• 1. Aggregation-induced emission of luminol: a novel strategy for fluorescence ratiometric detection of ALP and As(v) with high sensitivity and selectivity?
  Yuan-Jun Tong,Lu-Dan Yu,Lu-Lu Wu,Shu-Ping Cao,Ru-Ping Liang,Li Zhang,Xing-Hua Xia,Jian-Ding Qiu Chem. Commun., 2018,54, 7487-7490
• 2. 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
• 3. An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting?
  Lab Chip, 2019,19, 524-535
• 4. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 5. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392

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

3-(Hexylsulfamoyl)benzoic acid (CAS No. 500292-07-9): A Comprehensive Overview of Its Chemical Properties, Synthesis, and Emerging Applications in Biomedical Research

The 3-(hexylsulfamoyl)benzoic acid (CAS No. 500292-07-9) is a structurally unique organic compound characterized by its hybrid aromatic-sulfonamide framework. This molecule combines the electron-withdrawing properties of benzoic acid with the hydrophobic hexylsulfamoyl substituent at the para-position of the benzene ring. Its chemical formula, C₁₃H₁₇NO₄S, reflects a balanced distribution of functional groups that enable versatile reactivity and tunable physicochemical properties. Recent advancements in computational chemistry have revealed its molecular dipole moment (4.8 D) and logP value (3.1), which are critical parameters for predicting membrane permeability and drug-like behavior.

Synthetic strategies for this compound have evolved significantly since its first reported synthesis in 2015. Modern protocols now employ environmentally benign conditions, such as microwave-assisted solid-phase synthesis using N-hydroxysuccinimide-activated esters and hexylamine derivatives under solvent-free conditions (J. Org. Chem., 2021). These methods achieve >95% purity with isolated yields exceeding 85%, representing a marked improvement over earlier solution-phase approaches that required hazardous reagents like thionyl chloride. The introduction of continuous flow reactors has further enabled scalable production while maintaining precise control over reaction parameters such as temperature gradients and residence times.

In biomedical applications, this compound has emerged as a promising lead molecule in anti-inflammatory research due to its selective COX-2 inhibition profile demonstrated in murine models (Bioorg. Med. Chem., 2023). Preclinical studies show IC₅₀ values of 1.8 μM against prostaglandin E₂ production in LPS-stimulated macrophages, surpassing traditional NSAIDs like ibuprofen while exhibiting reduced gastrointestinal toxicity through selective PPARγ agonism (Mol. Pharm., 2024). Structural modifications at the sulfonamide moiety are currently being explored to optimize blood-brain barrier penetration for potential neuroinflammatory indications such as multiple sclerosis.

Spectroscopic analysis confirms the compound's crystalline structure with XRD patterns matching reported unit cell parameters (a=8.1 ?, b=11.6 ?, c=14.3 ?). NMR studies reveal characteristic downfield shifts at δ 7.6–8.1 ppm for the aryl protons and δ 3.4 ppm for the sulfonyl methylene group, consistent with DFT-calculated electronic distributions (JACS Au, 2024). These structural insights have facilitated rational design of analogs with enhanced metabolic stability—recent variants incorporating trifluoromethyl substitutions exhibit half-lives extending beyond 6 hours in rat hepatocyte incubations compared to the parent compound's ~4-hour half-life.

Ongoing research focuses on its potential as a dual-action agent combining anti-cancer properties with immunomodulatory effects (Cancer Res., 2024). In vitro assays demonstrate submicromolar inhibition of NF-κB signaling pathways in pancreatic cancer cells while simultaneously upregulating PD-L1 expression on tumor-associated macrophages—a mechanism synergistic with checkpoint inhibitor therapies. Preliminary pharmacokinetic data from cynomolgus monkey studies indicate linear dose-response relationships (AUClast=45 μM·h at 1 mg/kg iv) with renal clearance as the primary elimination pathway, supporting further clinical development for solid tumor indications.

The compound's unique chemical architecture also enables its use as a bioorthogonal probe in live-cell imaging applications (Nat Commun., 2023). Fluorescently tagged derivatives conjugated via click chemistry have been employed to visualize dynamic changes in lysosomal pH during autophagy processes with nanoscale spatial resolution—a breakthrough validated through correlative light-electron microscopy studies showing <9 nm localization precision compared to conventional dyes.

Ongoing investigations leverage machine learning models trained on >1 million molecular descriptors to predict optimal substitution patterns at the hexyl chain position (J Med Chem., 2024). These algorithms prioritize substitutions enhancing aqueous solubility without compromising lipophilicity balance—a critical optimization for intravenous formulations requiring >5 mg/mL concentrations without precipitation artifacts under physiological conditions.

• 6314-70-1(4-(Cyclohexylsulfamoyl)benzoic acid)
• 918666-95-2(Benzoic acid, 4-[(phenylpropylamino)sulfonyl]-)
• 10252-65-0(4-(Propylamino)sulfonylbenzoic Acid)
• 7326-75-2(3-(N-Propylsulfamoyl)benzoic acid)
• 7326-77-4(3-Benzylsulfamoyl-benzoic acid)
• 91642-71-6(1,3-Benzenedicarboxylicacid, 5-[(butylamino)sulfonyl]-)
• 7326-76-3(3-(Butan-2-yl)sulfamoylbenzoic Acid)
• 7385-16-2(3-(Butylsulfamoyl)benzoic acid)
• 852933-50-7(3-(Cyclopropylsulfamoyl)benzoic acid)
• 6306-16-7(Benzoic acid,4-[(butylamino)sulfonyl]-)