Literature DB >> 21041085

Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth.

Cassia S Mizuno1, Shiby Paul, Nanjoo Suh, Agnes M Rimando.   

Abstract

Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids was designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid like moiety was introduced through Friedel-Crafts alkylation of toluene. Among the synthesized compounds, the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile 8 showed submicromolar inhibitory activity with an IC(50) of 0.66 μM. Published by Elsevier Ltd.

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Year:  2010        PMID： 21041085      PMCID： PMC3018291          DOI： 10.1016/j.bmcl.2010.10.038

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


  23 in total

1.  A safety study of oral tangeretin and xanthohumol administration to laboratory mice.

Authors:  Barbara W Vanhoecke; Femke Delporte; Eva Van Braeckel; Arne Heyerick; Herman T Depypere; Margareta Nuytinck; Denis De Keukeleire; Marc E Bracke
Journal:  In Vivo       Date:  2005 Jan-Feb       Impact factor: 2.155

2.  Antileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis.

Authors:  S F Nielsen; S B Christensen; G Cruciani; A Kharazmi; T Liljefors
Journal:  J Med Chem       Date:  1998-11-19       Impact factor: 7.446

3.  In vitro and in vivo studies on stilbene analogs as potential treatment agents for colon cancer.

Authors:  Shiby Paul; Cassia S Mizuno; Hong Jin Lee; Xi Zheng; Sarah Chajkowisk; John M Rimoldi; Allan Conney; Nanjoo Suh; Agnes M Rimando
Journal:  Eur J Med Chem       Date:  2010-05-15       Impact factor: 6.514

4.  [Antitumor chemotherapy. IX. Cytotoxic activity in cultured tumor cells of chalcone substituants and related compounds].

Authors:  J C Doré; C Viel
Journal:  J Pharm Belg       Date:  1974 Jul-Aug

5.  Synthesis of novel retinoid X receptor-selective retinoids.

Authors:  M M Faul; A M Ratz; K A Sullivan; W G Trankle; L L Winneroski
Journal:  J Org Chem       Date:  2001-08-24       Impact factor: 4.354

6.  Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids.

Authors:  H Kagechika; E Kawachi; Y Hashimoto; K Shudo
Journal:  J Med Chem       Date:  1989-04       Impact factor: 7.446

7.  Khellinone derivatives as blockers of the voltage-gated potassium channel Kv1.3: synthesis and immunosuppressive activity.

Authors:  Jonathan B Baell; Robert W Gable; Andrew J Harvey; Nathan Toovey; Tanja Herzog; Wolfram Hänsel; Heike Wulff
Journal:  J Med Chem       Date:  2004-04-22       Impact factor: 7.446

8.  Azulenic retinoids: novel nonbenzenoid aromatic retinoids with anticancer activity.

Authors:  A E Asato; A Peng; M Z Hossain; T Mirzadegan; J S Bertram
Journal:  J Med Chem       Date:  1993-10-15       Impact factor: 7.446

9.  Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents.

Authors:  Marinella Roberti; Daniela Pizzirani; Daniele Simoni; Riccardo Rondanin; Riccardo Baruchello; Caterina Bonora; Filippo Buscemi; Stefania Grimaudo; Manlio Tolomeo
Journal:  J Med Chem       Date:  2003-07-31       Impact factor: 7.446

10.  In vitro antimalarial activity of chalcones and their derivatives.

Authors:  R Li; G L Kenyon; F E Cohen; X Chen; B Gong; J N Dominguez; E Davidson; G Kurzban; R E Miller; E O Nuzum
Journal:  J Med Chem       Date:  1995-12-22       Impact factor: 7.446
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  3 in total

Review 1.  Retinoic acid signaling pathways in development and diseases.

Authors:  Bhaskar C Das; Pritam Thapa; Radha Karki; Sasmita Das; Sweta Mahapatra; Ting-Chun Liu; Ingrid Torregroza; Darren P Wallace; Suman Kambhampati; Peter Van Veldhuizen; Amit Verma; Swapan K Ray; Todd Evans
Journal:  Bioorg Med Chem       Date:  2013-11-22       Impact factor: 3.641

2.  Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies.

Authors:  Katarina Jakovljević; Milan D Joksović; Ivana Z Matić; Nina Petrović; Tatjana Stanojković; Dušan Sladić; Miroslava Vujčić; Barbara Janović; Ljubinka Joksović; Snežana Trifunović; Violeta Marković
Journal:  Medchemcomm       Date:  2018-08-23       Impact factor: 3.597

Review 3.  Hybrid curcumin compounds: a new strategy for cancer treatment.

Authors:  Marie-Hélène Teiten; Mario Dicato; Marc Diederich
Journal:  Molecules       Date:  2014-12-12       Impact factor: 4.411
  3 in total

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