5122-38-3

Upstream product

• 870-63-3 prenyl bromide 
• 87-42-3 6-chloropurine 
• 169558-41-2 6-chloro-9-(3-methylbut-2-en-1-yl)-9H-purine 
• 66224-66-6 adenine 

Downstream Products

• 4121-39-5 9-allyl-9H-adenine 
• 13532-34-8 3-Allyladenin 
• 1464851-21-5 (Z)-6-amino-9-(prop-1-en-1-yl)-9H-purine 
• 1446486-33-4 (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine 

Relevant academic research and scientific papers

Synthesis of certain alkenyl purines and purine analogs as inhibitors of tumor necrosis factor alpha (TNFα)

The preparation of 2-penten-1-yl and 3-methyl-2-buten-1-yl derivatives of adenine 2a,b, 7-deazaadenine 2c,d, 2-aminopurine 4a,b and 5a,b, 4-aminopyrazolo[3,4-d]pyrimidine 7a,b and 7-amino-v-triazolo-[4,5-d]pyrimidine 8a-10a and 8b-10b is described. The synthesis of compounds 2a-d was accomplished by the functional group transformation reaction, whereas the synthesis of 4a-8a and 4b-8b was performed by the alkylation of the sodium salt of the heterocycles with alkenyl bromides. These alkenyl derivatives prepared as congeners of pentoxifylline (methylxanthine) were evaluated for their anti-tumor necrosis factor α activity in human monocytic leukemia cells. Only compounds 7a and 7b exhibited significant activity and a poor toxicity profile in this assay. In peripheral blood mononuclear cells, compounds 7a and 7b, inhibited tumor necrosis factor α production in a dose dependent manner.

Synthesis of N-alkenylpurines by rearrangements of the corresponding N-allyl isomers: Scopes and limitations

N-9- and N-7-alkenylpurines have been synthesized by rearrangement of the corresponding N-allyl derivatives, often in good yields and with high stereoselectivity. Base promoted and transition metal mediated rearrangements have been studied. Simple allylpurines were easily rearranged with catalytic amounts of RuClH(CO)(PPh3)3. The efficiency of base promoted rearrangement was highly dependent on the detailed structure of the starting material, but this reaction often occurred with surprisingly high Z-selectivity. N-Alkenylpurines have been synthesized, often in good yields, from the corresponding more readily available N-allyl isomers by a double bond migration. The scope and limitation of the rearrangement in the presence of various bases or transition metal complexes have been studied.

BRANCHED-CHAIN DERIVATIVES OF ACYCLIC ADENOSINE ANALOGS: ALKYL AND HYDROXYMETHYL DERIVATIVES OF S-ADENOSYL-L-HOMOCYSTEINASE INHIBITORS SUBSTITUTED AT THE 2- AND 3-POSITION OF THE SIDE CHAIN

Reaction of 1,3-dichloro-2-propanone (VII) with methylmagnesium chloride, followed by alkaline hydrolysis, afforded 2-methylpropane-1,2,3-triol (VIII) which on treatment with 2,2-dimethoxypropane and subsequent tosylation give 4-(p-toluenesulfonyloxymethyl)-2,2,4-trimethyl-1,3-dioxolane (IXb).Compound IXb was condensed with sodium salt of adenine and the intermediate X was acid-hydrolysed to give 9-(RS)-(2,3-dihydroxy-2-methylpropyl)adenine (XI).Oxidation of XI with sodium periodate led to 9-(2-oxopropyl)adenine (XII). 9-(RS)-(2-Hydroxy-2-hydroxymethyloctyl)adenine (XVI) was obtained analogously from compound VII and hexylmagnesium bromida via triol XIV.Methyl 2-bromomethyl-2-propenoate (XVII) reacted with sodium salt of adenine and the resulting methyl 2-(adenin-9-ylmethyl)-2-propenoate (XVIII) was hydroxylated with sodium perchlorate and osmium tetroxide.The obtained methyl (RS)-2-(adenin-9-ylmethyl)-2,3-dihydroxypropanoate (XIX) was alkali-hydrolysed to give sodium salt of the acid XX.Reduction of ester XIX with sodium borohydride furnished 9-(RS)-(2,3-dihydroxy-2-hydroxymethylpropyl)adenine (XXI). 1-Nonen-3-ol (XXIII), obtained by reaction of propenal with hexylmagnesium bromide, was converted by hydroxylation with osmium tetroxide into nonane-1,2,3-triol (XXIVa) and further into its 1-O-p-toluenesulfonate XXIVb which reacted with 2,2-dimethoxypropane to give 2,2-dimethyl-4-hexyl-5-(p-toluenesulfonyloxymethyl)-1,3-dioxolane (XXV).Compound XXV reacted with adenine and the resulting intermediate XXVI was converted into 9-(RS)-(2,3-dihydroxynonyl)adenine (XXVII) by acid hydrolysis. 9-(3-Methyl-2-buten-1-yl)adenine (XXVIII), obtained by alkylation of sodium salt of adenine with 1-bromo-3-methyl-2-butene, was oxidized with potassium permanganate in an acid medium to give 9-(3-hydroxy-2-oxo-3-methylbutyl)adenine (XXIX).This compound was converted into 9-(RS)-(2,3-dihydroxy-3-methylbutyl)adenine (XXX) by reduction with sodium borohydride. 4-C-Hydroxymethyl-1,2-O-isopropylidene-α-D-xylofuranose (XXXII) reacted with 2,2-dimethoxypropane under formation of 4-C-hydroxymethyl-1,2:3,5-di-O-isopropylidene derivative XXXIIIa whose p-toluenesulfonyl derivative XXXIIIb on treatment with adenine afforded 4-C-(adenin-9-yl)methyl-1,2:3,5-di-O-isopropylidene-α-D-xylofuranose (XXXIV).Acid hydrolysis of this compound, followed by oxidation in an alkaline medium, gave (2S,3R)-4-(adenin-9-yl)-3-hydroxymethyl-2,3-dihydroxybutanoic acid, isolated as its ethyl ester XXXVI.