51-66-1Relevant articles and documents
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
Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
, p. 2820 - 2826 (2021/02/01)
A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.
A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
supporting information, p. 1955 - 1958 (2021/03/02)
Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides
Gudun, Kristina A.,Hayrapetyan, Davit,Khalimon, Andrey Y.,Segizbayev, Medet,Slamova, Ainur,Zakarina, Raikhan
, (2021/11/30)
The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.
Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds
Ran, Maogang,He, Jiaxin,Yan, Boyu,Liu, Wenbo,Li, Yi,Fu, Yunfen,Li, Chao-Jun,Yao, Qiuli
supporting information, p. 1970 - 1975 (2021/03/16)
We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.
Visible-light induced one-pot hydrogenation and amidation of nitroaromatics with carboxylic acids over 2D MXene-derived Pt/N-TiO2/Ti3C2
Jiang, Heyan,Hu, Zujie,Gan, Chuan,Sun, Bin,Kong, Shuzhen,Bian, Fengxia
, (2021/03/03)
Pt nanoparticles supported on N doped titanium dioxide/titanium carbide (MXene) heterojunctions were employed as photocatalysts for the tandem reactions between aromatic nitro compounds and carboxylic acids to produce amide products. The 3%Pt/N-TiO2/Ti3C2 heterojunction was prepared by in situ grew TiO2 on Ti3C2 nanosheets and then N doped TiO2 with melamine, Pt nanoparticles with 3.3 nm mean diameter well dispersed on N-TiO2/Ti3C2. 3%Pt/N-TiO2/Ti3C2 had excellent amidation activity and chemoselectivity under visible-light irradiation. The elevated catalytic performance of 3%Pt/N-TiO2/Ti3C2 was owing to the improvement in photogenerated electron and hole separation efficiency through charge short-range directional transmission caused by the intimate contact between the TiO2 and the conductive Ti3C2. This direct hydrogenation along with amidation between nitroaromatics and carboxylic acids own actual merits in the amides produce with no harmful byproducts. In situ DRIFTS spectra verified that the amidation activation with visible light irradiation at 25 °C was much faster than heating.
