20788-06-1

Upstream product

• 303-07-1 2,6-Dihydroxybenzoic acid 
• 106-47-8 4-chloro-aniline 
• 20788-05-0 phenyl 2,6-dihydroxybenzoate 

Downstream Products

• 31936-02-4 N-(4-Chloro-phenyl)-2,6-dihydroxy-3-isobutyryl-benzamide 
• 31936-08-0 3-Butyryl-N-(4-chloro-phenyl)-2,6-dihydroxy-benzamide 
• 59402-80-1 3-(4-chlorophenyl)-5-hydroxy-2H-1,3-benzoxazine-2,4(3H)-dione 
• 30533-95-0 5-Jod-3-nitro-2,6-dihydroxy-benzoesaeure-4'-chloranilid 
• 25995-59-9 3-Bromo-N-(4-chloro-phenyl)-2,6-dihydroxy-5-nitro-benzamide 
• 25995-57-7 3-Chloro-N-(4-chloro-phenyl)-2,6-dihydroxy-5-nitro-benzamide 
• 51754-42-8 C₂₇H₁₈Cl₃N₃O₅ 
• 51754-45-1 Methoxymethyl-carbamic acid 4,6-dichloro-2-(4-chloro-phenylcarbamoyl)-3-methoxymethylcarbamoyloxy-phenyl ester 
• 51754-44-0 Dimethyl-carbamic acid 4,6-dichloro-2-(4-chloro-phenylcarbamoyl)-3-dimethylcarbamoyloxy-phenyl ester 
• 51754-43-9 Methyl-carbamic acid 4,6-dichloro-2-(4-chloro-phenylcarbamoyl)-3-methylcarbamoyloxy-phenyl ester 
• 41109-88-0 N-(4-chlorophenyl)-3,5-dichloro-2,6-dihydroxybenzamide 

Relevant academic research and scientific papers

Synthesis and antifungal evaluation of hydroxy-3-phenyl-2H-1,3-benzoxazine- 2,4(3H)-diones and their thioanalogs

(Chemical Equation Presented) A series of substituted 5-, 6-, 7-, and 8-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones (5-8) was synthesized by cyclization of corresponding dihydroxy-N-phenylbenzamides (1-4) with methyl chloroformate. The starting compounds 1-4 were prepared by the reaction of the respective dihydroxybenzoic acid, aniline and phosphorus trichloride via microwave irradiation. Thionation of compounds 8a-d employing Lawesson's reagent was used to prepare 5-hydroxy-3-phenyl-4-thioxo-3,4-dihydro-2H-1,3-benzoxazin- 2-ones (10a-d) and 5-hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones (11a-d). The position of sulfur in monothionated derivatives 9c and 10a-d was confirmed by 2D NMR methods. Attempts to prepare dithionated derivatives from the isomeric 6-, 7- or 8-hydroxy compounds 5-7 failed. All compounds were tested for their in vitro antifungal activity against eight test strains. Compounds 1-4 showed moderate activity and the cyclization to corresponding hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones (5-8) resulted in a decrease in antifungal activity. No antifungal activity was observed in thionated compounds 9c and 10-11.

2,6 Dihydroxybenzoic acid derivatives as anthelmintics

The 2,6 dihydroxybenzoic acid anilides have marked cesticidal properties when a specific form of substitution by halogen atoms or methyl groups is made in the anilide portion of the molecule. Optimum activity is achieved with 2,6 dihydroxybenzoic acid 4' bromanilide. This compound interferes with the energy metabolism of cestodes, inhibiting the breakdown of glucose and lowering the ATP level. The introduction of halogen atoms in the 3 and 5 position of the benzoic acid portion increases the activity but the toxicity as well. Activity against the liver fluke is also observed and prevails when an electronegative substituent is introduced in the 3 position. The most effective compounds are the 3 nitro 2,6 dihydroxybenzoic acid anilides, followed by the 3 acyl 2,6 dihydroxybenzoic acid anilides. The choice of substituents in the anilide portion is restricted to halogens, methyl groups, tri halogenated methyls, i.e. substituents which improve the lipoid solubility. Optimum efficacy is achieved with 3 nitro 2,6 dihydroxybenzoic acid 3',5' bis trifluoromethyl anilide. A description of the chemical methods of synthesis is given.