Literature DB >> 25108300

Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.

Sergey Vshyvenko1, Mary Rose Reisenauer2, Snezna Rogelj2, Tomas Hudlicky3.   

Abstract

Several unnatural derivatives of narciclasine were prepared in which the C-7 carbon was replaced with nitrogen. The 7-aza derivative and its N-oxide were prepared by the coupling of iodopicolinic acid with a conduramine unit derived chemoenzymatically from bromobenzene. Intramolecular Heck reaction was used to construct the isocarbostyryl ring system. The compounds were submitted to biological screening against cancer cell lines. Full experimental and spectra data are provided for all new compounds.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Amaryllidaceae; Anticancer; Biotransformation; Narciclasine; Narciclasine analogs

Mesh：

Substances：

Year:  2014        PMID： 25108300      PMCID： PMC4146675          DOI： 10.1016/j.bmcl.2014.07.034

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  22 in total

1.  Stereospecific biocatalytic synthesis of pancratistatin analogues.

Authors:  Anh Nga Phung; Maria Teresa Zannetti; Gregg Whited; Wolf-Dieter Fessner
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-13       Impact factor: 15.336

2.  A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore.

Authors:  James McNulty; Vladimir Larichev; Siyaram Pandey
Journal:  Bioorg Med Chem Lett       Date:  2005-09-23       Impact factor: 2.823

3.  Synthesis and evaluation of C-ring aromatized analogues of phenanthridone alkaloids.

Authors:  Seokwoo Lee; Soonho Hwang; Shuai Yu; Wonyoung Jang; Yun Mi Lee; Sanghee Kim
Journal:  Arch Pharm Res       Date:  2011-08-03       Impact factor: 4.946

Review 4.  Chemistry, biology, and medicinal potential of narciclasine and its congeners.

Authors:  Alexander Kornienko; Antonio Evidente
Journal:  Chem Rev       Date:  2008-05-20       Impact factor: 60.622

5.  Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents.

Authors:  Artem S Kireev; Oleg N Nadein; Vincent J Agustin; Nancy E Bush; Antonio Evidente; Madhuri Manpadi; Marcia A Ogasawara; Shiva K Rastogi; Snezna Rogelj; Scott T Shors; Alexander Kornienko
Journal:  J Org Chem       Date:  2006-07-21       Impact factor: 4.354

6.  Total synthesis of epi-7-deoxypancratistatin via aza-Payne rearrangement and intramolecular cyclization.

Authors:  Uwe Rinner; Peter Siengalewicz; Tomas Hudlicky
Journal:  Org Lett       Date:  2002-01-10       Impact factor: 6.005

7.  Synthesis and cytotoxicity of (+/-)-7,9-dideoxy-pancratistatin analogues.

Authors:  Olaia Nieto-García; Ricardo Alonso
Journal:  Org Biomol Chem       Date:  2012-12-03       Impact factor: 3.876

8.  synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues.

Authors:  James McNulty; Jerald J Nair; Carly Griffin; Siyaram Pandey
Journal:  J Nat Prod       Date:  2008-01-29       Impact factor: 4.050

9.  Synthesis of structurally simplified analogues of pancratistatin: truncation of the cyclitol ring.

Authors:  Madhuri Manpadi; Artem S Kireev; Igor V Magedov; Jeff Altig; Paul Tongwa; Mikhail Yu Antipin; Antonio Evidente; Willem A L van Otterlo; Alexander Kornienko
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

10.  Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents.

Authors:  Laurent Ingrassia; Florence Lefranc; Janique Dewelle; Laurent Pottier; Véronique Mathieu; Sabine Spiegl-Kreinecker; Sébastien Sauvage; Mohamed El Yazidi; Mischaël Dehoux; Walter Berger; Eric Van Quaquebeke; Robert Kiss
Journal:  J Med Chem       Date:  2009-02-26       Impact factor: 7.446
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  6 in total

Review 1.  The role of biocatalysis in the asymmetric synthesis of alkaloids - an update.

Authors:  Emmanuel Cigan; Bettina Eggbauer; Joerg H Schrittwieser; Wolfgang Kroutil
Journal:  RSC Adv       Date:  2021-08-20       Impact factor: 3.361

2.  Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity.

Authors:  Lihi Habaz; Korey Bedard; Mitchell Smith; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Molecules       Date:  2022-06-14       Impact factor: 4.927

3.  Synthesis and biological evaluation of 10-benzyloxy-Narciclasine.

Authors:  Vincenzo Ticli; Zhenze Zhao; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Tetrahedron       Date:  2021-10-18       Impact factor: 2.457

4.  Asymmetric Entry into 10b-aza-Analogues of Amaryllidaceae Alkaloids Reveals a Pronounced Electronic Effect on Antiviral Activity.

Authors:  Carla E Brown; Tiffany Kong; James F Britten; Nick H Werstiuk; James McNulty; Leonardo D'Aiuto; Matthew Demers; Vishwajit L Nimgaonkar
Journal:  ACS Omega       Date:  2018-09-20

5.  Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine.

Authors:  Juana Goulart Stollmaier; Jared Thomson; Mary Ann Endoma-Arias; Razvan Simionescu; Alexandra Vernaza; Nakya Mesa-Diaz; Mitchell Smith; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Molecules       Date:  2022-06-28       Impact factor: 4.927

6.  Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.

Authors:  Gábor Varró; Balázs Pogrányi; Alajos Grün; András Simon; László Hegedűs; István Kádas
Journal:  Monatsh Chem       Date:  2018-10-26       Impact factor: 1.451
  6 in total

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