65996-58-9

Usage

Uses

Used in Pharmaceutical Industry:
4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro(9CI) is used as a therapeutic agent for the management of T cell-related conditions. Its application as an inhibitor of purine nucleoside phosphorylase (PNP) makes it a valuable compound in the treatment of T cell cancers, autoimmune diseases, and the prevention of tissue transplant rejection. By controlling the activity of PNP, this nucleoside analog can help regulate immune responses and potentially improve patient outcomes in these areas.

InChI:InChI=1/C6H6N4O/c7-6-9-3-1-2-8-4(3)5(11)10-6/h1-2,8H,(H3,7,9,10,11)

Upstream product

• 570386-22-0 N,N-dimethyl-N'-[4-(2-dimethylaminovinyl)-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl]formamidine 
• 4214-85-1 2-amino-6-methyl-5-nitro-4(3H)-oxopyrimidine 
• 180059-05-6 2-Methoxycarbonylamino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid methyl ester 
• 914496-92-7 (E)-N'-(1-benzyl-4-((E)-2-(dimethylamino)vinyl)-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)-N,N-dimethylformimidamide 
• 914496-91-6 (E)-N'(1-benzyl-4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)-N,N-dimethylformimidamide 
• 914496-90-5 (E)-N,N-dimethyl-N'-(4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)formimidamide 
• 111869-50-2 2-<(Dimethylamino)methylenamino>-3,7-dihydro-4H-pyrrolo-<2,3-d>pyrimidin-4-on 
• 34840-23-8 1,3-Dicarbomethoxy-S-methylisothiourea 
• 252932-48-2 3-amino-2-ethoxycarbonylpyrrole 
• 224946-82-1 2-amino-3-benzyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one 
• 151587-57-4 2,2-Dimethyl-propionic acid 2-(dimethylamino-methyleneamino)-4-((E)-2-dimethylamino-vinyl)-5-nitro-6-oxo-6H-pyrimidin-1-ylmethyl ester 
• 151587-55-2 2-<<(N,N-Dimethylamino)methylene>amino>-6-methyl-5-nitro-4(3H)-oxo-3-<(pivaloyloxy)methyl>pyrimidine 
• 3977-29-5 2-amino-6-methyl-3H-pyrimidin-4-one 
• 180059-04-5 3-amino-1H-pyrrole-2,4-dicarboxylic acid dimethyl ester 

Downstream Products

• 864155-80-6 2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one 
• 132138-67-1 2-Amino-3,5-dihydro-7-(phenylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one 
• 102731-45-3 9-deazaguanosine 
• 129872-83-9 5-benzyl-2,4-dichloro-5H-pyrrolo<3,2-d>pyrimidine 
• 914497-06-6 4-(5-benzyl-4-(4-((dimethylamino)methyl)-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile 
• 914496-24-5 4-(5-benzyl-4-(2,6-dimethyl-4-nitrophenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile 

Relevant academic research and scientific papers

9-Benzoyl 9-deazaguanines as potent xanthine oxidase inhibitors

A novel potent xanthine oxidase inhibitor, 3-nitrobenzoyl 9-deazaguanine (LSPN451), was selected from a series of 10 synthetic derivatives. The enzymatic assays were carried out using an on-flow bidimensional liquid chromatography (2D LC) system, which allowed the screening the measurement of the kinetic inhibition constant and the characterization of the inhibition mode. This compound showed a non-competitive inhibition mechanism with more affinity for the enzyme-substrate complex than for the free enzyme, and inhibition constant of 55.1 ± 9.80 nM, about thirty times more potent than allopurinol. Further details of synthesis and enzymatic studies are presented herein.

HETEROCYCLIC GTP CYCLOHYDROLASE 1 INHIBITORS FOR THE TREATMENT OF PAIN

The present invention relates to the field of small molecule heterocyclic inhibitors of GTP cyclohydrolase (GCH-I), or a tautomer, prodrug, or pharmaceutically acceptable salt thereof. The invention also features pharmaceutical compositions of the compounds and the medical use of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, or neuropathic pain).

9-Deazaguanine and its methyl derivatives: Synthesis, antitumor activity in vitro and effects on purine nucleoside phosphorylase gene expression

9-Deazaguanine 9-DG, 1-methyl-9-deazaguanine AG-19-K1 and 1,7-dimethyl-9-deazaguanine AG-3 were synthesized and their antiproliferative activity against five leukemia and four solid tumor cell lines as well as inhibitory properties vs. calf spleen purine nucleoside phosphorylase (PNP) were tested. Synthesis of 9-DG involves reaction of 2-amino-6-methyl-5- nitropyrimidin-4(3H)-one (2) with DMF-dimethylacetal (amount ratio, n(2) / n(DMF-dimethylacetal) = 1:2.5) and use of the benzyloxymethyl group to protect the N-3 position of 2-(N-dimethylaminomethylene) amino-6-methyl-5- nitropyrimidin-4(3H)-one (4). Reaction of 2 with DMF-dimethylacetal (amount ratio, n(2) / n(DMF-dimethylacetal) = 1:6) gave the N-3 methyl substituted intermediate 3. Dithionite reduction of this product afforded N-methyl derivatives AG-19-K1 and AG-3. AG-19-K1 and AG-3 were inactive vs. calf spleen PNP at a concentration of 75 μmol dm-3. Cytotoxic effects of 9-deazaguanine derivatives on cell growth were determined by the MTT assay. Investigated derivatives showed moderate antiproliferative activity towards examined tumor cells. At a concentration of 10-3 mol dm-3, AG-19-K1 inhibited the growth of JURKAT, K562 and AGS cells by approximately 80 %. At the same concentration, AG-3 and 9-DG inhibited cell proliferation by 40-50 % of all tested lines, except MOLT-4 and HL-60. The PNP gene expression was changed in treated leukemia cells after exposure to AG-19-K1 and 9-DG in a time-dependent manner.

DIARYL-PURINE, AZAPURINES AND -DEAZAPURINES AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS FOR TREATMENT OF HIV

This application concerns certain 2-phenylamino-6-aryl amino-, 6-aryloxy-, and 6- arylthio- purines, -azapurines and -deazapurines. These compounds are non-nucleoside reverse transcriptase inhibitors and have potential as anti-HIV treatment.

Process for preparing 2-pyrrolidinyl-1H-pyrrolo[3,2-d]pyrimidine inhibitors of nucleoside metabolism

A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted all, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of the formula (II) ?with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX), ?to form a compound of formula (XX) The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).

An improved synthesis of 9-deazaguanine

A new, improved synthesis of 9-deazaguanine is described. The method involves use of the benzyloxymethyl group to protect the N3-position of 2-[(dimethylaminomethylene)-amino]-6-methyl-5-nitro-4(3H)-pyrimidinone, followed by treatment with DMF-dimethylacetal, reductive cyclization, treatment with ethanolic ammonia and removal of the protecting group by catalytic hydrogenation.

A short, facile synthesis of 2-amino-1,5-dihydro-4H-pyrrolo[3,2-d]- pyrimidin-4-one (9-deazaguanine)

9-Deazaguanine has been synthesized in four steps in an overall isolated yield of 18% from ethyl (ethoxymethylene)cyanoacetate and diethyl aminomalonate.

Pyrrolopyrimidine Folate Analogues: "Inverted" Analogues of the Cytotoxic Agent LY231514

N-pyrimidin-5-yl)ethyl>benzoyl>-L-glutamic acid (3a) and N-pyrimidin-5-yl)propyl>benzoyl>-L-glutamic acid (3b) were synthesized as potential anticancer agents.

An expeditious synthesis of 2-amino-4(3H)-oxo-5H-pyrrolo[3,2-d]pyrimidine (9-deazaguanine)

9-Deazaguanine has been synthesized in five steps from 2-amino-6-methyl-5-nitro-4(3H)-pyrimidinone by a modification of the Batcho-Leimgruber indole synthesis.