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Upstream product

• 108-44-1 1-amino-3-methylbenzene 
• 108-95-2 phenol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 2028-72-0 m-toluenediazonium chloride 

Relevant academic research and scientific papers

Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

Background and Purpose: Because of gastrointestinal irritation and kidney toxicity associated with non-steroidal anti-inflammatory drugs and the cardiovascular problems of Coxibs use, developing novel anti-inflammatory agents with reduced toxicity and improved selectivity remains a major challenge. Depending on our previous work, a novel series of pyridopyrimidinones IIIa-i has been synthesized via reaction of 6-amino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (I) and phenyldiazenyl aromatic aldehydes (IIa-i). All the new constructed compounds were fully characterized by elemental and spectral analysis. Methods: The target compounds IIIa–i were investigated for their potential towards COX inhibition, anti-inflammatory properties using carrageenan induced edema model in rat paw, and the ulcer indices of the most active members. Results: The ethyl pyridopyrmidinone-benzoates IIIf, IIIg and IIIh showed superior inhibitory activity of carrageenan induced edema to celecoxib. Furthermore, the pyridopyrimidinones IIId, IIIf, IIIg, and IIIi exerted improved COX-2 inhibitory activity (IC50 = 0.67–1.02 μM) comparing to celecoxib (IC50 = 1.11 μM). Moreover, the gastric ulcerogenic potential assay of compounds IIIf– h revealed their lower ulcerogenic liability than indomethacin with comparable effect to celecoxib. Conclusion: Virtual docking investigation of the most active candidates IIId, IIIf, IIIg and IIIi in the active site of COX-2 enzyme showed that these compounds implied interaction and binding motif similar to the cocrystallized ligand bromocelecoxib.

The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors

In this paper, a micro-fluidic optimized process for the continuous flow synthesis of azo compounds is presented. The continuous flow synthesis of Sudan II azo dye was used as a model reaction for the study. At found optimal azo coupling reaction temperature and pH an investigation of the optimum flow rates of the reactants for the diazotization and azo coupling reactions in Little Things Factory-MS microreactors was performed. A conversion of 98% was achieved in approximately 2.4 minutes and a small library of azo compounds was thus generated under these reaction conditions from couplers with aminated or hydroxylated aromatic systems. The scaled up synthesis of these compounds in PTFE tubing (i.d. 1.5 mm) was also investigated, where good reaction conversions ranging between 66-91% were attained.

Modified clays as efficient acid-base catalyst systems for diazotization and diazocoupling reactions

Diazotization and diazocoupling reactions of aniline and its substituted derivatives with phenol and other aromatic amines over ecofriendly clay catalysts is described. This inexpensive, non-corrosive and reusable catalysts were found to exhibit bifunctional catalytic properties for these reactions. No considerable decrease in the efficiency of the catalysts were observed after five cycles of operation. The new method totally avoids the use of acids and alkalies.

Antifungal agents

The present invention provides azo and stilbene compounds having the structure: wherein XY is N=N, CH=CH, (C=O)-NH or NH-(C=O); wherein Z is CR6 or N; wherein R1, R2 and R5 are independently hydrogen, halogen, NO2 or CF3; wherein R3 is hydrogen, halogen, CF3, aryl or heteroaryl, NO2 or OCF3; wherein R4 is hydrogen, halogen, CF3, aryl or heteroaryl, NO2 or linear or branched chain alkoxy; wherein R6 is hydrogen or linear or branched alkyl; wherein R7 is hydrogen, cyano, hydroxyalkyl, carboxyl, halogen, hydroxyl, formyl, NO2 or halogen; and wherein R8 is hydroxyl or substituted or unsubstituted amino; and wherein R9 and R10 are independently hydrogen, CN or hydroxyalkyl. Said compounds are useful as antifungal therapeutics, fungicides and fungistats. The present invention also provides methods of inhibiting fungal RNA transcription and treating fungal infections in human and animal subjects and fungal infestations in plants.

Mannich bases of phenolic azobenzenes possessing cytotoxic activity

A number of arylazophenols 1 were converted into the corresponding mono Mannich bases 2 from which two quaternary salts 3a,b and an ester 3c were prepared. A series of bis Mannich bases 4 were also synthesized. The angles (φ) made between one of the aryl rings and the adjacent azo linkage were determined by electronic absorption spectroscopy. X-ray crystallographic data were obtained for some of the Mannich bases. The compounds were evaluated against murine P388 D1 and L1210 cells and two human T-lymphocyte (Molt 4, CEM) lines, and most of the derivatives were also screened against a panel of human tumour cell lines. A number of correlations were noted between cytotoxicity and various physicochemical constants as well as some structural features determined by X-ray crystallography. Several of the Mannich bases were shown to have mutagenic properties using the λ RK mutatest; the compounds in series 2 and 4 have the ability to penetrate the central nervous system, as revealed by their anticonvulsant properties. While series 2-4 have the potential to deaminate forming ortho quinone methides which would be capable of alkylating cellular thiols, the results of stability studies suggest that the bioactivities noted were due to the molecules per se.