An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene:  Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963

Kauffman, Goss S.; Harris, Gregory D.; Dorow, Roberta L.; Stone, Benjamin R. P.; Parsons, Rodney L.; Pesti, Jaan A.; Magnus, Nicholas A.; Fortunak, Joseph; Confalone, Pat N.; Nugent, William A.

doi:10.1021/ol006321x

Cited by 184 publications

(69 citation statements)

References 17 publications

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“…Quinoline and their derivatives play important roles in the synthesis of natural products and as therapeutic agents, and constitute an important class of compounds for new drug development. They have been synthesized by many researchers as model compounds 14 and found to exhibit different pharmacological activities covering anti-cancer, anti-mycobacterial, anti-microbial, anti-convulsant, anti-inflammatory, and cardiovascular activities [15][16][17][18][19] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Püsküllü

Shirinzadeh

Nenni

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Overproduction of reactive oxygen species results in oxidative stress that can cause fatal damage to vital cell structures. It is known that the use of antioxidants could be beneficial in the prevention or delay of numerous diseases associated with oxidative stress. Melatonin (MLT) is known as a powerful free-radical scavenger and antioxidant. It was found that indole ring of MLT can be employed by bioisosteric replacement by other aromatic rings. Quinoline derivatives constitute an important class of compounds for new drug development. Owing to quinoline and hydrazones appealing physiological properties and are mostly found in numerous biologically active compounds a series of quinoline-2-carbaldehyde hydrazone derivatives were synthesized as bioisosteric analogues of MLT, characterized and in vitro antioxidant activity was investigated by evaluating their reducing effect against oxidation of a redox-sensitive fluorescent probe. Cytotoxicity potential of all compounds was investigated both by lactate dehydrogenase leakage assay and by MTT assay.

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Püsküllü

Shirinzadeh

Nenni

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…This reaction belongs among C-C couplings producing chiral propargylamines which represent important intermediates in synthesis of various chiral nitrogen compounds (heterocyclic, in particular) [32][33][34][35][36]. It is well known [37] that Cu(I) complexes are highly efficient catalysts in this reaction.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, copper(II) complexes and catalytic activity of substituted 6-(1,3-oxazolin-2-yl)pyridine-2-carboxylates

Drabina

Funk

Růžička

et al. 2010

Transition Met Chem

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The optically pure 6-(4-alkyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine-2-carboxylates have been prepared from 6-methoxycarbonylpyridine-2-carboxylic acid by a sequence of three reactions with the overall yield of 40-50%. Some of these compounds form stable complexes with Cu(II) ions in non-aqueous medium. Their polymeric structure was determined in the solid phase by X-ray diffraction analysis. The Cu(II) complexes were also used as catalysts for addition reactions of terminal alkynes to imines giving substituted propargylamines with maximum yield 64% and 37% ee.

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“…[63] In 2004, Jiang and co-workers managed the synthesis of 4-methoxybenzyl ether (PMB)-protected DPC 961 65 by means of a chiral amino alcohol (64 a) mediated enantioselective alkynylation addition reaction (Scheme 20). [64] However, a drawback of these two preliminary studies is the use of a stoichiometric amount of chiral mediator, which prompted chemists to investigate catalytic asymmetric ways to achieve the same result.…”

Section: Chiral Trifluoromethylated Dihydroquinazolinones (Cf 3 -Dihymentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF₃ Stereogenic Center

Huang

Yang

Chen

et al. 2015

Chemistry A European J

133

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Given the important agricultural and medicinal application of optically pure heterocycles bearing a trifluoromethyl group at the stereogenic carbon center in the heterocyclic framework, the exploration of efficient and practical synthetic strategies to such types of molecules remains highly desirable. Catalytic enantioselective synthesis has one clear advantage that it is more cost-effective than other synthetic methods, but remains limited by challenges in achieving excellent yield and stereoselectivities with a low catalyst loading. Thus far, numerous models of organo- and organometal-catalyzed asymmetric reactions have been exploited to achieve this elusive goal over the past decade. This review article describes recent progress on this research topic, and focuses on an understanding of the catalytic asymmetric protocols exemplified in the catalytic enantioselective synthesis of a wide range of complex enantioenriched trifluoromethylated heterocycles.

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An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene: Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963

Cited by 184 publications

References 17 publications

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Synthesis, copper(II) complexes and catalytic activity of substituted 6-(1,3-oxazolin-2-yl)pyridine-2-carboxylates

Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF₃ Stereogenic Center

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An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene: Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963

Cited by 184 publications

References 17 publications

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues

Synthesis, copper(II) complexes and catalytic activity of substituted 6-(1,3-oxazolin-2-yl)pyridine-2-carboxylates

Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF3 Stereogenic Center

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Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF₃ Stereogenic Center