35168-64-0Relevant academic research and scientific papers
Experimental and theoretical studies of 2-Mercaptobenzothiazole with 2-Bromomethylmesitylene and 1,4-Bis(bromomethyl)durene
Asha, R. Nandini,Bhuvanesh, N.,Daisy, Caroline,Kumar, G. S. Suresh,Nayagam, B. Ravindran Durai,Vadivel, E.
, (2020)
Biologically important 2-(2,4,6-trimethylbenzylthio)benzo[d]thiazole[BTM1] and 2-(4-((benzo[d]thiazol-2-ylthio)methyl)-2,3,5,6-tetramethylbenzylthio)benzo[d]thiazole [BTD2] were synthesized and characterised using FT-IR, NMR and single-crystal XRD (SCXRD). SCXRD revealed that both compounds were crystallized as a triclinic system and were associated through weak intermolecular interactions like H-bondings (CH…N, sp3-, and sp2-CH…π), π-π stackings and Vander Waals interactions. These weak intermolecular interactions in BTM1 and BTD2 were studied using Crystal Explorer and Gaussian. The interaction of title compounds with epidermal growth factor receptor (EGFR)tyrosine kinase protein was performed using AutoDock Vina. Molecular docking study revealed an efficient interaction of compounds with the protein resulting in good anti-cancer activity. DNA binding studies were explored against calf thymus (CT) DNA using a spectrophotometric titration method and was found that benzothiazole compounds showed hyperchromism and good binding efficiency. In-vitro anti-microbial activities against some bacterial and fungal strains were investigated. BTM1exhibited a better inhibition against bacterial (Bacillus subtilis and Staphylococcus aureus) and fungal (Aspergillus niger) strains than BTD2.
Intervalence (Charge-Resonance) Transitions in Organic Mixed-Valence Systems. Through-Space versus Through-Bond Electron Transfer between Bridged Aromatic (Redox) Centers
Sun,Rosokha,Lindeman,Kochi
, p. 15950 - 15963 (2003)
Intervalence absorption bands appearing in the diagnostic near-IR region are consistently observed in the electronic spectra of mixed-valence systems containing a pair of aromatic redox centers (Ar+/Ar) that are connected by two basically different types of molecular bridges. The through-space pathway for intramolecular electron transfer is dictated by an o-xylylene bridge in the mixed-valence cation radical 3.+ with Ar = 2,5-dimethoxy-p-tolyl (T), in which conformational mobility allows the proximal syn disposition of planar T.+/T redox centers. Four independent experimental probes indicate the large through-space electronic interaction between such cofacial Ar.+/Ar redox centers from the measurements of (a) sizable potential splitting in the cyclic voltammogram, (b) quinonoidal distortion of T.+/T centers by X-ray crystallography, (c) "doubling" of the ESR hyperfine splittings, and (d) a pronounced intervalence charge-resonance band. The through (br)-bond pathway for intramolecular electron transfer is enforced in the mixed-valence cation radical 2a.+ by the p-phenylene bridge which provides the structurally inflexible and linear connection between Ar.+/Ar redox centers. The direct comparison of intramolecular rates of electron transfer (kET) between identical T.+/T centers in 3.+ and 2a.+ indicates that through-space and through-bond mechanisms are equally effective, despite widely different separations between their redox centers. The same picture obtains for 3.+ and 2a.+ from theoretical computations of the first-order rate constants for intramolecular electron transfer from Marcus-Hush theory using the electronic coupling elements evaluated from the diagnostic intervalence (charge-transfer) transitions. Such a strong coherence between theory and experiment also applies to the mixed-valence cation radical 7.+, in which the aromatic redox S center is sterically encumbered by annulation.
Preparation, crystal structures and conformations of six complexes based on 1,4-bis(benzimidazol-1-ylmethyl)-2,3,5,6-tetramethylbenzene
Liu, Qing-Xiang,Zhao, Zhi-Xiang,Zhao, Xiao-Jun,Bi, Yue,Yu, Jie,Wang, Xiu-Guang
, p. 7023 - 7036 (2014)
Reaction of ligands (L or LA) with metal salts affords six new metal complexes {[Mn(L)3](ClO4)2}n (1), [Cu(L)(SO4)(H2O)]·1.5H2O (2), [Co(L)(LA)(CH3OH)2]·2CH3OH (3), [Co(L)(DMF)(NO3)2]n (4), [Cd(L)(DMF)(NO3)2]n (5) and [Cu(L)(DMF)(NO 3)2]n (6) (L = 1,4-bis(benzimidazol-1-ylmethyl) -2,3,5,6-tetramethylbenzene, LA = fumarate). These complexes are structurally characterized by X-ray diffraction analyses. Analyses of crystal structures of complexes 1 and 2 show that 2D layers with metallomacrocycles are formed via ligand L and metal atoms (Mn(ii) for 1 and Cu(ii) for 2). The 2D layer with metallomacrocycles in complex 3 is formed via ligand L, fumarate groups and Co(ii) atoms. 1D polymeric chains in complexes 4-6 are formed via ligand L and metal atoms (Co(ii) for 4, Cd(ii) for 5 and Cu(ii) for 6). In the crystal packing of complexes 1-6, 3D supramolecular frameworks are formed via intermolecular weak interactions, including π-π interactions and C-H...π contacts. π-π interactions between benzimidazole rings are compared. The conformations of metal complexes based on dibenzimidazolyl bidentate ligands with flexible or semi-rigid linkers are described and compared. Additionally, the fluorescence emission spectra of ligand L and metal complexes and the magnetic properties of complexes 2-4 are reported. This journal is the Partner Organisations 2014.
Synthesis, structural, spectral, antidiabetic, DNA interactions and molecular docking investigations of a piperidine derivative
Asha, Radhakrishnan Nandini,Bhuvanesh, Nattamai,Nayagam, Balasingh Ravindran Durai,Sankarganesh, Murugesan
, (2021/10/26)
A new organic piperidine derivative named as 4‐methyl‐1‐({2,3,5,6‐tetramethyl‐4‐[(4‐methylpiperidinyl)methyl]phenyl}methyl)piperidine (D24MP) was synthesized and characterized by single crystal X-ray diffraction (SCXRD) and diverse spectroscopic (1H &13C NMR and FT-IR) techniques. The monoclinic structure of D24MP crystallises with the space group P-1. Density Function theory (DFT) using the B3LYP/6–31++G(d,p) level basis set was used to get the optimised geometry and non-linear optical properties. MEP surface analysis was used to investigate the crystal's nucleophilic and electrophilic reactive sites. The molecular shape and intermolecular interactions in the crystal structure were determined using Hirshfeld surface analysis and fingerprint plots. The physicochemical, pharmacokinetic and toxicological properties of D24MP have been evaluated by using drug-likeness and insilico ADMET studies. The molecule's first hyperpolarizability (β) estimation is 3.65 times higher than urea. Antidiabetic, antioxidant and DNA binding ability of D24MP were investigated by experimental and theoretical techniques. The obtained results suggest that D24MP possesses better antidiabetic, antioxidant and DNA binding abilities. Gel-electrophoretic method results suggest that D24MP has better cleaving capability against CT-DNA at higher concentrations (100 μg).
Refining the model to design α-chymotrypsin superactivators: The role of the binding mode of quaternary ammonium salts
Gabriele, Francesco,Goracci, Laura,Germani, Raimondo,Spreti, Nicoletta
, p. 20823 - 20833 (2020/12/28)
A number of quaternary ammonium salts with bulky hydrophobic moieties are known to provoke the superactivation of α-chymotrypsin (α-CT) in aqueous solution. In particular, benzyl-substituted ammonium and dicationic ammonium-based salts have recently emerged as promising classes of compounds to induce α-CT superactivation and stabilization. Preliminary in silico modelling suggested the α-CT residue tryptophan 215 to be the major anchor point of these additives. In order to achieve a broader knowledge of the enzyme-additive interactions and to validate the modelling studies, new ammonium-based additives were designed and tested. The hydrophobic interaction resulted in being critical to improving superactivation, with [(2,3,5,6-tetramethyl-p-phenylene)dimethylene]bis[triethylammonium bromide] (bisEDuEAB) resulting as the most effective quaternary ammonium superactivating agent studied so far. Finally, a general agreement between in silico outcomes and kinetic parameters was observed, and data interpretation is discussed based on the proposed α-CT/additive binding modes. This journal is
Asymmetric epoxidation of unfunctionalized olefins with C2-symmetrical diphenol-derived axially coordinated homogeneous chiral bi-Mn(III) salen complexes
Dong, Tianyi,Wu, Xiaoju,Cai, Jiali,Huang, Jing
, p. 57 - 61 (2019/01/19)
A novel type of C2-symmetrical diphenol-derived and axially coordinated homogeneous chiral bi-Mn(III) salen complexes are synthesized and their catalytic effects in asymmetric epoxidation of unfunctionalized olefins are investigated in details. The results show that excellent enantioselectivities and high activities are achieved (enantioselectivities up to >99% in 99.9%) in the absence of expensive NMO. Compared with Jacobsen's catalyst, the configuration of C2-symmetrical homogeneous chiral bi-Mn(III) salen complex contribute to the catalytic reactivity and stability. Furthermore, these new homogeneous catalysts could be easily recovered and reused for 5 cycles without significant loss of their properties.
Cyclic bis-benzimidazole hexafluorophosphate compound as well as preparation method and application thereof
-
Paragraph 0015, (2018/03/26)
The invention discloses a preparation method of a cyclic bis-benzimidazole hexafluorophosphate compound and application thereof. The preparation method comprises the following steps: taking 2,3,5,6-tetramethylbenzene as a raw material in an organic solvent, and reacting with paraformaldehyde, glacial acetic acid, concentrated sulfuric acid and potassium bromide so as to obtain 1,4-bisbromomethyl-2,3,5,6-tetramethylbenzene; reacting with benzimidazole to obtain an intermediate (Y), reacting with 1,8-bis(2-bromoethoxy) anthraquinone so as to obtain a bromide (1) of a cyclic bis-benzimidazole salt; and exchanging the cyclic bis-benzimidazole salt and hexafluorophosphate, thereby obtaining the cyclic bis-benzimidazole hexafluorophosphate compound (2). The cyclic bis-benzimidazole hexafluorophosphate compound disclosed by the invention has the advantages of being simple in preparation and obvious in fluorescent sensitization effect, can be used for manufacturing a fluorescent molecular recognition system and is mainly applied to the technical field of fluorescent recognition.
Macrocyclic Receptor for Precious Gold, Platinum, or Palladium Coordination Complexes
Liu, Wenqi,Oliver, Allen G.,Smith, Bradley D.
supporting information, p. 6810 - 6813 (2018/05/31)
Two macrocyclic tetralactam receptors are shown to selectively encapsulate anionic, square-planar chloride and bromide coordination complexes of gold(III), platinum(II), and palladium(II). Both receptors have a preorganized structure that is complementary to its precious metal guest. The receptors do not directly ligate the guest metal center but instead provide an array of arene π-electron donors that interact with the electropositive metal and hydrogen-bond donors that interact with the outer electronegative ligands. This unique mode of supramolecular recognition is illustrated by six X-ray crystal structures showing receptor encapsulation of AuCl4-, AuBr4-, PtCl4-2, or Pd2Cl6-2. In organic solution, the 1:1 association constants correlate with specific supramolecular features identified in the solid state. Technical applications using these receptors are envisioned in a wide range of fields that involve precious metals, including mining, recycling, catalysis, nanoscience, and medicine.
Chiral and achiral basket-handle porphyrins: Short synthesis and stereostructures of these versatile building blocks
Gehrold, Andreas C.,Bruhn, Torsten,Schneider, Heidi,Radius, Udo,Bringmann, Gerhard
, p. 210 - 213 (2015/03/05)
Both, chiral and achiral basket-handle porphyrins were synthesized via a short, reliable, and efficient route in multigram quantities. Standard synthetic protocols such as metalation of the macrocycle, halogenation, and borylation of the porphyrin core or alkyl- and arylation with lithium organyls were successfully adapted. The planar-chiral representatives were resolved into their enantiomers, whose absolute configurations were determined by comparison of experimental CD spectra with TDCAM-B3LYP calculated ones.
Zinc metal-organic frameworks based on a flexible benzylaminetetracarboxylic acid and bipyridine colinkers
Wang, Chao,Tang, Sifu,Lv, Xiaoxia,Li, Liangjun,Zhao, Xuebo
supporting information, p. 3133 - 3139 (2014/07/21)
Three new metal-organic frameworks (MOFs), [Zn2(L)(H 2O)]·3DMF·1.5H2O (1), [Zn 2(L)(4,4-bpy)1.5(H2O)2] ·2DMF·2H2O (2), and [Zn2(L)(2,2-bpy) 2(DMF)2]·2DMF·4H2O (3) [H 4L = 5,5-(2,3,5,6-tetramethyl-1,4-phenylene)bis(methylene) bis(azanediyl)diisophthalic acid, 4,4-bpy = 4,4-bipyridine, 2,2-bpy = 2,2-bipyridine, DMF = N,N-dimethylformamide], were synthesized under solvothermal conditions and characterized by single-crystal X-ray diffraction analysis, elemental analysis, IR spectroscopy, powder X-ray diffraction (PXRD), and thermogravimetric analysis (TGA). The L4- ligands in 1-3 display different coordination modes, and the introduction of bipyridine colinkers brings significant structural variation into the frameworks. Complex 1 is constructed from dinuclear carboxylate [Zn2O(COO)4] secondary building units (SBUs) and H4L ligands and exhibits a binodal (4,4)-connected pts net with 54.6 % solvent-accessible void. Complex 2 exhibits an unprecedented tetranodal (3,4,4,4)-connected net, which is constructed from two types of crystallographically independent ZnII ions, H4L ligands, and the 4,4-bipyridine colinker. Complex 3 is constructed from parallel 1D molecular ladders stacked along the a axis that generate 1D channels (7.8 × 10.4 A?) and are hydrogen bonded to form 2D layers. The thermal stabilities and luminescence properties of 1-3 have also been studied in detail. Copyright
