161105-54-0Relevant academic research and scientific papers
Controlling Intramolecular Interactions in the Design of Selective, High-Affinity Ligands for the CREBBP Bromodomain
Brand, Michael,Clayton, James,Moroglu, Mustafa,Schiedel, Matthias,Picaud, Sarah,Bluck, Joseph P.,Skwarska, Anna,Bolland, Hannah,Chan, Anthony K. N.,Laurin, Corentine M. C.,Scorah, Amy R.,See, Larissa,Rooney, Timothy P. C.,Andrews, Katrina H.,Fedorov, Oleg,Perell, Gabriella,Kalra, Prakriti,Vinh, Kayla B.,Cortopassi, Wilian A.,Heitel, Pascal,Christensen, Kirsten E.,Cooper, Richard I.,Paton, Robert S.,Pomerantz, William C. K.,Biggin, Philip C.,Hammond, Ester M.,Filippakopoulos, Panagis,Conway, Stuart J.
, p. 10102 - 10123 (2021/07/31)
CREBBP (CBP/KAT3A) and its paralogue EP300 (KAT3B) are lysine acetyltransferases (KATs) that are essential for human development. They each comprise 10 domains through which they interact with >400 proteins, making them important transcriptional co-activa
Acylation of β-Amino Esters and Hydrolysis of β-Amido Esters: Candida antarctica Lipase A as a Chemoselective Deprotection Catalyst
M?enp??, Harri,Kanerva, Liisa T.,Liljeblad, Arto
, p. 1226 - 1232 (2016/04/05)
N-Acylation by lipase A from Candida antarctica (CAL-A) in ethyl butanoate was applied to the kinetic resolution of tert-butyl esters of 3-amino-3-phenylpropanoic acid (E>100), 3-amino-4-methylpentanoic acid (E>100) and 3-aminobutanoic acid (E=60) on 1.0-2.0 m scale. With the N-acylated resolution products, the exceptional ability of CAL-A to hydrolyse amides and bulky tert-butyl esters was then studied. In all N-acylated tert-butyl esters, chemoselectivity favoured the amide bond cleavage. The tert-butyl ester bond was left intact with 3-amino-3-phenylpropanoate, whereas with 3-amino-4-methylpentanoate and 3-aminobutanoate the CAL-A-catalysed hydrolysis of tert-butyl ester followed the amide hydrolysis.
Parallel synthesis of homochiral β-amino acids
Davies, Stephen G.,Mulvaney, Andrew W.,Russell, Angela J.,Smith, Andrew D.
, p. 1554 - 1566 (2008/02/09)
The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.
Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide
Sakai, Takeo,Doi, Hirohisa,Tomioka, Kiyoshi
, p. 8351 - 8359 (2007/10/03)
Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoat
Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl} amine
Fleck, Thomas J.,McWhorter Jr., William W.,DeKam, Richard N.,Pearlman, Bruce A.
, p. 9612 - 9617 (2007/10/03)
N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl} amine (1)1 is a key intermediate in the preparation of premafloxacin (2), which was under development as an antibiotic for use against pathogens of veterinary importance. This paper describes the development of a practical, efficient, and stereoselective process for the preparation of 1 from isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]-amino}butanoate (5c). The key steps in the synthetic sequence are an asymmetric Michael addition, which yields 5c, and a stereoselective alkylation, which yields (3S,4S)-3-allyl-1,4-dimethylazetidin-2-one (17).
NOVEL BETA-LACTAM COMPOUNDS AND PROECSS FOR PRODUCING THE SAME
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, (2008/06/13)
1. A β-lactam compound of the formula [1]; ???wherein R1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y2 is hydrogen, an alkyl, cyano, -C(R3)=NR4 (wherein R3 and R4 are hydrogen, an amino, an alkyl, etc., or R3 and R4 may combine each other together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has an excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.
Peptide based inhibitors of interleukin-8: Structural simplification and enhanced potency
Attwood, Michael R.,Conway, Elizabeth A.,Dunsdon, Rachel M.,Greening, John R.,Handa, Balraj K.,Jones, Philip S.,Jordan, Steven C.,Keech, Elizabeth,Wilson, Francis X.
, p. 429 - 432 (2007/10/03)
Important areas of a lead peptide inhibitor of IL-8 had been previously identified. Chemical modification led to the identification of key amide bonds which allowed the replacement of the central section of the peptide with modified amino acids and spacers. This approach led to inhibitors of lower molecular weight and of increased potency.
Lithium (α-Methylbenzyl)allylamide: A Differentially Protected Chiral Ammonia Equivalent for the Asymmetric Synthesis of β-Amino Acids and β-Lactams
Davies, Stephen G.,Fenwick, David R.
, p. 1109 - 1110 (2007/10/02)
The addition products from the highly stereoselective conjugate additions of lithium (αS)-(α-methylbenzyl)allylamide to α,β-unsaturated tert-butyl esters are efficiently deallylated with tris(triphenylphosphine)rhodium(I) chloride and converted, after tra
