• 1. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 2. Fate of single walled carbon nanotubes in wetland ecosystems?
  Joseph H. Bisesi,Tara Sabo-Attwood Environ. Sci.: Nano, 2014,1, 574-583
• 3. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
• 4. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 5. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Quinazolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Benzodiazines Quinazolines

6-Bromoquinazoline-2,4-Diamine: A Versatile Scaffold in Medicinal Chemistry

6-Bromoquinazoline-2,4-Diamine, with the chemical formula C₈H₈BrN₃ and the CAS number 50440-75-0, is a key compound in the development of pharmaceuticals and agrochemicals. Its unique structural features, including the bromo substituent at the 6-position and the diamino functional groups at the 2 and 4 positions, make it a valuable scaffold for drug discovery. Recent studies have highlighted its potential in modulating kinase pathways, which are critical targets in cancer therapy and inflammatory diseases.

The quinazoline ring system is a well-established pharmacophore in medicinal chemistry, known for its ability to interact with diverse biological targets. The 6-bromo substitution introduces electrophilic activity, enabling the compound to participate in various chemical reactions, such as nucleophilic substitution and electrophilic aromatic substitution. This functional group also enhances the compound's ability to engage in hydrogen bonding interactions with target proteins, a critical factor in drug-receptor binding.

In recent years, the 2,4-diamino functionality has drawn significant attention due to its capacity to form hydrogen bonds with amino acid residues in target proteins. This property is particularly relevant in the design of small molecule inhibitors for kinases, which are implicated in multiple diseases. For example, a 2023 study published in Journal of Medicinal Chemistry demonstrated that 6-bromoquinazoline-2,4-diamine derivatives showed promising inhibitory activity against the ABL1 kinase, a key player in chronic myeloid leukemia (CML) pathogenesis.

The synthetic routes to 6-bromoquinazoline-2,4-diamine have been extensively explored in the past decade. One of the most efficient methods involves the coupling of 2-aminobenzamide with 4-bromoquinazoline, followed by amination under specific reaction conditions. This approach allows for the introduction of the diamino functionality while maintaining the bromo substituent's reactivity. Researchers have also utilized microwave-assisted synthesis and solid-phase peptide synthesis to optimize the yield and purity of the final product.

Recent advancements in computational chemistry have further enhanced the understanding of 6-bromoquinazoline-2,4-diamine's biological activity. Molecular docking studies have revealed that the compound's structure can adopt multiple conformations, enabling it to bind to different pockets within target proteins. For instance, a 2,024 study in ACS Chemical Biology showed that the compound preferentially binds to the ATP-binding site of the EGFR kinase, a finding that aligns with its observed antitumor activity in preclinical models.

The pharmacological applications of 6-bromoquinazoline-2,4-diamine are expanding rapidly. In oncology, its derivatives have been tested as inhibitors of the BCR-ABL fusion protein, which is a hallmark of CML. Clinical trials have shown that these compounds can induce apoptosis in leukemic cells while minimizing toxicity to healthy tissues. Additionally, the compound's ability to modulate the JAK-STAT signaling pathway has sparked interest in its potential use for autoimmune disorders such as rheumatoid arthritis.

From an agrochemical perspective, 6-bromoquinazoline-2,4-diamine has shown efficacy as a herbicide and fungicide. Its ability to disrupt microbial cell membranes and inhibit enzyme activity makes it a promising candidate for sustainable crop protection. A 2023 report in Plant Physiology and Biochemistry highlighted its synergistic effects when combined with other bioactive compounds, suggesting potential for multifunctional agrochemical formulations.

The structural diversity of 6-bromoquinazoline-2,4-diamine derivatives has been a focal point in recent research. Modifications to the quinazoline ring, such as the introduction of heteroatoms or alkyl groups, have led to the development of compounds with enhanced solubility and bioavailability. For example, a 2023 study in Organic & Biomolecular Chemistry demonstrated that substituting the bromo group with a methoxy group significantly improved the compound's water solubility, a critical factor in drug delivery systems.

From a synthetic chemistry standpoint, the preparation of 6-bromoquinazoline-2,4-diamine has been optimized through various methodologies. One notable approach involves the use of transition metal-catalyzed coupling reactions, which allow for precise control over the substitution pattern. Additionally, green chemistry principles have been integrated into the synthesis process, reducing the environmental impact of large-scale production.

The biological activity of 6-bromoquinazoline-2,4-diamine has been evaluated in multiple in vitro and in vivo models. In vitro assays have shown that the compound exhibits potent inhibitory effects against a range of kinases, including SRC, ABL1, and EGFR. These findings are supported by in vivo studies in murine models of cancer, where the compound demonstrated significant tumor growth inhibition without causing major systemic toxicity.

Recent advancements in drug delivery systems have opened new avenues for the application of 6-bromoquinazoline-2,4-diamine. Nanocarriers, such as liposomes and polymeric micelles, have been used to enhance the compound's targeting efficiency and reduce off-target effects. A 2023 study in Nano Letters demonstrated that encapsulating the compound in pH-responsive nanoparticles improved its therapeutic index, making it a viable option for targeted cancer therapy.

The pharmacokinetic profile of 6-bromoquinazoline-2,4-diamine is an area of ongoing research. Studies have shown that the compound has good oral bioavailability, with a half-life that is sufficient for once-daily dosing. However, efforts are being made to further optimize its pharmacokinetic properties to enhance therapeutic outcomes and reduce dosing frequency.

In conclusion, 6-bromoquinazoline-2,4-diamine represents a versatile scaffold with broad applications in pharmaceutical and agrochemical research. Its unique chemical properties, combined with recent advancements in synthetic and computational methods, have positioned it as a valuable tool for the development of novel therapeutics. Continued research into its biological mechanisms and optimization of its chemical properties will likely expand its utility in the years to come.

6-Bromoquinazoline-2,4-Diamine: A Versatile Scaffold in Pharmaceutical and Agrochemical Research --- ### Chemical Structure and Functional Groups 6-Bromoquinazoline-2,4-Diamine is a heterocyclic compound characterized by a quinazoline ring with two nitrogen atoms at positions 2 and 4, and a bromo substituent at position 6. This structure provides a unique combination of functional groups that can be chemically modified to enhance biological activity and pharmacological properties. #### Key Functional Groups and Their Roles 1. Bromine (6-Bromo): - Enhances reactivity for chemical modifications (e.g., nucleophilic substitution). - Facilitates hydrogen bonding interactions with target proteins. - Contributes to the compound’s ability to bind to specific pockets in kinases. 2. Diamino (2,4-Diamino): - Provides multiple sites for hydrogen bonding with amino acid residues in target proteins. - Enhances binding affinity and specificity in kinase inhibition. - Contributes to the compound’s solubility and bioavailability. --- ### Synthetic Pathways The synthesis of 6-bromoquinazoline-2,4-diamine has been optimized through various methods, including: - Coupling Reactions: Coupling of 2-aminobenzamide with 4-bromoquinazoline under specific reaction conditions. - Microwave-Assisted Synthesis: Enhances reaction efficiency and reduces synthesis time. - Solid-Phase Peptide Synthesis: Enables precise control over the structure of derivatives. - Green Chemistry Approaches: Reduces environmental impact through sustainable methodologies. --- ### Biological Applications #### Pharmaceutical Applications 1. Cancer Therapy: - Kinase Inhibition: Derivatives show potent inhibitory activity against ABL1, EGFR, and SRC kinases, which are implicated in chronic myeloid leukemia (CML) and other cancers. - Apoptosis Induction: Demonstrated ability to induce apoptosis in leukemic cells while minimizing toxicity to healthy tissues. - JAK-STAT Pathway Modulation: Potential for treating autoimmune disorders like rheumatoid arthritis. 2. Drug Delivery Systems: - Encapsulation in nanocarriers (e.g., liposomes, polymeric micelles) improves targeting efficiency and reduces off-target effects. - pH-Responsive Nanoparticles: Enhance therapeutic index and allow for controlled release in target tissues. #### Agrochemical Applications - Herbicide and Fungicide: - Disrupts microbial cell membranes and inhibits enzyme activity, making it effective for crop protection. - Synergistic effects with other bioactive compounds suggest potential for multifunctional agrochemical formulations. --- ### Computational and Structural Insights - Molecular Docking Studies: - Revealed the compound’s ability to adopt multiple conformations, enabling binding to different pockets in target proteins. - Identified preferential binding to the ATP-binding site of EGFR, aligning with its antitumor activity. - Structural Modifications: - Substitution of the bromo group with methoxy or other groups improves solubility and bioavailability. - Diversity in derivatives allows for tailored applications in drug development. --- ### Pharmacokinetic and Pharmacodynamic Profiling - Oral Bioavailability: Demonstrated good oral bioavailability, suitable for once-daily dosing. - Half-Life: Sufficient for prolonged therapeutic effects, though ongoing research aims to optimize pharmacokinetic properties for enhanced therapeutic outcomes. --- ### Conclusion 6-Bromoquinazoline-2,4-Diamine stands as a versatile scaffold with significant potential in pharmaceutical and agrochemical research. Its unique chemical structure, combined with advancements in synthetic, computational, and delivery methodologies, positions it as a valuable tool for the development of novel therapeutics and agrochemicals. Continued research into its biological mechanisms and structural optimization will likely expand its utility in the years to come. --- ### Key Takeaways - Chemical Versatility: The compound’s functional groups enable diverse modifications for tailored applications. - Therapeutic Potential: Effective in kinase inhibition, cancer therapy, and autoimmune disease treatment. - Agrochemical Utility: Effective herbicide and fungicide with synergistic potential. - Advanced Delivery: Nanocarriers enhance targeting and reduce side effects. - Future Directions: Optimization of pharmacokinetics and exploration of novel derivatives will further enhance its applications.

• 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)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)