期刊
JOURNAL OF MOLECULAR STRUCTURE
卷 1244, 期 -, 页码 -出版社
ELSEVIER
DOI: 10.1016/j.molstruc.2021.130944
关键词
Acrylamide; X-ray crystallography; Hirshfeld surface maps; Anticancer activity
资金
- Facultad de Ciencias at the Universidad de los Andes [FAPA-P18.160422.043, INV-2019-84-1800]
- Direccion de Investigaciones at the Universidad Pedagogica y Tecnologica de Colombia [SGI-3073]
This study reported the stereoselective synthesis of novel (E)-2-cyano-3-(het)arylacrylamides 3 through a Knoevenagel condensation reaction, with high yields and moderate anti-cancer activity against various cancer cell lines.
We report the stereoselective synthesis of novel (E)-2-cyano-3-(het)arylacrylamides 3 in high yields by a triethylamine-catalyzed Knoevenagel condensation of cyanoacetamide ( 1 ) with (het)arylaldehydes 2 in ethanol under mild reaction conditions. The products were full characterized by IR, 1D and 2D NMR spectroscopy, mass spectrometry, and elemental analysis. Additionally, structures 3 were studied and confirmed by single-crystal X-ray diffraction, observing that the cyanoacrylamide fragment affects considerably the crystal growth. The cooperative non-covalent interactions and Hirshfeld surface analysis are discussed. Moreover, quantum chemical descriptors such as frontier molecular orbitals and HOMO-LUMO energy gap, as well as global reactivity descriptors were computed by the B3LYP method with 6-31G(d,p) basis set implemented in CrystalExplorer using the crystallographic information files (.cif) obtained from the X-ray diffraction measurements. Ultimately, the (E)-2-cyano-3-(het)arylacrylamides 3 exhibited moderate activity against T-47D breast, UACC-62 melanoma, NCI-H522 non-small cell lung, SR leukemia, and SNB-75 ovarian cancer cell lines with%GI values ranging from 7.98 to 14.83%. (c) 2021 Elsevier B.V. All rights reserved.
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