Abstract
AbstractDerivatives of 2‐chloro‐2′‐deoxyadenosine (1a) containing secondary 6‐NH2 groups (5a‐c) or a 8‐Br substituent (9) were synthesized. They were tested together with ring‐modified congeners containing a pyrrolo[2,3‐b]pyridine, pyrrolo[3,2‐c]pyridine, or pyrazolo[3,4‐d]pyrimidine ring system as inhibitors of various leukemic cell lines. Only the 8‐Br derivatives 9 showed inhibitory activity, whereas the base‐modified congeners were not active. Compound 1a was protonated at a pKa = 1.4 (2′‐deoxyadenosine at pKa = 3.8). Protonation occurred at N(7) and not at N(1) as observed for dA.
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