5H-Pyrrolo[3,2-d]pyrimidine, 2-[3-(3-methylphenyl)-1H-pyrazol-1-yl]-6-(1-methyl-1H-pyrazol-3-yl)-4-(4-morpholinyl)-, hydrochloride (1:1)

5H-Pyrrolo[3,2-d]pyrimidine, 2-[3-(3-methylphenyl)-1H-pyrazol-1-yl]-6-(1-methyl-1H-pyrazol-3-yl)-4-(4-morpholinyl)-, hydrochloride (1:1) (CAS: 2877704-17-9) is a highly functionalized heteroaromatic kinase inhibitor scaffold widely used in medicinal chemistry, oncology drug discovery, and advanced structure-based drug design. Featuring a fused pyrrolo[3,2-d]pyrimidine core decorated with multiple nitrogen-rich heterocycles, including pyrazole and morpholine substituents in hydrochloride salt form, it provides a multi-point interaction framework for ATP-binding kinase domains. The compound is primarily applied in kinase inhibition research, hit-to-lead optimization, and preclinical candidate development targeting cancer, inflammatory, and immune-related signaling pathways, supporting biochemical assays, SAR studies, and molecular modeling workflows. Its primary applications are outlined below:

1. Medicinal Chemistry & Kinase Inhibitor Development

Selective Kinase Targeting Scaffold

This compound serves as a privileged heteroaromatic scaffold for designing ATP-competitive kinase inhibitors. The pyrrolo[3,2-d]pyrimidine core mimics adenine-like interactions within kinase hinge regions, enabling strong hydrogen bonding and high binding affinity across multiple kinase families. Researchers utilize this scaffold in oncology-focused programs targeting PI3K, JAK, EGFR, and other clinically relevant signaling pathways.

Lead Optimization in Oncology Drug Discovery

The compound is widely used in hit-to-lead and lead optimization workflows to improve potency, selectivity, and pharmacokinetic properties of kinase inhibitor candidates. Structural modifications on pyrazole and morpholine substituents allow fine-tuning of solubility, permeability, and metabolic stability.

2. Structure–Activity Relationship (SAR) Studies

Multi-Substituent Pharmacophore Mapping

The presence of multiple heterocyclic motifs enables systematic SAR exploration across binding pocket regions. Researchers investigate how variations in pyrazole substitution patterns and morpholine polarity influence kinase binding affinity, selectivity profiles, and off-target interactions.

Conformational Constraint and Binding Optimization

The fused heteroaromatic system provides structural rigidity, reducing conformational entropy loss upon target binding. This enhances receptor interaction efficiency and supports rational drug design strategies based on X-ray crystallography and molecular docking models.

3. Chemical Biology & Mechanistic Research

Signal Transduction Pathway Modulation

The compound is used as a chemical tool to investigate kinase-driven signaling pathways involved in cell proliferation, apoptosis, angiogenesis, and immune regulation. It enables functional validation of kinase targets in disease models.

Target Engagement and Selectivity Profiling

Researchers employ this scaffold in kinase panel screening assays to evaluate selectivity and off-target binding profiles, supporting the identification of safer and more selective therapeutic candidates.

4. Pharmaceutical Process Development

Scalable Intermediate for Drug Candidate Synthesis

The compound is applied in process chemistry for evaluating synthetic routes toward complex kinase inhibitors. Its defined heteroaromatic structure and salt form improve handling, crystallinity, and reproducibility in multi-step synthesis workflows.

Analytical Method Development Standard

It is used as a reference standard in LC-MS and HPLC method development for impurity profiling, stability testing, and quality control of related heterocyclic drug substances.

5. Bioactivity Screening & Drug Discovery Platforms

High-Throughput Screening (HTS) Scaffold

This compound is frequently included in kinase-focused screening libraries due to its privileged binding architecture, making it suitable for identifying novel bioactive hits in oncology and immunology programs.

Fragment Expansion and Library Design Template

Its modular heterocyclic framework makes it a valuable template for fragment-based drug design (FBDD), enabling systematic expansion into diverse chemical libraries for lead generation.

6. Handling & Storage

Storage Conditions

Store in tightly sealed containers under dry, dark conditions at 2–8 °C. Protect from moisture and prolonged light exposure to maintain structural integrity, particularly due to its multi-heteroaromatic system and protonated hydrochloride form.

Intended Use

This compound is intended strictly for laboratory research use, including medicinal chemistry, chemical biology, and pharmaceutical R&D applications. It is not intended for human or veterinary therapeutic use without appropriate regulatory approval. Standard laboratory safety procedures and protective equipment should be used during handling.

Summary

The value of 5H-Pyrrolo[3,2-d]pyrimidine, 2-[3-(3-methylphenyl)-1H-pyrazol-1-yl]-6-(1-methyl-1H-pyrazol-3-yl)-4-(4-morpholinyl)-, hydrochloride (1:1) lies in its highly optimized kinase-targeting heteroaromatic architecture, enabling strong hinge-region binding, tunable physicochemical properties, and versatile SAR exploration. Its multi-functional pharmacophore design makes it a powerful scaffold for kinase inhibitor discovery, oncology drug development, and advanced medicinal chemistry research. The compound supports hit identification, lead optimization, and mechanistic signaling studies, making it a valuable asset in modern precision drug discovery programs.

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