- Two asymmetric syntheses of AMG 221, an inhibitor of 11β- hydroxysteroid dehydrogenase type 1
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(Chemical Equation Presented) Two asymmetric syntheses of AMG 221 (2), an inhibitor of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) discovered in our laboratories, are reported. One of the syntheses utilizes chiral trimethylsilyl cyanohydrin 12 as s
- Caille, Seb,Cui, Sheng,Hwang, Tsang-Lin,Wang, Xiang,Faul, Margaret M.
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experimental part
p. 3833 - 3842
(2009/11/30)
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- Oxazolones as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1
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2,5,5-Trisubstituted oxazolones were identified as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). The synthesis, structure-activity relationship and metabolic stability of these compounds are presented.
- Sutin, Lori,Andersson, Soeren,Bergquist, Lars,Castro, Victor M.,Danielsson, Eva,James, Stephen,Henriksson, Martin,Johansson, Lars,Kaiser, Christina,Flyren, Katarina,Williams, Meredith
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p. 4837 - 4840
(2008/02/11)
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- A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins
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A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).
- Nanda, Samik,Kato, Yasuo,Asano, Yasuhisa
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p. 10908 - 10916
(2007/10/03)
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- Studies on phosphoroheterocycle chemistry III: An unusual way to 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives
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An unusual but efficient method for the synthesis of phosphoroheterocycles, 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives, by the reaction of Lawesson's reagent with a variety of α-hydroxy nitriles has been developed. The possible mechanism of the reaction is proposed to involve thiation of hydroxy group in a first step, sequential addition of P-SH to the nitrile and rearrangement resulting in the title phosphoroheterocycles. The preliminary bioassays show that these heterocyclic compounds have herbicidal properties.
- Deng, ShengLou,Chen, RuYu
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p. 2527 - 2531
(2007/10/03)
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- Naturally occurring cyanohydrins, analogues and derivatives as potential insecticides
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Several naturally occurring cyanohydrins were tested for fumigation toxicity to two insect species, the house fly (Musca domestica L) and the lesser grain borer (Rhyzopertha dominica (F)). Synthetic analogues of these compounds were tested as well. Most of the cyanohydrins tested were more toxic as fumigants to M domestica and R dominica than chloropicrin; some compounds were nearly as toxic as dichlorvos. Naturally occurring cyanohydrins were among the most toxic tested. (C) 2000 Society of Chemical Industry.
- Peterson, Chris J.,Tsao, Rong,Coats, Joel R.
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p. 615 - 617
(2007/10/03)
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- KINETIC RESOLUTION OF KETONE CYANOHYDRIN ACETATES WITH A MICROBIAL ENZYME
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Incubation of dl-1-cyano-1-metylalkyl (or alkenyl) acatates (methyl ketone cyanohydrin acetates) with cells of Pichia miso IAM 4682 afforded optically active acetates and the corresponding ketones via asymmetric hydrolysis.Resulting (S)-2-cyano-2-undecyl acetate was converted to the aminofuranone derivative without losing its optical purity.
- Ohta, Hiromichi,Kimura,Yoichi,Sugano, Yasushi
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p. 6957 - 6960
(2007/10/02)
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- PHEROMONE SYNTHESIS-63 SYNTHESIS OF BOTH THE ENANTIOMERS OF 2,3-DIHYDRO-2-ISOPROPYL-2,5-DIMETHYLFURAN, A SEX SPECIFIC COMPOUND IN FEMALES OF THE BEETLE HYLECOETUS DERMESTOIDES L
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Both the enantiomers of 2,3-dihydro-2-isopropyl-2,5-dimethylfuran were synthesized employing the Sharpless asymmetric epoxidation reaction.The (R)-(-)-enantiomer of this cyclic enol ether was also synthesized from (R)-(-)-linalool.
- Mori, Kenji,Ebata, Takashi,Takechi, Shozo
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p. 1761 - 1766
(2007/10/02)
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