Chalcogen and Hydrogen Bonds at the Periphery of Arylhydrazone Metal Complexes

Gurbanov, Atash V.; Kuznetsov, Maxim L.; Resnati, Giuseppe; Mahmudov, Kamran T.; Pombeiro, Armando J. L.

doi:10.1021/acs.cgd.2c00322

Cited by 17 publications

(6 citation statements)

References 58 publications

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“…The chalcogen bond (ChB) has been recently exploited as a supramolecular tool for crystal growth and design involving metal complexes as tectons. 8,19–21 In this work, we have demonstrated that the simple design of ligands with a ChB donor selenium centre can contribute to the molecular oxygen and one-pot nitrile activation in copper( ii )-mediated synthesis. The tetravalent selenium atom acts as a ChB donor towards coordinated halogen atoms (Cl or Br) in the secondary coordination sphere of copper( ii ) complexes (see 2 , 3 and 5 in Scheme 3 and Fig.…”

Section: Discussionmentioning

confidence: 92%

Chalcogen bonding in copper(ii)-mediated synthesis

et al. 2023

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Section: Discussionmentioning

confidence: 92%

Chalcogen bonding in copper(ii)-mediated synthesis

et al. 2023

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“…Benzenesulfonamide derivatives AL56, AL106, AL107, AL109 (Figure 1A) AL34 and AL110 (Figure 1B) were synthesized as described in the Methods section. The purity of AL56, AL106, AL107, AL109 derivatives (>95%) were verified from the melting point, Nuclear Magnetic Resonance (NMR) spectrum, elemental analysis and mass spectrometry measurements as reported in [14,15]. The 1 H-NMR spectra of AL34 and AL110 in DMSO-d 6 , and CH=N is observed at 10.25 and 9.93 ppm, respectively.…”

Section: Benzenesulfonamide Derivatives' Interaction With Receptor Ty...mentioning

confidence: 96%

Benzenesulfonamide Analogs: Synthesis, Anti-GBM Activity and Pharmacoprofiling

Murugesan,

Konda Mani,

Thiyagarajan

et al. 2023

IJMS

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The tropomyosin receptor kinase A (TrkA) family of receptor tyrosine kinases (RTKs) emerge as a potential target for glioblastoma (GBM) treatment. Benzenesulfonamide analogs were identified as kinase inhibitors possessing promising anticancer properties. In the present work, four known and two novel benzenesulfonamide derivatives were synthesized, and their inhibitory activities in TrkA overexpressing cells, U87 and MEF cells were investigated. The cytotoxic effect of benzenesulfonamide derivatives and cisplatin was determined using trypan blue exclusion assays. The mode of interaction of benzenesulfonamides with TrkA was predicted by docking and structural analysis. ADMET profiling was also performed for all compounds to calculate the drug likeness property. Appropriate QSAR models were developed for studying structure–activity relationships. Compound 4-[2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl]-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfon-amide (AL106) and 4-[2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazinyl]-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (AL107) showed acceptable binding energies with the active sites for human nerve growth factor receptor, TrkA. Here, AL106 was identified as a potential anti-GBM compound, with an IC50 value of 58.6 µM with a less toxic effect in non-cancerous cells than the known chemotherapeutic agent, cisplatin. In silico analysis indicated that AL106 formed prominent stabilizing hydrophobic interactions with Tyr359, Ser371, Ile374 and charged interactions with Gln369 of TrkA. Furthermore, in silico analysis of all benzenesulfonamide derivatives revealed that AL106 has good pharmacokinetics properties, drug likeness and toxicity profiles, suggesting the compound may be suitable for clinical trial. Thus, benzenesulfonamide analog, AL106 could potentially induce GBM cell death through its interaction with TrkA and might be an attractive strategy for developing a drug targeted therapy to treat glioblastoma.

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“…The results of QTAIM analysis are summarized in Tables 1 and 2 The QTAIM analysis demonstrates the presence of appropriate bond critical points (3, −1) for HB, XB and ChB in model supramolecular associates (Table 1). The low magnitude of the electron density, positive values of the Laplacian of electron density and zero or very close to zero positive energy density in these bond critical points (3, −1) and estimated strengths for appropriate short contacts are typical for such non-covalent interactions is similar chemical systems [38,41,[48][49][50][51]. The balance between the Lagrangian kinetic energy G(r) and potential energy density V(r) at the bond critical points (3, −1) corresponding for HB, XB and ChB in model supramolecular associates reveals that a covalent contribution is absent in these contacts (−G(r)/V(r) > 1) [52].…”

Section: Contactmentioning

confidence: 97%

Halogen Bond-Assisted Supramolecular Dimerization of Pyridinium-Fused 1,2,4-Selenadiazoles via Four-Center Se2N2 Chalcogen Bonding

Dukhnovsky,

Novikov,

Kubasov

et al. 2024

IJMS

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The synthesis and structural characterization of α-haloalkyl-substituted pyridinium-fused 1,2,4-selenadiazoles with various counterions is reported herein, demonstrating a strategy for directed supramolecular dimerization in the solid state. The compounds were obtained through a recently discovered 1,3-dipolar cycloaddition reaction between nitriles and bifunctional 2-pyridylselenyl reagents, and their structures were confirmed by the X-ray crystallography. α-Haloalkyl-substituted pyridinium-fused 1,2,4-selenadiazoles exclusively formed supramolecular dimers via four-center Se···N chalcogen bonding, supported by additional halogen bonding involving α-haloalkyl substituents. The introduction of halogens at the α-position of the substituent R in the selenadiazole core proved effective in promoting supramolecular dimerization, which was unaffected by variation of counterions. Additionally, the impact of cocrystallization with a classical halogen bond donor C6F3I3 on the supramolecular assembly was investigated. Non-covalent interactions were studied using density functional theory calculations and topological analysis of the electron density distribution, which indicated that all ChB, XB and HB interactions are purely non-covalent and attractive in nature. This study underscores the potential of halogen and chalcogen bonding in directing the self-assembly of functional supramolecular materials employing 1,2,4-selenadiazoles derived from recently discovered cycloaddition between nitriles and bifunctional 2-pyridylselenyl reagents.

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Chalcogen and Hydrogen Bonds at the Periphery of Arylhydrazone Metal Complexes

Cited by 17 publications

References 58 publications

Chalcogen bonding in copper(ii)-mediated synthesis

Chalcogen bonding in copper(ii)-mediated synthesis

Benzenesulfonamide Analogs: Synthesis, Anti-GBM Activity and Pharmacoprofiling

Halogen Bond-Assisted Supramolecular Dimerization of Pyridinium-Fused 1,2,4-Selenadiazoles via Four-Center Se2N2 Chalcogen Bonding

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