Literature DB >> 18343127

Enantiospecific synthesis and cytotoxicity of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one enantiomers.

F Scott Kimball1, Brandon J Turunen, Keith C Ellis, Richard H Himes, Gunda I Georg.   

Abstract

An enantiospecific synthesis was developed to generate both enantiomers of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one. A biological assay utilizing the HCT-116 colon cancer cell line to determine the cytotoxicity of these analogs revealed that only the (R)-enantiomer exhibited appreciable cytotoxicity with an IC(50) value of 0.2 microM.

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Year:  2008        PMID： 18343127      PMCID： PMC2408685          DOI： 10.1016/j.bmc.2008.02.073

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


  3 in total

1.  Cytotoxic alkaloids from Tylophora indica.

Authors:  M Ali; S H Ansari; M R Grever
Journal:  Pharmazie       Date:  2001-02       Impact factor: 1.267

2.  Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents.

Authors:  Vedula M Sharma; K V Adi Seshu; C Vamsee Krishna; P Prasanna; V Chandra Sekhar; A Venkateswarlu; Sriram Rajagopal; R Ajaykumar; Dhanvanthri S Deevi; N V S Rao Mamidi; R Rajagopalan
Journal:  Bioorg Med Chem Lett       Date:  2003-05-19       Impact factor: 2.823

3.  Synthesis, in vitro and in vivo cytotoxicity of 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-ones.

Authors:  F Scott Kimball; Ashok Rao Tunoori; Samuel F Victory; Dinah Dutta; Jonathan M White; Richard H Himes; Gunda I Georg
Journal:  Bioorg Med Chem Lett       Date:  2007-06-13       Impact factor: 2.823
  3 in total
  4 in total

1.  Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors:  Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

2.  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

3.  Metal-free [3 + 2 + 1]/[2 + 2 + 1] biscyclization: stereospecific construction with concomitant functionalization of indolizin-5(1H)-one.

Authors:  Tuan-Jie Li; Zhong-Qiu Liu; Hong-Mei Yin; Chang-Sheng Yao; Bo Jiang; Xiang-Shan Wang; Shu-Jiang Tu; Xiu-Ling Li; Guigen Li
Journal:  J Org Chem       Date:  2013-11-07       Impact factor: 4.354

4.  In search of constrained FTY720 and phytosphingosine analogs as dual acting anticancer agents targeting metabolic and epigenetic pathways.

Authors:  Jean-Baptiste Garsi; Lorenzo Sernissi; Vito Vece; Stephen Hanessian; Alison N McCracken; Grigor Simitian; Aimee L Edinger
Journal:  Eur J Med Chem       Date:  2018-09-21       Impact factor: 6.514
  4 in total

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