Triazolo[n,m-a]Pyridine&Pyrimidine

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Introduction

In recent years, heterocyclic compounds have great biological significance as active centers. In particular, heterocyclic compounds containing nitrogen atoms are widely found in various drugs. As one of the most important classes, triazolo pyrimidines (C₄H₃N₅) have attracted extensive interest and played important biological roles in the past few years. The triazolo pyrimidine ring is a ubiquitous structural feature of many active compounds with different pharmacological effects. The skeleton of triazolo pyrimidine contains a triazole ring and a pyrimidine ring. There are mainly six isomers of triazolo pyrimidine according to the position of nitrogen atom, specifically as follows: [1,2,4]triazolo[1,5-a]pyrimidine, [1,2,4]triazolo[4,3-a]pyrimidine, [1,2,4]triazolo[1,5-c]pyramidine, [1,2,3]triazolo[1,5-a]pyramidine, [1,2,3]triazolo-[1,5-a]pyrimidine, the 7aH-[1,2,3]triazolo[4,5-d]pyrimidine (Figure 1).

Figure 1. Six tautomeric forms of triazolo pyrimidine ^[1].

Triazolo pyrimidines and their derivatives are increasingly accepted because of their diverse forms and powerful efficacy, and are becoming the first choice of researchers. As organic chemicals, triazolo pyrimidines and their derivatives have the following applications in drug synthesis:

Figure 2. Triazolo pyrimidines derivatives.

In 2008, Mostafa et al. synthesized novel compounds of triazolo pyrimidine derivatives that containing a pyrrole ring and sulfonamide moieties ^[2]. When evaluating the compound's antitumor activity, compound 1 (IC50 = 67.5 µM) enhanced in vitro antitumor activity compared to the reference drug doxorubicin. Compound 2 ^[3] possesses excellent analgesic, anticonvulsant and anti-inflammatory pharmacological activities. On the other hand, research shows that compound 2 is more effective than prednisolone as an anti-inflammatory agent. In 2004, Prakash et al. ^[4] synthesized new 1,2,4-triazolo[4,3-a] pyrimidines, which showed antibacterial activity in vitro. At the lowest inhibitory concentration (10 μg/mL), the antibacterial activity of 3-(4'-pyridyl)-substituted (Compound 3) and 3-(3',4'-dimethoxyphenyl) substituted (compound 4) was significantly higher than that of some commercial antibiotics against Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Salmonella typhi. It is worth mentioning that compound 5 ^[5] (para-CF₃ substituted) showed equal potency against Pf DHODH and Pb DHODH (IC₅₀ values of 0.28 and 0.38 µM, respectively), and exhibited good plasma exposure after oral dosing in mice, with significant plasma concentrations remaining for a sufficient time to allow once daily or twice daily dosing to suppress parasite growth.

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References

Renyu, Q. et al. Recent applications of triazolopyrimidine-based bioactive compounds in medicinal and agrochemical chemistry. Mini Rev Med Chem. 2018, 18(9): 781-793.
Dalal, A.E. et al. Molecular modeling study and synthesis of novel pyrrolo 2,3-d pyrimidines and pyrrolotriazolopyrimidines of expected antitumor and radioprotective activities. Bioorg. Med. Chem. 2008, 16(5): 2391-2402.
Said, S.A. et al. Analgesic, anticonvulsant and anti-inflammatory activities of some synthesized benzodiazipine, triazolopyrimidine and bis-imide derivatives. Eur. J. Med. Chem. 2009, 44(12): 4787-4792.
Prakash, O. et al. Organoiodine (III) mediated synthesis of 3-aryl/hetryl-5,7-dimethyl-1,2,4-triazolo 4,3-a pyrimidines as antibacterial agents. Eur. J. Med. Chem. 2004, 39(12): 1073-1077.
Gujjar, R. et al. Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice. J. Med. Chem. 2009, 52(7): 1864-1872.

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