Literature DB >> 22542017

Bio-inspired synthesis and biological evaluation of a colchicine-related compound library.

K C Nicolaou1, Roman A Valiulin, Jonathan K Pokorski, Vicki Chang, Jason S Chen.   

Abstract

A bio-inspired investigation of the reactions of substrates of type 1 with VOF(3) and PIFA [phenyliodine(III) bis(trifluoroacetate)] led to a collection of colchicine-like compounds 2-5 and related systems. Biological evaluation revealed that some of the synthesized products had significant cytotoxic properties against the colon cancer cell line HT-29.
Copyright © 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID： 22542017      PMCID： PMC3353021          DOI： 10.1016/j.bmcl.2012.04.007

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


  26 in total

1.  Eribulin induces irreversible mitotic blockade: implications of cell-based pharmacodynamics for in vivo efficacy under intermittent dosing conditions.

Authors:  Murray J Towle; Kathleen A Salvato; Bruce F Wels; Kimberley K Aalfs; Wanjun Zheng; Boris M Seletsky; Xiaojie Zhu; Bryan M Lewis; Yoshito Kishi; Melvin J Yu; Bruce A Littlefield
Journal:  Cancer Res       Date:  2010-12-02       Impact factor: 12.701

2.  Androcymbine--position of substituents on ring A.

Authors:  P Sedmera; A Husek; V Simánek
Journal:  Acta Univ Palacki Olomuc Fac Med       Date:  1991

3.  Design, synthesis, and biological evaluation of a biyouyanagin compound library.

Authors:  K C Nicolaou; Silvano Sanchini; David Sarlah; Gang Lu; T Robert Wu; Daniel K Nomura; Benjamin F Cravatt; Beatrice Cubitt; Juan C de la Torre; Ann J Hessell; Dennis R Burton
Journal:  Proc Natl Acad Sci U S A       Date:  2011-01-18       Impact factor: 11.205

4.  Alkaloid biosynthesis. XVII. The structure and chemistry of androcymbine.

Authors:  A R Battersby; R B Herbert; L Pijewska; F Santavý; P Sedmera
Journal:  J Chem Soc Perkin 1       Date:  1972

5.  Studies on the syntheses of heterocyclic compounds. 700. Syntheses of isoquinoline alkaloids with cuprous chloride and oxygen in pyridine as an enzymic model.

Authors:  T Kametani; M Ihara; M Takemura; Y Satoh; H Terasawa
Journal:  J Am Chem Soc       Date:  1977-05-25       Impact factor: 15.419

6.  Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B.

Authors:  Naoko Yasobu; Mariko Kitajima; Noriyuki Kogure; Yoshiyuki Shishido; Takeshi Matsuzaki; Masato Nagaoka; Hiromitsu Takayama
Journal:  ACS Med Chem Lett       Date:  2011-03-04       Impact factor: 4.345

7.  Phytochemical study and cytotoxicity evaluation of Colchicum stevenii Kunth (Colchicaceae): a Jordanian meadow saffron.

Authors:  Mohsen S Al-Mahmoud; Feras Q Alali; Khaled Tawaha; Rana M Qasaymeh
Journal:  Nat Prod Res       Date:  2006-02       Impact factor: 2.861

8.  Induction of morphological and biochemical apoptosis following prolonged mitotic blockage by halichondrin B macrocyclic ketone analog E7389.

Authors:  Galina Kuznetsov; Murray J Towle; Hongsheng Cheng; Takanori Kawamura; Karen TenDyke; Diana Liu; Yoshito Kishi; Melvin J Yu; Bruce A Littlefield
Journal:  Cancer Res       Date:  2004-08-15       Impact factor: 12.701

9.  1-phenethylisoquinoline alkaloids. IV. Isolation, structural elucidation, and synthesis of c-homoaporphines.

Authors:  A R Battersby; R B Bradbury; R B Herbert; M H Munro; R Ramage
Journal:  J Chem Soc Perkin 1       Date:  1974

10.  From nature to the laboratory and into the clinic.

Authors:  K C Nicolaou; Jason S Chen; Stephen M Dalby
Journal:  Bioorg Med Chem       Date:  2008-11-06       Impact factor: 3.641
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  7 in total

1.  New Colchicine-Derived Triazoles and Their Influence on Cytotoxicity and Microtubule Morphology.

Authors:  Persefoni Thomopoulou; Julia Sachs; Nicole Teusch; Aruljothi Mariappan; Jay Gopalakrishnan; Hans-Günther Schmalz
Journal:  ACS Med Chem Lett       Date:  2015-12-29       Impact factor: 4.345

Review 2.  Reviewing Colchicaceae alkaloids - perspectives of evolution on medicinal chemistry.

Authors:  Sonny Larsson; Nina Rønsted
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

3.  Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings.

Authors:  Lei Li; Zhong-Liang Li; Fu-Li Wang; Zhen Guo; Yong-Feng Cheng; Na Wang; Xiao-Wu Dong; Chao Fang; Jingjiang Liu; Chunhui Hou; Bin Tan; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2016-12-22       Impact factor: 14.919

4.  A Catalytic Asymmetric Pictet-Spengler Platform as a Biomimetic Diversification Strategy toward Naturally Occurring Alkaloids.

Authors:  Manuel J Scharf; Benjamin List
Journal:  J Am Chem Soc       Date:  2022-08-17       Impact factor: 16.383

5.  Antiproliferative Activity and Molecular Docking of Novel Double-Modified Colchicine Derivatives.

Authors:  Urszula Majcher; Greta Klejborowska; Mahshad Moshari; Ewa Maj; Joanna Wietrzyk; Franz Bartl; Jack A Tuszynski; Adam Huczyński
Journal:  Cells       Date:  2018-11-01       Impact factor: 6.600

6.  Synthesis and Antiproliferative Screening Of Novel Analogs of Regioselectively Demethylated Colchicine and Thiocolchicine.

Authors:  Dominika Czerwonka; Szymon Sobczak; Ewa Maj; Joanna Wietrzyk; Andrzej Katrusiak; Adam Huczyński
Journal:  Molecules       Date:  2020-03-05       Impact factor: 4.411

7.  Discovery and engineering of colchicine alkaloid biosynthesis.

Authors:  Ryan S Nett; Warren Lau; Elizabeth S Sattely
Journal:  Nature       Date:  2020-07-22       Impact factor: 49.962
  7 in total

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