The crystal structures of five 6-mercaptopurine derivatives, viz. 2-[(9-acetyl-9H-purin-6-yl)sulfanÂyl]-1-(3-methÂoxyÂphenÂyl)ethan-1-one (1), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanÂyl]-1-(4-methÂoxyÂphenÂyl)ethan-1-one (2), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanÂyl]-1-(4-chloroÂphenÂyl)ethan-1-one (3), C15H11ClN4O2S, 2-[(9-acetyl-9H-purin-6-yl)sulfanÂyl]-1-(4-bromoÂphenÂyl)ethan-1-one (4), C15H11BrN4O2S, and 1-(3-methÂoxyÂphenÂyl)-2-[(9H-purin-6-yl)sulfanÂyl]ethan-1-one (5), C14H12N4O2S. Compounds (2), (3) and (4) are isomorphous and accordingly their molÂecular and supraÂmolecular structures are similar. An analysis of the dihedral angles between the purine and exocyclic phenyl rings show that the molÂecules of (1) and (5) are essentially planar but that in the case of the three isomorphous compounds (2), (3) and (4), these rings are twisted by a dihedral angle of approximately 38°. With the exception of (1) all molÂecules are linked by weak C—Hâ‹ŻO hydrogen bonds in their crystals. There is π–π stacking in all compounds. A Cambridge Structural Database search revealed the existence of 11 deposited compounds containing the 1-phenyl-2-sulfanylÂethanone scaffold; of these, only eight have a cyclic ring as substituent, the majority of these being heterocycles.
Keywords: crystal structure, mercaptopurines, supraÂmolecular structure
Go to:
Chemical context Â
Purines, purine nucleosides and their analogs, are nitroÂgen-containing heterocycles ubiquitous in nature and present in biological systems like man, plants and marine organisms (Legraverend, 2008 â–¸). These types of heterocycles take part of the core structure of guanine and adenine in nucleic acids (DNA and RNA) being involved in diverse in vivo catabolic and anabolic metabolic pathways.
6-Mercaptopurine is a water insoluble purine analogue, which attracted attention due to its antiÂtumor and immunosuppressive properties. The drug is used, among others, in the treatment of rheumathologic disorders, cancer and prevent
Step-by-step explanation: