119109-58-9Relevant academic research and scientific papers
Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
Surcshbabu, Vommina V.,Sudarshan,Chennakrishnareddy
experimental part, p. 574 - 579 (2009/12/06)
The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
Synthesis of N-urethane protected β-amino alcohols employing N-(protected-α-aminoacyl)benzotriazoles
Sureshbabu, Vommina V.,Sudarshan,Muralidhar,Narendra
, p. 683 - 685 (2008/09/20)
A simple and racemisation-free synthesis of N-urethane protected α-amino/peptidyl alcohols by the reduction of the corresponding easily accessible N-acylbenzotriazoles is described. The method is practical, straightforward, fast and efficient for the synt
Novel matrix metalloproteinase inhibitors: Generation of lead compounds by the in silico fragment-based approach
Takahashi, Kanji,Ikura, Masahiro,Habashita, Hiromu,Nishizaki, Minoru,Sugiura, Tsuneyuki,Yamamoto, Shingo,Nakatani, Shingo,Ogawa, Koji,Ohno, Hiroyuki,Nakai, Hisao,Toda, Masaaki
, p. 4527 - 4543 (2007/10/03)
Generation of structurally new matrix metalloproteinase inhibitors was successfully carried out using an in silico technique. In order to identify the small fragment interacting with residues in the S1′ pocket of MMP-1 through hydrogen bonds, we performed in silico screening using the LUDI program. As a result, acetyl-l-alanyl-(N-methyl)amide (Ac-l-Ala-NHMe) was selected to link with another fragment, hydroxamic acid that interacted with catalytic zinc. By this approach, the l-glutamic acid derivative 2b was discovered to be a new type of matrix metalloproteinase inhibitor. Further transformation to reduce its peptidic nature and improve activity yielded nonpeptidic lead compounds as inhibitors of MMP-1, -2, -3, and -9.
A novel synthetic route to chiral γ-lactams from α-amino acids via Rh-catalyzed intramolecular C-H insertion
Yoon, Cheol Hwan,Flanigan, David L.,Chong, Byong-Don,Jung, Kyung Woon
, p. 6582 - 6584 (2007/10/03)
Highly functionalized γ-lactams are key intermediates for the synthesis of numerous biologically significant natural products. We herein described the synthesis of various chiral γ-lactams via intramolecular C-H insertion of α-diazo-α-(phenylsulfonyl)acetamides derived from α-amino acids, which possess various functional groups. The cyclizations were highly regio- and stereoselective to afford chiral γ-lactam motifs in high yields.
REVERSE HYDROXAMATE INHIBITORS OF MATRIX METALLOPROTEINASES
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, (2008/06/13)
Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.
A synthetic approach to diaryl ethers using the Robinson annulation
Feng, Xianqi,Edstrom, Eric D.
, p. 99 - 105 (2007/10/03)
An alternative synthetic approach to diaryl ethers has been developed. In the key transformation, Robinson annulation of nonracemic aldehydes 16a,b, derived from L-glutamic acid 5-methyl ester and phenoxymethylvinyl ketone, provided α-phenoxyenones 17a,b.
A Convenient One-Pot Conversion of N-Protected Amino Acids and Peptides into Alcohols
Kokotos, George
, p. 299 - 301 (2007/10/02)
N-Protected amino acids and peptides are converted to alcohols by chemoselective reduction of their corresponding mixed anhydrides with sodium borohydride in tetrahydrofuran with dropwise addition of methanol.
