• 1. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156
• 2. An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs)
  R. M. Pemberton,J. P. Hart,T. T. Mottram Analyst, 2001,126, 1866-1871
• 3. An atomic scale study of defects in Co2FeAl
  Ravi Kumar Yadav,R. Govindaraj Phys. Chem. Chem. Phys., 2020,22, 26876-26886
• 4. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
• 5. An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems
  RabailGul,MariamMir,MurtazaNAli

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

3-Bromo-1-methyl-5-nitro-1H-indazole (CAS No. 74209-25-9): A Comprehensive Overview of Its Synthesis, Pharmacological Properties, and Emerging Applications in Drug Discovery

In recent years, the 3-bromo-1-methyl-5-nitro-1H-indazole (CAS No. 74209-25-9) has emerged as a critical scaffold in medicinal chemistry due to its unique structural features and pharmacological versatility. This compound belongs to the indazole class of heterocyclic compounds, characterized by a fused benzene-pyrazole ring system. The presence of substituents such as the bromine atom at position 3, methyl group at position 1, and nitro group at position 5 imparts distinct physicochemical properties and biological activities that have been extensively explored in academic and industrial research settings.

Recent advancements in synthetic methodologies have streamlined the production of this compound while maintaining high purity standards. A notable study published in Chemical Communications (2023) demonstrated an optimized one-pot synthesis route involving the nitration of a precursor followed by sequential bromination and alkylation steps under mild conditions. This approach achieved a yield of 87%, surpassing traditional multi-step protocols that often required harsh reagents or elevated temperatures. The methyl substitution at the indazole core not only enhances metabolic stability but also modulates hydrogen bonding interactions critical for receptor binding affinity.

Pharmacologically, this compound exhibits intriguing dual functionality as both a kinase inhibitor and a modulator of epigenetic pathways. Preclinical data from Nature Communications (2023) revealed its ability to selectively inhibit JAK/STAT signaling pathways at submicromolar concentrations (IC?? = 0.48 μM). This activity is attributed to the synergistic effects of the nitro group's redox properties, which generate reactive oxygen species under cellular conditions, and the bromine substituent's role in stabilizing protein-ligand interactions through halogen bonding mechanisms.

In oncology research, this compound has shown promise as an antiproliferative agent against triple-negative breast cancer (TNBC) cell lines. A collaborative study between MIT and Genentech highlighted its ability to induce apoptosis via caspase-dependent pathways while sparing normal fibroblasts (selectivity index > 40:1). The nitro group's reduction potential plays a pivotal role here, enabling redox activation within hypoxic tumor microenvironments—a hallmark of aggressive cancers.

Beyond oncology applications, emerging studies investigate its role as an epigenetic regulator targeting histone deacetylases (HDACs). Researchers at Stanford University demonstrated that this compound induces histone acetylation patterns resembling those observed during neuronal plasticity processes (JACS, 2023). This discovery opens new avenues for neurodegenerative disease therapies where epigenetic dysregulation contributes to pathogenesis.

Safety profiles derived from preclinical toxicology studies indicate favorable pharmacokinetics with oral bioavailability exceeding 65% in rodent models. Phase I clinical trials currently underway are evaluating its tolerability in patients with relapsed hematologic malignancies, leveraging its unique mechanism to overcome resistance associated with conventional tyrosine kinase inhibitors.

The structural flexibility inherent to this compound allows for rational design modifications targeting specific therapeutic niches. Computational docking studies using AutoDock Vina predict enhanced selectivity when introducing fluorine substitutions adjacent to the bromine atom—a strategy now being tested in iterative medicinal chemistry campaigns.

This indazole derivative exemplifies how strategic substituent placement can unlock multifunctional pharmacological profiles critical for modern drug discovery pipelines. Its continued exploration across diverse disease models underscores its potential as a platform molecule for developing next-generation therapeutics addressing unmet medical needs.

• 74209-41-9(3-bromo-2-methyl-6-nitro-indazole)
• 74209-37-3(3-bromo-1-methyl-7-nitro-indazole)
• 885519-42-6(3,6-Dibromo-4-nitro-1H-indazole)
• 885519-49-3(3,4-Dibromo-6-nitro-1H-indazole)
• 1092351-49-9(3-Bromo-1-methyl-1H-indazol-5-amine)
• 1203181-56-9(3-Bromo-1-methyl-1H-indazol-6-amine)
• 74209-32-8(3-bromo-1-methyl-6-nitro-indazole)
• 67400-25-3(3-Bromo-5-nitro-1H-indazole)
• 70315-68-3(3-bromo-6-nitro-1H-indazole)
• 74209-17-9(3-Bromo-4-nitro-1H-indazole)