53940-12-8Relevant academic research and scientific papers
Luminescent Zn(ii) and Cd(ii) complexes with chiral 2,2′-bipyridine ligands bearing natural monoterpene groups: synthesis, speciation in solution and photophysics
Agafontsev, Alexander M.,Baranov, Andrey Y.,Bushuev, Mark B.,Glinskaya, Ludmila A.,Kokina, Tatyana E.,Komarov, Vladislav Y.,Plyusnin, Pavel E.,Rakhmanova, Marianna I.,Shekhovtsov, Nikita A.,Sheludyakova, Liliya A.,Tkachev, Alexey V.
, p. 7552 - 7563 (2020)
Mononuclear zinc(ii) and cadmium(ii) complexes, ZnLCl2(1), CdLCl2(2), ZnL1Cl2·2H2O (3), and CdL1Cl2·2H2O (4), with chiral ligands containing a 2,2′-bipyridine moiety and natural terpene (+)-limonene (L) or (+)-3-carene (L1) moieties were synthesized. In these complexes theLandL1ligands are shown to coordinate Zn2+and Cd2+ions through the 2,2′-bipyridine moiety. The acetamide group of the ligands interacts with M2+ions by forming N?M2+and C-O?M2+contacts and N-H?Cl hydrogen bonds with coordinated Cl?ions. In solutions the complexes have several conformers differing by the degree of the turn of the acetamide moiety relative to the ligand core and the type of its interaction with the coordination core. The ligands and complexes exhibit luminescence with the quantum yield increasing in the order: ligand 1-S0and T1-S0
Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
Roscales, Silvia,Csáky, Aurelio G.
supporting information, p. 8728 - 8732 (2021/03/16)
A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.
An Efficient Cyclic Di-AMP Based Artificial Metalloribozyme for Enantioselective Diels–Alder Reactions
Qi, Qianqian,Lv, Shuting,Hao, Min,Dong, Xingchen,Gu, Youkun,Wu, Peizhe,Zhang, Wenyue,Chen, Yashao,Wang, Changhao
, p. 4417 - 4424 (2020/06/17)
The diverse structures of nucleic acids as scaffolds have brought the significant advancement for DNA-based enantioselective catalysis, yet RNA-based enantioselective catalysis is lacking investigation. Herein, we report a small, natural RNA of cyclic di-AMP (c-di-AMP) and Cu2+ ions assemble into an artificial metalloribozyme (c-di-AMP·Cu2+), that could effectively catalyze the enantioselective Diels–Alder reactions with up to 80 percent ee. The enantioselective catalytic performance of c-di-AMP·Cu2+ has been studied by thorough investigations of different metal cofactors, c-di-AMP/Cu2+ molar ratios, additives, buffers and c-di-AMP analogues. In addition, the assembly of c-di-AMP·Cu2+ gives rise to 300-fold and 5-fold rate acceleration compared to the uncatalyzed reaction and Cu2+ ions, respectively. This work provides a simple and efficient strategy to construct the RNA-based catalysts that would expand the current nucleic acids-based catalysis and might hint the possible catalytic RNA in primordial chemistry.
Design, synthesis and neuropharmacological evaluation of new 2,4-disubstituted-1,5-benzodiazepines as CNS active agents
Bhatia, Rohit,Kumar, Bhupinder,Mehan, Sidharth,Monga, Vikramdeep,Singh, Gurpreet,Verma, Ramesh
, (2020/07/03)
Benzodiazepines (BZDs) represent a class of privilege scaffold in the modern era of medicinal chemistry as CNS active agents and BZD based drugs are used to treat different psychotic disorders. Inspired from the therapeutic potential of BZDs as promising CNS active agents, in the present work three different series of 1,5-benzodiazepines bearing various substitutions at position 2 and 4 of the benzodiazepine core were synthesized by condensing different substituted chalcones with o-phenylenediamine in the presence of piperidine as a base catalyst. Structural characterization of title compounds was done by using various analytical techniques such as IR, NMR, elemental analysis and mass spectral data. All the synthesized compounds (9a-d, 10a-e and 11a-c) were subjected to in vivo neuropharmacological studies to evaluate their CNS depressant and antiepileptic activity. Results of in vivo evaluation data showed that analogue 11b exhibited potent CNS depressant activity which was comparable to the standard drug diazepam. Compounds 10b and 10c displayed significant antiepileptic activity however they were less potent than the standard drug phenobarbitone. Molecular docking studies were performed using MOE software to find the interaction pattern and binding mode at the GABAA receptor (PDB Id: 6HUP). The results of the docking studies were in good agreement with the observed in vivo activity and revealed the satisfactory binding mode of the compounds within the binding site of the protein. The docking scores for the most promising candidates 10c, 11b and Diazepam were found to be ?9.18, ?9.46 and ?9.88, respectively. Further, the compounds showed compliance with the Lipinski's ‘rule of five’ and exhibited favourable drug-likeness scores. The identified leads can be explored further for the design and development of new BZD based psychotropic agents.
Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow
Laroche, Benjamin,Saito, Yuki,Ishitani, Haruro,Kobayashi, Shū
supporting information, p. 961 - 967 (2019/05/02)
A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.
Design, synthesis, pharmacological evaluation and DNA interaction studies of binuclear Pt(II) complexes with pyrazolo[1,5-a]pyrimidine scaffold
Lunagariya, Miral V.,Thakor, Khyati P.,Waghela, Bhargav N.,Pathak, Chadramani,Patel, Mohan N.
, (2018/01/22)
Substituted pyrazolo[1,5-a]pyrimidine ligands were synthesized by cyclization, using 3-(thiophen-2-yl)-1H-pyrazol-5-amine with substituted enones (3-phenyl-1-(pyridin-2-yl)prop-2-en-1-one) in presence of KOH and DMF as solvent to form cyclic aromatic compounds. The substituted pyrazolo[1,5-a] pyrimidine based binuclear PtII complexes containing neutral tetradentated ligands have general formula [Pt2(5a–5f)Cl4], (where, (5a -5f) = pyrazolo[1,5-a] pyrimidine ligand). This compounds were characterized by physicochemical and spectroscopic method like elemental analyses, UV-Visible, FT-IR, EDX, TGA, molar conductivity, magnetic susceptibility measurements, mass spectroscopy, 1H and 13C NMR method. The square planar geometry was predicted by electronic spectral study. All PtII compounds were evaluated by antimicrobial assay, in vitro brine shrimp assay, in vivo cellular level bioassay using S. Pombe cells and anti-tuberculosis study. LC50 (50% lethal concentration) values of compounds are observed between 6.450 - 102.07?μg/mL. UV-vis absorption titration, competitive displacement assay, molecular docking and viscosity measurement were carried out to examine the binding type and binding strength of complexes. The binding studies suggest partial intercalative binding mode of the complexes and the observed binding constant (Kb) values are found in the order of 6d > 6b > 6c > 6a > 6e > 6?f. The anti-proliferative cytotoxicity of the synthesized PtII complexes (6a-6f) were tested against the HCT-116 (Human Colorectal Carcinoma) cancer cell line.
Synthesis and structures of CuI,II complexes with a 2,2′-bipyridine derivative bearing a (+)-3-carene moiety
Kokina,Glinskaya,Piryazev,Baranov, A. Yu.,Agafontsev,Eremina, Yu. A.,Vorontsova,Bogomyakov,Naumov, D. Yu.,Tkachev,Larionov
, p. 1251 - 1260 (2018/10/15)
The complex salt {[CuL2][Cu4I6]?MeCN}n (1) and the compound [Cu4L3I4]?3 MeCN (2) (L is a chiral ligand bearing a natural monoterpene (+)-3-carene moiety) were synthesized. The crystal structures of compounds 1 and 2 were determined by X-ray diffraction. The structure of compound 1 consists of complex cations [CuL2]2+ (N3O2 polyhedron is a trigonal bipyramid) and CuI coordination polymers (CuI4 polyhedron is a tetrahedron) as anions. The experimental magnetic moment μeff at 300 K is 1.90 μB, which is consistent with the X-ray diffraction data and the assumption that compound 1 is mixed-valence. The structure of compound 2 comprises a tetranuclear CuI complex, in which three Cu atoms are coordinated by two N atoms of the ligand L and two I atoms, and the fourth Cu atom is coordinated by four I atoms (coordination polyhedra are distorted tetrahedra). Compounds L and 2 were found to influence the viability of human laryngeal carcinoma cells (Hep2). The IC50 value for complex 2 (13.0±1.7 μM) is substantially smaller than IC50 for compound L (30.5±0.5 μM).
N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones
Rajkiewicz, Adam A.,Kalek, Marcin
, p. 1906 - 1909 (2018/04/16)
An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives
Lauzon, Samuel,Keipour, Hoda,Gandon, Vincent,Ollevier, Thierry
supporting information, p. 6324 - 6327 (2017/12/08)
A highly enantioselective FeII-catalyzed thia-Michael addition to α,β-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to α,β-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantioselective event. DFT calculations support the proposed model for observed stereoselectivities.
Solvent-free enantioselective conjugate addition and bioactivities of nitromethane to Chalcone containing pyridine
Zhang, Guoping,Zhu, Chun,Liu, Dengyue,Pan, Jianke,Zhang, Jian,Hu, Deyu,Song, Baoan
, p. 129 - 136 (2016/12/23)
A series of chiral thioureas derived from quinine were tested as catalysts in the enantioselective Michael additions of nitromethane to α,β-unsaturated ketones containing pyridine. The best results were obtained with the bifunctional catalyst prepared from 3,5-di(trifluoromethyl)-aniline under solvent-free conditions. This thiourea promoted the reaction with high enantioselectivities and chemical yields for aryl ketones. The origins of enantioselectivity were further investigated via experiment and computation. Meanwhile, the products from our reaction showed potent antibacterial activities against rice bacterial leaf blight, with the S-enantiomer performing much better than the R-enantiomer. Given the promising bioactivity of this class of molecules, our work is expected to offer important applications in developing future generations for drug design.
