Structure and syntheses of texazone. 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid, an actinomycete metabolite.

نویسندگان

  • N N Gerber
  • H L Yale
  • W A Taber
  • I Kurobane
  • L C Vining
چکیده

Cultures of actinomycete strain WRAT-210 produced a dark red crystalline metabolite which was named texazone. Spectroscopic evidence suggested that the structure of texazone is 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid. The structure was confirmed by chemical synthesis through oxidative dimerization of ethyl 3-amino-4-hydroxybenzoate with 2-(N-methylamino)phenol and subsequent hydrolysis of the resultant phenoxazinone ester.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Hydroxylated 2-amino-3H-phenoxazin-3-one derivatives as products of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) biotransformation by Chaetosphaeria sp., an endophytic fungus from Aphelandra tetragona.

The biotransformation of the phytoanticipin HBOA and its major degradation metabolites 2-hydroxy-N-(2-hydroxyphenyl)acetamide (7) and N-(2-hydroxyphenyl)acetamide (8) by Chaetosphaeria sp., an endophytic fungus isolated from Aphelandra tetragona, was studied. Three new metabolites could be identified as 2-amino-7-hydroxy-3H-phenoxazin-3-one (12), 2-acetylamino-7-hydroxy-3H-phenoxazin-3-one (13)...

متن کامل

SYNTHESES, ANTIBACTERIAL AND ANTIFUNGAL ACTIVITIES OF 2-ARYL-4- QUINOLINE- CARBOXAMIDE DERIVATIVES

Reaction of aryl methyl ketone with isatin in the presence of a base afforded 2- arylquinoline-4-carboxylic acid (3). Reaction of diazomethane with compound 3 yielded the ester 4. Compound 5 was prepared from the reaction of N, N'-dialkylethyl (or propyl) arnine with 4. Addition of hydrazine hydrate to compound 4a gave 2- (2- pyridyl) quinoline-4-carboxylic acid hydrazide (6). Reaction of l...

متن کامل

Inhibitive Assessment of N-(8-bromo-3H-phenoxazin-3-ylidene)-N,N’-Dimethylaminium, as a Novel Corrosion Inhibitor for Mild Steel in 1.0 M HCl

The inhibition effect of N-(8-bromo-3H-phenoxazin-3-ylidene)-N,N’-dimethylaminium (DPhDMA) on the corrosion behavior of mild steel in 1.0 M HCl solution has been studied. Weight loss measurements, potentiodynamic polarization, electrochemical impedance spectroscopy (EIS) and quantum chemical calculations were used in this study. Electrochemical results revealed that DPhDMA is an effective mixed...

متن کامل

SYNTHESES, ANTIFUNGAL AND ANTIBACTERIAL ACTIVITIES OF SUBSTITUTED 1,2, CTRIMOLES

The reaction of readily available 1 -methyl-4-nitropyrrole-2- carboxylic acid (1) with thionyl chloride afforded the corresponding acyl chloride 2. The reaction of compound 2 with thiosemicarbazides yielded 1-(1 -methyl-4-nitrop yrrole-2-carbony1)- thiosemicarbazides (3) which cyclized in basic medium to 5-(1-methyl-4-nitropyrrole- 2-y1)-2,4-dihydro-3H- l,2,4-triazole-3- thione 4. Alkylatio...

متن کامل

Identification and characterization of in vitro metabolites of 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz [de,h]isoquinoline-1,3-dione (Azonafide).

Azonafide (2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de, h]isoquinoline-1,3-dione) is the parent of a new series of anthracene-containing antitumor agents. Its structure is based on amonafide but lacks a primary amine and has an anthracene chromophore rather than a naphthalene chromophore. Using a rat liver cytosol incubation and HPLC/MS detection, we have identified four metabolites re...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • The Journal of antibiotics

دوره 36 6  شماره 

صفحات  -

تاریخ انتشار 1983