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Synthesis and Characterization of Novel Pyridine Periodic Mesoporous Organosilicas and Its Catalytic Activity in the Knoevenagel Condensation Reaction.

ABSTRACT: The preparation of novel organic-inorganic hybrid mesoporous organosilica containing pyridinedicarboxamide functional groups uniformly distributed inside the nanostructured pore walls has been addressed. The mesoporosity and uniformity of the synthesized nanomaterials were characterized by different techniques such as nitrogen adsorption/desorption measurements and powder X-ray diffraction (PXRD). Additionally, the presence of the pyridinedicarboxamide in the pore walls of the nanomaterials was assessed by Fourier-transform infrared spectroscopy (FT-IR), as well as 29Si and 13C solid-state cross-polarization and magic angle spinning nuclear magnetic resonance (CP/MAS-NMR). The Knoevenagel condensation of aldehydes with active methylene compounds was carried out over the pyridinedicarboxamide functionalized mesoporous organosilica, which has been proven to be an efficient heterogeneous basic catalyst in the presence of ethanol as solvent. The catalytic activity of the investigated materials was investigated in the Knoevenagel condensation between malononitrile and several benzaldehyde derivatives exhibiting a high conversion (>90%) and excellent selectivity toward the final condensation products under very mild reaction conditions. Furthermore, the catalyst stability is noteworthy as it could be recycled and reused at least twelve times without any significant change in the performance.

SUBMITTER: Rajabi F

PROVIDER: S-EPMC7084680 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Synthesis and Characterization of Novel Pyridine Periodic Mesoporous Organosilicas and Its Catalytic Activity in the Knoevenagel Condensation Reaction.

Rajabi Fatemeh F Ebrahimi Arezoo Zare AZ Rabiee Ahmad A Pineda Antonio A Luque Rafael R

Materials (Basel, Switzerland) 20200302 5

The preparation of novel organic-inorganic hybrid mesoporous organosilica containing pyridinedicarboxamide functional groups uniformly distributed inside the nanostructured pore walls has been addressed. The mesoporosity and uniformity of the synthesized nanomaterials were characterized by different techniques such as nitrogen adsorption/desorption measurements and powder X-ray diffraction (PXRD). Additionally, the presence of the pyridinedicarboxamide in the pore walls of the nanomaterials was ...[more]

PMID: 32121622

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Project description:A series of arylidenes derivatives was synthesized under ultrasonic methodology via Knoevenagel condensation reaction of cyanoacetohydrazide derivative with the appropriate aldehydes and/or ketone. The anticancer properties of the newly synthesized compounds were tested against four different human cancer cell lines (HEPG-2, MCF-7, HCT-116, and PC-3); compounds 5d and 6 demonstrated the greatest anticancer activity against all cancer cell lines. The MLR technique was used to create the QSAR model using five molecular descriptors (AATS6p, AATS7p, AATS8p, AATS0i, and SpMax4_Bhv). The examination of the constructed QSAR model equations revealed that the selected descriptors influence the tested compound's anti-proliferative activity. The descriptors identified in this work by QSAR models can be utilized to predict the anticancer activity levels of novel arylidenes derivatives. This will allow for significant cost savings in the drug development process and synthesis at pharmaceutical chemistry laboratories. According to the physicochemical properties, the results revealed that all of these compounds comply with Lipinski's Rule of Five, indicating that they may have high permeability across biological membranes and reveal drug-relevant properties. The Swiss Target Prediction webtool was used to assess the probable cellular mechanism for the promising candidate compounds (5d and 6), and the results revealed that adenosine A1 receptor (ADORA1) was a common target for both compounds. ADORA1 is involved in the regulation of cell metabolism and gene transcription. ADORA1 overexpression has been linked to a variety of cancers, including colon cancer, breast cancer, leukemia, and melanoma. The docking study of tested compounds 5d and 6 revealed that their binding scores to ADORA1 are more favorable than those of its co-crystalized ligand (DU172, selective ADORA1 antagonist) and adenosine (ADORA1 endogenous agonist), implying that they may hold great promise as an anti-cancer therapy. Density functional theory (DFT) with a (B3LYP)/6-31G (d,p) basis set was used to calculate the physicochemical parameters of these compounds. The theoretical data from the DFT computation was found to be in good agreement with the experimental values.

Dataset Information

Synthesis and Characterization of Novel Pyridine Periodic Mesoporous Organosilicas and Its Catalytic Activity in the Knoevenagel Condensation Reaction.

Publications

Synthesis and Characterization of Novel Pyridine Periodic Mesoporous Organosilicas and Its Catalytic Activity in the Knoevenagel Condensation Reaction.

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