Literature DB >> 20196574

Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

Xiaoming Yang1, Qian Shi, Kenneth F Bastow, Kuo-Hsiung Lee.   

Abstract

A new versatile synthetic methodology for the synthesis of enantiomerically pure natural phenanthroindolizidines and phenanthroquinolizidines has been established and described. Natural products R-antofine and R-cryptopleurine, as well as a novel E-ring expanded analogue 13c (E7), 12-oxo-S-antofine (17), and 12N-methyl-12-aza-S-antofine (18) were synthesized with the new method. This strategy will greatly facilitate future SAR studies on the natural alkaloids with E-ring variations.

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Year:  2010        PMID： 20196574      PMCID： PMC2849728          DOI： 10.1021/ol902819j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  First asymmetric total synthesis of (-)-antofine by using an enantioselective catalytic phase transfer alkylation.

Authors:  Sanghee Kim; Jaekwang Lee; Taeho Lee; Hyeung-geun Park; Deukjoon Kim
Journal:  Org Lett       Date:  2003-07-24       Impact factor: 6.005

2.  [Stereospecific synthesis of two 9,11,12,13, 13a, 14-hexahydrodibenzo(f,h)pyrrolo(1,2-beta)isoquinolines (author's transl)].

Authors:  L Faber; W Wiegrebe
Journal:  Helv Chim Acta       Date:  1976-09-29       Impact factor: 2.164

3.  Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Org Chem       Date:  2008-06-28       Impact factor: 4.354

4.  Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.

Authors:  Alois Fürstner; Jason W J Kennedy
Journal:  Chemistry       Date:  2006-09-25       Impact factor: 5.236

5.  Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Synthesis of (-)-Septicine and (-)-Tylophorine.

Authors:  Daniel L. Comins; Xinghai Chen; Lawrence A. Morgan
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

6.  Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.

Authors:  Sherry R Chemler
Journal:  Curr Bioact Compd       Date:  2009-03-01

7.  Total synthesis of phenanthroindolizidine alkaloids (+/-)-antofine, (+/-)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity.

Authors:  Chung-Ren Su; Amooru G Damu; Po-Cheng Chiang; Kenneth F Bastow; Susan L Morris-Natschke; Kuo-Hsiung Lee; Tian-Shung Wu
Journal:  Bioorg Med Chem       Date:  2008-04-18       Impact factor: 3.641

8.  Asymmetric total syntheses of (-)-antofine and (-)-cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol.

Authors:  Sanghee Kim; Taeho Lee; Eunjung Lee; Jaekwang Lee; Gao-jun Fan; Sang Kook Lee; Deukjoon Kim
Journal:  J Org Chem       Date:  2004-04-30       Impact factor: 4.354

9.  Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents.

Authors:  Wenli Gao; Scott Bussom; Susan P Grill; Elizabeth A Gullen; You-Cai Hu; Xueshi Huang; Sanbao Zhong; Conrad Kaczmarek; Julio Gutierrez; Samson Francis; David C Baker; Shishan Yu; Yung-Chi Cheng
Journal:  Bioorg Med Chem Lett       Date:  2007-05-16       Impact factor: 2.823

10.  Novel mode of action of tylophorine analogs as antitumor compounds.

Authors:  Wenli Gao; Wing Lam; Sanbao Zhong; Conrad Kaczmarek; David C Baker; Yung-Chi Cheng
Journal:  Cancer Res       Date:  2004-01-15       Impact factor: 12.701
  10 in total
  7 in total

1.  Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.

Authors:  Xiaoming Yang; Qian Shi; Chin-Yu Lai; Chi-Yuan Chen; Emika Ohkoshi; Shuenn-Chen Yang; Chih-Ya Wang; Kenneth F Bastow; Tian-Shung Wu; Shiow-Lin Pan; Che-Ming Teng; Pan-Chyr Yang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2012-07-23       Impact factor: 7.446

2.  Total synthesis of (+)-antofine and (-)-cryptopleurine.

Authors:  Weijiang Ying; James W Herndon
Journal:  European J Org Chem       Date:  2013-05-01

3.  Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.

Authors:  Xiaoming Yang; Qian Shi; Shuenn-Chen Yang; Chi-Yuan Chen; Sung-Liang Yu; Kenneth F Bastow; Susan L Morris-Natschke; Pei-Chi Wu; Chin-Yu Lai; Tian-Shung Wu; Shiow-Lin Pan; Che-Ming Teng; Jau-Chen Lin; Pan-Chyr Yang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2011-06-28       Impact factor: 7.446

4.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

5.  Lead Optimization: Synthesis and Biological Evaluation of PBT-1 Derivatives as Novel Antitumor Agents.

Authors:  Lan Xie; Masuo Goto; Xiaoyan Chen; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  ACS Med Chem Lett       Date:  2021-11-17       Impact factor: 4.345

6.  Cryptopleurine analogs with modification of e ring exhibit different mechanism to rac-cryptopleurine and tylophorine.

Authors:  Ying Wang; Hui-Chyn Wong; Elizabeth A Gullen; Wing Lam; Xiaoming Yang; Qian Shi; Kuo-Hsiung Lee; Yung-Chi Cheng
Journal:  PLoS One       Date:  2012-12-10       Impact factor: 3.240

7.  Use of chiral-pool approach into epi-thieno analogues of the scarce bioactive phenanthroquinolizidine alkaloids.

Authors:  Peter Šafář; Štefan Marchalín; Nadežda Prónayová; Viktor Vrábel; Ata Martin Lawson; Mohamed Othman; Adam Daïch
Journal:  Tetrahedron       Date:  2016-04-21       Impact factor: 2.457
  7 in total

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