928840-99-7

Usage

Uses

Used in Medicinal Chemistry:
2,4-Dichloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine is utilized as a chemical intermediate for the synthesis of novel drugs. Its unique structure and functional groups allow for the exploration of new therapeutic agents that can modulate specific biological pathways, potentially leading to the discovery of treatments for various medical conditions.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,4-Dichloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine serves as a key component in the development of new drugs. Its potential biological activities and chemical properties make it a valuable asset in the creation of medications that address unmet medical needs, offering hope for improved patient outcomes and novel treatment options.
Further research on 2,4-Dichloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine is essential to fully understand its capabilities and optimize its use in medicinal applications, ensuring that its potential is harnessed to contribute to advancements in healthcare.

InChI:InChI=1/C6H2Cl2IN3/c7-5-4-3(2(9)1-10-4)11-6(8)12-5/h1,10H

Upstream product

• 63200-54-4 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine 

Downstream Products

• 928841-01-4 5-(benzyloxymethyl)-2,4-dichloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine 
• 928841-21-8 5-(benzyloxymethyl)-2-chloro-7-[(trimethylsilyl)ethynyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine 
• 928841-16-1 5-(benzyloxymethyl)-2,4-dichloro-7-[(trimethylsilyl)ethynyl]-5H-pyrrolo[3,2-d]pyrimidine 
• 928841-23-0 1-[4-amino-5-(benzyloxymethyl)-2-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl]ethane-1,2-diol 
• 928841-18-3 5-(benzyloxymethyl)-2-chloro-7-ethynyl-5H-pyrrolo[3,2-d]pyrimidin-4-amine 
• 928841-12-7 5-(benzyloxymethyl)-2,4-dichloro-7-vinyl-5H-pyrrolo[3,2-d]pyrimidine 
• 928841-17-2 5-(benzyloxymethyl)-2,4-dichloro-7-ethynyl-5H-pyrrolo[3,2-d]pyrimidine 
• 928841-22-9 5-(benzyloxymethyl)-2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidin-4-amine 

Relevant academic research and scientific papers

EIF4E-INHIBITING 4-OXO-3,4-DIHYDROPYRIDO[3,4-D]PYRIMIDINE COMPOUNDS

The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X1, X2, X3, X4, X5, X6, Q, L1, L2, Y, R1, R2, R3, R4, R5, R6, R7, R8 and rings A, B and C are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4e and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

Anticancer Properties of Halogenated Pyrrolo[3,2-d]pyrimidines with Decreased Toxicity via N5 Substitution

Halogenated pyrrolo[3,2-d]pyrimidine analogues have shown antiproliferative activity in recent studies, with cell accumulation occurring in the G2/M stage without apoptosis. However, the mechanism of action and pharmacokinetic (PK) profile of these compounds has yet to be determined. To investigate the PK profile of these compounds, a series of halogenated pyrrolo[3,2-d]pyrimidine compounds was synthesized and first tested for activity in various cancer cell lines followed by a mouse model. EC50 values ranged from 0.014 to 14.5 μm, and maximum tolerated doses (MTD) in mice were between 5 and 10 mg kg?1. This indicates a wide variance in activity and toxicity that necessitates further study. To decrease toxicity, a second series of compounds was synthesized with N5-alkyl substitutions in an effort to slow the rate of metabolism, which was thought to be leading to the toxicity. The N-substituted compounds demonstrated comparable cell line activity (EC50 values between 0.83–7.3 μm) with significantly decreased toxicity (MTD=40 mg kg?1). Finally, the PK profile of the active N5-substituted compound shows a plasma half-life of 32.7 minutes, and rapid conversion into the parent unsubstituted analogue. Together, these data indicate that halogenated pyrrolo[3,2-d]pyrimidines present a promising lead into potent antiproliferative agents with tunable activity and toxicity, and rapid metabolism.

THIENO- AND PYRROLOPYRIMIDINE ANALOGUES AS ANTICANCER AGENTS AND METHODS OF USE THEREOF

The present invention provides for the design and synthesis of halogenated thieno- and pyrrolopyrimidine compounds that exhibit cancer proliferation inhibitory activity and the use thereof for cancer treatment.

Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines

In vitro evaluation of the halogenated pyrrolo[3,2-d]pyrimidines identified antiproliferative activities in compounds 1 and 2 against four different cancer cell lines. Upon screening of a series of pyrrolo[3,2-d]pyrimidines, the 2,4-Cl compound 1 was foun

C-Functionalization of 9-deazapurines by cross-coupling reactions

C-Functionalization of pyrrolo[3,2-d]pyrimidine scaffold in positions 2, 4, and 7 using cross-coupling reactions was performed. Thus, 2-(5-(benzyloxymethyl)-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)ethanol, a versatile synthetic precursor for 9-deazapurines and?4,6-diazaindoles, was prepared by vinylation of the corresponding iodide followed by hydroboration of the double bond. A synthesis of 9-(1,2-dihydroxyethyl)-9-deazaadenine, a 9-deaza-1′-nor congener to antiviral DHPA, was developed. In addition, an abnormal regioselectivity in methylalumination of the terminal triple bond in position 7 of the pyrrolo[3,2-d]pyrimidine scaffold leading to a transformation into (Z)-prop-1-enyl was observed.