15136-34-2Relevant academic research and scientific papers
Oxidative couplings on tryptophan-based diketopiperazines leading to fused and bridged chemotypes
Mendive-Tapia, Lorena,Albornoz-Grados, Arantxa,Bertran, Alexandra,Albericio, Fernando,Lavilla, Rodolfo
, p. 2740 - 2743 (2017)
New chemotypes are obtained from tryptophan-containing diketopiperazines through selective C-C or C-N intramolecular oxidative couplings. The choice of the oxidant source dictates the outcome of the reaction.
A [3,3] sigmatropic and novel ipso [3,3] sigmatropic rearrangement of 1-hydroxyindole chemistry
Fukui, Yoshikazu,Kobayashi, Tetsuya,Kawasaki, Toshiya,Yamada, Fumio,Somei, Masanori
, p. 465 - 483 (2019/08/02)
Utilizing 1-aryloxyindole derivatives, we found a new type of [3,3] sigmatropic rearrangement reaction. We named it as ipso [3,3] sigmatropic rearrangement. The product structures are strictly determined by X-ray crystallographic analysis. Normal [3,3] sigmatropic rearrangement of 1-hydroxyindole derivative was found to be a useful synthetic method for 2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione derivative.
Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds
Skiredj, Adam,Beniddir, Mehdi A.,Evanno, Laurent,Poupon, Erwan
supporting information, p. 2954 - 2958 (2016/07/11)
Drimentines are a family of tetracyclic alkaloids biosynthetically originating from the condensation of sesquiterpene units onto cyclic dipeptides. A straightforward assembly of the fused “pyrroloindoline–diketopiperazine” core of drimentines is described herein and used for the synthesis of Δ8′-isodrimentine A. The strategy involves a bio-inspired indole dearomatization of a tryptophan-containing cyclodipeptide by a drimane-type decaline followed by the intramolecular trapping of the resulting indolenine intermediate in an uninterrupted reactive sequence. The starting diketopiperazine was prepared by classical peptidic coupling and the drimane-type decaline from (+)-sclareolide. A fully biomimetic approach with a linear sesquiterpene unit is also reported and led to farnesylated pyrroloindoline–diketopiperazines, which correspond to the proposed biosynthetic precursors of both drimentines A and D. The end product Δ8′-isodrimentine A and its congeners were evaluated in vitro for their cytotoxic activities against three human tumor cell lines.
Cyclic dipeptides exhibit potency for scavenging radicals
Furukawa, Tadashi,Akutagawa, Takashi,Funatani, Hitomi,Uchida, Toshikazu,Hotta, Yoshihiro,Niwa, Masatake,Takaya, Yoshiaki
, p. 2002 - 2009 (2012/05/04)
Twenty kinds of cyclic dipeptides containing l-leucine were synthesized, and their antioxidant activity against .OH and O2·- was investigated. Compounds possessing polar amino acid residues, such as Asp, Cys, Glu, Lys, Pro, Ser, and Trp, exhibited higher antioxidant activity against .OH than vitamin E. However, only cyclo(l-Cys-l-Leu) scavenged O2·-.
Three types of induced tryptophan optical activity compared in model dipeptides: Theory and experiment
Hudecová, Jana,Horní?ek, Jan,Budě?ínsky, Milo?,?ebestík, Jaroslav,?afa?ík, Martin,Zhang, Ge,Keiderling, Timothy A.,Bou?, Petr
experimental part, p. 2748 - 2760 (2012/10/08)
The tryptophan (Trp) aromatic residue in chiral matrices often exhibits a large optical activity and thus provides valuable structural information. However, it can also obscure spectral contributions from other peptide parts. To better understand the indu
Simple synthesis of 1,3,4,5a,6,10b,11,11a-octahydro-2H-pyrazino[1′,2′:1,5]pyrrolo[2, 3-b]indole derivatives based on 1-hydroxyindole chemistry
Fukui, Yoshikazu,Somei, Masanori
, p. 2055 - 2057 (2007/10/03)
3-Substituted (3S,6S)-6-(1-hydroxyindol-3-ylmethyl)-2,5-piperazinediones are prepared for the first time. They are shown to be suitable intermediates for the synthesis of 3,10b-disubstituted (3S,5aR,10bS,11as)-1,3,4,5a,6,10b,11, 11a-octahydro-2H-pyrazino[
