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• 3. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
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• 4. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl alkyl sulfoxides
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl sulfoxides Benzyl alkyl sulfoxides

2-[(2,4-Dichlorophenyl)Methanesulfinyl]Acetohydrazide (CAS No. 956159-44-7): A Comprehensive Overview

As a sulfanylhydrazide derivative with the chemical name 2-[(2,4-dichlorophenyl)methanesulfinyl]acetohydrazide, this compound (CAS No. 956159-44-7) represents an intriguing structure for advanced chemical and biological investigations. Its unique combination of a methanesulfinyl group attached to a dichlorophenyl moiety, coupled with an acetohydrazide functional unit, positions it at the intersection of organosulfur chemistry and bioactive molecule design. Recent studies have highlighted its potential in targeted drug delivery systems, particularly in modulating enzyme activities through redox-sensitive mechanisms.

The molecular architecture of this compound exhibits notable stability under physiological conditions while retaining reactivity toward reactive oxygen species (ROS). This dual characteristic was experimentally validated in a 2023 study published in the Journal of Medicinal Chemistry, where researchers demonstrated its ability to form disulfide bonds with glutathione under cellular redox environments. The acetohydrazide segment acts as a pH-responsive trigger, enabling controlled release of bioactive payloads in tumor microenvironments with acidic pH levels. Such properties make this compound a promising candidate for developing prodrug strategies targeting cancer cells without systemic toxicity.

Synthetic advancements have recently optimized the preparation of this compound through microwave-assisted synthesis reported in the European Journal of Organic Chemistry. The method employs a one-pot approach combining chlorination and sulfoxidation steps, achieving yields exceeding 85% compared to traditional multi-step protocols. Structural characterization via X-ray crystallography confirmed the precise configuration of the dichlorophenyl ring, which adopts an eclipsed conformation relative to the sulfinyl group - a critical factor influencing its interaction with biological targets.

In pharmacological evaluations, this compound has shown selective inhibition against matrix metalloproteinase (MMP)-9 at sub-micromolar concentrations without affecting MMP-2 activity. This selectivity was attributed to the steric hindrance imposed by the dichlorinated phenyl group during enzyme-substrate docking simulations performed using AutoDock Vina software. These findings were corroborated by in vivo studies demonstrating reduced tumor angiogenesis in murine xenograft models treated with conjugates containing this compound's hydrazide moiety.

Ongoing research focuses on exploiting its redox-triggered properties for constructing smart nanocarriers. A collaborative study between MIT and Weill Cornell Medicine recently engineered lipid nanoparticles functionalized with this compound's sulfoxide group, achieving targeted delivery efficiency over 70% in pancreatic cancer models. The methanesulfinyl functionality facilitated intracellular reduction by thioredoxin reductase, enabling payload release specifically within hypoxic tumor regions.

The compound's structural versatility has also led to investigations in non-biological applications such as electrochemical sensing systems. Researchers at ETH Zurich integrated it into graphene oxide-based biosensors through Schiff base formation with its hydrazide group, achieving femtomolar detection limits for hydrogen peroxide - critical for monitoring oxidative stress biomarkers in clinical diagnostics.

Critical reviews published in 2023 highlight its role as a privileged scaffold for designing multitarget agents addressing complex pathologies like neurodegenerative diseases. Molecular dynamics simulations revealed that the dichlorophenyl substituent enhances blood-brain barrier permeability while maintaining selectivity for amyloid-beta aggregation inhibition - properties validated through in vitro assays using Alzheimer's disease cellular models.

Current safety assessments indicate favorable pharmacokinetic profiles when administered intravenously at therapeutic doses, with plasma half-life exceeding 8 hours due to metabolic stability from its sulfone-like sulfoxide group. These attributes align with FDA guidelines for biocompatible drug carriers while avoiding interactions with cytochrome P450 enzymes - a significant advantage over traditional hydrazone-based linkers.

Emerging applications now explore its use in CRISPR-based gene editing systems as a delivery enhancer through membrane permeabilization mechanisms observed during cell uptake studies. This novel direction opens possibilities for precision medicine approaches requiring efficient intracellular delivery of genetic material without viral vectors.

The integration of computational chemistry tools like DFT modeling has further accelerated structure-property relationship studies around this molecule's core framework. These analyses predict that substituting one chlorine atom on the phenyl ring could enhance water solubility by up to 30%, suggesting promising avenues for formulation optimization without compromising bioactivity.

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