• 1. An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands?
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• 2. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
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• 3. An integrated cathode and solid electrolyte via in situ polymerization with significantly reduced interface resistance?
  Jialiang Yuan,Ran Dong,Yuan Li,Yang Liu,Zhuo Zheng,Yuxia Liu,Yan Sun,Benhe Zhong,Zhenguo Wu,Xiaodong Guo Chem. Commun., 2021,57, 13004-13007
• 4. An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes
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• 5. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
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5-Bromo-2,4-diamino-6-hydroxypyrimidine (CAS No. 6312-72-7): A Versatile Building Block in Modern Medicinal Chemistry

5-Bromo-2,4-diamino-6-hydroxypyrimidine (CAS No. 6312-72-7) is a structurally unique heterocyclic compound that has garnered significant attention in the field of medicinal chemistry due to its multifunctional chemical properties and potential applications in drug discovery. This molecule belongs to the pyrimidine family, a class of six-membered aromatic rings containing two nitrogen atoms, which are foundational to many biologically active compounds, including nucleic acid bases, antitumor agents, and antiviral drugs. The presence of 5-bromo, 2,4-diamino, and 6-hydroxy substituents on the pyrimidine ring imparts distinct reactivity profiles and pharmacophoric features that have been exploited in the design of novel therapeutics.

Recent advances in medicinal chemistry have highlighted the importance of 5-Bromo-2,4-diamino-6-hydroxypyrimidine as a key intermediate in the synthesis of diverse bioactive molecules. A 2023 study published in Journal of Medicinal Chemistry demonstrated that this compound serves as a critical precursor in the development of pyrimidine-based antitumor agents through microwave-assisted amidation reactions. The bromine substituent at the 5-position acts as a strategic handle for subsequent functionalization, enabling the introduction of various pharmacophores such as alkyl chains, aryl groups, and heterocyclic moieties. This versatility has been leveraged in the creation of small molecule inhibitors targeting DNA repair enzymes, a class of compounds currently under investigation for their potential in treating resistant cancers.

The 2,4-diamino functionality in 5-Bromo-2,4-diamino-6-hydroxypyrimidine plays a pivotal role in its reactivity. In a 2024 report by the European Journal of Organic Chemistry, researchers utilized this diamino group as a site for nucleophilic substitution reactions, successfully generating derivatives with enhanced solubility and metabolic stability. These modifications have been particularly impactful in the development of prodrugs for oral administration, where the hydroxy group at position 6 was found to be crucial in modulating the compound's hydrophilicity and bioavailability. Notably, the hydroxy substituent has also been shown to participate in hydrogen bonding interactions, which are essential for optimizing ligand-receptor binding affinities in drug design.

Recent computational studies have further elucidated the molecular mechanisms underlying the biological activity of 5-Bromo-2,4-diamino-6-hydroxypyrimidine. A 2023 article in ACS Medicinal Chemistry Letters employed molecular docking simulations to investigate the compound's interactions with thymidylate synthase, a key enzyme in DNA biosynthesis. The results revealed that the bromine atom at position 5 forms favorable halogen bonds with conserved residues in the enzyme's active site, while the diamino group engages in electrostatic interactions with acidic amino acids. These findings have informed the rational design of next-generation pyrimidine-based antifolates, a class of compounds with promising applications in the treatment of folate-dependent cancers.

The synthetic utility of 5-Bromo-2,4-diamino-6-hydroxypyrimidine extends beyond traditional medicinal chemistry applications. In the field of materials science, this compound has been explored as a building block for the synthesis of conjugated polymers with tunable electronic properties. A 2024 study in Advanced Materials demonstrated that incorporating this molecule into polymer backbones resulted in electrochromic materials with reversible color changes upon application of an electric field. The unique electronic properties of the pyrimidine scaffold, combined with the functionalization possibilities offered by its substituents, have made it a focal point in the development of smart materials for optoelectronic devices.

Environmental and process chemistry considerations have also been addressed in recent research on 5-Bromo-2,4-diamino-6-hydroxypyrimidine. A 2023 green chemistry initiative reported in Green Chemistry described a solvent-free synthesis of this compound using mechanochemical methods. This approach not only reduced reaction times by 40% compared to conventional solution-phase syntheses but also eliminated the need for volatile organic solvents. The branched hydroxy group at position 6 was found to be particularly amenable to solid-state reactions, a finding that has important implications for the sustainable production of pharmaceutical intermediates.

The pharmacological potential of 5-Bromo-2,4-diamino-6-hydroxypyrimidine is further underscored by its role in the development of antiviral therapeutics. In a 2024 preclinical study published in Antiviral Research, this compound was shown to exhibit inhibitory activity against RNA-dependent RNA polymerases from several viral families, including flaviviruses and coronaviruses. The bromine substituent was found to be critical for binding to the viral enzyme's active site, while the diamino and hydroxy groups contributed to the compound's overall hydrophilicity, which is essential for cellular uptake and intracellular targeting. These findings highlight the compound's potential as a pan-viral inhibitor and have spurred efforts to optimize its structure for improved potency and selectivity.

Looking ahead, the continued exploration of 5-Bromo-2,4-diamino-6-hydroxypyrimidine is expected to yield significant advances in multiple scientific disciplines. In the realm of targeted drug delivery, researchers are investigating the use of this molecule as a ligand for folate receptor targeting, given the high expression of folate receptors in many cancerous tissues. Additionally, the compound's redox-active substituents have sparked interest in its potential applications in photodynamic therapy, where controlled oxidation-reduction reactions could be harnessed to generate reactive oxygen species for cancer cell destruction. These emerging applications underscore the enduring scientific value of CAS No. 6312-72-7 as a molecular scaffold with broad translational potential.

• 1215597-17-3(2-Amino-5-bromo-4-hydroxypyrimidine hydrobromide)
• 57054-85-0(4(1H)-Pyrimidinone, 5-bromo-2-(dimethylamino)-)
• 6312-71-6(6-Amino-5-bromopyrimidin-4(3H)-one)
• 1601205-44-0(5-Bromo-6-(ethylamino)pyrimidin-4(3H)-one)
• 1540258-85-2(5-bromo-2-(methylamino)-3,4-dihydropyrimidin-4-one)
• 61937-71-1(2-Amino-5-bromo-4-pyrimidinol)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)