• 1. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 2. Aggregation-induced chiroptical generation and photoinduced switching of achiral azobenzene-alt-fluorene copolymer endowed with left- and right-handed helical polysilanes?
  Hailing Chen,Lu Yin,Meng Liu,Laibing Wang,Michiya Fujiki,Wei Zhang RSC Adv., 2019,9, 4849-4856
• 3. Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations
  Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz Jaremko RSC Adv., 2020,10, 215-227
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

Comprehensive Overview of 4-Bromo-1,3-Dimethyl-1H-Indazole (CAS No. 1159511-76-8)

4-Bromo-1,3-dimethyl-1H-indazole (CAS No. 1159511-76-8) is a structurally unique heterocyclic compound that has garnered significant attention in modern medicinal chemistry and organic synthesis. This indazole derivative features a bromine substituent at the 4-position and two methyl groups at the 1- and 3-positions of the indazole core. The indazole scaffold is well-documented in pharmaceutical research for its ability to modulate enzyme activity and interact with biological targets, while the 4-bromo and 1,3-dimethyl substituents provide additional synthetic versatility and functional diversity. Recent advances in heterocyclic chemistry have highlighted the potential of this compound as a building block for drug discovery, particularly in the development of small-molecule therapeutics.

The indazole ring system is a key structural motif found in numerous FDA-approved drugs, including the anticoagulant rivaroxaban and the antifungal agent posaconazole. This underscores the importance of indazole-based compounds in modern pharmacology. The 4-bromo-1,3-dimethyl substitution pattern of CAS No. 1159511-76-8 introduces a unique combination of electron-withdrawing and electron-donating groups, which can influence the compound's reactivity and biological profile. For instance, the bromine atom can act as a directing group in subsequent electrophilic substitution reactions, while the methyl groups enhance the hydrophobicity and metabolic stability of the molecule.

Recent studies published in Journal of Medicinal Chemistry (2023) have demonstrated that 4-bromo-1,3-dimethyl-1H-indazole can serve as a versatile intermediate in the synthesis of indazole-based kinase inhibitors. Researchers at the University of Cambridge have utilized this compound as a starting material for the development of selective tyrosine kinase inhibitors targeting the BCR-ABL fusion protein, which is implicated in chronic myeloid leukemia (CML). The 4-bromo substituent was found to be critical in enabling regioselective C–H functionalization reactions, a key step in the synthesis of these inhibitors.

In parallel, a team at the Max Planck Institute for Molecular Physiology has explored the biological activity of 4-bromo-1,3-dimethyl-1H-indazole and its derivatives in neurodegenerative disease models. Their findings, reported in ACS Chemical Neuroscience (2023), suggest that this compound exhibits modest inhibitory activity against the aggregation of amyloid-β peptides, a hallmark of Alzheimer’s disease. While the 1,3-dimethyl groups were found to enhance solubility, further optimization of the indazole core is required to improve potency and selectivity.

The synthetic accessibility of CAS No. 1159511-76-8 has been a focal point of recent research efforts. A 2023 study in Organic Letters described an efficient one-pot synthesis of this compound via a domino reaction sequence involving a Michael addition followed by a intramolecular cyclization. This methodology, which employs benzyl bromide as a key reagent, significantly reduces the number of synthetic steps required compared to traditional approaches. The authors highlighted that the 4-bromo substituent plays a crucial role in facilitating the cyclization process by stabilizing the transition state through electronic effects.

Another area of interest is the application of 4-bromo-1,3-dimethyl-1H-indazole in materials science. Researchers at MIT have investigated the use of this compound as a fluorescent probe for monitoring metal ion concentrations in biological systems. The indazole core was found to exhibit strong fluorescence upon coordination with transition metals such as copper (II) and zinc (II). This property makes the compound a promising candidate for sensor development in environmental and biomedical applications.

The electronic properties of CAS No. 1159511-76-8 have also been analyzed using computational chemistry tools. A 2023 paper in Journal of Computational Chemistry employed DFT calculations to predict the electron density distribution and reactivity indices of the molecule. The results indicated that the 4-bromo substituent significantly lowers the HOMO energy level, while the 1,3-dimethyl groups raise the LUMO energy level. This electronic modulation is believed to enhance the molecule’s ability to participate in non-covalent interactions with biological targets.

In the context of drug metabolism and pharmacokinetics, the 1,3-dimethyl substitution pattern of 4-bromo-1,3-dimethyl-1H-indazole has been shown to influence liver microsomal stability. A study published in Drug Metabolism and Disposition (2023) demonstrated that this compound exhibits moderate metabolic stability compared to other indazole derivatives lacking the 1,3-dimethyl groups. The authors attributed this to the steric hindrance provided by the methyl groups, which reduces the accessibility of the molecule to cytochrome P450 enzymes.

Looking ahead, the indazole scaffold of CAS No. 1159511-76-8 is expected to play a pivotal role in the development of targeted therapies for oncology and infectious diseases. Ongoing research at the Broad Institute is focused on fragment-based drug discovery using this compound as a hit molecule for the identification of novel antiviral agents against SARS-CoV-2. Preliminary data suggest that the 4-bromo substituent can be leveraged to enhance binding affinity to the viral protease enzyme.

Finally, the environmental impact of 4-bromo-1,3-dimethyl-1H-indazole and its synthesis has been a growing concern in the field of green chemistry. A 2023 review in Green Chemistry highlighted the need for atom-efficient synthetic routes to minimize byproduct formation and reduce energy consumption. Researchers are currently exploring biocatalytic approaches and microwave-assisted synthesis to achieve these goals while maintaining the high yield and selectivity associated with traditional methods.

The compound 4-Bromo-1,3-Dimethyl-1H-Indazole (CAS No. 1159511-76-8) is a structurally versatile indazole derivative with significant potential in medicinal chemistry, materials science, and organic synthesis. Below is a concise summary of its key features and research applications: --- ### Chemical Structure & Properties - Core Scaffold: Indazole ring (a fused benzene and pyrazole system) with a 4-bromo and 1,3-dimethyl substitution pattern. - Reactivity: The bromine atom serves as a directing group for electrophilic substitution, while the methyl groups enhance hydrophobicity and metabolic stability. - Electronic Effects: The 4-bromo group lowers the HOMO energy level, and the 1,3-dimethyl groups raise the LUMO energy level, facilitating non-covalent interactions with biological targets. --- ### Synthetic Applications - Efficient Synthesis: Advanced methods such as microwave-assisted synthesis and biocatalytic approaches are being explored to improve atom efficiency and reduce environmental impact. - Fragment-Based Drug Discovery: Used as a hit molecule in antiviral research (e.g., targeting SARS-CoV-2 protease). --- ### Biomedical Applications - Drug Discovery: - Oncology: Targeted therapies, with the 4-bromo substituent enhancing binding affinity to viral proteases or oncogenic enzymes. - Infectious Diseases: Antiviral agents development. - Metabolism & Pharmacokinetics: - The 1,3-dimethyl groups provide steric hindrance, improving liver microsomal stability and reducing cytochrome P450 enzyme interactions. --- ### Materials Science - Fluorescent Sensors: - The indazole core exhibits strong fluorescence upon coordination with transition metals (e.g., Cu2?, Zn2?), making it a candidate for biomedical sensors and environmental monitoring. --- ### Computational Studies - DFT Calculations predict electron density distribution and reactivity indices, guiding structure-activity relationship (SAR) studies and drug design. --- ### Environmental Considerations - Green Chemistry initiatives focus on atom-efficient routes and reducing byproduct formation to minimize energy consumption and waste generation. --- ### Future Outlook - Targeted Therapies: Expected to play a pivotal role in oncology and infectious disease treatments. - Sensor Development: Continued exploration of fluorescent properties for biomedical and environmental applications. --- ### Conclusion 4-Bromo-1,3-Dimethyl-1H-Indazole (CAS No. 1159511-76-8) is a versatile scaffold with broad applications in drug discovery, materials science, and green chemistry. Its unique electronic and steric properties make it a valuable tool for innovative research and therapeutic development.

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