Literature DB >> 27338157

Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.

Wenyu Wang1, Regina Cencic2, Luke Whitesell3, Jerry Pelletier2, John A Porco4.   

Abstract

Synthesis of aza-rocaglates, nitrogen-containing analogues of the rocaglate natural products, is reported. The route features ESIPT-mediated (3+2) photocycloaddition of 1-alkyl-2-aryl-3-hydroxyquinolinones with the dipolarophile methyl cinnamate. A continuous photoflow reactor was utilized for photocycloadditions. An array of compounds bearing the hexahydrocyclopenta[b]indole core structure was synthesized and evaluated in translation inhibition assays.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  ESIPT; flow chemistry; heterocycles; photocycloaddition; rocaglate

Year:  2016        PMID： 27338157      PMCID： PMC5224829          DOI： 10.1002/chem.201602953

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  29 in total

1.  Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies.

Authors:  Christina M Rodrigo; Regina Cencic; Stéphane P Roche; Jerry Pelletier; John A Porco
Journal:  J Med Chem       Date:  2011-12-19       Impact factor: 7.446

2.  Enantioselective synthesis of the complex rocaglate (-)-silvestrol.

Authors:  Baudouin Gerard; Regina Cencic; Jerry Pelletier; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 3.  Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species.

Authors:  Li Pan; John L Woodard; David M Lucas; James R Fuchs; A Douglas Kinghorn
Journal:  Nat Prod Rep       Date:  2014-05-02       Impact factor: 13.423

4.  Simplified silvestrol analogues with potent cytotoxic activity.

Authors:  Bill C Hawkins; Lisa M Lindqvist; Duong Nhu; Phillip P Sharp; David Segal; Andrew K Powell; Michael Campbell; Eileen Ryan; Jennifer M Chambers; Jonathan M White; Mark A Rizzacasa; Guillaume Lessene; David C S Huang; Christopher J Burns
Journal:  ChemMedChem       Date:  2014-03-27       Impact factor: 3.466

5.  Novel flavaglines displaying improved cytotoxicity.

Authors:  Frédéric Thuaud; Nigel Ribeiro; Christian Gaiddon; Thierry Cresteil; Laurent Désaubry
Journal:  J Med Chem       Date:  2010-12-13       Impact factor: 7.446

6.  Steric control of the excited-state intramolecular proton transfer in 3-hydroxyquinolones: steady-state and time-resolved fluorescence study.

Authors:  Dmytro A Yushchenko; Volodymyr V Shvadchak; Andrey S Klymchenko; Guy Duportail; Vasyl G Pivovarenko; Yves Mély
Journal:  J Phys Chem A       Date:  2007-08-24       Impact factor: 2.781

7.  Thiyl radical-mediated cleavage of allylic C-N bonds: scope, limitations, and theoretical support to the mechanism.

Authors:  Stéphanie Escoubet; Stéphane Gastaldi; Vitaliy I Timokhin; Michèle P Bertrand; Didier Siri
Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419

Review 8.  Flavaglines: potent anticancer drugs that target prohibitins and the helicase eIF4A.

Authors:  Christine Basmadjian; Frédéric Thuaud; Nigel Ribeiro; Laurent Désaubry
Journal:  Future Med Chem       Date:  2013-12       Impact factor: 3.808

9.  Translation Inhibition by Rocaglates Is Independent of eIF4E Phosphorylation Status.

Authors:  Jennifer Chu; Regina Cencic; Wenyu Wang; John A Porco; Jerry Pelletier
Journal:  Mol Cancer Ther       Date:  2015-11-19       Impact factor: 6.261

10.  Remodeling natural products: chemistry and serine hydrolase activity of a rocaglate-derived β-lactone.

Authors:  Neil J Lajkiewicz; Armand B Cognetta; Micah J Niphakis; Benjamin F Cravatt; John A Porco
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419
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  11 in total

1.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

2.  A photochemical flow reactor for large scale syntheses of aglain and rocaglate natural product analogues.

Authors:  Han Yueh; Qiwen Gao; John A Porco; Aaron B Beeler
Journal:  Bioorg Med Chem       Date:  2017-06-11       Impact factor: 3.641

3.  Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited-State Intramolecular Proton-Transfer Photocycloaddition.

Authors:  Wenyu Wang; Anthony Clay; Retheesh Krishnan; Neil J Lajkiewicz; Lauren E Brown; Jayaraman Sivaguru; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-13       Impact factor: 15.336

4.  Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors.

Authors:  Wenhan Zhang; Jennifer Chu; Andrew M Cyr; Han Yueh; Lauren E Brown; Tony T Wang; Jerry Pelletier; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-30       Impact factor: 15.419

Review 5.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

6.  An efficient Nozaki-Hiyama allenylation promoted by the acid derived MIL-101 MOF.

Authors:  Yi Luan; Zonghui Cai; Xiujuan Li; Daniele Ramella; Zongcheng Miao; Wenyu Wang
Journal:  RSC Adv       Date:  2019-03-07       Impact factor: 4.036

7.  Chemical Synthesis Enables Structural Reengineering of Aglaroxin C Leading to Inhibition Bias for Hepatitis C Viral Infection.

Authors:  Wenhan Zhang; Shufeng Liu; Rayelle I Maiga; Jerry Pelletier; Lauren E Brown; Tony T Wang; John A Porco
Journal:  J Am Chem Soc       Date:  2019-01-11       Impact factor: 15.419

8.  Oxo-aglaiastatin-Mediated Inhibition of Translation Initiation.

Authors:  Rayelle Itoua Maïga; Regina Cencic; Jennifer Chu; Daniel D Waller; Lauren E Brown; William G Devine; Wenhan Zhang; Michael Sebag; John A Porco; Jerry Pelletier
Journal:  Sci Rep       Date:  2019-02-04       Impact factor: 4.379

9.  Targeting translation initiation by synthetic rocaglates for treating MYC-driven lymphomas.

Authors:  Xuan Zhang; Chengfeng Bi; Ting Lu; Weiwei Zhang; Ting Yue; Cheng Wang; Tian Tian; Xiaoyan Zhang; Yuhua Huang; Matthew Lunning; Xinbao Hao; Lauren E Brown; William G Devine; Julie Vose; John A Porco; Kai Fu
Journal:  Leukemia       Date:  2019-06-06       Impact factor: 11.528

Review 10.  Continuous Flow Photochemistry for the Preparation of Bioactive Molecules.

Authors:  Mara Di Filippo; Cormac Bracken; Marcus Baumann
Journal:  Molecules       Date:  2020-01-15       Impact factor: 4.411
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