential anti-tubercular and anti-malarial agents.

  • The structure-activity relationship is also discussed for the further rational design of novel tetrazoles.

Abstract

Tetrazole, a bioisostere of the carboxylic acid group, can replace the carboxyl group in drugs to increase the lipophilicity, bioavailability and reduce side effects. Tetrazole derivatives possess a broad-spectrum of biological properties including anti-tubercular and anti-malarial activities, and some tetrazole-based compounds have already been used in clinics for the treatment of various diseases. Therefore, tetrazole is an important pharmacophore in the development of new drugs. This review covers the recent advances of tetrazole derivatives as potential anti-tubercular and anti-malarial agents, and the structure-activity relationship is also discussed for the further rational design of tetrazole derivatives.

Graphical abstract

This review covers the recent advances of tetrazole derivatives as potential anti-tubercular and anti-malarial agents. The structure-activity relationship is also discussed for the further rational design of novel tetrazole candidates.

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Introduction

Tetrazole (Fig. 1) with poly-nitrogen electron-rich planar structural features contains a five-membered ring of four nitrogen, one carbon and two hydrogen atoms [1,2]. Tetrazole is a bioisostere of the carboxylic acid group, which can replace carboxyl group in drug molecules to increase lipophilicity, bioavailability and reduce side effects [3,4]. Tetrazoles can interact with various enzymes and receptors in organisms through noncovalent interactions to exhibit broad biological properties such as anti-bacterial [5], anti-cancer [6], anti-fungal [7], anti-inflammatory [8], anti-malarial [9], anti-tubercular [10] and anti-viral [11,12] activities. Moreover, a great number of medicinally important compounds containing tetrazole moiety such as anti-bacterial agent Ceforanide and anti-asthmatic drug Tomelukast (Fig. 1) which have been approved by US Food and Drug Administration for the treatment of various diseases. Thus, tetrazole derivatives play an intriguing role in the development of new drugs [13].

In recent years, a variety of tetrazole derivatives have been screened for their anti-tubercular and anti-malarial activities, and some of them exhibited promising in vitro and in vivo potency. This review covers the recent advances of tetrazole derivatives and their in vitro and in vivo anti-tubercular and anti-malarial properities. The structure-activity relationship (SAR) is also discussed to pave the way for the reasonable design of tetrazole derivatives.

Section snippets

Anti-tubercular activity

Mycobacterium tuberculosis (MTB) is globally spread, and is the main causative agent of tuberculosis (TB) [14,15]. Around 1.7 billion people have been infected with MTB globally, and 5–10% of individuals will develop TB disease during their lifetime [16]. TB is the leading cause of death from a single infectious agent, and World Health Organization (WHO) estimated that 1.6 million people died from the disease in 2017 [16]. TB co-infected with HIV and drug-resistant TB (DR-TB) present tremendous

Anti-malarial activity

Malaria, which is usually caused by protozoan parasites of the genus Plasmodium including P. falciparum, P. vivax, P. malariae, P. ovale and P. knowlesi species of human malaria parasite, is one of the most widespread and deadliest disease throughout the world [[48], [49], [50]]. In 2016, there were estimated 216 million cases of malaria, an increase of about 5 million cases over 2015. In the same year, 445,000 people died from malaria, a similar number to 2015 [51]. The most lethal human

Conclusion

Tetrazole derivatives, which have already been used in current drug molecules, exhibit various biological and pharmacological properties can be a useful pharmacophore in new drug discovery.

Some tetrazole derivatives exhibited promising in vitro and in vivo anti-tubercular and anti-malarial activities against both drug-sensitive and drug-resistant strains, and have no cross-resistance with the current used drugs. It is noted that compounds 21l, 23f, 23g, 23i and 23l with MIC of 0.03 μM against

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