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Aktywność biologiczna pochodnych tiazolo[4,5-d]pirymidyny

Becan L.

Wiadomości Chemiczne

2013

[Z] 67, 11-12

1051--1074

Thiazolo[4,5-d]pyrimidine is one of the six structural isomers of the bicyclic ring system containing thiazole moiety fused with the pyrimidine. There are six structural isomers depending on the position of the nitrogen atoms. The isomer [4,5-d] does not contain the bridge-head nitrogen and can be considered as 7-thio analogue of the natural purine bases such as guanine and adenine. Due to the great of their biological potential the newly synthesized compounds are evaluated for various pharmacological activities. This review presents numerous thiazolo[4,5-d]pyrimidine derivatives reported for their interesting biological activity including antibacterial [2, 3, 5, 7, 8, 10, 19], antifungal [2–6, 9, 10], antiviral [11–13], analgesic [18, 19], antidepressant [17] and anticancer properties [23–26]. Some urea and thiourea derivatives exhibited significant antiparkinsonian activity [14–16]. Tumor necrosis factor (TNF) promotes an inflammatory response, which in turn causes many of the clinical problems associated with autoimmune disorders. Ethyl 4-(2-amino-5,7-dioxo-3,4,5,7-tetrahydro-thiazolo[4,5-d]pyrimidin- 6(2H)-yl)butanoate derivatives 29 (Fig. 24) as a TNFα inhibitors have a potential use in the treatment of diseases such as refractory asthma, psoriasis, rheumatoid arthritis, irritable bowel syndrome, and other [21]. Blocade of the CXCR2 receptor by thiazolo[4,5-d]pyrimidine-2(3H)-ones also represents an attractive strategy for treatment of inflammatory diseases [20]. Recently there have been developed CX3CR1 receptor antagonists for the treatment of multiple sclerosis [22]. Isatoribine, 5-amino-3-β-D-ribofuranosyl-3H-thiazolo[4,5-d]pyrimidin-2-one (20) (Fig. 15) is a small molecule toll-like receptor 7 (TLR7) agonist and an activator of innate immunity. Its orally bioavailable analogue ANA 975 (Fig. 16) has been reported for probable use in treating disease states associated with abnormal cell growth, such as cancer and has anti HCV activity [13]. Thiazolo[4,5-d]pyrimidines inhibit the growth of the weeds which implies that they have a potential as herbicides [27].