Synthesis and biological evaluation of pyrimidine analogs of antimycobacterial purines.

Pyrimidine analogs of antimycobacterial 6-aryl-9-benzylpurines have been synthesized and screened for antibacterial activity against Mycobacterium tuberculosis H(37)Rv in vitro. Several active compounds were identified and the best results were observed for 5-formamidopyrimidines. These compounds generally displayed IC(90) values < or =1microg/mL, and they exhibited low toxicity towards mammalian cells.

Synthesis, structure, and antimycobacterial activity of 6-[1(3H)-isobenzofuranylidenemethyl]purines and analogs.

6-Benzofuryl-, styryl, benzyl, and furfurylpurines as well as 6-[1(3H)-isobenzofuranylidenemethyl]purines have been synthesized and their activities against Mycobacterium tuberculosis (Mtb) determined. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian cells. NMR and X-ray crystallography were employed to determine the detailed structures and the results were supported by quantum chemical calculations.

Synthesis and antimycobacterial activity of 5-formylaminopyrimidines; analogs of antibacterial purines.

Pyrimidine analogs of antimycobacterial purines have been synthesized and their biological activities evaluated. Several 5-formamidopyrimidines exhibited profound activity against Mycobacterium tuberculosis in vitro (IC(90)< or =1.5 microg/mL), and they were essentially inactive against other bacteria.

Synthesis, biological activity, and SAR of antimycobacterial 2- and 8-substituted 6-(2-furyl)-9-(p-methoxybenzyl)purines.

A number of 6-(2-furyl)-9-(p-methoxybenzyl)purines carrying a variety of substituents in the 2- or 8-position have been synthesized and their ability to inhibit growth of Mycobacterium tuberculosis in vitro has been determined. It is demonstrated that sterical hindrance in the purine 8-position reduces activity and that C-8 should be unsubstituted. In the purine 2-position small, hydrophobic substituents are beneficial.

2-Chloro-6-(2-furyl)-9-(4-methoxybenzyl)-9H-purine.

The title compound, C(17)H(13)ClN(4)O(2), displays profound and selective activity against Mycobacterium tuberculosis. In the crystal structure, there are two independent molecules in the asymmetric unit. Intermolecular hydrogen bonding between a CH group of the purine ring and the O atom of the furan ring, and also pi-pi stacking in another direction, builds the three-dimensional network.

Selective anti-tubercular purines: synthesis and chemotherapeutic properties of 6-aryl- and 6-heteroaryl-9-benzylpurines.

6-Aryl- and 6-heteroaryl-9-benzylpurines have been synthesized employing palladium-catalyzed coupling reactions in the step forming the C-C or C-N bond between the aryl- or heteroaryl and the purine. The compounds were screened for activity against Mycobacterium tuberculosis as well as representative Gram+ and Gram- bacteria, and for cytotoxic effects on mammalian cells. Several potent antimycobacterials were identified.