Literature DB >> 29056779

Synthesis of indolo[4,3-bc]phenanthridine-6,11(2H,12H)-diones using the Schiff base-homophthalic anhydride cyclization reaction.

Mohamed S A Elsayed1, Matthias Zeller2, Mark Cushman1.   

Abstract

A novel indolophenanthridine ring system has been synthesized via the Schiff base-homophthalic anhydride cyclization followed by thionyl chloride-mediated dehydrogenation and intramolecular Friedel-Crafts acylation. This adds to the array of heterocyclic systems that are available through the cycloaddition reaction of imines with cyclic dicarboxylic acid anhydrides. The cytotoxicities of the indolophenanthridines were investigated in human cancer cell cultures, and the results documented significant antitumor activity in a variety of human cancer cell lines. This provides a new heterocyclic scaffold for anticancer drug design.

Entities:  

Keywords:  Indolophenanthridine; Schiff base; anticancer; cytotoxicity; homophthalic anhydride

Year:  2016        PMID： 29056779      PMCID： PMC5646376          DOI： 10.1080/00397911.2016.1232409

Source DB:  PubMed          Journal:  Synth Commun        ISSN： 0039-7911            Impact factor:   2.007


  18 in total

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Authors:  Marcos González-López; Jared T Shaw
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

2.  Synthesis of pharmacologically active nitrogen analogs of the tetrahydrocannabinols.

Authors:  M Cushman; N Castagnoli
Journal:  J Org Chem       Date:  1974-05-31       Impact factor: 4.354

3.  The condensation of succinic anhydride with benzylidinemethylamine. A stereoselective synthesis of trans- and cis-1-methyl-4-carbosy-5-phenyl-2-pyrrolidinone.

Authors:  N Castagnoli
Journal:  J Org Chem       Date:  1969-10       Impact factor: 4.354

4.  Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles.

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5.  Azaindenoisoquinolines as topoisomerase I inhibitors and potential anticancer agents: a systematic study of structure-activity relationships.

Authors:  Evgeny Kiselev; Keli Agama; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2012-02-13       Impact factor: 7.446

6.  Identification, synthesis, and biological evaluation of metabolites of the experimental cancer treatment drugs indotecan (LMP400) and indimitecan (LMP776) and investigation of isomerically hydroxylated indenoisoquinoline analogues as topoisomerase I poisons.

Authors:  Maris A Cinelli; P V Narasimha Reddy; Peng-Cheng Lv; Jian-Hua Liang; Lian Chen; Keli Agama; Yves Pommier; Richard B van Breemen; Mark Cushman
Journal:  J Med Chem       Date:  2012-12-07       Impact factor: 7.446

7.  Toward lead-oriented synthesis: one-pot version of Castagnoli condensation with nonactivated alicyclic anhydrides.

Authors:  Sergey V Ryabukhin; Dmitriy M Panov; Dmitry S Granat; Eugeniy N Ostapchuk; Dmitriy V Kryvoruchko; Oleksandr O Grygorenko
Journal:  ACS Comb Sci       Date:  2014-02-06       Impact factor: 3.784

8.  Dibenzo[c,h][1,5]naphthyridinediones as topoisomerase I inhibitors: design, synthesis, and biological evaluation.

Authors:  Evgeny Kiselev; Nicholas Empey; Keli Agama; Yves Pommier; Mark Cushman
Journal:  J Org Chem       Date:  2012-05-15       Impact factor: 4.354

9.  Optimization of the lactam side chain of 7-azaindenoisoquinoline topoisomerase I inhibitors and mechanism of action studies in cancer cells.

Authors:  Evgeny Kiselev; Dhriti Sooryakumar; Keli Agama; Mark Cushman; Yves Pommier
Journal:  J Med Chem       Date:  2014-02-06       Impact factor: 7.446

10.  Synthesis and biological evaluation of new carbohydrate-substituted indenoisoquinoline topoisomerase I inhibitors and improved syntheses of the experimental anticancer agents indotecan (LMP400) and indimitecan (LMP776).

Authors:  Daniel E Beck; Keli Agama; Christophe Marchand; Adel Chergui; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2014-02-11       Impact factor: 7.446
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  1 in total

1.  Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.

Authors:  Claire L Jarvis; Neyra M Jemal; Spencer Knapp; Daniel Seidel
Journal:  Org Biomol Chem       Date:  2018-06-13       Impact factor: 3.876
  1 in total

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