51-66-1Relevant academic research and scientific papers
Exploiting the potential of aryl acetamide derived Zn(II) complexes in medicinal chemistry: Synthesis, structural analysis, assessment of biological profile and molecular docking studies
Sultana, Kishwar,Zaib, Sumera,Hassan Khan, Najm Ul,Khan, Imtiaz,Shahid, Khadija,Simpson, Jim,Iqbal, Jamshed
, p. 7084 - 7094 (2016)
In the medical arena, advancements in the rational design of metal-based therapeutic agents showcase increasingly significant research efforts towards the development of new compounds with fewer toxic side effects. In this context, our present manuscript explicitly encapsulates the design and synthesis of Zn(ii) complexes derived from different aryl acetamides, as potential frontline enzyme inhibitors as well as antileishmanial and anticancer agents. The structures of the synthesized metal complexes were established on the basis of spectro-analytical data and, in the case of 4c, by single crystal X-ray diffraction analysis. The X-ray structure of the Zn(ii) complex, dichlorido-bis[N-(4-methoxyphenyl)acetamide-O]-zinc(ii), 4c, showed that the zinc atom and the chloride ligands lie on a mirror plane, with the acetamide ligands in general positions. The coordination geometry of the zinc atom was tetrahedral, with the N-(4-methoxyphenyl)acetamide ligands bound to zinc via the acetamide oxygen atoms. The designed coordination complexes were analysed for their enzyme inhibition potential, and anticancer and antileishmanial efficacy. Detailed kinetic studies for complex 4b, the most active carbonic anhydrase and alkaline phosphatase inhibitor, indicated competitive and uncompetitive modes of inhibition against carbonic anhydrase and tissue non-specific alkaline phosphatase, respectively. The bioactivity results and molecular docking analysis revealed that the synthesized coordination complexes (4a-c) have great potential as enzyme inhibitors, in addition to being anticancer and anti-parasitic drug candidates.
1,1-Bis(3,5-dimethyl-1-pyrazolyl)- and 1-amino-1-(3,5-dimethyl-1-pyrazolyl) -4,4-dichloro-1-buten-3-ones
Potkin,Petkevich,Kaberdin,Kurman
, p. 1508 - 1511 (2004)
Reaction of 1,1,4,4-tetrachloro-3-buten-2-one with 3,5-dimethylpyrazole gave 1,1-dichloro- 4,4-bis-(3,5-dimethyl-1-pyrazolyl)-3-buten-2-one. Treatment of the latter with amines resulted in replacement of one pyrazole ring by the amine residue with formati
Synthesis of new dihydropyrrol-2-one derivatives bearing sulfonamide groups and studies their antibacterial activity
Bavadi, Masoume,Niknam, Khodabakhsh,Gharibi, Marzieh
, p. 1025 - 1034 (2017)
Abstract: A novel series of dihydropyrrol-2-one compounds bearing sulfonamide groups were synthesized and assayed for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Streptococcus epidermidis bacteria. Antibacterial results showed that most of the compounds exhibited the antibacterial activity against P. aeruginosa and S. epidermidis and displayed no inhibition against S. aureus and E. coli. Interestingly, most of the screened compounds were more active than the reference drug trimethoprim-sulfamethoxazole against P. aeruginosa. Among them, one compound exhibited good antibacterial activity in comparison with the reference drugs against P. aeruginosa and may make it as potential an antibacterial agent. Graphical abstract: [Figure not available: see fulltext.].
Iron oxide nanospheres and nanocubes modified with carboxyphenyl porphyrin and their magnetic, optical properties and photocatalytic activities in room temperature amide synthesis
Insin, Numpon,Krause, Stefan,Saengruengrit, Chalathan,Saetan, Trin,Salvan, Georgeta,Sattayaporn, Suchinda,Sharma, Apoorva,Solonenko, Dmytro,Thamyongkit, Patchanita,Wacharasindhu, Sumrit,Zahn, Dietrich R. T.
, (2021)
Superparamagnetic iron oxide nanoparticles of different shapes and sizes combined with 5-(4-carboxyphenyl)-10,15,20-triphenylporphinatozinc(II) (SPION-ZnCTPP) were prepared and investigated as a novel and potent magnetically responsive photocatalyst. Nanospheres and nanocubes of SPIONs in the sizes of 10 and 20 nm were synthesized using thermal decomposition method before coating with ZnCTPP. Morphologies of SPIONs were observed using a transmission electron microscope (TEM). Herein the attachment of ZnCTPP on particles was studied using various techniques including infrared spectroscopy (IR) and UV–visible spectroscopy and Inductively Coupled Plasma Optical Emission Spectroscopy (ICP-OES). Moreover, the obtained particles showed superparamagnetic character with saturation magnetization in a range of 10 to 76 emu/g, depending on the size and shape of the SPIONs. The SPION-ZnCTPP showed high photocatalytic activity (52% yield) for amide synthesis between potassium ethanethioate and 4-methoxyaniline under irradiation with a 19 W LED lamp, and this heterogeneous catalyst could be well separated from a solution under the induction of an external magnetic field.
Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols
Alinejad, Sara,Donyapeyma, Ghazaleh,Rahmatpour, Ali
, (2022/01/24)
Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec
Cu(OTf)2-Mediated Cross-Coupling of Nitriles and N-Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products**
Bell, Nicola L.,Xu, Chao,Fyfe, James W. B.,Vantourout, Julien C.,Brals, Jeremy,Chabbra, Sonia,Bode, Bela E.,Cordes, David B.,Slawin, Alexandra M. Z.,McGuire, Thomas M.,Watson, Allan J. B.
supporting information, p. 7935 - 7940 (2021/03/03)
Metal-catalyzed C–N cross-coupling generally forms C?N bonds by reductive elimination from metal complexes bearing covalent C- and N-ligands. We have identified a Cu-mediated C–N cross-coupling that uses a dative N-ligand in the bond-forming event, which, in contrast to conventional methods, generates reactive cationic products. Mechanistic studies suggest the process operates via transmetalation of an aryl organoboron to a CuII complex bearing neutral N-ligands, such as nitriles or N-heterocycles. Subsequent generation of a putative CuIII complex enables the oxidative C–N coupling to take place, delivering nitrilium intermediates and pyridinium products. The reaction is general for a range of N(sp) and N(sp2) precursors and can be applied to drug synthesis and late-stage N-arylation, and the limitations in the methodology are mechanistically evidenced.
Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines
Amirsoleimani, Mina,Khalilzadeh, Mohammad A.,Zareyee, Daryoush
, (2020/08/22)
Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.
An efficient, economical and eco-friendly acylation of alcohols and amines by alum doped nanopolyaniline under solvent free condition
Behera, Satyaranjan,Patra, Braja N.
, (2021/08/06)
We report acylation of alcohols and amines employing acetic acid as an acylating agent in solvent free condition by using alum doped nanopolyaniline (NDPANI) as a catalyst. This environmentally benign method does not use corrosive acid anhydrides and acid chlorides for acylation and does not produce waste product. Also, a non-toxic potash alum was used for doping of polyaniline rather than corrosive acids. The reaction conditions represent an advance over established method not only in omitting the need for expensive catalysts or solvents but also in shortening the reaction time significantly. The advantages of this catalyst are non-hazardous, cheap, reusable, easy to prepare and handling.
Hybrid quinoline-thiosemicarbazone therapeutics as a new treatment opportunity for Alzheimer’s disease-synthesis, in vitro cholinesterase inhibitory potential and computational modeling analysis
Alsaab, Hashem O.,Aqsa, Sehar,Asif, Tahira Tasneem,Ibrar, Aliya,Kausar, Naghmana,Khan, Imtiaz,Munir, Rubina,Shahid, Noorma,Younas, Muhammad Tayyab,Zaib, Sumera
, (2021/12/10)
Alzheimer’s disease (AD) is a progressive neurodegenerative disorder and the leading cause of dementia worldwide. The limited pharmacological approaches based on cholinesterase inhibitors only provide symptomatic relief to AD patients. Moreover, the adverse side effects such as nausea, vomiting, loss of appetite, muscle cramps, and headaches associated with these drugs and numerous clinical trial failures present substantial limitations on the use of medications and call for a detailed insight of disease heterogeneity and development of preventive and multifactorial therapeutic strategies on urgent basis. In this context, we herein report a series of quinoline-thiosemicarbazone hybrid therapeutics as selective and potent inhibitors of cholinesterases. A facile multistep synthetic approach was utilized to generate target structures bearing multiple sites for chemical modifications and establishing drug-receptor interactions. The structures of all the synthesized compounds were fully established using readily available spectroscopic techniques (FTIR, 1H- and 13C-NMR). In vitro inhibitory results revealed compound 5b as a promising and lead inhibitor with an IC50 value of 0.12 ± 0.02 μM, a 5-fold higher potency than standard drug (galantamine; IC50 = 0.62 ± 0.01 μM). The synergistic effect of electron-rich (methoxy) group and ethylmorpholine moiety in quinolinethiosemicarbazone conjugates contributes significantly in improving the inhibition level. Molecular docking analysis revealed various vital interactions of potent compounds with amino acid residues and reinforced the in vitro results. Kinetics experiments revealed the competitive mode of inhibition while ADME properties favored the translation of identified inhibitors into safe and promising drug candidates for pre-clinical testing. Collectively, inhibitory activity data and results from key physicochemical properties merit further research to ensure the design and development of safe and high-quality drug candidates for Alzheimer’s disease.
Dehydrative Beckmann rearrangement and the following cascade reactions
Liu, Yinghui,Wei, Yongjiao,Xie, Lan-Gui
supporting information, (2021/11/16)
The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.
