1-Phenazinecarboxamide

ChEBI: An aromatic amide that is phenazine substituted at C-1 with a carbamoyl group.

Phenazine-1-carboxamide is an aromatic amide that is phenazine substituted at C-1 with a carbamoyl group. It is a member of phenazines, an aromatic amide and a monocarboxylic acid amide.

Add aniline and 2-bromo-3-nitrobenzoic acid to 2, 3-butanediol, add CuCl, Cu powder and N-ethylmorpholine, and heat and stir at 70 C for 15h.Wash with 0.1M ammonia, filter, The resulting solution was slowly poured into 2M HCl to obtain the intermediate 3-nitro-2-phenylaminobenzoic acid;Add it and NaBH4 to a solution in 2M NaOH, reflux for 5h, and cool in an ice bath.Acidified with dilute hydrochloric acid to obtain phenazine-1-carboxylic acid;Under ice-bath conditions, phenazine-1-carboxylic acid was dissolved in dichloromethane, and oxalyl chloride and N, N-dimethylformamide were added dropwise under the protection of nitrogen. After stirring at room temperature for 16 hours, Remove the volatiles in vacuo and cool to 0 C.Add ammonia dropwise and stir for half an hour, The reaction was filtered to give a solid, After drying, it was recrystallized from ethyl acetate.Phenazine-1-carboxamide is obtained;The mixture with 1, 3-dichloroacetone was heated at 130 C for 1 h, and after cooling to room temperature, It was quenched by adding water, and the mixture was extracted with dichloromethane. The organic phase was dried over sodium sulfate, filtered, Concentrated under reduced pressure, Column chromatography gave 2- (1-phenazine) -4-chloromethyloxazole.Yellow liquid, 68% yield.

Oxychloroaphine (1-phenazinecarboxamide) is a simple phenazine produced by several species of Pseudomonas. Oxychloroaphine is a weakly active antifungal metabolite that plays a role in the biocontrol of plant diseases by several Pseudomonas strains. Oxychloroaphine and related phenazines are important dereplication standards in discovery research to eliminate leads due to high amounts of weakly potent actives.

Molecular Weight:223.23
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:223.074561919
Monoisotopic Mass:223.074561919
Topological Polar Surface Area:68.9
Heavy Atom Count:17
Complexity:307
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes