56941-94-7Relevant academic research and scientific papers
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
, p. 2954 - 2958 (2016)
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.
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.
Oxidative couplings on tryptophan-based diketopiperazines leading to fused and bridged chemotypes
Mendive-Tapia, Lorena,Albornoz-Grados, Arantxa,Bertran, Alexandra,Albericio, Fernando,Lavilla, Rodolfo
supporting information, p. 2740 - 2743 (2017/03/10)
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.
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[
