Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest

Singh, Sukhpreet; Ramaswamy, Sridhar; Paul, Abir Kumar; Layek, Mohosin; Jayaprakash, Sarva; Reddy, K.T. Ramakrishna; Deora, Girdhar Singh; Mukherjee, Somenath; Pal, Manojit

doi:10.1016/j.tetlet.2013.07.126

Cited by 47 publications

(17 citation statements)

References 16 publications

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“…One-pot synthesis of benzofuran fused N-heterocycles 39 and 40a–g ( Figure 18 ) has been achieved by AlCl 3 -mediated C–C followed by C–O bond formation between 2,3-dichloropyrazine or its derivatives and phenols. Synthesized compounds were tested in vitro for their PDE4B inhibitory activity [ 57 ]. Compound 39 showed significant PDE4B inhibition at 30 µM in comparison to the reference compound rolipram.…”

Section: Selective Pde4b Inhibitorsmentioning

confidence: 99%

Selective Phosphodiesterase 4B Inhibitors: A Review

Azam¹

2014

Sci. Pharm.

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Phosphodiesterase 4B (PDE4B) is a member of the phosphodiesterase family of proteins that plays a critical role in regulating intracellular levels of cyclic adenosine monophosphate (cAMP) by controlling its rate of degradation. It has been demonstrated that this isoform is involved in the orchestra of events which includes inflammation, schizophrenia, cancers, chronic obstructive pulmonary disease, contractility of the myocardium, and psoriatic arthritis. Phosphodiesterase 4B has constituted an interesting target for drug development. In recent years, a number of PDE4B inhibitors have been developed for their use as therapeutic agents. In this review, an up-to-date status of the inhibitors investigated for the inhibition of PDE4B has been given so that this rich source of structural information of presently known PDE4B inhibitors could be helpful in generating a selective and potent inhibitor of PDE4B.

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Section: Selective Pde4b Inhibitorsmentioning

confidence: 99%

Selective Phosphodiesterase 4B Inhibitors: A Review

Azam¹

2014

Sci. Pharm.

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“…Isatin (indole‐2,3‐dione; Figure 1) is ubiquitous in naturally occurring compounds and its derivatives have the potential to act on various biological targets like histone deacetylase, β‐carbonic anhydrase, tyrosine kinase, phosphodiesterase 4B, and tubulin, causing apoptosis of diverse pathogens and influencing the expression of certain apoptosis‐related genes. [ 9–12 ] Thus, isatin derivatives possess broad‐spectrum therapeutic properties, such as antibacterial, [ 12,13 ] antimalarial, [ 14,15 ] antitubercular, [ 16,17 ] and anticancer [ 18–22 ] activities. Moreover, many anticancer agents such as semaxanib, sunitinib, nintedanib, and hesperadin (Figure 1) bear an isatin moiety, [ 23 ] demonstrating that isatin is a fruitful matrix for the development of novel anticancer drugs.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in isatin hybrids as potential anticancer agents

Ding

Zhou

Zeng

2020

Archiv der Pharmazie

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The isatin framework is a useful template for the development of novel anticancer agents. This is exemplified by the fact that several isatin‐based anticancer agents, such as semaxanib, sunitinib, nintedanib, and hesperadin, are already in use or under clinical trials for the treatment of diverse kinds of cancers. Isatin‐based hybrids could be obtained by incorporating other anticancer pharmacophores into the isatin skeleton and they have the potential to overcome drug resistance with reduced side effects. Thus, isatin‐based hybrids may provide attractive scaffolds for the development of novel anticancer agents. This review covers the recent advances of isatin‐based hybrids with anticancer activity, covering articles published between 2001 and 2019. The anticancer activities of these molecules and the structure–activity relationships are also discussed. The purpose of this review article is to set up the direction for the design and development of isatin‐based hybrids with high efficacy and low toxicity.

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“…[ 10,11 ] Hence many reports are available in the literature for such cycloadditions, especially by using electron‐deficient alkenes and alkynes as dipolarophiles such as α,β‐unsaturated carbonyl compounds and nitro compounds. [ 12–15 ] The resulting adducts find enormous applications in pharmaceutics, catalysis, and agrochemicals. [ 16,17 ]…”

Section: Introductionmentioning

confidence: 99%

One‐pot three‐component 1,3‐dipolar cycloaddition of azomethineylides to nitrofuran containing acetylenic ketones and molecular docking studies of the cycloadducts

Kadambar

Kalluraya

Kumar

2020

Journal of Heterocyclic Chem

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One‐pot three‐component 1,3‐dipolar cycloaddition reaction of azomethineylides generated from various combinations of isatin and ninhydrin with α‐aminoacids to 5‐nitrofurancontaining acetylenic ketones was carried out under thermal and microwave methods. The study of the regiochemical trend during the cycloaddition suggested that the nitrofuran ring exert no effect on the regiochemistry of the reaction as observed in the case of nitrofuran containing chalcones. The reason for the nil influence of the nitrofuran group is attributed to the increased electron density due to the triple bond. The newly synthesized compounds were docked to the active site of human anaplastic lymphoma kinase (ALK) to know the cancer cell toxicity in silico. The compounds 4b and 5a showed good binding interactions with the target in the active site.

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Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest

Cited by 47 publications

References 16 publications

Selective Phosphodiesterase 4B Inhibitors: A Review

Selective Phosphodiesterase 4B Inhibitors: A Review

Recent advances in isatin hybrids as potential anticancer agents

One‐pot three‐component 1,3‐dipolar cycloaddition of azomethineylides to nitrofuran containing acetylenic ketones and molecular docking studies of the cycloadducts

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