(11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate

نویسندگان

  • Sundar Neelakantan
  • Sean Parkin
  • Peter A. Crooks
چکیده

Crystals of the title salt, C(17)H(28)NO(3) (+)·C(4)H(3)O(4) (-), were obtained by reacting parthenolide with dimethyl-amine followed by conversion of the amine adduct into a water-soluble fumarate salt. Subsequent crystallization of the fumarate salt from water afforded colorless ortho-rhom-bic crystals. The amine addition is highly stereospecific yielding exclusively a single diastereomer with R-configuration at the newly formed C-11 chiral carbon. In the crystal, intermolecular O-H⋯O and N-H⋯O hydrogen bonds help to establish the packing.

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

(11R)-13-[2-(4-Hydroxy­phen­yl)ethyl­amino]-4,5-ep­oxy-11,13-dihydro­costunolide monohydrate

THE TITLE COMPOUND (SYSTEMATIC NAME 12-{[2-(4-hydroxyphenyl)ethyl]aminomethyl}-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one monohydrate), C(23)H(31)NO(4)·H(2)O, was obtained by the reaction of tyramine with parthenolide. The configuration of the new chiral center in the title compound is R, establishing the stereospecificity of the amination reaction. The water molecule is ...

متن کامل

(11R,13R)-13-(Tetra­lin-1-ylamino)-4,5-ep­oxy-11,13-dihydro­costunolide

THE TITLE COMPOUND [SYSTEMATIC NAME: (12R)-4,8-dimethyl-12-[(1'R)-1',2',3',4'-tetrahydro-1'-naphthyl)aminomethyl]-3,14-dioxatricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one}, C(25)H(33)NO(3), was formed from the reaction of (1R)-1-amino-tetra-lin with parthenolide in methano-lic solution. X-ray crystal structure analysis determined that the configuration of the new chiral center in the title compound...

متن کامل

Synthesis and In Vitro Cytotoxic Activity of Novel [1,3] Dioxolo[4,5-g]Chromen-8-ones as a Chalcone-Like Agent

In this investigation, new structures based on homoisoflavonoids were designed. Homoisoflavonoids are considered as an important class of flavonoids with various biological properties such as cytotoxicity. A new series of benzylidene-6,7-dihydro-8H-[1,3]dioxolo[4,5-g] chromen-8-one derivatives were developed and their cytotoxic activities evaluated for all compounds on three human breast cancer...

متن کامل

Synthesis and properties of imidazolo-fused benzotriazinyl radicals.

1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one, the oxidation product of 1,3-diphenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl (Blatter's radical), reacts with N'-arylbenzamidines in PhMe at ca. 100 °C in the presence of N,N-diisopropylethylamine (Hünig's base) (1 equiv.) to give N'-aryl-N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzimidamides in 49-95% yield. In neat AcOH heated at...

متن کامل

Rational Design, Synthesis and Computational Structure-Activity Relationship of Novel 3-(4-Chlorophenyl)-5-(3-Hydroxy-4-Ethoxyphenyl)-4,5-Dihydro-1H-Pyrazole-1-Carboxamide

Densely functionalized 3-(4-chlorophenyl)-5-(3-hydroxy-4-etoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide was  synthesized in an expedient manner through specification and transamidation  respectively, of ester-functionalized pyrazoles. This synthetic protocol allowed for three diversifying steps in which appendages on the pyrazole scaffold were adjusted to optimize inhibition of protein kina...

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:

دوره 65  شماره 

صفحات  -

تاریخ انتشار 2009