• 1. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 2. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 3. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 4. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 5. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

Introduction to 5-Bromo-4-methyl-1H-indazole (CAS No. 1082041-34-6)

5-Bromo-4-methyl-1H-indazole, identified by the Chemical Abstracts Service Number (CAS No.) 1082041-34-6, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the indazole family, characterized by a fused benzene and pyrrole ring system, which endows it with unique electronic and steric properties. The presence of both bromine and methyl substituents on the indazole core enhances its reactivity, making it a valuable intermediate in the synthesis of more complex molecules.

The structural features of 5-Bromo-4-methyl-1H-indazole make it a versatile building block in medicinal chemistry. The bromine atom, located at the 5-position of the indazole ring, serves as a versatile handle for further functionalization via cross-coupling reactions such as Suzuki-Miyaura, Stille, or Buchwald-Hartwig couplings. These reactions are pivotal in constructing biaryl structures, which are prevalent in many bioactive compounds. Additionally, the methyl group at the 4-position introduces steric and electronic effects that can influence the compound's interactions with biological targets.

In recent years, 5-Bromo-4-methyl-1H-indazole has been explored in various therapeutic areas due to its structural framework. One of the most promising applications is in the development of anticancer agents. The indazole scaffold is known to exhibit cytotoxic properties, and modifications at key positions can enhance potency and selectivity. For instance, studies have shown that indazole derivatives can inhibit kinases and other enzymes involved in tumor proliferation and survival. The brominated derivative, in particular, has been investigated for its ability to disrupt microtubule formation and induce apoptosis in cancer cells.

Another area where 5-Bromo-4-methyl-1H-indazole has shown promise is in antimicrobial research. The unique electronic properties of the indazole ring contribute to its ability to interact with bacterial enzymes and DNA gyrase, leading to inhibition of bacterial growth. Researchers have synthesized various derivatives of this compound and found that modifications at the 3- and 5-positions can significantly enhance antimicrobial activity against Gram-positive and Gram-negative bacteria. This has led to interest in developing novel antibiotics based on this scaffold.

The synthesis of 5-Bromo-4-methyl-1H-indazole typically involves multi-step organic reactions starting from readily available precursors. A common synthetic route begins with the condensation of acetanilide with glyoxal or an aldehyde derivative to form an intermediate indole derivative. Subsequent bromination using bromine or N-bromosuccinimide (NBS) introduces the bromine atom at the desired position. Finally, methylation using methyl iodide or dimethyl sulfate installs the methyl group at the 4-position. These steps highlight the compound's synthetic accessibility, which is crucial for large-scale production and further derivatization.

Recent advances in computational chemistry have also contributed to the study of 5-Bromo-4-methyl-1H-indazole. Molecular modeling techniques allow researchers to predict binding affinities and optimize lead structures before experimental synthesis. This approach has been particularly useful in designing analogs with improved pharmacokinetic properties. For example, virtual screening has identified derivatives with enhanced solubility and reduced toxicity, making them more suitable for clinical development.

The pharmaceutical industry has taken notice of 5-Bromo-4-methyl-1H-indazole due to its potential as a drug candidate or intermediate. Several companies have patented derivatives of this compound for their anticancer and antimicrobial applications. Clinical trials are ongoing for some of these derivatives, with early results indicating promising efficacy against various diseases. The success of these trials could pave the way for new treatments targeting cancer and infectious diseases.

Environmental considerations also play a role in the research and development of 5-Bromo-4-methyl-1H-indazole. Given its importance as an intermediate, sustainable synthetic methods are being explored to minimize waste and reduce environmental impact. Green chemistry principles are being applied, such as using catalytic systems that improve efficiency and reduce byproduct formation. These efforts align with global initiatives to promote sustainable chemical manufacturing.

In conclusion, 5-Bromo-4-methyl-1H-indazole (CAS No. 1082041-34-6) is a multifaceted compound with significant potential in pharmaceutical research. Its unique structural features make it a valuable tool for synthesizing bioactive molecules, particularly in anticancer and antimicrobial applications. Advances in synthetic chemistry, computational modeling, and green chemistry are enhancing our understanding and utilization of this compound. As research continues, it is likely that new derivatives will emerge with even greater therapeutic potential.

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