Stereoselective reactions of nitro compounds in the synthesis of natural compound analogs and active pharmaceutical ingredients

Sukhorukov, Alexey Yu.; Sukhanova, Anna; Zlotin, Sergei G.

doi:10.1016/j.tet.2016.07.067

Cited by 125 publications

(77 citation statements)

References 540 publications

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“…An alternative to the soluble base used as catalyst, which requires additional work‐up steps, is the use of metal‐organic frameworks as heterogeneous catalysts . Michael addition steps allow to obtain Rolipram (compound 5 in Figure ), a selective phosphodiesterase‐4 inhibitor, or Warfarin (compound 6 in Figure ), a vitamin K antagonist and one of the most effective anticoagulants …”

Section: Mofs and Enzymes As Catalysts For C−c Bond Formationsmentioning

confidence: 99%

Engineered MOFs and Enzymes for the Synthesis of Active Pharmaceutical Ingredients

Cirujano

2019

ChemCatChem

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The latest strategies in the design and synthesis of metalorganic frameworks as heterogeneous catalysts in organic synthesis are compared with biocatalyzed transformations, as a step forward to a more convenient industrial production of pharmaceuticals. Relevant CÀ C and CÀ N bond forming reactions that are both chemo-and bio-catalyzed by synthetic MOFs and in vitro evolved and/or promiscuous enzymes with the aim of obtaining key bioactive scaffolds in a sustainable, competitive and cost-efficient manner, are thoroughly discussed in this mini review.

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Section: Mofs and Enzymes As Catalysts For C−c Bond Formationsmentioning

confidence: 99%

Engineered MOFs and Enzymes for the Synthesis of Active Pharmaceutical Ingredients

Cirujano

2019

ChemCatChem

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“…It was approved by the U.S. Food and Drug Administration for the treatment of Alzheimer's disease (AD) on April 21, 2000 . Isoprenaline or isoproterenol (trade names Medihaler‐Iso and Isuprel) is a medication used for the treatment of bradycardia (slow heart rate), heart block, and rarely for asthma …”

Section: Introductionmentioning

confidence: 99%

“…[13] Isoprenaline or isoproterenol (trade names Medihaler-Iso and Isuprel) is a medication used for the treatment of bradycardia (slow heart rate), heart block, and rarely for asthma. [14] Selective asymmetric reduction can be carried out by using either isolated enzymes or whole cells. There are reports using yeasts and bacteria for the asymmetric reduction of the carbonyl moiety to chiral alcohols.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD87E6 as a Biocatalyst

Öksüz

Şahin

Dertli

2018

Chemistry & Biodiversity

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Global sales of single enantiomeric drug products are growing at an alarming rate every year. A total of 7 bacterial strains were screened for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Lactobacillus paracasei BD87E6 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent Lactobacillus paracasei BD87E6, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of 3‐methoxyacetophenone (1h) by Lactobacillus paracasei BD87E6 gave (R)‐1‐(3‐methoxyphenyl)ethanol (2h) with 92% yield and 99% enantiomeric excess. Compound 2h could be used for the synthesis of (S)‐rivastigmine which has a great potential for the treatment of Alzheimer's disease. This study demonstrates that Lactobacillus paracasei BD87E6 can be used as a biocatalyst to obtain chiral carbinol with excellent yield and selectivity. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that Lactobacillus paracasei BD87E6 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest.

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“…23 This class of compound is quite limited and therefore insufficiently studied. In addition, the pyrrolidine moiety (including fused pyrrolidines) is considered as a "privileged" structural fragment and a key component of efficient organocatalysts, 24 enzyme inhibitors, 25 etc.…”

Section: Introductionmentioning

confidence: 99%

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

Bastrakov¹,

Kucherova²,

Fedorenko³

et al. 2017

Arkivoc

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An efficient and convenient one-step method for the synthesis of decahydrodipyrrolo [3,4-b:3',4'-d]pyridine derivatives was developed on the basis of 1,3-dipolar cycloaddition of unstabilized N-methyl azomethine ylide with 2-substituted 3,5-dinitropyridines. This novel heterocyclic system contains two 3-nitropyrrolidine fragments fused to a partially saturated pyridine ring. Such types of compound, as follows from the literature, can be considered as potential nitric oxide donors.

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Stereoselective reactions of nitro compounds in the synthesis of natural compound analogs and active pharmaceutical ingredients

Cited by 125 publications

References 540 publications

Engineered MOFs and Enzymes for the Synthesis of Active Pharmaceutical Ingredients

Engineered MOFs and Enzymes for the Synthesis of Active Pharmaceutical Ingredients

Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD87E6 as a Biocatalyst

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

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