6657-02-9

Upstream product

• 17333-84-5 3-chlorobenzenediazonium 
• 108-95-2 phenol 
• 108-42-9 3-chloro-aniline 

Relevant academic research and scientific papers

Synthesis of diaryl-azo derivatives as potential antifungal agents

As compared with a commercially available agricultural fungicide hymexazol, some phenyl-azo phenol derivatives (e.g., 4a, 4b, 4f, 4n, 4q, 4u, and 4v) exhibited the more promising and pronounced antifungal activities in vitro against seven phytopathogenic fungi. It seemed that 4-((un)substituted phenylazo)-phenol and 4-((un)substituted phenylazo)-3-methylphenol might be considered as new lead structures for further design of agricultural fungicides.

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.