Literature DB >> 21190371

Polycyclic compounds by Ugi-Pictet-Spengler sequence.

Wei Wang1, Sarah Ollio, Eberhardt Herdtweck, Alexander Dömling.   

Abstract

A general approach to architecturally stimulating polycyclic structures is described by a concise, two-step procedure including a Ugi MCR (multicomponent reaction) and a subsequent Pictet-Spengler reaction starting from phenylethylamine-derived isocyanides. Ten compounds are described in full experimental detail, and yields range from medium to very good. Some of the reactions run with a high degree of stereoselectivity. The compound structures resemble steroid hormones and alkaloid classes of natural products. Exemplary products have been fully reduced to their tertiary amines. As such they could potentially become interesting biological probes.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 21190371      PMCID： PMC3101332          DOI： 10.1021/jo102058s

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

Review 1.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

2.  The discovery of GSK221149A: a potent and selective oxytocin antagonist.

Authors:  John Liddle; Michael J Allen; Alan D Borthwick; David P Brooks; David E Davies; Richard M Edwards; Anne M Exall; Chris Hamlett; Wendy R Irving; Andrew M Mason; Gerald P McCafferty; Fabrizio Nerozzi; Simon Peace; Joanne Philp; Derek Pollard; Mark A Pullen; Shaila S Shabbir; Steve L Sollis; Timothy D Westfall; Pat M Woollard; Charlene Wu; Deirdre M B Hickey
Journal:  Bioorg Med Chem Lett       Date:  2007-11-06       Impact factor: 2.823

3.  Polycyclic indole alkaloid-type compounds by MCR.

Authors:  Wei Wang; Eberhardt Herdtweck; Alexander Dömling
Journal:  Chem Commun (Camb)       Date:  2009-12-11       Impact factor: 6.222

4.  Efficient and diverse synthesis of indole derivatives.

Authors:  Haixia Liu; Alexander Dömling
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

5.  Praziquantel analogs with activity against juvenile Schistosoma mansoni.

Authors:  Yuxiang Dong; Jacques Chollet; Mireille Vargas; Nuha R Mansour; Quentin Bickle; Yazen Alnouti; Jiangeng Huang; Jennifer Keiser; Jonathan L Vennerstrom
Journal:  Bioorg Med Chem Lett       Date:  2010-03-04       Impact factor: 2.823

6.  Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents.

Authors:  Guoqiang Dong; Chunquan Sheng; Shengzheng Wang; Zhenyuan Miao; Jianzhong Yao; Wannian Zhang
Journal:  J Med Chem       Date:  2010-11-11       Impact factor: 7.446

7.  Discovery of the HCV NS3/4A protease inhibitor (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3- [2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]- 6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (Sch 503034) II. Key steps in structure-based optimization.

Authors:  Andrew J Prongay; Zhuyan Guo; Nanhua Yao; John Pichardo; Thierry Fischmann; Corey Strickland; Joseph Myers; Patricia C Weber; Brian M Beyer; Richard Ingram; Zhi Hong; Winifred W Prosise; Lata Ramanathan; S Shane Taremi; Taisa Yarosh-Tomaine; Rumin Zhang; Mary Senior; Rong-Sheng Yang; Bruce Malcolm; Ashok Arasappan; Frank Bennett; Stephane L Bogen; Kevin Chen; Edwin Jao; Yi-Tsung Liu; Raymond G Lovey; Anil K Saksena; Srikanth Venkatraman; Viyyoor Girijavallabhan; F George Njoroge; Vincent Madison
Journal:  J Med Chem       Date:  2007-04-20       Impact factor: 7.446

Review 8.  Isocyanide-based multicomponent reactions in drug discovery.

Authors:  Irini Akritopoulou-Zanze
Journal:  Curr Opin Chem Biol       Date:  2008-03-14       Impact factor: 8.822

9.  Synthesis and antifungal activities in vitro of novel pyrazino [2,1-a] isoquinolin derivatives.

Authors:  Hui Tang; Canhui Zheng; Jiaguo Lv; Juan Wu; Yanan Li; Hui Yang; Bingyue Fu; Chuntong Li; Youjun Zhou; Ju Zhu
Journal:  Bioorg Med Chem Lett       Date:  2009-12-21       Impact factor: 2.823

10.  Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence.

Authors:  Anass Znabet; Job Zonneveld; Elwin Janssen; Frans J J De Kanter; Madeleine Helliwell; Nicholas J Turner; Eelco Ruijter; Romano V A Orru
Journal:  Chem Commun (Camb)       Date:  2010-09-27       Impact factor: 6.222
View more
  11 in total

1.  MCR synthesis of a tetracyclic tetrazole scaffold.

Authors:  Pravin Patil; Kareem Khoury; Eberhardt Herdtweck; Alexander Dömling
Journal:  Bioorg Med Chem       Date:  2014-12-20       Impact factor: 3.641

Review 2.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

3.  Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Org Lett       Date:  2013-05-29       Impact factor: 6.005

4.  Various cyclization scaffolds by a truly Ugi 4-CR.

Authors:  Mantosh K Sinha; Kareem Khoury; Eberhardt Herdtweck; Alexander Dömling
Journal:  Org Biomol Chem       Date:  2013-06-13       Impact factor: 3.876

5.  Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds.

Authors:  Shima Dianat; Mohammad Mahdavi; Setareh Moghimi; Arash Mouradzadegun; Abbas Shafiee; Alireza Foroumadi
Journal:  Mol Divers       Date:  2015-08-01       Impact factor: 2.943

6.  A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy.

Authors:  Taofeng Shao; Zhiming Gong; Tianyi Su; Wei Hao; Chao Che
Journal:  Beilstein J Org Chem       Date:  2017-05-04       Impact factor: 2.883

7.  Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions.

Authors:  Yuanze Wang; Pravin Patil; Katarzyna Kurpiewska; Justyna Kalinowska-Tluscik; Alexander Dömling
Journal:  Org Lett       Date:  2019-04-29       Impact factor: 6.005

8.  One-Pot Diastereoselective Synthesis of Pyrrolopiperazine-2,6-diones by a Ugi/Nucleophilic Substitution/N-Acylation Sequence.

Authors:  Beatriz González-Saiz; Israel Carreira-Barral; Pablo Pertejo; Javier Gómez-Ayuso; Roberto Quesada; María García-Valverde
Journal:  J Org Chem       Date:  2022-06-27       Impact factor: 4.198

9.  The outcome of the oxidations of unusual enediamide motifs is governed by the stabilities of the intermediate iminium ions.

Authors:  Muneer Ahamed; Bun Chan; Paul Jensen; Matthew H Todd
Journal:  PLoS One       Date:  2012-10-19       Impact factor: 3.240

Review 10.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.