Azaguanine

yellow powderChEBI: A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.

8-azaguanine is a triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively. It has a role as an antimetabolite, an antineoplastic agent and an EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor. It is a member of triazolopyrimidines and a nucleobase analogue.|8-azaguanine is one of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.|8-Azaguanine is a purine analogue with potential antineoplastic activity. 8-Azaguanine interferes with the modification of transfer ribonucleic acid (tRNA) by competing with guanine for incorporation into tRNA catalyzed by the enzyme tRNA-guanine ribosyltransferase (tRNA-guanine transglycosylase). Altered guanine modification of tRNA has been implicated in cellular differentiation and neoplastic transformation. 8-Azaguanine also inhibits the formation of 43S and 80S initiation complexes, thereby interfering with initiation of translation and inhibiting protein synthesis. This agent inhibits tumor cell growth and stimulates cell differentiation. (NCI04)|One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.

It is obtained from 2, 4-diamino-6-hydroxypyrimidine by nitrosation, reduction, diazotization and cyclization. (1) Nitrification to obtain 2, 4-diamino-5-nitroso-6-hydroxypyrimidine: add sodium nitrite to the aqueous solution of 2, 4-diamino-6-hydroxypyrimidine below 15℃, Concentrated hydrochloric acid was added dropwise to precipitate a rose-red precipitate with a pH of about 3.5. Filter and wash to neutrality to obtain 2, 4-diamino-5-nitroso-6-hydroxypyrimidine (nitroso). (2) Reduction to obtain 2, 4, 5-triamino-6-hydroxypyrimidine sulfate (triamino): Suspend the nitroso in water, and gradually put the powder into the powder under stirring. Subsequently, sodium hydroxide solution was added to make pH=9, and it was heated to boiling, so that the reaction solution changed from red to light yellow. Add activated carbon to decolorize and filter. After the filtrate was cooled, it was adjusted to acidic Congo red with sulfuric acid, and a yellow precipitate was deposited. Filter and wash with ethanol to obtain triamino. (3) Diazotization and cyclization to obtain 8-azaguanine: suspend the triamino compound in water, add sodium hydroxide solution, and dissolve by heating. Then add sodium nitrite, stir and dissolve and add glacial acetic acid. Heated to 90℃ for 1h. Cool and filter to obtain crude 8-azaguanine, which is refined to obtain finished product.

Antineoplastic;Purine antimetabolite

Molecular Weight:152.11
XLogP3:-1.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Exact Mass:152.04465877
Monoisotopic Mass:152.04465877
Topological Polar Surface Area:109
Heavy Atom Count:11
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes