65996-58-9

Basic information

• Product Name: 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI)
• Synonyms: 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI);2-AMINO-3,5-DIHYDRO-PYRROLO[3,2-D]PYRIMIDIN-4-ONE ;4H-Pyrrolo3,2-dpyrimidin-4-one, 2-amino-1,5-dihydro-;9-deazaguanine;2-amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one;2-Amino-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one;NSC 344522;2-amino-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one
• CAS NO: 65996-58-9
• Molecular Formula: C₆H₆N₄O
• Molecular Weight: 150.13804
• Product Categories: AMINEPRIMARY;PYRIMIDINE;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 65996-58-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: >300 °C(Solv: water (7732-18-5))
• Boiling Point: 452.7°Cat760mmHg
• Flash Point: 227.6°C
• Appearance: /
• Density: 1.87g/cm³
• Vapor Pressure: 2.2E-08mmHg at 25°C
• Refractive Index: 1.89
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 10.85±0.20(Predicted)
• CAS DataBase Reference: 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI)(65996-58-9)
• EPA Substance Registry System: 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI)(65996-58-9)

Safety Data

• Hazardous Substances Data: 65996-58-9(Hazardous Substances Data)

Usage

Description

4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro(9CI) is a nucleoside analog that functions as a potent inhibitor of purine nucleoside phosphorylase (PNP). 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro(9CI) is characterized by its unique chemical structure, which allows it to effectively target and inhibit the enzyme PNP, playing a significant role in the regulation of T cell proliferation.

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

• 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 
• 180059-05-6 2-Methoxycarbonylamino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid methyl ester 
• 180059-04-5 3-amino-1H-pyrrole-2,4-dicarboxylic acid dimethyl ester 
• 4214-85-1 2-amino-6-methyl-5-nitro-4(3H)-oxopyrimidine 
• 518316-53-5 3-benzyloxymethyl-2-[(dimethylamino)methyleneimino]-6-[(2-dimethylamino)ethenyl]-5-nitro-4(3H)-oxopyrimidine 

Downstream Products

• 132138-67-1 2-Amino-3,5-dihydro-7-(phenylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one 
• 129872-88-4 2-amino-5-benzyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one 
• 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 
• 914497-04-4 1-(4-(5-benzyl-2-chloro-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylphenyl)ethanone 
• 914496-98-3 4-(5-benzyl-2-fluoro-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile 
• 914496-23-4 4-(4-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile 

Relevant articles and documents

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.

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.

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).