Absolute configurations of four isomers of 3-formamido-4-hydroxy-.ALPHA.-[[N-(p-methoxy-.ALPHA.-methylphenethyl)amino]methyl]benzyl alcohol, a potent .BETA.-adrenoreceptor stimulant.

Murase, Kiyoshi; Mase, Toshiyasu; Ida, Hisashi; Takahashi, Kozo; Murakami, Masuo

doi:10.1248/cpb.26.1123

Cited by 34 publications

(20 citation statements)

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“…For example, (S)-amphetamine has higher pharmacologically activity as stimulant [4] and hyperthermic agent [5] than its (R)-enantiomer; (R)-4-phenylbutan-2-amine (2a) is a precursor of the anti-hypertensive dilevalol, [6] and (R)-p-methoxyamphetamine (2d) is a constituent of (R,R)-formoterol, a potent bronchodilator. [7] Furthermore 1-phenyl-1-propylamine (2c) is a precursor of the corticotropin-releasing factor type-1 receptor antagonist, a potent anti-depressive agent. [8] Consequently, there is a need for efficient methods to obtain the desired (R)-or (S)-enantiomer in optically pure form starting from easily accessible ketone.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Optically Pure Pharmacologically Relevant Amines Employing ω‐Transaminases

et al. 2008

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Abstract:Various w-transaminases were tested for the synthesis of enantiomerically pure amines from the corresponding ketones employing d-or l-alanine as amino donor and lactate dehydrogenase to remove the side-product pyruvate to shift the unfavourable reaction equilibrium to the product side. Both enantiomers, (R)-and (S)-amines, could be prepared with up to 99% ee and > 99% conversions within 24 h at 50 mM substrate concentration. The activity and stereoselectivity of the amination reaction depended on the w-transaminase and substrate employed; furthermore the co-solvent significantly influenced both the stereoselectivity and activity of the transaminases. Best results were obtained by employing ATA-117 to obtain the (R)-enantiomer and ATA-113 or ATA-103 to access the (S)-enantiomer with 15% v v À1 DMSO.

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Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Optically Pure Pharmacologically Relevant Amines Employing ω‐Transaminases

et al. 2008

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“…Because of the two stereocenters in the molecule structure, there are four different stereoisomers that demonstrate different pharmacological potencies, respectively, the order is (R,R)>(R,S))(S,R)>(S,S). 1 Toxicology studies indicated that the (S,S)-isomer is toxic in a manner independent of b 2 -adrenoceptor binding and may increase the toxicological burden of the racemic drug. 2 Therefore, the use of (R,R)-Formoterol for asthma could eliminate adverse effects of (S,S)-Formoterol that arise during therapeutic use.…”

Section: Introductionmentioning

confidence: 99%

“…Despite the unique strongpoint of (R,R)-Formoterol, there were few reports of the asymmetric synthesis of this useful chiral drug. Murase et al 1 described a preparation employing a resolution process of two enantiomers. Trofast et al 3 reported a HPLC-semipreparative separation of diastereomers.…”

Section: Introductionmentioning

confidence: 99%

The asymmetric synthesis of (R,R)‐formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water

et al. 2009

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(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro-acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild conditions. With a mixture of PEG 2000 and water as the reaction media, the catalyst system could be recycled four times.

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“…The order of potency is (R,R ) » (R,S ) = (S,R) > (S,S) [57]. The order of potency is (R,R ) » (R,S ) = (S,R) > (S,S) [57].…”

Section: Formoterol-perforomistmentioning

confidence: 99%

Drugs for Treating Respiratory System Diseases

Vardanyan

Hruby

2016

Synthesis of Best-Seller Drugs

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Absolute configurations of four isomers of 3-formamido-4-hydroxy-.ALPHA.-[[N-(p-methoxy-.ALPHA.-methylphenethyl)amino]methyl]benzyl alcohol, a potent .BETA.-adrenoreceptor stimulant.

Cited by 34 publications

References 0 publications

Asymmetric Synthesis of Optically Pure Pharmacologically Relevant Amines Employing ω‐Transaminases

Asymmetric Synthesis of Optically Pure Pharmacologically Relevant Amines Employing ω‐Transaminases

The asymmetric synthesis of (R,R)‐formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water

Drugs for Treating Respiratory System Diseases

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