Synthesis and characterization of new substituted adenines

The reaction of the 5-aminoimidazole-4-carbonitrile 3 with hydroxylamine hydrochloride, followed by cyclization with triethyl orthoformate gave the 6-aminopurine-l-oxide-derivative 5. Quarternization of 5 with alkyl iodides afforded the unexpected purinium iodide salts 7, which were obtained also from reacting the 6-aminopurine 6 with the same alkyl iodides. Treatment of 7 with alkali gave the rearranged products 9. The triazolopurines 15 and 16 were synthesized from the 6-hydrazinopurine 13 and 1-amino-6 iminopurine 12, respectively. Rearrangement of 15 to the triazole 16 was also carried out. The 3-[5-amino-1-[p-chlorophenyl] imidazol-4-yl]-1,2,4-triazole 17 was obtained from treating 16 with alkali. The imidazotriazolo-triazine 18 and substituted triazoles 19 and 20 were afforded from reacting 17 with nitrous acid and dimethyl sulfate, respectively. The reaction of 3 with methyl-, ethyl- and phenyl-isothiocyanates gave the imidazothiazine derivatives 22. Whereas, when the reaction was carried out with n-butyl- isothiocyanate, the 6-[-n-butyl] amino-2-[n-butyl] dithiocarbamylpurine 23 was obtained

Synthesis and antitumor properties of some 9-benzylpurine derivatives

During the past few years numerous synthetic purines have been claimed to have multitude of useful biological and pharmacological activities. For example, the antitumour [1-3] and antiviral [4,5]properties of many purine derivatives have been reported. Also, some alkoxy/aryloxycaffiene derivatives have been reported to exhibit cytostatic action against tumour cells in tissue culture [6]. Moreover, 6-methoxypurine has been proved to show activity at 250 and 125 mg/kg versus L 1210 leukaemia [7] Therefore, the interest in the present work was directed for synthesizing some newer purine derivatives with the target to evaluate their potential antitumour properties

Newer 1H- 2-pyrazolines and their related derivatives of anticipated biological activity

1 H-delta2-pyrazolines 2 were prepared from the reaction of 2- propen-1-ones 1 with hydrazine hydrate in absolute ethanol at room temperature. Reactions of 2 with acetyl, benzenesulphonyl-, p- toluenesulphonyl-chlorides and ethyl chloroformate gave the corresponding 1-substituted pyrazolines 3 and 4. Compounds 2 reacted also with different isocyanates and isothiocyanates to give carbanilides and thiocarbanilides 5. The pyrazoles 6 were obtained by reaction of the pyrazolines 2 with tetrachloro-O-benzoquinone

New purine derivatives with useful plant-growth regulating properties

The corresponding 6-substituted amino-9-aryl-9H-purines 4a-k are synthesized from reactions of 6-chloro-9-[p-anisyl]-or 9-[p- chlorophenyl]-9H-purines 3c and d with primary amines. Products 4d and k are also obtained by fusing 6-methylthiopurines 5 a and b with benzyl and p-anisyl amines. Most of the products 4a-k have been screened for activity as plant-growth regulating factors for wheat plant. Ring closure of 5-acetylamino 1-arylimidazole-4-carboxamides 6 by methanolic sodium hydroxide solution afforded the corresponding 9-aryl 2-methyl-hypoxantlines 7. The action of phosphoryl chloride on the latter products gave their 6-chloro derivatives 8. Treatment of 8b with p-toludine yielded its 9-[p-anisyl]-2-methyl-6-[p-tolylamino] purine 4 I