Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

Anderson, David R.; Hegde, Shridhar G.; Reinhard, Emily J.; Gomez, Leslie; Vernier, William F.; Lee, Len; Liu, Shuang; Sambandam, Aruna; ., Snider, Patricia, R.; Masih, Liaqat

doi:10.1016/j.bmcl.2005.01.067

Cited by 270 publications

(121 citation statements)

References 6 publications

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“…6-8. Some among them are extremely effective against such kind of diseases which influenced by nitrogen-activated protein kinase enzyme inhibitors. Some of them have antimicrobial activity , 11 cytotoxic effect against human cancer cells, 12 antiallergic activity, 13 central nervous system influencing activity, 14 antiproliferation activty. 15 Several derivatives are also widely used as agrochemicals, 16 antioxidant 17 and antiinflammatory agent.…”

Section: Introductionmentioning

confidence: 99%

An Expeditious and Green Approach for the Synthesis of 2-Amino-4h-Chromenes Using a Catalyst of Natural Origin

Bhosale¹,

Shisodia²,

Ingle³

et al. 2018

ECB

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A highly efficient three-component one step system for the synthesis of 2-amino-4H-chromens is developed. Excellent yields were obtained simply by mixing malononitrile, aromatic aldehyde and α-napthol in lemon juice as a catalyst of natural origin and solvent, avoiding using hazardous organic solvents. The main advantages of this method are its green method character, short reaction time and simple workup procedures and the lack of using any metal containing catalysts. * Corresponding Authors

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Section: Introductionmentioning

confidence: 99%

An Expeditious and Green Approach for the Synthesis of 2-Amino-4h-Chromenes Using a Catalyst of Natural Origin

Bhosale¹,

Shisodia²,

Ingle³

et al. 2018

ECB

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“…An important source with various applications in biology, pharmacology and diseases therapy is 4H-Pyran nucleus. These compounds are also employed in industrial and biodegradable agrochemicals [13][14][15][16][17][18][19][20][21][22] . Organic chemists encouraged to develop efficiencies and procedures for synthesis of these kinds of compounds [23][24][25][26] .…”

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confidence: 99%

Insights into the Reaction Mechanism of the Tetrahydrobenzo [b] pyran by means of Kinetic Studies in the Presence of Fructose as a Green Catalyst

Ghalandarzehi¹,

Habibi‐Khorassani²,

Shahraki³

2016

Orient. J. Chem

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Extensive kinetic studies were performed to investigate the mechanism of the reaction between 4-methoxybenzaldehyde 1, malononitrile 2, and dimedone 3 in the presence of fructose as a catalyst in a mixture of water and ethanol. The synthesis reaction of tetrahydrobenzo[b]pyran followed second-order kinetics. The partial orders with respect to 1, 2 were one and one, respectively. Temperature effect has been investigated on the reaction rate, and relevant parameters have been determined with two linearized forms of Eyring equation. The proposed mechanism theoretical rate law were compatible with the experimental data. From the temperature, concentration and solvent studies, the activation energy (E a = 70.05 ± 1.39 kJmol

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“…1). Examples of structurally relevant biologically active compounds are benzopyranopyridines B, found to inhibit mitogen-activated protein kinase-activated protein kinase 2 and attenuate the production of pro-inflammatory TNFα, 12 and C, reported to inhibit histamine-stimulated gastric acid secretion in animals. 13 We previously disclosed a one-step three-component synthesis of 3,5-dicyanopyridines D starting from various aldehydes, thiols and malononitrile (Fig.…”

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Convenient One‐Step Synthesis of a Medicinally Relevant Benzopyranopyridine System.

et al. 2007

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Benzopyrano [2,3-b]pyridine is an important privileged medicinal scaffold. A three-component reaction of salicylaldehydes, thiols and 2 equiv of malononitrile that leads to the formation of a series of compounds incorporating 2,4-diamino-3-cyano-5-sulfanylbenzopyrano[2,3-b]pyridine framework is described. A proposed mechanism with the supporting experimental data is presented. KeywordsMulticomponent reaction; Privileged medicinal scaffold; Drug-like heterocycle The rapid assembly of molecular diversity utilizing multi-component reactions has received a great deal of attention, most notably for the construction of heterocyclic `drug-like' libraries. 1 These methodologies are of particularly great utility when they lead to the formation of `privileged medicinal scaffolds,' defined as molecular frameworks serving as the basis for the generation of ligands for functionally and structurally discreet biological receptors. 2 Such chemistry greatly facilitates the development of pharmaceutical agents for diverse applications.Benzopyrano [2,3-b]pyridine scaffold is of a significant medicinal relevance. The examples of approved therapeutic agents incorporating this molecular framework include amlexanox and pranoprofen (Fig. 1).In addition, many of these compounds possess anti-pro-liferative, 3 cancer chemopreventive, 4 anti-bacterial (including anti-tubercular), 5 anti-myopic, 6 anti-histaminic, 7 hypotensive, 8 anti-rheumatic 9 and anti-asthmatic activities. 10 processes allowing the synthesis of previously inaccessible analogues for biological evaluation. In this letter, we describe a multi-component strategy for the rapid preparation of library A (Fig. 1). Examples of structurally relevant biologically active compounds are benzopyranopyridines B, found to inhibit mitogen-activated protein kinase-activated protein kinase 2 and attenuate the production of pro-inflammatory TNFα, 12 and C, reported to inhibit histamine-stimulated gastric acid secretion in animals. 13 We previously disclosed a one-step three-component synthesis of 3,5-dicyanopyridines D starting from various aldehydes, thiols and malononitrile (Fig. 2). 14 In an attempt to extend the method for the preparation of pyridines E we employed salicylic aldehydes and obtained a library of compounds whose elemental analysis data and the NMR spectra were inconsistent with the expected structures. The X-ray analysis showed these compounds to have a benzopyrano[2,3-b]pyridine framework A (Fig. 3). 15 The reaction works well for all salicylaldehyde and thiol combinations tested. The products precipitate from refluxing ethanolic solutions and are isolated by simple filtration. The yields of recrystallized benzopyranopyridines are given in Table 1. 16,17 Our proposed mechanistic interpretation of the divergence in reaction paths for o,ounsubstituted aldehydes, leading to formation of pyridines D, and salicylic aldehydes, resulting in benzopyranopyridines A, is shown in Figure 4.Base-catalyzed Michael addition of thiols to Knoevenagel adducts F, produced fr...

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Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

Cited by 270 publications

References 6 publications

An Expeditious and Green Approach for the Synthesis of 2-Amino-4h-Chromenes Using a Catalyst of Natural Origin

An Expeditious and Green Approach for the Synthesis of 2-Amino-4h-Chromenes Using a Catalyst of Natural Origin

Insights into the Reaction Mechanism of the Tetrahydrobenzo [b] pyran by means of Kinetic Studies in the Presence of Fructose as a Green Catalyst

Convenient One‐Step Synthesis of a Medicinally Relevant Benzopyranopyridine System.

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