Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

Paizs, Csaba; Toşa, Monica Ioana; Majdik, Cornelia; Moldovan, Paula; Novák, Lajos; Kolonits, Pál; Marcovici, Adriana; Irimie, Florin Dan; Poppe, László

doi:10.1016/s0957-4166(03)00222-2

Cited by 51 publications

(22 citation statements)

References 24 publications

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“…To determine the absolute confi guration of the novel heteroarylethanols, a known retrosynthetic pathway was employed (Paizs et al 2003). Thus, the known optically active diols (Bencze et al 2010(Bencze et al , 2011 ( S )-3a,c-e were selectively mesylated at the primary hydroxyl group, followed by a reduction of the mesylated intermediates with LiAlH 4 , yielding the corresponding optically active heteroarylethanols ( S )-2a,c-e (Scheme 1b).…”

Section: Resultsmentioning

confidence: 99%

“…Highly enantiomerically enriched benzofuranyl-, benzo[ b ]thiophenyl-, pyridinyl-and furanyl-ethanols have been synthesised in high yield by whole cell reduction (To ş a et al 2008, Paizs et al 2003, Busto et al 2006, Takeshita et al 1987). Due to its high substrate specifi city, only 1-substituted ethanones are accepted as substrates by yeast alcohol dehydrogenase (YADH), the main oxidoreductase from yeast.…”

Section: Introductionmentioning

confidence: 99%

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Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast

Trif

Kalló

Naghi

et al. 2011

Biocatalysis and Biotransformation

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Baker ' s yeast mediated reduction of various phenylfuran-2-yl-ethanones has been studied. The infl uence of the reaction conditions, the type and position of the substituents, as well the presence of various additives on the enantiomeric composition of the products and the reaction yield are discussed. The absolute confi guration of the reaction products was established using a retrosynthetic procedure.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast

Trif

Kalló

Naghi

et al. 2011

Biocatalysis and Biotransformation

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“…Reaction of 14 with hydroxylamine hydrochloride afforded the amidoxime (15). Treatment of 15 with acetyl chloride in pyridine gave the 2-(5-methyloxadiazol-3-yl) benzo[b] furan (17) by cyclization to the 1,2,4-oxadiazole ring.…”

Section: Preparation Of 2-isoxazolylbenzo[b] Furans (9-12)mentioning

confidence: 99%

“…The 2-pyrazoly-(8), 2-isoxazolyl-(12), 2-oxadiazolylbenzo [b] furans (15,(17)(18)(19) were inactive (Tables 1, 2). Unfortunately, inhibitory activity of the carboxylic acids (6c, e, 21k) could not be determined, because they are fluorescent compounds.…”

Section: Preparation Of 2-isoxazolylbenzo[b] Furans (9-12)mentioning

confidence: 99%

Preparation of Benzo[<i>b</i>]furans Having Five-Membered Heterocycles at the 2-Position and 2-(4-Alkylcarbamoylbuta-1,3-dienyl)benzo[<i>b</i>]furans, and Their Cysteinyl Leukotriene Receptor (cysLT1, cysLT2) Inhibitory Activity

Akai

Tabuchi

Ando

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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1-5) CysLTs mediate their effects through two different receptors, cysLT1 and cysLT2. 6) CysLT1 selective antagonists, such as pranlukast, montelukast and zafirlukast, have been shown to be clinically beneficial against chronic asthma. However, the synthesis of cysLT1 and/or cysLT2 antagonist still remains challenging. BAY u9773 was reported to be a dual cysLT1 and cysLT2 antagonist and a partial agonist of cysLT2.7,8) DUO-LT was also shown to be a dual antagonist (Fig. 1). 4) However, no selective cysLT2 antagonist has yet been developed for clinical applications. Recently, increased expression of cysLT2 receptor has been reported in colon cancer 9) and myocardial ischemia-reperfusion injury.10) The development of a dual antagonist and/or selective cysLT2 antagonist should be of great therapeutic value.In previous papers, we reported the preparation of sev-furan derivatives (A) and their cysLT1 and cysLT2 inhibitory activities 11,12) (Fig. 2). In our current work on leukotriene, we found that (E)-(2-diethylcarbamoyl-1-methylvinyl)-benzo [b] furans (B) showed potent leukotoriene B 4 (LTB 4 ) inhibitory activity, 13,14) and that compound (C) showed more potent LTB 4 inhibitory activity than compounds B. 15,16) In this time, in order to increase the inhibitory activity of the cycLTs receptor, acidic and amide moieties were introduced to the benzo [b] furan skeleton on the compound D on the basis of the structure of the compounds A and characteristic cysLTs molecular structures (Fig. 3). In addition, 2-(4-alkylcarbamoylbuta-1,3-dienyl) benzo [b] furans (E) having a wide range of conjugated systems were also prepared. In our design of compounds D and E, the structure of LTC 4 could be divided into the lipophilic, acidic and amide moieties. In the design of compound D, the benzo[b] furan ring having a fivemembered heterocyclic ring at the 2-position, the 4-oxypropanoic acid and the amide group on the heterocycle could be considered to correspond to the lipophilic, acidic and amide moieties in LTC 4 , respectively. Compound E was designed in the same manner as compound D, as shown in Fig. 3. Here Note * To whom correspondence should be addressed. e-mail: ikuo_k@mukogawa-u.ac.jp; nishide@mukogawa-u.ac.jp; ymohishi@kcc.zaq.ne.jp (1) 17,18) were treated with 2 eq of POCl 3 in N,N-dimethylformamide to give 2-(1-chloro-2-formylvinyl)-benzo [b] furans (2), 19,20) of which the stereochemistry of the (Z)-olefin is discussed below. Aldehydes (2) were converted to 2-(1-chloro-2-cyanovinyl) benzo [b] furans (3a, b) in two steps. 21)Cleavage of the methyl ether of 3b by treatment with BBr 3 afforded the 7-hydroxyl compound (3c) (Chart 1).Preparation of 2-Thienylbenzo[b] furans (4-6) Thiophene ring formation by treatment of 3 with ethyl thioglyco late proceeded smoothly to give 2-(3-amino-2-ethoxycarbonylthiophen-5-yl) benzo [b] furans (4a-c).21,22) The 7-hydroxyl compound (4c) was treated with several alkyl halides to afford the corresponding 7-alkyloxy-2-thienylbenzo[b]-furans (4d-e). Acylation of the 3-aminothiophene co...

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“…Since the need for the production of optically active compounds as single enantiomers is growing rapidly, we have previously studied the lipase-catalyzed enantiomerselective kinetic resolutions of the racemic 1-heteroarylethanols 2a-d. 1,2 The main drawback of the enantiomer selective reactions is that maximum conversion for the desired enantiomer can only be 50%, which in turn can be overcome by performing an enantioselective transformation, with 100% theoretical conversion.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols

Toşa

Podea

Paizs

et al. 2008

Tetrahedron: Asymmetry

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Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

Cited by 51 publications

References 24 publications

Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast

Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast

Preparation of Benzo[<i>b</i>]furans Having Five-Membered Heterocycles at the 2-Position and 2-(4-Alkylcarbamoylbuta-1,3-dienyl)benzo[<i>b</i>]furans, and Their Cysteinyl Leukotriene Receptor (cysLT1, cysLT2) Inhibitory Activity

Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols

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