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Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.005 A Ê R factor = 0.045 wR factor = 0.116 Data-to-parameter ratio = 10.2 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2002 International Union of Crystallography Printed in Great Britain ± all rights reservedThe title compound, C 19 H 14 O 6 , is a derivative of 2,3-dioxo-2,3dihydrofuran. The furan ring is essentially planar and the phenyl rings in the methoxyphenyl and methoxybenzoyl groups are not parallel to each other. The furan and phenyl rings are not coplanar. In the crystal, there are two weak CÐ HÁ Á ÁO-type intermolecular interactions. Comment

In the title compound, C23H16N2O3·CH4O, the N—N bond distance in the pyrazole ring, which is planar within 0.008 Å, is 1.3634 (18) Å. The crystal packing is stabilized by O—H⋯O, O—H⋯N and C—H⋯O intermolecular hydrogen bonds.

The 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2,3-furandione (1) and various semi-/thiosemicarbazones 2a-h combine with loss of carbondioxide and water yielding l-methylenaminopyrimidine-2-one and -thione derivatives 3a-h, in moderate yields (43-59%). Hydrolysis of 5-(4-methylbenzoyl)-l-(methyl-4methylphenyimethylenamino)-4-(4-methylphenyl)-1 //-pyrimidine-2-one (3c) and 5-(4-methylbenzoyl)-4-(4methylphenyl)-l-(phenylmethylenamino)-l//-pyrimidine-2-thione (3h) lead to the l-amino-5-(4methylbenzoyl)-4-(4-methylphenyl)-l//-pyrimidine-2-one (4) and the l-amino-5-(4-methylbenzoyl)-4-(4-). The newly synthesized compounds were characterized by elemental analyses, IR, 'H and l3 C NMR spectral data. All were compared with their previous analogues. Brought to you by | Purdue University Libraries Authenticated Download Date | 5/27/15 6:26 AM Vol. 13, Nos. 2-3, 2007 Reactions of 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2,3-Furandione with semi-thiosemi-carbazones much interest for biological and medical reasons, thus their chemistry have been investigated extensively 25 . In particulary, various analogues of pyrimidines possess effective herbicidal, antibacterial, antifungal, antiviral 26 ' 27 . Some of them are frequently encountered in many drugs used for the treatment of hypothyroidy, hypertension, cancer chemotherapy or HIV infection 28 31 . In the present study, we carried out the reactions of 1 with several semi-/thiosemi-carbazones 2a-h, obtained from semi-/thiosemi-carbazide and the corresponding carbonyl compounds in our laboratories, yielding the new series of l-methyleneaminopyrimidine-2-one and -thione derivatives 3a-h. The l-Amino-5-(4-methylbenzoyl)-4-(4-methylphenyl)-l//-pyrimidine-2-thione (5).20 mL of water and 5 mL of acetic acid were added to a solution of 1 g 3h in 20 mL of butanol and the mixture was the heated under reflux for 45-50 minutes. With cooling 0.46g (58%) of 5 precipitated and was recrystallized from ethanol; m.p.

The in vitro cytotoxic potentials of Furo[3,2-c]pyran-4-one derivatives in human lymphocytes were investigated. Blood samples were obtained from six healthy donors, non-smoking volunteers, which were incubated and exposed to increasing concentrations (0.05, 0.1, 0.5, 1 and 2 mg/mL) of Furo[3,2-c] pyran-4-one derivatives which are methyl 2-methoxy-7-(4-methylbenzoyl)-6-(4-methylphenyl)-4-oxo-4H-furo [3,2-c]pyran-3-carboxylate (1a) and methyl 2-methoxy-7-(4-methoxybenzoyl)-6-(4-methoxyphenyl)-4-oxo-4H-furo[3,2-c]pyran-3-carboxylate (1b). Compounds 1a and 1b induced micronucleus, mitotic and replication indexes in human lymphocytes (1 and 2 mg/mL). The increases of micronucleus, mitotic and replication indexes show that compounds at high concentrations may become cytotoxic, genotoxic and carcinogenic.