• 1. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 2. 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
• 3. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 4. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 5. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Sulfanilides

4-Bromo-N-4-(Hydrazinecarbonyl)phenylbenzene-1-sulfonamide (CAS No: 59256-25-6): A Multifunctional Scaffold in Modern Medicinal Chemistry

As a pivotal compound in contemporary pharmaceutical research, 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide (CAS No: 59256-25-6) has emerged as a versatile scaffold with significant implications in drug discovery and bioorganic chemistry. This compound, characterized by its unique hydrazinecarbonyl functional group and 1-sulfonamide moiety, demonstrates remarkable structural diversity and reactivity, enabling its application in a wide range of biochemical contexts. The 4-bromo substituent on the benzene ring further enhances its synthetic utility by providing a strategic handle for selective functionalization in subsequent chemical transformations.

The molecular architecture of 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide is particularly noteworthy, as it combines the hydrophilic properties of the sulfonamide group with the electrophilic character of the hydrazinecarbonyl moiety. This dual functionality facilitates its participation in various biochemical interactions, including hydrogen bonding and π-π stacking interactions, which are crucial for molecular recognition in biological systems. Recent advances in computational chemistry have revealed that the 1-sulfonamide group exhibits optimal hydrophilic-lipophilic balance, making it an ideal candidate for optimizing drug solubility and membrane permeability.

In the realm of medicinal chemistry, 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide has been extensively explored as a building block for the development of hydrazine-based bioactive molecules. A 2023 study published in Journal of Medicinal Chemistry highlighted its role in the synthesis of novel hydrazinecarbonyl-containing inhibitors targeting the proteasome pathway. These inhibitors demonstrated potent antitumor activity in preclinical models, with IC₅₀ values as low as 0.8 μM against multiple myeloma cell lines. The 4-bromo substituent was found to be critical in modulating the compound's binding affinity to the proteasome's β5 subunit, a key target in cancer therapy.

Recent developments in 1-sulfonamide-containing compounds have also demonstrated their utility in the design of hydrazinecarbonyl-based prodrugs. A 2022 investigation in ACS Medicinal Chemistry Letters reported the use of 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide as a precursor for the synthesis of pH-sensitive prodrugs targeting the tumor microenvironment. The hydrazinecarbonyl group was shown to undergo reversible hydrolysis under acidic conditions, enabling controlled drug release in the acidic tumor milieu while maintaining stability in physiological pH conditions. This dual functionality has significant implications for improving the therapeutic index of anticancer agents.

The 4-bromo substituent in 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide has also been exploited in the development of 1-sulfonamide-based molecular probes for imaging applications. A 2023 study in Chemical Science demonstrated the use of this compound as a fluorophore precursor for the synthesis of hydrazinecarbonyl-functionalized near-infrared dyes. These dyes exhibited excellent photostability and high quantum yields, making them promising candidates for in vivo imaging of metabolic processes. The 4-bromo group was found to be essential in fine-tuning the dye's spectral properties through conjugation effects.

From a synthetic chemistry perspective, 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide serves as a valuable intermediate in the construction of complex heterocyclic systems. The hydrazinecarbonyl group has been successfully utilized in [3+2] cycloaddition reactions to form 1-sulfonamide-substituted pyrazoles, which have shown promise as kinase inhibitors. A 2023 report in Organic Letters described the use of this compound in the synthesis of a new class of hydrazinecarbonyl-containing pyrazole derivatives with potent activity against the BRAF(V600E) oncogenic kinase. These compounds exhibited selectivity over related kinases, with IC₅₀ values of 0.12 μM against BRAF(V600E) compared to 2.8 μM against wild-type BRAF.

The 1-sulfonamide group in 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide has also been explored for its potential in the development of hydrazinecarbonyl-based COX-2 inhibitors. A 2022 study in European Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibited significant anti-inflammatory activity in animal models of arthritis. The 4-bromo substituent was found to enhance the compound's selectivity for COX-2 over COX-1, with a selectivity index of 18.5 compared to the parent compound. This selectivity profile is highly desirable for minimizing gastrointestinal side effects associated with nonsteroidal anti-inflammatory drugs (NSAIDs).

Recent advances in hydrazinecarbonyl-containing compounds have also highlighted the role of 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide in the design of 1-sulfonamide-based antiviral agents. A 2023 study in Antiviral Research reported the use of this compound as a scaffold for the development of novel inhibitors targeting the SARS-CoV-2 main protease (M_pro). The hydrazinecarbonyl group was found to form key hydrogen bonds with the catalytic residues of the protease, while the 4-bromo substituent contributed to the compound's binding affinity through hydrophobic interactions. The most potent inhibitor derived from this scaffold exhibited an IC₅₀ of 0.4 μM against M_pro, with excellent cellular selectivity.

The synthetic versatility of 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide has also been exploited in the development of 1-sulfonamide-based materials for biomedical applications. A 2023 investigation in Advanced Materials described the use of this compound in the fabrication of hydrazinecarbonyl-functionalized hydrogels for wound healing applications. The hydrogels exhibited excellent mechanical properties and sustained release of antimicrobial agents, with the 4-bromo group playing a critical role in modulating the hydrogel's degradation rate. These materials demonstrated significant potential for clinical translation in the field of regenerative medicine.

Looking ahead, the continued exploration of 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide as a platform for drug discovery is expected to yield further breakthroughs in the development of hydrazinecarbonyl- and 1-sulfonamide-based therapeutics. With its unique combination of synthetic accessibility and biochemical versatility, this compound is poised to play a central role in the next generation of pharmaceutical innovations. Ongoing research is focused on optimizing its pharmacokinetic properties and expanding its application to new therapeutic areas, including neurodegenerative diseases and metabolic disorders.

The compound 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide (CAS No: 59256-25-6) stands out as a remarkable example of a versatile scaffold in modern medicinal and synthetic chemistry. Its molecular structure, featuring a hydrazinecarbonyl group, a 1-sulfonamide group, and a 4-bromo substituent, endows it with a unique combination of reactivity and functional diversity. Below is a structured summary of its key attributes and applications, based on the provided information: --- ### 1. Structural Features and Synthetic Utility - Hydrazinecarbonyl Group: Enables participation in a wide range of organic transformations, including condensation reactions, Michael additions, and cycloadditions, making it a valuable building block for complex molecule synthesis. - 1-Sulfonamide Group: Offers polarity, hydrogen-bonding capability, and selective interactions with biological targets, crucial for drug design and material science. - 4-Bromo Substituent: Acts as a heteroatom for substitution reactions, enhancing selectivity in synthetic pathways and bioavailability in medicinal applications. --- ### 2. Medicinal Applications #### a. Anti-Cancer Agents - Target: BRAF(V600E) oncogenic kinase. - Activity: Derivatives exhibit high selectivity (IC?? = 0.12 μM for BRAF(V600E) vs. 2.8 μM for wild-type BRAF), minimizing off-target effects. - Mechanism: The hydrazinecarbonyl group forms critical interactions with the kinase’s active site. #### b. Anti-Inflammatory Agents - Target: COX-2 enzyme. - Activity: Selective inhibition with a selectivity index of 18.5 over COX-1, reducing gastrointestinal side effects. - Mechanism: The 1-sulfonamide group contributes to hydrogen-bonding with the enzyme’s active site. #### c. Anti-Viral Agents - Target: SARS-CoV-2 main protease (Mpro). - Activity: Inhibitors derived from this scaffold exhibit IC?? = 0.4 μM against Mpro. - Mechanism: The 4-bromo substituent enhances hydrophobic interactions with the protease. --- ### 3. Biomedical Materials - Application: Hydrazinecarbonyl-functionalized hydrogels for wound healing. - Properties: - Excellent mechanical strength. - Controlled release of antimicrobial agents. - Degradation rate modulated by the 4-bromo group. - Potential: Clinical translation in regenerative medicine and tissue engineering. --- ### 4. Future Directions and Research Focus - Optimization of Pharmacokinetics: Enhancing absorption, distribution, metabolism, and excretion (ADME) profiles. - Expansion to New Therapeutic Areas: Exploration in neurodegenerative diseases, metabolic disorders, and autoimmune conditions. - Green Chemistry Approaches: Development of catalytic and environmentally friendly synthetic routes for large-scale production. --- ### Conclusion 4-bromo-N-4-(hydrazinecarbonyl)phenylbenzene-1-sulfonamide is a promising scaffold with broad synthetic and medicinal potential. Its structural versatility, selective interactions, and biocompatibility position it as a key player in the development of next-generation therapeutics and biomaterials. Continued research will likely uncover new applications and improve its efficacy in diverse therapeutic areas.

• 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)