Alkylammonium Guest Induced‐Fit Recognition by a Flexible Dihomo­oxacalix[4]arene Derivative

Talotta, Carmen; Gaeta, Carmine; Rosa, Margherita De; Ascenso, José R.; Marcos, Paula M.; Neri, Placido

doi:10.1002/ejoc.201501319

Cited by 38 publications

(15 citation statements)

References 66 publications

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“…Interestingly, only in 33 % of the cases were the NMR shielding tensors computed at the level of theory reported in the seminal publication (B3LYP/6‐31G(d,p)//MMFF) –. In the remaining 67 %, the geometry optimization steps was conducted at higher levels, such as B3LYP or mPW1PW91 DFT functionals, coupled with double‐ or triple‐ζ basis sets –. Hereafter, three representative examples of the use of CP3 in solving different types of structural problems are given.…”

Section: Cp3mentioning

confidence: 99%

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Grimblat

Sarotti

2016

Chemistry A European J

187

147

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The calculations of NMR properties of molecules using quantum chemical methods have deeply impacted several branches of organic chemistry. They are particularly important in structural or stereochemical assignments of organic compounds, with implications in total synthesis, stereoselective reactions, and natural products chemistry. In studying the evolution of the strategies developed to support (or reject) a structural proposal, it becomes clear that the most effective and accurate ones involve sophisticated procedures to correlate experimental and computational data. Owing to their relatively high mathematical complexity, such calculations (CP3, DP4, ANN-PRA) are often carried out using additional computational resources provided by the authors (such as applets or Excel files). This Minireview will cover the state-of-the-art of these toolboxes in the assignment of organic molecules, including mathematical definitions, updates, and discussion of relevant examples.

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Section: Cp3mentioning

confidence: 99%

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Grimblat

Sarotti

2016

Chemistry A European J

187

147

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“…Calixarenes show a central hydrophobic cavity of controllable size, in addition to a wide upper rim and a narrow lower rim. The synthetic and structural versatility of these macrocycles make them suitable for different applications, (Böhmer, 1995 ; Gaeta et al, 2002 ; De Rosa et al, 2015 ; Neri et al, 2016 ; Talotta et al, 2017 ) including molecular recognition and sensing (Guo et al, 2011 , 2012 , 2013 ; Gaeta et al, 2012 ; Guo and Liu, 2014 ; Sun et al, 2016 ; Talotta et al, 2016 ; Yeon et al, 2016 ; Zheng et al, 2018 ), self-assembly processes (Rebek, 2000 ; Rudkevic, 2001 ; Díaz- Moscoso et al, 2016 ), synthesis of interpenetrated architectures (Gaeta et al, 2013 , 2016 ; Arduini et al, 2016 ; De Rosa et al, 2017c ; La Manna et al, 2017 ; Talotta et al, 2018 ), and catalysis (Cacciapaglia and Mandolini, 2000 ; Li et al, 2011 ; Deraedt and Astruc, 2016 ; Stoikov et al, 2016 ; Yilmaz and Sayin, 2016 ).…”

Section: Reaction Organocatalyzed By Cavity-containing Macrocyclic Scmentioning

confidence: 99%

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

et al. 2018

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In the last decades many efforts have been devoted to design supramolecular organocatalysts able to work in water as the reaction medium. The use of water as solvent provides promising benefits with respect to environmental impact. In this context, macrocyclic compounds played a role of primary importance thanks to their ease of synthesis and their molecular recognition abilities toward the reactants. The aim of this review is to give an overview of the recent advances in the field of supramolecular organocatalysis in water, focusing the attention on calixarene and cyclodextrins derivatives. Calixarenes and cyclodextrins, thanks to their hydrophobic cavities, are able to host selectively the substrates isolating they from the reaction environment. In addition, the synthetic versatilities of these macrocycles permits to introduce useful functional groups in close proximity of the hydrophobic binding sites. Regarding the cyclodextrins (CDs), we have here reviewed the their most recent uses as organocatalysts for the synthesis of heterocyclic compounds, in multi-component reactions and in carbon-carbon bond forming reactions. Examples have been reported in which CD catalysts are able to drive the regiochemistry of common organic reactions. In addition, cyclodextrins bearing catalytically active chiral groups, have shown excellent enantioselectivity in the catalysis of organic reactions. Recently reported results have shown that calixarene derivatives are able to accelerate organic reaction under “on-water” conditions with a significant selectivity toward the reactants. Under “on-water conditions” the hydrophobic effect, induced by insoluble calixarene derivatives, forces the reactants and the catalyst to aggregate and thus accelerating the reaction between them thanks to an amplification of weak secondary interactions. Regarding the use of water-soluble calixarene organocatalysts, we have here reviewed their role in the acceleration of common organic reactions.

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“…Dihomooxacalix [4]arene was initially reported by Gutsche et al (1981). However, over the past several years, dihomooxacalix [4]arene macrocycles and their functional derivatives were used for ion-binding application (Marcos et al, 2006(Marcos et al, , 2014Gaeta et al, 2012;Talotta et al, 2016;Liu et al, 2017Liu et al, , 2018An et al, 2018). It would seem surprising that as yet few works are so far known about the bioactivity-based approach (Harris, 1995).…”

Section: Introductionmentioning

confidence: 99%

Structural Design, Synthesis, and Preliminary Biological Evaluation of Novel Dihomooxacalix[4]arene-Based Anti-tumor Agents

Wang

Han

et al. 2019

Front. Chem.

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Calixarene and its derivatives have extensively served as promising anti-tumor agents. Previously, we have synthesized a series of calix[n]arene polyhydroxyamine derivatives (n = 4, 6, 8) and found that 5,11,17,23-tetra-tert-butyl-25,27-bis [N-(2-hydroxyethyl)aminocarbonylmethoxyl] calix[4]arene (CLX-4) displayed significant effect toward SKOV3, A549, SW1990, HeLa, Raji, and MDA-MB-231 cancer cells. In the present work, we find a replacement of calix[4]arene bone and synthesized 19 novel structurally related dihomooxacalix[4]arene amide derivatives 4A−4S to optimize its efficacy. Their abilities to induce cytotoxicity in human lung carcinoma (A549) cells, breast cancer (MCF-7) cells, cervical cancer (HeLa) cells, hepatocellular carcinoma (HepG2) cells, as well as human umbilical vein endothelial (HUVEC) cells are evaluated in vitro. Encouraging results show that the majority of dihomooxacalix[4]arene amide derivatives are effective at inhibiting A549 cell proliferation with the corresponding IC 50 ranging from 0.6 to 20.1 µM. In particular, compounds 4A, 4D, and 4L explore markedly increased potency (IC 50 value is 2.0 ± 0.5 µM, 0.7 ± 0.1 µM, and 1.7 ± 0.4 µM) over the cytotoxicity profiles of control CLX-4, whose IC 50 value is 2.8 ± 0.3 µM. More interestingly, 4A also demonstrates the perfect cytotoxic effect against MCF-7, HeLa, and HepG2 cells with IC 50 values of 1.0 ± 0.1 µM, 0.8 ± 0.2 µM, and 2.7 ± 0.4 µM. In addition, the results proved that our synthesized 4A has much lower toxicity (41%) to normal cells at a concentration of 10 µM than that of 4D (90%). To reveal the mechanisms, the key indicators including the cell cycle and apoptosis are observed by the flow cytometry analysis in MCF-7 cells. The results demonstrate that both 4A and 4D can induce the MCF-7 cell cycle arrest in G0/G1 phase and cell apoptosis. Therefore, our finding proves that the dihomooxacalix[4]arene amide derivatives are convenient platforms for potential supramolecular anticancer agents.

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Alkylammonium Guest Induced‐Fit Recognition by a Flexible Dihomooxacalix[4]arene Derivative

Cited by 38 publications

References 66 publications

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

Structural Design, Synthesis, and Preliminary Biological Evaluation of Novel Dihomooxacalix[4]arene-Based Anti-tumor Agents

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Alkylammonium Guest Induced‐Fit Recognition by a Flexible Dihomo­oxacalix[4]arene Derivative

Cited by 38 publications

References 66 publications

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

Structural Design, Synthesis, and Preliminary Biological Evaluation of Novel Dihomooxacalix[4]arene-Based Anti-tumor Agents

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Alkylammonium Guest Induced‐Fit Recognition by a Flexible Dihomooxacalix[4]arene Derivative