Synthesis and biological evaluation of biaryl analogs of antitubulin compounds

Tozatti, Camila Santos Suniga; Khodyuk, Rejane Gonçalves Diniz; Silva, Adriano Olímpio da; Santos, Edson dos Anjos dos; Amaral, Marcos Serrou do; Lima, Dênis Pires de; Hamel, Ernest

doi:10.1590/s0100-40422012000900010

Cited by 2 publications

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References 17 publications

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“…Phenyl benzoate and their fluoro-derivatives (Scheme ) have been synthesized and characterized via 1 H NMR, Fourier transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC) and powder X-ray diffraction (Figures S1–S11). The synthetic procedure was undertaken using well established procedures and is provided in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of the Role of Isostructurality in Fluorinated Phenyl Benzoates

Dey

Chopra

2017

Crystal Growth & Design

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In this report, the occurrence of three-, two-, and one-dimensional (3D, 2D, and 1D) isostructurality in phenyl benzoate (D00) and their fluorinated analogues was investigated in terms of their molecular assembly in solid state structures. A one-dimensional C–H···OC chain is observed as a robust motif (∼ −21 kJ/mol) in the formation of the supramolecular architectures in these isostructural compounds. The isomorphous crystal structures exhibit 3D isostructurality or vice versa. The crystal packing shows that weak intermolecular C–H···F, C–H···O, C–H···π interactions, and π···π stacking are the main contributors providing stability toward the crystal lattice. The nature and energetics of all the geometrically or energetically equivalent building blocks associated with similar or different intermolecular interactions delineate the role of different molecular pairs in the crystal structures. The fingerprint plots of the isostructural set of crystal structures help to understand the similarities and the differences in the various interatomic contacts. A comparison of these crystal structures with fluorinated N-phenyl benzamides shows the change in supramolecular assembly in terms of intermolecular interactions as well as the lattice energy due to the participation of a strong donor (N–H).

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Section: Methodsmentioning

confidence: 99%