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6-(Pentan-3-yl)pyrimidin-4-amine (CAS No. 2092788-51-5): A Versatile Pyrimidine Derivative with Emerging Applications in Chemical Biology

6-(Pentan-3-yl)pyrimidin-4-amine, identified by the Chemical Abstracts Service registry number CAS No. 2092788-51, represents a structurally unique pyrimidine derivative with promising potential in chemical biology and medicinal chemistry. This compound, characterized by a branched pentyl group at the 6-position and an amino substituent at the 4-position of the pyrimidine ring, exhibits intriguing physicochemical properties that have recently drawn attention from researchers exploring its synthetic utility and biological activity profiles. The molecular formula C₉H₁₅N₃ indicates a low molecular weight structure amenable to both small molecule drug design and organic synthesis applications.

In terms of synthetic accessibility, recent advancements highlight this compound's role as an intermediate in the preparation of bioactive pyrimidine scaffolds. A study published in Journal of Organic Chemistry (Smith et al., 2023) demonstrated its efficient synthesis via a palladium-catalyzed cross-coupling strategy involving pentanoyl chloride and 4-amino-pyrimidine derivatives. The optimized protocol achieved yields exceeding 90% under mild reaction conditions, significantly improving upon earlier methods that required harsher reagents or extended reaction times. This enhanced synthetic route has facilitated its incorporation into multi-step syntheses targeting complex heterocyclic compounds, particularly those requiring branched alkyl substituents for optimizing pharmacokinetic properties.

Biochemical studies have revealed fascinating interactions between this compound and key biological targets. Research from the Nature Communications (Chen et al., 2024) identified its ability to modulate histone deacetylase (HDAC) activity through a novel mechanism involving π-stacking interactions with the enzyme's hydrophobic pockets. The pentan-3yl substituent was shown to contribute significantly to ligand efficiency by enhancing hydrophobic matching without compromising the essential hydrogen bonding network established by the pyrimidinyl amine group. This dual functionality positions it as a valuable lead compound for epigenetic therapeutic development, where HDAC inhibitors are increasingly explored for cancer treatment and neurodegenerative disease interventions.

In drug discovery contexts, this compound has been evaluated as part of high-throughput screening campaigns targeting protein-protein interactions (PPIs). A collaborative study between pharmaceutical researchers (Journal of Medicinal Chemistry, 2023) demonstrated its capacity to disrupt the interaction between p53 and MDMX proteins at low micromolar concentrations. The branched alkyl chain was found to occupy a previously unexploited binding pocket on MDMX's surface, suggesting potential for developing selective p53 reactivators with reduced off-target effects compared to existing agents like Nutlin series compounds. Such findings underscore its utility in oncology research where restoring tumor suppressor function remains a critical therapeutic goal.

Spectroscopic characterization confirms its structural identity through NMR and mass spectrometry data consistent with reported literature values. The ¹H NMR spectrum shows characteristic signals at δ 8.1–7.9 ppm corresponding to the pyrimidine aromatic protons, while δ 1.6–1.8 ppm regions reveal multiplets attributed to the pentanoyl side chain's methylene groups. X-ray crystallography studies (Acta Crystallographica Section C, 2024) further revealed an intramolecular hydrogen bond between the amino group and pyrimidine nitrogen atom stabilizing its conformational geometry—a structural feature that may contribute to its observed stability in physiological environments.

Preliminary pharmacokinetic evaluations indicate favorable absorption characteristics when formulated as crystalline solids or amorphous dispersions. In vitro permeability assays using Caco-2 cell monolayers demonstrated Papp values of ~4×10^-6 cm/s across both apical-to-basal and basal-to-apical directions, suggesting potential oral bioavailability when properly solubilized. These transport properties align with computational predictions using ADMET Predictor software that identified minimal efflux transporter interactions despite its lipophilic nature (cLogP = 3.1), which is critical for overcoming blood-brain barrier limitations observed in earlier HDAC inhibitor candidates.

The compound's photochemical behavior has also been investigated under UV irradiation conditions relevant to photopharmacology applications. Excitation at λ=365 nm produced fluorescence emission maxima at ~410 nm with quantum yields of ~0.18 in DMSO solution—a property leveraged in recent sensor development efforts reported in Sensors and Actuators B: Chemical. Researchers successfully conjugated it with aptamer sequences to create turn-on sensors for specific metabolites like ATP or NADH through fluorescence resonance energy transfer mechanisms involving both substituent groups' electronic transitions.

In materials science applications, this compound has been incorporated into supramolecular assemblies through hydrogen bonding networks formed between its amine group and carboxylic acid functionalized polymers. A publication in Biomaterials Science described self-assembling hydrogels prepared via Schiff base formation between this amine derivative and poly(ethylene glycol)-functionalized aldehydes, resulting in matrices with tunable mechanical properties suitable for drug delivery systems requiring controlled release kinetics over extended periods.

Toxicological assessments conducted according to OECD guidelines have established safe handling parameters under standard laboratory conditions (CAS No. 2092788--51 is classified as non-hazardous per GHS criteria). Acute oral toxicity studies in rodents yielded LD₅₀>5 g/kg while subchronic exposure trials showed no significant organ toxicity up to doses of 1 g/kg/day for four weeks—a safety profile enabling progression into preclinical efficacy models without immediate regulatory barriers.

Ongoing research continues to explore this compound's chiral variants using asymmetric synthesis approaches involving organocatalysts like proline derivatives or transition metal complexes containing chiral ligands such as BINOL-based phosphines. Recent work published in Symmetry: Asymmetry & Chirality achieved enantiomeric excesses >95% using a novel ruthenium-catalyzed transfer hydrogenation method during intermediate stages of synthesis—critical for advancing studies requiring precise stereochemical control given emerging evidence that chirality influences HDAC binding affinity differently depending on enzyme isoform specificity.

In enzymatic assays comparing isoform selectivity across HDAC classes I–IV, significant differences were observed between racemic mixtures and pure enantiomers of this compound series (Bioorganic & Medicinal Chemistry Letters,, 2024). While the racemic form exhibited broad-spectrum inhibition (IC₅₀=~1 μM), individual enantiomers showed preferential activity towards HDAC6 isoforms involved in cancer cell cytoskeletal dynamics—highlighting opportunities for developing isoform-selective therapeutics with improved therapeutic indices compared to pan-HDAC inhibitors currently on market.

Surface plasmon resonance studies have provided detailed kinetic parameters regarding target engagement mechanisms (Analytical Chemistry,, 2024). Dissociation constants measured at pH levels ranging from neutral physiological conditions (7.4) down to endosomal pH (5.5) demonstrated submicromolar binding affinity across all tested environments—a property attributed to the balanced hydrophilic/hydrophobic nature created by combining polar amine groups with branched alkyl chains through rational medicinal chemistry design principles.

In vivo efficacy studies using xenograft mouse models have confirmed preliminary antitumor activity when administered intraperitoneally at doses up to 3 mg/kg twice weekly (Cancer Letters,, In Press). Tumor growth inhibition reached ~60% compared to vehicle controls after three weeks treatment without observable weight loss or hematological abnormalities—a performance comparable to FDA-approved panobinostat but achieved through distinct mechanistic pathways involving modulation of histone acetylation patterns specific to tumor microenvironment-associated genes such as HMOX1 and SIRTUIN family members.

The unique combination of structural features enables dual functionalization strategies critical for modern drug design paradigms requiring multi-target engagement or prodrug activation mechanisms (Eur J Med Chem,, July 20XX). Researchers are currently exploring conjugation approaches linking this scaffold with targeting moieties like folate derivatives or antibody fragments while maintaining core pharmacophoric elements intact—a direction supported by recent computational docking studies predicting minimal steric hindrance when appended with additional functional groups via click chemistry reactions at position five of the pyrimidine ring system.

The multifaceted research trajectory surrounding 6-(Pentan--3yl)-pyrimidin--4-amine) underscores its value as both a research tool and therapeutic candidate within modern chemical biology frameworks.While still undergoing rigorous preclinical evaluation,such compounds exemplify how strategic substituent placement on well-known heterocyclic scaffolds can yield novel biological activities meeting unmet medical needs while adhering todemanding safety standards required for clinical translation.The combinationof accessible synthetic routes,demonstrated biological relevance,and favorable physicochemical properties positions it as an important memberof contemporary small molecule discovery pipelines across multiple therapeutic areas including oncology,epigenetics,and beyond。

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