79762-35-9Relevant academic research and scientific papers
A facile preparation of α-aryl carboxylic acid via one-flow arndt-eistert synthesis
Fuse, Shinichiro,Otake, Yuma,Mifune, Yuto,Tanaka, Hiroshi
, p. 1657 - 1661 (2015/11/10)
An efficient, one-flow Arndt-Eistert synthesis was demonstrated. A sequence of acid chloride formation-nucleophilic acyl substitution-Wolff rearrangement-nucleophilic addition was performed in a microflow system without isolating any intermediates, which
Synthesis of Curvulone B Using the 2-Chlorobenzyl Protecting Group
Bates, Roderick W.,Wang, Kongchen,Zhou, Guanying,Kang, Dave Zhihong
supporting information, p. 751 - 754 (2015/03/30)
A total synthesis of curvulone B has been completed using a Friedel-Crafts reaction and a highly cis-selective intramolecular oxa-Michael addition. The 2-chlorobenzyl protecting group was employed and found to have much greater Lewis acid stability compared to the simple benzyl group.
Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates
Resch, Verena,Lechner, Horst,Schrittwieser, Joerg H.,Wallner, Silvia,Gruber, Karl,MacHeroux, Peter,Kroutil, Wolfgang
supporting information, p. 13173 - 13179 (2013/01/15)
Fluorine is commonly applied in pharmaceuticals to block the degradation of bioactive compounds at a specific site of the molecule. Blocking of the reaction center of the enzyme-catalyzed ring closure of 1,2,3,4- tetrahydrobenzylisoquinolines by a fluoro moiety allowed redirecting the berberine bridge enzyme (BBE)-catalyzed transformation of these compounds to give the formation of an alternative regioisomeric product namely 11-hydroxy-functionalized tetrahydroprotoberberines instead of the commonly formed 9-hydroxy-functionalized products. Alternative strategies to change the regioselectivity of the enzyme, such as protein engineering, were not applicable in this special case due to missing substrate-enzyme interactions. Medium engineering, as another possible strategy, had clear influence on the regioselectivity of the reaction pathway, but did not lead to perfect selectivity. Thus, only substrate tuning by introducing a fluoro moiety at one potential reactive carbon center switched the reaction to the formation of exclusively one regioisomer with perfect enantioselectivity. Custom-made substrates: Employing customized substrates with a fluoro atom at the normally preferred reaction site switched the regioselectivity of the berberine-bridged enzyme. With this strategy, it was possible to get access to (S)-11-hydroxy-functionalized berbines in an asymmetric fashion by using the wild-type enzyme (see scheme). Copyright
Characterization of a fungal thioesterase having claisen cyclase and deacetylase activities in melanin biosynthesis
Vagstad, Anna L.,Hill, Eric A.,Labonte, Jason W.,Townsend, Craig A.
, p. 1525 - 1534 (2013/02/25)
Melanins are a broad class of darkly pigmented macromolecules formed by oxidative polymerization of phenolic monomers. In fungi, melanins are known virulence factors that contribute to pathogenicity. Their biosynthesis generally involves polymerization of 1,8-dihydroxynaphthalene via a 1,3,6,8- tetrahydroxynaphthalene (THN) precursor assembled by multidomain, nonreducing polyketide synthases. Convergent routes to THN have evolved in fungi. Parallel heptaketide and hexaketide pathways exist that utilize conventional C-terminal thioesterase/Claisen cyclase domains and separate side-chain deacylases. Here, in vitro characterization of Pks1 from Colletotrichum lagenarium establishes a true THN synthase with a bifunctional thioesterase (TE) catalyzing both cyclization and deacetylation of an enzyme-bound hexaketide substrate. Chimeric TE domains were generated by swapping lid regions of active sites between classes of melanin TEs to gain insight into this unprecedented catalysis of carbon-carbon bond making and breaking by an α/β-hydrolase fold enzyme.
A diastereoselective formal synthesis of berkelic acid
Wenderski, Todd A.,Marsini, Maurice A.,Pettus, Thomas R. R.
supporting information; experimental part, p. 118 - 121 (2011/04/15)
A formal synthesis of berkelic acid is reported. The strategy employs the combination of a chiral exocyclic enol ether and an achiral isochromanone to afford the chroman spiroketal core via a base-triggered generation and cycloaddition of an o-quinone met
1,3,5 TRI-SUBTITUTED BENZENES FOR TREATMENT OF ALZHEIMER'S DISEASE AND OTHER DISORDERS
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Page/Page column 93-94, (2009/06/27)
The present disclosure relates to novel 1,3,5 tri-substituted benzenes of general formula (I), (II) or (III) and the use of such compounds in the treatment of diseases associated with the deposition of -amyloid in the brain.
PIPERIDINYL AND PIPERAZINYL MODULATORS OF y-SECRETASE
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Page/Page column 29, (2009/05/29)
The present invention relates to compounds of Formula I as shown below, wherein the definitions of Het, R0, R1 R2, R3, R4, R5, R6, R7, R8, and R9 are provided in the specification. Compounds of Formula I are useful for the treatment of diseases associated with γ-secretase activity, including Alzheimer's disease.
CARBON LINKED MODULATORS OF gamma-SECRETASE
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Page/Page column 17, (2009/05/29)
The present invention relates to compounds of Formula I as shown below, wherein the definitions of A, X, R1, R3, R4, R5, R6, R7, R8, and R9 are provided in the specification. Compounds of Formula I are useful for the treatment of diseases associated with γ-secretase activity, including Alzheimer's disease.
AMINE LINKED MODULATORS OF y-SECRETASE
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Page/Page column 23, (2009/05/29)
The present invention relates to compounds of Formula I as shown below, wherein the definitions of A, X, Y, R1 R2, R3, R4, R5, R6, R7, R8, and R9 are provided in the specification. Compounds of Formula I are useful for the treatment of diseases associated with γ-secretase activity, including Alzheimer's disease.
BIPHENYL CARBOXYLIC ACIDS AND DERIVATIVES THEREOF
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Page/Page column 9, (2009/05/29)
The present invention relates to compounds having the general Formula (I) with the definitions of R1, R2, R3, and R4 given below, and/or a salt or ester thereof. Furthermore the invention relates to the use of s
