Studies on biotransformation of (±)-1-(4′-chlorophenyl)-2-phenylethanol

Bustillo, Antonio; García-Pajón, Carlos Mario; Aleu, Josefina; Hernández-Galán, Rosario; Collado, Isidro G.

doi:10.1016/j.tetasy.2003.08.026

Cited by 7 publications

(12 citation statements)

References 16 publications

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“…Detoxification by these fungi was studied and suggests that they probably would not persist in the environment for long periods post-application (7,10).…”

Section: Resultsmentioning

confidence: 99%

Global Antifungal Profile Optimization of Chlorophenyl Derivatives against Botrytis cinerea and Colletotrichum gloeosporioides

Saı́z-Urra

Pérez

Cruz-Monteagudo

et al. 2009

J. Agric. Food Chem.

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Twenty-two aromatic derivatives bearing a chlorine atom and a different chain in the para or meta position were prepared and evaluated for their in vitro antifungal activity against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. The results showed that maximum inhibition of the growth of these fungi was exhibited for enantiomers S and R of 1-(4 0 -chlorophenyl)-2-phenylethanol (3 and 4). Furthermore, their antifungal activity showed a clear structure-activity relationship (SAR) trend confirming the importance of the benzyl hydroxyl group in the inhibitory mechanism of the compounds studied. Additionally, a multiobjective optimization study of the global antifungal profile of chlorophenyl derivatives was conducted in order to establish a rational strategy for the filtering of new fungicide candidates from combinatorial libraries. The MOOP-DESIRE methodology was used for this purpose providing reliable ranking models that can be used later.

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“…Detoxification by these fungi was studied and suggests that they probably would not persist in the environment for long periods post-application (7,10).…”

Section: Resultsmentioning

confidence: 99%

Global Antifungal Profile Optimization of Chlorophenyl Derivatives against Botrytis cinerea and Colletotrichum gloeosporioides

Saı́z-Urra

Pérez

Cruz-Monteagudo

et al. 2009

J. Agric. Food Chem.

Self Cite

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“…The reaction mixtures were stirred for 20 h. The solvent was then removed and the crude reaction product chromatographed to give (±)-1-(4 -chlorophenyl)-1-cyclopropyl methyl acetate (5) (94.1%) and (±)-1-(4-chlorophenyl)-2-phenylethyl acetate (6) [14] (93.2%).…”

Section: Synthesis Of Racemic Substratesmentioning

confidence: 99%

“…The chemical preparation of the (S)-enantiomer of 1-(4 -chlorophenyl)-2-phenylethanol (S)-4 was previously reported with excellent yield and enantiomeric excess [14]. Thus, in order to obtain (R)-1-(4 -chlorophenyl)-2-phenylethanol (R)-4 and both enantiomers of 1-(4 -chlorophenyl)-1-cyclopropyl methanol (3) [15], we employed the same chemical experimental procedure consisting of treatment of 4 -chlorophenyl cyclopropyl ketone (1) or benzyl 4 -chlorophenyl ketone (2) with BH 3 -THF and (R)-or (S)-methyl oxazaborolidine [17].…”

Section: Chemical Transformationsmentioning

confidence: 99%

“…After hydrolysis of the acetate derivatives with potassium hydroxide in methanol, the enantiopure alcohols were identified as (6) [14].…”

Section: Lipase-mediated Transformationsmentioning

confidence: 99%

“…Previous studies of the detoxification of 1-(4 -chlorophenyl)-2-phenylethanol (4) by B. cinerea and C. gloeosporioides suggest that it is not likely to persist in the environment for long periods postapplication [14].…”

Section: Introductionmentioning

confidence: 99%

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