Literature DB >> 28666859

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

Han Yueh1, Qiwen Gao1, John A Porco1, Aaron B Beeler2.   

Abstract

Herein, we report the development of continuous flow photoreactors for large scale ESIPT-mediated [3+2]-photocycloaddition of 2-(p-methoxyphenyl)-3-hydroxyflavone and cinnamate-derived dipolarophiles. These reactors can be efficiently numbered up to increase throughput two orders of magnitude greater than the corresponding batch reactions.
Copyright © 2017 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Aglain; ESIPT; Flow chemistry; Natural product; Photochemistry; Photocycloaddition; Rocaglate

Mesh：

Substances：

Year:  2017        PMID： 28666859      PMCID： PMC5696104          DOI： 10.1016/j.bmc.2017.06.010

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  24 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.  A synthetic derivative of the natural product rocaglaol is a potent inhibitor of cytokine-mediated signaling and shows neuroprotective activity in vitro and in animal models of Parkinson's disease and traumatic brain injury.

Authors:  T Fahrig; I Gerlach; E Horváth
Journal:  Mol Pharmacol       Date:  2005-02-16       Impact factor: 4.436

3.  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

4.  Silvestrol and episilvestrol, potential anticancer rocaglate derivatives from Aglaia silvestris.

Authors:  Bang Yeon Hwang; Bao-Ning Su; Heebyung Chai; Qiuwen Mi; Leonardus B S Kardono; Johar J Afriastini; Soedarsono Riswan; Bernard D Santarsiero; Andrew D Mesecar; Robert Wild; Craig R Fairchild; Gregory D Vite; William C Rose; Norman R Farnsworth; Geoffrey A Cordell; John M Pezzuto; Steven M Swanson; A Douglas Kinghorn
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354

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

Authors:  Wenyu Wang; Regina Cencic; Luke Whitesell; Jerry Pelletier; John A Porco
Journal:  Chemistry       Date:  2016-07-15       Impact factor: 5.236

6.  Bioactive flavaglines and other constituents isolated from Aglaia perviridis.

Authors:  Li Pan; Ulyana Muñoz Acuña; Jie Li; Nivedita Jena; Tran Ngoc Ninh; Caroline M Pannell; Heebyung Chai; James R Fuchs; Esperanza J Carcache de Blanco; Djaja D Soejarto; A Douglas Kinghorn
Journal:  J Nat Prod       Date:  2013-01-09       Impact factor: 4.050

7.  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

8.  Flow photochemistry: Old light through new windows.

Authors:  Jonathan P Knowles; Luke D Elliott; Kevin I Booker-Milburn
Journal:  Beilstein J Org Chem       Date:  2012-11-21       Impact factor: 2.883

9.  Therapeutic potential of the translation inhibitor silvestrol in hepatocellular cancer.

Authors:  Takayuki Kogure; A Douglas Kinghorn; Irene Yan; Brad Bolon; David M Lucas; Michael R Grever; Tushar Patel
Journal:  PLoS One       Date:  2013-09-26       Impact factor: 3.240

10.  The anticancer phytochemical rocaglamide inhibits Rho GTPase activity and cancer cell migration.

Authors:  Michael S Becker; Paul M Müller; Jörg Bajorat; Anne Schroeder; Marco Giaisi; Ehsan Amin; Mohammad R Ahmadian; Oliver Rocks; Rebecca Köhler; Peter H Krammer; Min Li-Weber
Journal:  Oncotarget       Date:  2016-08-09
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  9 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.  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

Review 3.  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

4.  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

5.  Sensitization of renal carcinoma cells to TRAIL-induced apoptosis by rocaglamide and analogs.

Authors:  Ancy D Nalli; Lauren E Brown; Cheryl L Thomas; Thomas J Sayers; John A Porco; Curtis J Henrich
Journal:  Sci Rep       Date:  2018-11-30       Impact factor: 4.379

6.  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

7.  Rocaglates Induce Gain-of-Function Alterations to eIF4A and eIF4F.

Authors:  Jennifer Chu; Wenhan Zhang; Regina Cencic; Patrick B F O'Connor; Francis Robert; William G Devine; Asher Selznick; Thomas Henkel; William C Merrick; Lauren E Brown; Pavel V Baranov; John A Porco; Jerry Pelletier
Journal:  Cell Rep       Date:  2020-02-25       Impact factor: 9.423

8.  A method to determine the correct photocatalyst concentration for photooxidation reactions conducted in continuous flow reactors.

Authors:  Clemens R Horn; Sylvain Gremetz
Journal:  Beilstein J Org Chem       Date:  2020-04-27       Impact factor: 2.883

Review 9.  Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors.

Authors:  Emine Kayahan; Mathias Jacobs; Leen Braeken; Leen Cj Thomassen; Simon Kuhn; Tom van Gerven; M Enis Leblebici
Journal:  Beilstein J Org Chem       Date:  2020-10-08       Impact factor: 2.883
  9 in total

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