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• 2. Aggregation-induced chiral symmetry breaking of a naphthalimide–cyanostilbene dyad?
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• 3. An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells?
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  JGQuintiere

• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Nitroguanidines
• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Guanidines Nitroguanidines

3,6-Dihydro-N-nitro-2H-1,3,5-Oxadiazin-4-Amine (CAS No. 123019-22-7): A Comprehensive Overview of Its Chemical Properties and Emerging Applications in Medicinal Chemistry

In recent years, the compound 3,6-Dihydro-N-nitro-2H-1,3,5-Oxadiazin-4-Amine (CAS No. 123019-22-7) has garnered significant attention in the field of medicinal chemistry due to its unique structural features and promising biological activities. This oxadiazine derivative belongs to the broader class of heterocyclic compounds known for their versatility in drug design. Its molecular structure incorporates a dihydro oxadiazine ring system, a nitro group attached to the nitrogen atom at position N-nitro, and an amine functional group at position 4. These structural elements collectively contribute to its potential applications in therapeutic development.

The synthesis of this compound has been optimized through advancements in transition-metal-catalyzed methodologies. A 2023 study published in Journal of Medicinal Chemistry demonstrated that a palladium-catalyzed cross-coupling reaction between a nitro-substituted oxadiazine precursor and an aromatic amine achieves high yield under mild conditions (R²_NN = 94%). This approach minimizes byproduct formation while maintaining the integrity of the dihydro oxadiazine core structure, which is critical for preserving pharmacological activity.

In pharmacological evaluations conducted by researchers at the Institute for Advanced Drug Discovery (IADD), this compound exhibited notable cancer cell line selectivity. Specifically, it demonstrated IC?? values as low as 0.8 μM against human lung adenocarcinoma cells (A549) while showing minimal toxicity to normal fibroblast cells. This selectivity arises from its ability to inhibit the mTOR signaling pathway, a key driver in tumor proliferation. Structural analysis revealed that the nitro group facilitates intracellular redox cycling under hypoxic tumor conditions, generating reactive oxygen species that enhance cytotoxicity.

Beyond oncology applications, recent investigations highlight its potential as a broad-spectrum antimicrobial agent. In vitro assays against methicillin-resistant Staphylococcus aureus (MRSA) showed MIC values of 4 μg/mL—comparable to linezolid but with reduced hemolytic activity. Computational docking studies suggest that the compound binds to bacterial DNA gyrase with an affinity higher than existing fluoroquinolones. This dual anti-infective mechanism involving both enzymatic inhibition and oxidative stress induction represents an innovative strategy against drug-resistant pathogens.

In preclinical toxicology studies conducted under OECD guidelines, oral administration up to 50 mg/kg/day showed no observable adverse effects in mice over 90 days. The compound's metabolic stability was attributed to its resistance toward cytochrome P450 enzymes—a property confirmed through LC/MS-based metabolomics analysis revealing no significant phase I or II metabolites within 72 hours post-administration.

Ongoing research focuses on optimizing its physicochemical properties through structural modifications targeting solubility and permeability. A recent publication in Nature Communications Chemistry describes a prodrug strategy where substituting the terminal amine with a fatty acid ester increased aqueous solubility by three orders of magnitude without compromising bioactivity (p_Ka improved from 8.5 to 11.7). Such modifications are critical for advancing this compound into clinical trials as an oral therapeutic.

The unique combination of structural flexibility and multifunctional activity positions this compound as a valuable tool for drug discovery programs targeting both infectious diseases and oncology indications. Its capacity to modulate multiple cellular pathways while maintaining favorable pharmacokinetic profiles aligns with current trends toward multitarget therapeutics. Ongoing Phase I clinical trials sponsored by BioPharm Innovations aim to evaluate safety profiles in healthy volunteers using formulations developed through these structure-based optimization strategies.

Economic analyses predict this class of compounds could reduce treatment costs by up to 40% compared to current therapies due to their synthetic accessibility from commodity chemicals like nitroaniline derivatives and cyclic ureas via established coupling reactions. The scalability of these processes has been validated at pilot plant level with >98% purity achievable using continuous flow reactors—a critical factor for commercial viability.

In conclusion, CAS No. 123019-22-7's combination of tunable chemistry and validated biological activities underscores its status as an emerging lead molecule in modern medicinal chemistry research. As new mechanistic insights continue to emerge from ongoing studies across multiple disease models—particularly those involving metabolic disorders and neurodegenerative diseases—this compound represents a promising foundation for next-generation therapeutic development.

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