Literature DB >> 31673310

Exploration of [2 + 2 + 2] cyclotrimerisation methodology to prepare tetrahydroisoquinoline-based compounds with potential aldo-keto reductase 1C3 target affinity.

Ana R N Santos1, Helen M Sheldrake1, Ali I M Ibrahim1, Chhanda Charan Danta1, Davide Bonanni2, Martina Daga2, Simonetta Oliaro-Bosso2, Donatella Boschi2, Marco L Lolli2, Klaus Pors1.   

Abstract

Tetrahydroisoquinoline (THIQ) is a key structural component in many biologically active molecules including natural products and synthetic pharmaceuticals. Here, we report on the use of transition-metal mediated [2 + 2 + 2] cyclotrimerisation of alkynes to generate tricyclic THIQs with potential to selectively inhibit AKR1C3. This journal is © The Royal Society of Chemistry 2019.

Entities:  

Year:  2019        PMID： 31673310      PMCID： PMC6786241          DOI： 10.1039/c9md00201d

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  16 in total

Review 1.  The changing landscape of cancer drug discovery: a challenge to the medicinal chemist of tomorrow.

Authors:  Klaus Pors; Frederick W Goldberg; Christopher P Leamon; Alan C Rigby; Scott A Snyder; Robert A Falconer
Journal:  Drug Discov Today       Date:  2009-07-26       Impact factor: 7.851

Review 2.  AKR1C3 as a target in castrate resistant prostate cancer.

Authors:  Adegoke O Adeniji; Mo Chen; Trevor M Penning
Journal:  J Steroid Biochem Mol Biol       Date:  2013-06-06       Impact factor: 4.292

3.  Bioisosteres of Indomethacin as Inhibitors of Aldo-Keto Reductase 1C3.

Authors:  Marco L Lolli; Irene M Carnovale; Agnese C Pippione; Weixiao Y Wahlgren; Davide Bonanni; Elisabetta Marini; Daniele Zonari; Margherita Gallicchio; Valentina Boscaro; Parveen Goyal; Rosmarie Friemann; Barbara Rolando; Renzo Bagnati; Salvatore Adinolfi; Simonetta Oliaro-Bosso; Donatella Boschi
Journal:  ACS Med Chem Lett       Date:  2019-01-28       Impact factor: 4.345

4.  Cancer statistics, 2016.

Authors:  Rebecca L Siegel; Kimberly D Miller; Ahmedin Jemal
Journal:  CA Cancer J Clin       Date:  2016-01-07       Impact factor: 508.702

5.  Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin.

Authors:  Andrew L Lovering; Jon P Ride; Christopher M Bunce; Julian C Desmond; Stephen M Cummings; Scott A White
Journal:  Cancer Res       Date:  2004-03-01       Impact factor: 12.701

6.  Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.

Authors:  Kshitij Verma; Tianzhu Zang; Trevor M Penning; Paul C Trippier
Journal:  J Med Chem       Date:  2019-03-25       Impact factor: 7.446

7.  Potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors based on the benzoisoxazole moiety: application of a bioisosteric scaffold hopping approach to flufenamic acid.

Authors:  Agnese Chiara Pippione; Irene Maria Carnovale; Davide Bonanni; Marcella Sini; Parveen Goyal; Elisabetta Marini; Klaus Pors; Salvatore Adinolfi; Daniele Zonari; Claudio Festuccia; Weixiao Yuan Wahlgren; Rosmarie Friemann; Renzo Bagnati; Donatella Boschi; Simonetta Oliaro-Bosso; Marco Lucio Lolli
Journal:  Eur J Med Chem       Date:  2018-03-16       Impact factor: 6.514

8.  Hydroxytriazole derivatives as potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors discovered by bioisosteric scaffold hopping approach.

Authors:  Agnese C Pippione; Alessandro Giraudo; Davide Bonanni; Irene M Carnovale; Elisabetta Marini; Clara Cena; Annalisa Costale; Daniele Zonari; Klaus Pors; Maria Sadiq; Donatella Boschi; Simonetta Oliaro-Bosso; Marco L Lolli
Journal:  Eur J Med Chem       Date:  2017-08-24       Impact factor: 6.514

9.  A route to 2-substituted tetrahydroquinolines via palladium-catalyzed intramolecular hydroamination of anilino-alkynes.

Authors:  Nitin T Patil; Huanyou Wu; Yoshinori Yamamoto
Journal:  J Org Chem       Date:  2007-07-18       Impact factor: 4.354

10.  Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity.

Authors:  Ratchanok Pingaew; Prasit Mandi; Chanin Nantasenamat; Supaluk Prachayasittikul; Somsak Ruchirawat; Virapong Prachayasittikul
Journal:  Eur J Med Chem       Date:  2014-05-06       Impact factor: 6.514
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