Recent Advances in the Schiff Bases and <i>N</i>‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

Kumar, Sumit

doi:10.1002/jhet.3504

Cited by 37 publications

(11 citation statements)

References 227 publications

(278 reference statements)

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“…Notably, the THN motif contains polar functionality similar to that of classical kinase hinge-binding small molecules such as 7-deazapurines while offering tunable substituents (via the α-trialkyl-ATA motif) which project toward the hydrophobic pocket of interest in these proteins . In addition to the medicinal value of our products, Schiff bases have been utilized as ligands for many transition metals, with the resultant complexes having a broad scope of applications due to their promising catalytic, biological, and chemotherapeutic activities . We suggest that the α-tertiary imine products generated by our transformation could serve as interesting scaffolds for future ligand design, with the redox neutral process enabling rapid access to a range of structurally diverse and sterically hindered imines that are challenging to access via classical methods.…”

Section: Resultsmentioning

confidence: 99%

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines

et al. 2021

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Molecules displaying an α-trialkyl-α-tertiary amine motif provide access to an important and versatile area of biologically relevant chemical space but are challenging to access through existing synthetic methods. Here, we report an operationally straightforward, multicomponent protocol for the synthesis of a range of functionally and structurally diverse α-trialkyl-α-tertiary amines, which makes use of three readily available components: dialkyl ketones, benzylamines, and alkenes. The strategy relies on the of use visible-light-mediated photocatalysis with readily available Ir(III) complexes to bring about single-electron reduction of an all-alkyl ketimine species to an α-amino radical intermediate; the α-amino radical undergoes Giese-type addition with a variety of alkenes to forge the α-trialkyl-α-tertiary amine center. The mechanism of this process is believed to proceed through an overall redox neutral pathway that involves photocatalytic redox-relay of the imine, generated from the starting amine-ketone condensation, through to an imine-derived product. This is possible because the presence of a benzylic amine component in the intermediate scaffold drives a 1,5-hydrogen atom transfer step after the Giese addition to form a stable benzylic α-amino radical, which is able to close the photocatalytic cycle. These studies detail the evolution of the reaction platform, an extensive investigation of the substrate scope, and preliminary investigation of some of the mechanistic features of this distinct photocatalytic process. We believe this transformation will provide convenient access to previously unexplored α-trialkyl-α-tertiary amine scaffolds that should be of considerable interest to practitioners of synthetic and medicinal chemistry in academic and industrial institutions.

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Section: Resultsmentioning

confidence: 99%

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines

et al. 2021

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“…[ 4 ] Transition metal complexes with these Schiff bases ligands have prolonged advantages in the areas of organometallic compounds and various aspects of bio coordination chemistry. [ 5 ] Derivatives prepared from 4‐aminoantipyrine show interesting pharmacological, [ 4 ] therapeutic, [ 2 ] analgesic, [ 6 ] anti‐inflammatory, [ 1 ] antipyretic, [ 3 ] antimicrobial, [ 5 ] and anticancer activities [ 7 ] . The complex formation behavior of the Schiff base varies depending on the nature of the substituents close to the imino nitrogen .…”

Section: Introductionmentioning

confidence: 99%

Co(II), Ni(II), Cu(II), and Zn(II) complexes of 4‐aminoantipyrine‐derived Schiff base. Synthesis, structural elucidation, thermal, biological studies, and photocatalytic activity

Chellaian

S.S

2021

Journal of Heterocyclic Chem

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The Schiff base ligand was prepared from 4‐aminoantipyrine, acetamide, and m‐phenylenediamine. Metal salts used for the synthesis of these complexes are Co(II), Ni(II), Cu(II), and Zn(II) acetates. The elemental analysis results are in accordance with proposed formula assigned to these complexes. In the IR spectra, the imine band is shifted to a lower wave number in the complexes. UV spectra and magnetic susceptibility measurements proposed square planar geometry for Co(II), Ni(II), and Cu(II) complexes and tetrahedral geometry for Zn(II) complex. The grain size of the metal complexes was estimated by the Scherrer formula using powder XRD. In the present study, the ligand and its metal complexes are found to be nanocrystalline. Thermal decomposition pattern is in agreement with the proposed formula of the complexes. Irreversible redox behavior of the complex was identified by cyclic voltammetric analysis. The photocatalytic activity of the synthesized complexes are high under UV‐spectra using methylene blue dye. DNA studies reveal that the synthesized complexes exhibit both DNA cleavage and DNA binding properties. Antibacterial and antifungal activities were done by the minimum inhibitory concentration (MIC) method. Anticancer activity shows that Cu(II) complex has the highest cytotoxic effect in SK‐MEL‐28 cell line.

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“…10 In addition to NHCs, Schiff base ligands are widely used in metal complexes due to their low cost, ease of access, simplicity of synthesis, and chemical and thermal stability. 11…”

Section: Introductionmentioning

confidence: 99%

Metal Complexes as DNA Synthesis and/or Repair Inhibitors: Anticancer and Antimicrobial Agents

Ngoepe

Clayton

2021

Pharmaceutical Fronts

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Medicinal inorganic chemistry involving the utilization of metal-based compounds as therapeutics has become a field showing distinct promise. DNA and RNA are ideal drug targets for therapeutic intervention in the case of various diseases, such as cancer and microbial infection. Metals play a vital role in medicine, with at least 10 metals known to be essential for human life and a further 46 nonessential metals having been involved in drug therapies and diagnosis. These metal-based complexes interact with DNA in various ways, and are often delivered as prodrugs which undergo activation in vivo. Metal complexes cause DNA crosslinking, leading to the inhibition of DNA synthesis and repair. In this review, the various interactions of metal complexes with DNA nucleic acids, as well as the underlying mechanism of action, were highlighted. Furthermore, we also discussed various tools used to investigate the interaction between metal complexes and the DNA. The tools included in vitro techniques such as spectroscopy and electrophoresis, and in silico studies such as protein docking and density-functional theory that are highlighted for preclinical development.

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Recent Advances in the Schiff Bases and N‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

Cited by 37 publications

References 227 publications

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines

Co(II), Ni(II), Cu(II), and Zn(II) complexes of 4‐aminoantipyrine‐derived Schiff base. Synthesis, structural elucidation, thermal, biological studies, and photocatalytic activity

Metal Complexes as DNA Synthesis and/or Repair Inhibitors: Anticancer and Antimicrobial Agents

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