Literature DB >> 28980696

Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin.

Elizabeth W Kelley1, Skylar G Norman, Jonathan R Scheerer.   

Abstract

The synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product, is described. The synthesis starts with the diketopiperazine nucleus intact and the side chains are installed using iterative aldol condensations. The route represents a general strategy for synthesis of a wide array of mono-alkylidene diketopiperazine structures, including those derived from non-canonical amino acid residues.

Entities:  

Mesh：

Substances：

Year:  2017        PMID： 28980696      PMCID： PMC5678964          DOI： 10.1039/c7ob02297b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  38 in total

Review 1.  Antifouling marine natural products.

Authors:  Nobuhiro Fusetani
Journal:  Nat Prod Rep       Date:  2010-11-16       Impact factor: 13.423

2.  Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines.

Authors:  Adriano Mollica; Roberto Costante; Serena Fiorito; Salvatore Genovese; Azzurra Stefanucci; Veronique Mathieu; Robert Kiss; Francesco Epifano
Journal:  Fitoterapia       Date:  2014-07-24       Impact factor: 2.882

3.  Total synthesis of (-)-spirotryprostatin B: synthesis and related studies.

Authors:  Christiane Marti; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

4.  Development of a new benzophenone-diketopiperazine-type potent antimicrotubule agent possessing a 2-pyridine structure.

Authors:  Yoshiki Hayashi; Haruka Takeno; Takumi Chinen; Kyohei Muguruma; Kohei Okuyama; Akihiro Taguchi; Kentaro Takayama; Fumika Yakushiji; Masahiko Miura; Takeo Usui; Yoshio Hayashi
Journal:  ACS Med Chem Lett       Date:  2014-07-23       Impact factor: 4.345

5.  Design, synthesis and cytotoxic activities of novel 2,5-diketopiperazine derivatives.

Authors:  Sheng-Rong Liao; Xiao-Chu Qin; Zhen Wang; Ding Li; Liang Xu; Jin-Sheng Li; Zheng-Chao Tu; Yonghong Liu
Journal:  Eur J Med Chem       Date:  2016-06-04       Impact factor: 6.514

6.  Brominated cyclodipeptides from the marine sponge Geodia barretti as selective 5-HT ligands.

Authors:  Erik Hedner; Martin Sjögren; Per-Anders Frändberg; Tobias Johansson; Ulf Göransson; Mia Dahlström; Per Jonsson; Fred Nyberg; Lars Bohlin
Journal:  J Nat Prod       Date:  2006-10       Impact factor: 4.050

7.  Synthesis and structure-activity relationship study of antimicrotubule agents phenylahistin derivatives with a didehydropiperazine-2,5-dione structure.

Authors:  Yuri Yamazaki; Koji Tanaka; Benjamin Nicholson; Gordafaried Deyanat-Yazdi; Barbara Potts; Tomoko Yoshida; Akiko Oda; Takayoshi Kitagawa; Sumie Orikasa; Yoshiaki Kiso; Hiroyuki Yasui; Miki Akamatsu; Takumi Chinen; Takeo Usui; Yuki Shinozaki; Fumika Yakushiji; Brian R Miller; Saskia Neuteboom; Michael Palladino; Kaneo Kanoh; George Kenneth Lloyd; Yoshio Hayashi
Journal:  J Med Chem       Date:  2012-01-20       Impact factor: 7.446

Review 8.  The environmental fate and effects of antifouling paint biocides.

Authors:  K V Thomas; S Brooks
Journal:  Biofouling       Date:  2010-01       Impact factor: 3.209

9.  Antitumor activity of phenylahistin in vitro and in vivo.

Authors:  K Kanoh; S Kohno; J Katada; Y Hayashi; M Muramatsu; I Uno
Journal:  Biosci Biotechnol Biochem       Date:  1999-06       Impact factor: 2.043

10.  Asymmetric conjugate reductions with samarium diiodide: asymmetric synthesis of (2S,3R)- and (2S,3S)-[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)-[2-(2)H,3-2H]-phenylalanine methyl ester.

Authors:  Stephen G Davies; Humberto Rodriguez-Solla; Juan A Tamayo; Andrew R Cowley; Carmen Concellon; A Christopher Garner; Alastair L Parkes; Andrew D Smith
Journal:  Org Biomol Chem       Date:  2005-03-17       Impact factor: 3.876
View more
  3 in total

1.  Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids.

Authors:  Nicholas H Angello; Robert E Wiley; Tristan G Elmore; Ryan S Perry; Jonathan R Scheerer
Journal:  Org Lett       Date:  2018-08-10       Impact factor: 6.005

2.  Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.

Authors:  Susanna K Maisto; Angela P Leersnyder; Gwyneth L Pudner; Jonathan R Scheerer
Journal:  J Org Chem       Date:  2020-06-30       Impact factor: 4.354

3.  A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor.

Authors:  Di Zhang; Wayne Wang
Journal:  R Soc Open Sci       Date:  2018-06-20       Impact factor: 2.963
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.