Structural Examination of 6-Methylsulphonylphenanthro-[9,10-C]-furan-1(3H)-one—A Rofecoxib Degradation Product
نویسنده
چکیده
In the attempt to discover a new polymorph of rofecoxib (Vioxx®), an unexpected product resulted. The product was characterised by chemical composition, thermal behaviour and structure and found to be 6-methylsulphonylphenanthro-[9,10-C] furan-1(3H)-one, a photo-cyclization degradation product of rofecoxib. This is a significant finding because it indicates that without appropriate control of the recrystallisation procedures, the structural integrity of rofecoxib may be seriously compromised.
منابع مشابه
Crystal structure of 3-(3,4-dimethylanilino)-2-benzofuran-1(3H)-one
In the title compound, C16H15NO2, the 2-benzo-furan-1(3H)-one and 3,4-di-methyl-aniline fragments are oriented with a dihedral angle of 89.12 (5)°. N-H⋯O hydrogen-bond inter-actions join mol-ecules into C(6) chains propagating along the a axis. In addition, there are π-π stacking inter-actions between the 2-benzo-furan-one benzene rings [centroid-centroid dis-tance = 3.7870 (13) Å] and C-H⋯π in...
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Chem. Abstr. Serv. Reg. No.: 126-07-8 Deleted CAS Nos: 8027-03-0; 8055-10-5; 3426-54-8; 11103-62-1; 24659-79-8 Chem. Abstr. Name: (1′S,6′R)-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro[benzofuran-2(3H),1′-[2]cyclohexene]-3,4′-dione IUPAC Systematic Name: 7-Chloro-2′,4,6-trimethoxy-6′β-methylspiro[benzofuran-2(3H),1′-[2]cyclohexene]-3,4′-dione Synonyms: (2S,4′R)-7-Chloro-2′,4,6-trimethoxy-4′-methyl...
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In the title compound, C(13)H(15)NO(3), the dihydro-furan-one ring is planar to within 0.012 (4) Å and it forms a dihedral angle of 42.8 (2)° with the benzene ring. The amino-ethyl-idene group is coplanar with the dihydro-furan-one ring. The meth-oxy group is slightly twisted away from the benzene ring. An intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring, is observed. In the crystal...
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The title compound, [Pd(4)(CH(2))(2)Cl(4)(C(28)H(40)P(2))(2)]·5C(4)H(8)O, possesses a tetra-nuclear palladium core with four bridging chlorido ligands and two bridging methyl-ene units, as well as two bridging anthracene-based bis-phosphine ligands. This tetra-nuclear complex can be considered as being composed of two μ-chlorido-bridged LPd(2) units. The structural motif of these LPd(2) units s...
متن کاملSynthesis and E/Z Configuration Determination of Novel Derivatives of 3-Aryl-2-(benzothiazol-2'-ylthio) Acrylonitrile 3-(Benzothiazol-2'-ylthio)-4-(furan-2''-yl)-3-buten-2-one and -(1-(Furan-2''-yl)-3'-oxobut-1''-en-2-ylthio)-3-phenylquinazolin-4(3H)-on
Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a–b exclusively, while the condensation of the compound 2 with benzaldehyde or parasubstituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c–e with preferentially formation of the E-isomer. Condensation of furan-2-carba...
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عنوان ژورنال:
دوره 3 شماره
صفحات -
تاریخ انتشار 2010