Cu-metal organic frameworks (Cu-MOF) as an environment-friendly and economical catalyst for one pot synthesis of tacrine derivatives

Mollabagher, Hoda; Taheri, Salman; Mojtahedi, Mohammad M.; Seyedmousavi, SeyedAmirhossein

doi:10.1039/c9ra10111j

Cited by 35 publications

(18 citation statements)

References 26 publications

(41 reference statements)

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“…As a peculiar consideration, it should be noted that tacrine and derivatives are easily synthesizable through environment-friendly and economical approaches ( e.g. , catalysis with cheap and nontoxic catalysts and solvent-free reactions) …”

Section: Results and Discussionmentioning

confidence: 84%

Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer’s Disease

et al. 2021

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The multifactorial nature of Alzheimer’s disease (AD) is a reason for the lack of effective drugs as well as a basis for the development of “multi-target-directed ligands” (MTDLs). As cases increase in developing countries, there is a need of new drugs that are not only effective but also accessible. With this motivation, we report the first sustainable MTDLs, derived from cashew nutshell liquid (CNSL), an inexpensive food waste with anti-inflammatory properties. We applied a framework combination of functionalized CNSL components and well-established acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) tacrine templates. MTDLs were selected based on hepatic, neuronal, and microglial cell toxicity. Enzymatic studies disclosed potent and selective AChE/BChE inhibitors ( 5 , 6 , and 12 ), with subnanomolar activities. The X-ray crystal structure of 5 complexed with BChE allowed rationalizing the observed activity (0.0352 nM). Investigation in BV-2 microglial cells revealed antineuroinflammatory and neuroprotective activities for 5 and 6 (already at 0.01 μM), confirming the design rationale.

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Section: Results and Discussionmentioning

confidence: 84%

Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer’s Disease

et al. 2021

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“…A simple procedure for the syn-Scheme 43. CuNPs catalyzed the synthesis of heterocycles [175,180,181,[183][184][185].…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

“…Tacrine derivatives are among the most investigated molecules for the treatment of Alzheimer’s disease ( Scheme 43 ) [ 182 ]. In order to prepare tacrine derivatives avoiding intermediates isolation, Seyedmousavi and co-workers developed a Cu/MOF-catalyzed domino one-pot three-step synthesis starting from aldehyde, malonitrile, hydroxynaphthalene-1,4-dione and cycloketone [ 183 ]. CuNPs supported on MOF were highly active towards the formation of tacrine derivatives bearing different functional groups.…”

Section: Copper Nanoparticlesmentioning

confidence: 99%

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

et al. 2021

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Metal nanoparticles have been deeply studied in the last few decades due to their attractive physical and chemical properties, finding a wide range of applications in several fields. Among them, well-defined nano-structures can combine the main advantages of heterogeneous and homogenous catalysts. Especially, catalyzed multi-step processes for the production of added-value chemicals represent straightforward synthetic methodologies, including tandem and sequential reactions that avoid the purification of intermediate compounds. In particular, palladium- and copper-based nanocatalysts are often applied, becoming a current strategy in the sustainable synthesis of fine chemicals. The rational tailoring of nanosized materials involving both those immobilized on solid supports and liquid phases and their applications in organic synthesis are herein reviewed.

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“…In bond connectivity, Zr 6 cluster is coordinated to BDC in 1:12 unit ratio three dimensionally thus affording a hierarchical framework 18 – 21 . There are several reports on the synthesis and catalytic applications of various MOF derivatives being synthesized from pre-modified ligands and post-immobilized metal ions or metal nanoparticles thereon 22 – 29 . However, synthetic organic applications of active metal adorned post-functionalized MOFs, has not been much explored and there are ample scopes to develop this area 30 – 34 .…”

Section: Introductionmentioning

confidence: 99%

Pd immobilization biguanidine modified Zr-UiO-66 MOF as a reusable heterogeneous catalyst in Suzuki–Miyaura coupling

Veisi

Abrifam

Kamangar

et al. 2021

Sci Rep

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In recent days, nanohybrid metal organic frameworks (MOF) have been considered as next generation catalysts due to their unique features like large surface to volume ratio, tailorable geometry, uniform pore sizes and homogeneous distribution of active sites. In this report, we address the biguanidine modified 3D Zr-centred MOF UiO-66-NH2 following a post synthetic modification approach. Utilizing the excellent chelating ability of biguanidine, Pd ions are immobilized over the host matrix MOF. The as-synthesized material was physicochemically characterized using a broad range of analytical techniques like FT-IR, electron microscopy, EDS, elemental mapping, XRD and ICP-OES. Subsequently the material has been catalytically employed in the classical Suzuki–Miyaura coupling towards the synthesis of diverse biphenyl derivatives at sustainable conditions. There are very few reports on the covalently modified MOFs towards the organic coupling reactions. The catalyst has been isolated by centrifugation and recycled in 9 consecutive runs with almost insignificant leaching and minute decrease in reactivity.

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Cu-metal organic frameworks (Cu-MOF) as an environment-friendly and economical catalyst for one pot synthesis of tacrine derivatives

Abstract: The present work describes the catalytic activity of Cu-MOF for the one-pot synthesis of tacrine derivatives via a four-component reaction of 2-hydroxynaphthalene-1,4-dione, aldehydes, malononitrile and cycloketones in the presence of AlCl3.

Cited by 35 publications

References 26 publications

Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer’s Disease

Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer’s Disease

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

Pd immobilization biguanidine modified Zr-UiO-66 MOF as a reusable heterogeneous catalyst in Suzuki–Miyaura coupling

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