14848-01-2

Usage

Uses

Used in Chemical Synthesis:
4-Azidobenzoyl chloride is used as a building block for the synthesis of various organic compounds, such as pharmaceuticals, dyes, and polymers. Its versatility in organic chemistry makes it a valuable component in the creation of new molecules.
Used in Click Chemistry:
4-Azidobenzoyl chloride is used as a reactant in click chemistry, a set of powerful and highly efficient reactions that are widely used in drug discovery and materials science. Its azide group allows for the introduction of azide functionality into molecules, enabling further chemical modifications and reactions.
Used in Pharmaceutical Industry:
4-Azidobenzoyl chloride is used as a reagent in the pharmaceutical industry for the synthesis of drug compounds. Its ability to introduce azide functionality into molecules can be utilized to create new drug candidates with specific properties and therapeutic effects.
Used in Dye and Polymer Industries:
4-Azidobenzoyl chloride is used as a precursor in the production of dyes and polymers. Its chemical properties allow for the development of new dyes with unique color characteristics and polymers with specific properties for various applications.
Safety Precautions:
When handling 4-azidobenzoyl chloride, care should be taken as it is corrosive and can cause irritation to the skin, eyes, and respiratory system. Proper safety measures, such as wearing protective clothing and using appropriate equipment, should be followed to minimize potential hazards.

InChI:InChI=1/C7H4ClN3O/c8-7(12)5-1-3-6(4-2-5)10-11-9/h1-4H

Upstream product

• 6427-66-3 4-azidobenzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 152564-58-4 3-(4-azidobenzoyl)-1,3-thiazolidine-2-thione 
• 92143-51-6 6-<(4-Azidobenzoyl)amino>-1-hexanol 
• 133295-96-2 3-(4-Azidobenzoyl)-6-methoxy-2-(4-methoxyphenyl)benzothiophene 
• 85287-36-1 6-<(4-Azidobenzoyl)amino>hexanoic acid 
• 326923-28-8 (3R,4S)-1-(4-Azido-benzoyl)-4-phenyl-3-triisopropylsilanyloxy-azetidin-2-one 
• 133295-94-0 3-(4-Aminobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)-benzothiophene 
• 131589-65-6 3-(4-Aminobenzoyl)-2-(4-hydroxyphenyl)-6-hydroxy-7-iodobenzothiophene 
• 131589-60-1 3-(4-Azidobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)-benzothiophene 
• 92143-48-1 6-<(4-Azidobenzoyl)amino>-1-bromohexane 
• 92143-46-9 6-<(4-Azidobenzoyl)amino>hexanoyl chloride 
• 92143-49-2 6-<(4-Azidobenzoyl)amino>-1-hexyl tosylate 
• 92143-50-5 1,7-Bis(9-acridinylamino)-4-<6-<(4-azidobenzoyl)amino>hexyl>-4-azaheptane 
• 64160-54-9 [5-methoxy-2-methyl-1-(4-nitro-benzoyl)-indol-3-yl]-acetic acid 

Relevant academic research and scientific papers

EPR Spectroscopy of Triplet Aryl Nitrenes Covalently Bound to α-Chymotrypsin. Application of Low-Temperature Methods to Photoaffinity Labeling

Reaction of α-chymotrypsin with various aryl azido acyl imidazoles leads to covalent attachment of the aryl azide to the enzyme via an ester linkage.Photolysis of frozen solutions of the modified enzymes at 77 K leads to intense EPR signals of the related triplet nitrenes.The position of the EPR resonance fields and the decay kinetics of the nitrenes can be interpreted in terms of the label being within or outside the binding pocket of the enzyme.Photolysis of methyl m-azidobenzoate in toluene at 298 K gives very little nitrene-derived product.At this temperature, ring expansion to a ketenimine that ultimately polymerizes is the major process.Photolysis of methyl m-azidobenzoate in frozen toluene at 77 K gives the triplet nitrene, which undergoes secondary photolysis leading to formal CH insertion into the solvent matrix.It is demonstrated that photolysis of α-chymotrypsin covalently modified with a m-azidobenzoyl group at serine-195 leads to more efficient labeling at 77 K than at 298 K.

Design and investigation of photoactivatable platinum(iv) prodrug complexes of cisplatin

Platinum(iv) carboxylate scaffolds have garnered considerable research interest because they can be engineered to function as prodrugs of clinical platinum(ii) anticancer drugs. These platinum(iv) prodrug complexes are stable and tunable, and activated by reduction to release their cytotoxic platinum(ii) cargo. Here we propose new platinum(iv) prodrug complexes designed to release cisplatin via photoreduction upon UV irradiation. The central strategy is to utilise aryl carboxylate ligands on the axial positions of that platinum(iv) scaffold that confer significant UV absorption and would stabilise carboxyl radical formation, thus favouring homolytic Pt-O bond cleavage. We isolated and identified aryl carboxyl radicals via spin-trapping and showed that the photoreduced platinum species mirror cisplatin reactivity toward DNA bases, thereby validating the efficacy of this approach.

Synthesis of C60 derivatives for photoaffinity labeling

In order to study the interaction of fullerenes with biological molecules, a novel photoaffinity labeling agent derived from C60 was designed and synthesized. As photosensitive functional groups, azide group, and aziridine group are utilized. A convenient synthetic route via fulleropyrrolidine 2 was employed to obtain compounds labeling agents 5 and 9.

Ethynylphosphonamidates for the Rapid and Cysteine-Selective Generation of Efficacious Antibody–Drug Conjugates

Requirements for novel bioconjugation reactions for the synthesis of antibody–drug conjugates (ADCs) are exceptionally high, since conjugation selectivity as well as the stability and hydrophobicity of linkers and payloads drastically influence the performance and safety profile of the final product. We report Cys-selective ethynylphosphonamidates as new reagents for the rapid generation of efficacious ADCs from native non-engineered monoclonal antibodies through a simple one-pot reduction and alkylation. Ethynylphosphonamidates can be easily substituted with hydrophilic residues, giving rise to electrophilic labeling reagents with tunable solubility properties. We demonstrate that ethynylphosphonamidate-linked ADCs have excellent properties for next-generation antibody therapeutics in terms of serum stability and in vivo antitumor activity.

Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors

We identified nitazoxanide (NTZ) as a moderate STAT3 pathway inhibitor through immunoblot analysis and a cell-based IL-6/JAK/STAT3 pathway activation assay. A series of thiazolide derivatives were designed and synthesized to further validate the thiazolide scaffold as STAT3 inhibitors. Eight out of 25 derivatives displayed potencies greater than that of NTZ, and their STAT3 pathway inhibitory activities were found to be significantly correlated with their antiproliferative activities in HeLa cells. Derivatives 15 and 24 were observed to be more potent than the positive control WP1066, which is under phase I clinical trials. Compared with NTZ, 15 also exhibited much improved in vivo pharmacokinetic parameters in rats and efficacies against proliferations in multiple cancer cell lines, indicating a broad-spectrum effect of these thiazolides as antitumor agents targeted on STAT3.

'Second-generation' 1,2,3-triazole-based inhibitors of: Porphyromonas gingivalis adherence to oral streptococci and biofilm formation

Several 'second-generation' click inhibitors of the multi-species biofilm propagated by the adherence of the oral pathogen Porphyromonas gingivalis to Streptococcus gordonii were synthesized and evaluated. The design of the structures was based on the results obtained with the first-generation diphenyloxazole 'click' inhibitors which bear suitable hydrophobic and polar groups within a dual scaffold molecule bearing a 1,2,3-triazole spacer. The structures of the synthetic targets reported herein now consist of a triazolyl(phenylsulfonylmethyl) and a triazolyl(phenylsulfinylmethyl) spacer which joins a 4,5-diphenyloxazole with both phenyl rings bearing lipophilic substituents. The triazolyl "linker" group is formed by a click reaction between the 4-azido(phenylsulfonyl/sulfinylmethyl) oxazoles and acetylenic components having aryl groups bearing hydrophobic substituents. The 1,3,5-trisubstituted-2,4,6-triazine scaffold of the most active click compounds were modeled after the structural motif termed the VXXLL nuclear receptor (NR) box. When substituted at the 3- and 5-positions with 2- and 4-fluorophenylamino and N,N-diethylamino units, the candidates bearing the 1,3,5-trisubstituted-2,4,6-triazine scaffold formed a substantial subset of the second-generation click candidates. Four of the click products, compounds 95, 111, 115 and 122 showed inhibition of the adherence of P. gingivalis to S. gordonii with an IC50 range of 2.3-4.3 μM and only 111 exhibited cytotoxic activity against telomerase immortalized gingival keratinocytes at 60 μM. These results suggest that compounds 95, 115, 122, and possibly 111 represent the most suitable compounds to evaluate for activity in vivo.

NEW TARGETED CYTOTOXIC RATJADONE DERIVATIVES AND CONJUGATES THEREOF

The present invention is directed to novel natural product-derived ratjadone-based compounds useful as payloads (or toxins) in drug-conjugates constructs with cell target binding moieties (CTBM) and payload-linker compounds useful in connection with drug conjugates. The present invention further relates to new ratjadone compositions including the aforementioned payloads, payload-linkers and drug conjugates, and methods for using these payloads, payload-linkers and drug conjugates, to treat pathological conditions including cancer, inflammatory and infectious diseases.

Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold

Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.

SURFACE-MODIFIED POLYMERIC SUBSTRATES GRAFTED WITH A PROPERTIES-IMPARTING COMPOUND USING CLIP CHEMISTRY

The present invention relates to an efficient method for grafting a properties-imparting compound onto a polymeric substrate containing carbon-hydrogen (C—H) bonds using clip chemistry. The method of the invention includes coating the substrate with the properties-imparting compound and irradiating it with a reactive light source, and repeating this sequence at least once. The present invention further relates to surface-modified polymeric substrates grafted with a properties-imparting compound, in particular obtained with the method of the invention, medical devices comprising same, and non-medical of said surface-modified polymeric substrates.

Synthesis and structures of zwitterionic polymers to induce electrostatic interaction with PDMS surface treated by air-plasma

Various zwitterionic polymers, sulfobetaine and phosphoryl choline derivatives were synthesized in order to investigate zwitterionic polymer structures toward surface modification of PDMS, where the adsorption of zwitterionic polymers on polydimethylsiloxane surface treated with air-plasma was induced by the electrostatic interaction,. The electrostatic interaction was evaluated with hydrophilicity. The results suggested that a sulfobetaine polymer with higher molecular weight, lower molecular weight distribution, and shorter alkyl chain afforded high electrostatic interaction. A sulfobetaine polymer bearing phenylazide group showed similar electrostatic interaction with the PDMS surface, and it is a promising material for surface modification ofpolydimethylsiloxane.