Experimental and theoretical investigation of the molecular and electronic structure of 5-(4-aminophenyl)-4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine.
ABSTRACT The title molecule, 5-(4-aminophenyl)-4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine (C(20)H(21)N(3)S), was prepared and characterized by (1)H-NMR, (13)C-NMR, IR and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2(1)/c with a = 9.4350(5) A, b = 11.2796(6) A, c = 18.4170(8) A and beta = 113.378(3) degrees . In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies, gauge including atomic orbital (GIAO) (1)H- and (13)C-NMR chemical shift values and atomic charges distribution of the title compound in the ground state have been calculated using the Hartree-Fock (HF) and density functional method (DFT) (B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of the title compound was obtained by semi-empirical (AM1) calculations with respect to two selected degrees of torsional freedom, which were varied from -180 degrees to +180 degrees in steps of 10 degrees . Besides, frontier molecular orbitals (FMO) analysis was performed by the B3LYP/6-31G(d) method.
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ABSTRACT: A correlation-energy formula due to Colle and Salvetti [Theor. Chim. Acta 37, 329 (1975)], in which the correlation energy density is expressed in terms of the electron density and a Laplacian of the second-order Hartree-Fock density matrix, is restated as a formula involving the density and local kinetic-energy density. On insertion of gradient expansions for the local kinetic-energy density, density-functional formulas for the correlation energy and correlation potential are then obtained. Through numerical calculations on a number of atoms, positive ions, and molecules, of both open- and closed-shell type, it is demonstrated that these formulas, like the original Colle-Salvetti formulas, give correlation energies within a few percent.Physical review. B, Condensed matter 02/1988; 37(2):785-789.
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ABSTRACT: A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio)carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I.Bioorganic & Medicinal Chemistry 04/1997; 5(3):601-21. · 2.90 Impact Factor
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ABSTRACT: A series of arylthioureas (1), aromatic aldehyde thiosemicarbazones (2) and 5-aryl-2-furfuraldehyde thiosemicarbazones (3) were condensed with 2,4-dichloro-5-fluorophenacyl bromide to yield respective arylaminothiazoles, arylidene/5-aryl-2-furfurylidene hydrazinothiazoles (4). The newly synthesized compounds were characterized by IR, 1H-NMR and mass spectral studies. These compounds were also screened for their antibacterial and anti-inflammatory activities. Two of the newly synthesized compounds showed anti-inflammatory activity comparable with that of Ibuprofen.European Journal of Medicinal Chemistry 04/2003; 38(3):313-8. · 3.50 Impact Factor