6-Oxo and 6-thio purine analogs as antimycobacterial agents

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Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring.

Purine analogs modified in the five-membered ring have been synthesized and examined for antibacterial activity against Mycobacterium tuberculosis H(37)Rv in vitro employing the microplate alamar blue assay (MABA). The 9-deaza analogs were only found to be weak inhibitors, but the 8-aza-, 7-deaza- and 8-aza-7-deazapurine analogs studied displayed excellent antimycobacterial activities, some eve...

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Haloalkyl purines i.e. 2,6-diamino-8-(chloromethyl) purine 10; 2, 6-diamino-X- (chloromethyl) purine 17; 2,6-diamino-8-(chloropropylp) urine 18; were synthesized by two distinct but facile methods. The N-alkylating potential of 2, 6-diamino-8- (chloromethyl) purine was investigated. The following products 2,6-diamino-8-(Nbenzyl- N-methyl) purine 11; 2,6-diamino-8-(4-nitro anilinomethyl) pur...

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6-Benzyl­sulfanyl-9H-purine

The phenyl ring of the title compound, C(12)H(10)N(4)S, a purine derivative, is oriented at a dihedral angle of 76.65 (6)° with respect to the purine ring system. An inter-molecular N-H⋯N hydrogen bonds stabilizes the crystal structure.

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6-(2-Methoxy­benzyl­amino)purine

The title compound, C(13)H(13)N(5)O, consists of discrete mol-ecules connected by N-H⋯N hydrogen bonds to form infinite chains, with N⋯N separations of 3.0379 (15) and 2.8853 (15) Å. The benzene and purine ring systems make a dihedral angle of 77.58 (3)°. The crystal structure is further stabilized by intra-molecular N⋯O inter-actions [2.9541 (12) Å] and inter-molecular C-H⋯C and C⋯C contacts [...

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6-Chloropurine and 6-chlorouric acid as substrates and inhibitors of purine-oxidizing enzymes.

Various examples of oxidation of purine molecules in positions 8 and 2 by xanthine oxidase have been reported. The conversions of the natural purine substrates, xanthine and hypoxanthine to uric acid (I) and of adenine to 2,8-dihydroxy-6-aminopurine, are well known. The oxidation of the purine antimetabolites, 6-mercaptopurine to 6-thiouric acid (2)) 2,6-diaminopurine to 2,6-diamino-6-hydroxy p...

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ژورنال

عنوان ژورنال: Bioorganic & Medicinal Chemistry

سال: 2013

ISSN: 0968-0896

DOI: 10.1016/j.bmc.2013.01.054