62160-25-2

Usage

Uses

Used in Medicinal Chemistry:
N-(4-Oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-2-yl)acetamide is used as a potential pharmaceutical candidate for various applications in medicinal chemistry. Its bioactivity, similar to other pyrrolopyrimidine compounds, makes it a promising molecule for the development of new drugs and therapeutic agents. N-(4-Oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-2-yl)acetamide's unique structure and functional groups may contribute to its potential interactions with biological targets, such as enzymes, receptors, or other macromolecules, which could lead to the discovery of novel treatments for various diseases and conditions.

InChI:InChI=1/C8H8N4O2/c1-4(13)10-8-11-6-5(2-3-9-6)7(14)12-8/h2-3H,1H3,(H3,9,10,11,12,13,14)

Upstream product

• 88062-66-2 2-acetamido-4-acetoxy-3,7-dihydropyrrolo<2,3-d>pyrimidine 
• 7355-55-7 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 75-36-5 acetyl chloride 

Downstream Products

• 96446-01-4 Benzoic acid 2-(2-acetylamino-4-oxo-3,4-dihydro-pyrrolo[2,3-d]pyrimidin-7-ylmethoxy)-ethyl ester 
• 96446-00-3 Benzoic acid 2-(2-acetylamino-4-oxo-4,7-dihydro-pyrrolo[2,3-d]pyrimidin-3-ylmethoxy)-ethyl ester 
• 96446-02-5 C₂₈H₂₈N₄O₈ 
• 118527-51-8 N-{6-[(Dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-acetamide 
• 88523-04-0 N-{5-[(Dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-acetamide 
• 84955-38-4 2-amino-3,7-dihydro-7-<(2-hydroxyethoxy)-methyl>-4H-pyrrolo<2,3-d>pyrimidin-4-one 

Relevant academic research and scientific papers

Denitrified purine compound and pharmaceutical composition, preparation method and application thereof

The invention relates to denitrified purine compound which has a structure as a following general formula 1, a preparation method of the denitrified purine compound, a pharmaceutical composition containing the denitrified compound and application of the denitrified compound. The compound has selective B-Raf V600E mutation cancer cell inhibition activity, so that the denitrified purine compound disclosed by the invention and the pharmaceutical composition of the denitrified purine compound can be applied to preparing medicine for treating tumor or cancer.

Docking-based structural splicing and reassembly strategy to develop novel deazapurine derivatives as potent B-Raf V600E inhibitors

The mutation of B-Raf V600E is widespread in a variety of human cancers. Its inhibitors vemurafenib and dabrafenib have been launched as drugs for treating unresectable melanoma, demonstrating that B-Raf V600E is an ideal drug target. This study focused on developing novel B-Raf V600E inhibitors as drug leads against various cancers with B-Raf V600E mutation. Using molecular modeling approaches, 200 blockbuster drugs were spliced to generate 283 fragments followed by molecular docking to identify potent fragments. Molecular structures of potential inhibitors of B-Raf V600E were then obtained by fragment reassembly followed by docking to predict the bioactivity of the reassembled molecules. The structures with high predicted bioactivity were synthesized, followed by in vitro study to identify potent B-Raf V600E inhibitors. A highly potent fragment binding to the hinge area of B-Raf V600E was identified via a docking-based structural splicing approach. Using the fragment, 14 novel structures were designed by structural reassembly, two of which were predicted to be as strong as marketed B-Raf V600E inhibitors. Biological evaluation revealed that compound 1m is a potent B-Raf V600E inhibitor with an IC 50 value of 0.05 μmol/L, which was lower than that of vemurafenib (0.13 μmol/L). Moreover, the selectivity of 1m against B-Raf WT was enhanced compared with vemurafenib. In addition, 1m exhibits desirable solubility, bioavailability and metabolic stability in in vitro assays. Thus, a highly potent and selective B-Raf V600E inhibitor was designed via a docking-based structural splicing and reassembly strategy and was validated by medicinal synthesis and biological evaluation.

Synthesis of Queuine, the Base of Naturally Occuring Hypermodified Nucleoside (Queuosine), and Its Analogues

A convenient new method for synthesizing queuine (1) pyrrolopyrimidin-4(3H)-one>, the base of the naturally occuring hypermodified nucleoside, queuosine, present in certain transfer RNAs, and its biosynthetic precursor, 2-amino-5-aminomethylpyrrolopyrimidin-4(3H)-one (2) (Pre Q1 base), was succesfully exploited.This method involved two critical rections: the Mannich reaction using dibenzylamine-formaldehyde of 2-acrylaminopyrrolopyrimidin-4(3H)-one (7), which resulted in the selective introduction of the dibenzylaminomethyl group into the 5-position of (7), and an amine exchange reaction of the 5-dibenzylamino function in the resulting Mannich base (17) with (1S,2R,3S)-2,3-isopropylidenedioxycyclopent-4-enylamine, which yielded the desired queuine (1).Similar reaction of (17) with ammonia gave the biosynthetic precursor of queuine (2) (Pre Q1 base).Thus, a series of queuine analogues with structural variations in their 5-aminomethyl side-chains was synthesized by the amine exchange reaction of (17) with appropriate amines or by acylation of (2) with appropriate acylating agents.

Reaction of 2-Acetamido-3,7-dihydropyrrolopyrimidin-4-one With Dimethylamine and Formaldehyde. Formation of Two Isomeric Mannich Bases

2-Acetamido-3,7-dihydropyrrolopyrimidin-4-one reacts with dimethylamine and formaldehyde in glacial acetic acid to afford the two isomeric Mannich products, 2-acetamido-3,7-dihydro-5-dimethylaminomethylpyrrolopyrimidin-4-one, and 2-acetamido-3,7-dihydro-6-dimethylaminomethylpyrrolopyrimidin-4-one, in a ratio of 3:1, respectively.