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.

A four dimensional quantitative structure activity relationship analysis was applied to a series of 50 flavonoid inhibitors of p56 lck protein tyrosine kinase by the molecular comparative electron topological method. It was found that the -log (IC50) values of the compounds were highly dependent on the topology, size and electrostatic character of the substituents at seven positions of the flavonoid scaffold in this study. Depending on the negative or positive charge of the groups correctly embedded in these substituents, three-dimensional bio-structure to increase or decrease -log (IC50) values in the training set of 39 compounds was predicted. The test set of 11 compounds was used to evaluate the predictivity of the model. To generate 4D-QSAR model, the defined function groups and pharmacophore used as topological descriptors in the calculation of activity were of sufficient statistical quality (R 2 = 0.72 and Q 2 = 0.69). Ligand docking approach by using Dock 6.0. These compounds include many flavonoid analogs, They were docked onto human families of p56lck PTKs retrieved from the Protein Data Bank, 1lkl.pdb.

The reaction of 1-amino-5-(4-methylbenzoyl)-4-(4-methylphenyl)pyrimidin-2(1H)-one/-thione (1a,b) with ethyl acetoacetate (EA) afforded moderate to good yields (59-63%) of ethyl 2-methyl-4-(4-methylbenzoyl)-5-(4-methylphenyl)-7-oxo/-thioxo-3,3a-dihydropyrazolo[1,5-c]pyrimidine-3-carboxylate (2a,b). The newly synthesized compounds were characterized by elemental analyses, IR, 1 H and 13 C NMR spectral data. All were compared with their previous analogues. The reaction mechanism of 1 with EA was studied by means of the B3LYP/6-31G(d,p) method. In addition, for reactants Fukui functions were performed using the data calculated with the Becke3-Lee-Yang-Parr (B3LYP) hybrid function.

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The molecule of the title compound, C(22)H(19)N(3)O(2)S, is not planar. The dihedral angle between the two phenyl rings is 27.46 (7) degrees and in the dihydropyrazolopyrimidine ring the total puckering amplitude Q(T) is 0.526 (3) A. The structure is stabilized by both intra- and intermolecular C-H.O interaction, and by an intermolecular N-H.S hydrogen bond.

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In the title mol­ecule, C27H23N3O2, the three benzene rings make dihedral angles of 84.4 (1), 36.6 (1) and 59.3 (1)° with the central pyrimidine ring. In the crystal structure, mol­ecules associate into centrosymmetric dimers via weak C—H⋯O hydrogen‐bonding inter­actions.