Literature DB >> 15177450

Synthesis and anticancer activity of side chain analogs of the crambescidin alkaloids.

Zachary D Aron1, Halina Pietraszkiewicz, Larry E Overman, Fredrick Valeriote, Carman Cuevas.   

Abstract

Twenty three side chain analogs of the crambescidin alkaloids were prepared from the corresponding pentacyclic zwitterionic core acid. In the crambescidin 800 and 657 series, potency increased with increasing chain length. In addition, substantial variations in tumor selectivity with structure were seen. Crambescidin analogs having short, nonpolar side chains were identified for the first time as promising anticancer agents.

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Year:  2004        PMID： 15177450     DOI： 10.1016/j.bmcl.2004.04.071

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


  15 in total

Review 1.  Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids.

Authors:  Yunlong Shi; Yasamin Moazami; Joshua G Pierce
Journal:  Bioorg Med Chem       Date:  2017-03-12       Impact factor: 3.641

Review 2.  Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

Authors:  Jeffrey S Cannon; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

3.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

4.  Concise synthesis of guanidine-containing heterocycles using the Biginelli reaction.

Authors:  Bradley L Nilsson; Larry E Overman
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

5.  Accelerating the discovery of biologically active small molecules using a high-throughput yeast halo assay.

Authors:  Nadine C Gassner; Craig M Tamble; Jonathan E Bock; Naomi Cotton; Kimberly N White; Karen Tenney; Robert P St Onge; Michael J Proctor; Guri Giaever; Corey Nislow; Ronald W Davis; Phillip Crews; Theodore R Holman; R Scott Lokey
Journal:  J Nat Prod       Date:  2007-02-10       Impact factor: 4.050

6.  Mechanism of cytotoxic action of crambescidin-816 on human liver-derived tumour cells.

Authors:  J A Rubiolo; H López-Alonso; M Roel; M R Vieytes; O Thomas; E Ternon; F V Vega; L M Botana
Journal:  Br J Pharmacol       Date:  2014-04       Impact factor: 8.739

7.  Guanidine alkaloid analogs as inhibitors of HIV-1 Nef interactions with p53, actin, and p56lck.

Authors:  Allison Olszewski; Ken Sato; Zachary D Aron; Frederick Cohen; Aleishia Harris; Brenda R McDougall; W Edward Robinson; Larry E Overman; Gregory A Weiss
Journal:  Proc Natl Acad Sci U S A       Date:  2004-09-15       Impact factor: 11.205

8.  Crambescidin-816 acts as a fungicidal with more potency than crambescidin-800 and -830, inducing cell cycle arrest, increased cell size and apoptosis in Saccharomyces cerevisiae.

Authors:  Juan A Rubiolo; Eva Ternon; Henar López-Alonso; Olivier P Thomas; Félix V Vega; Mercedes R Vieytes; Luis M Botana
Journal:  Mar Drugs       Date:  2013-11-08       Impact factor: 5.118

9.  Spherulization as a process for the exudation of chemical cues by the encrusting sponge C. crambe.

Authors:  Eva Ternon; Lina Zarate; Sandrine Chenesseau; Julie Croué; Rémi Dumollard; Marcelino T Suzuki; Olivier P Thomas
Journal:  Sci Rep       Date:  2016-07-06       Impact factor: 4.379

10.  Guanidine Alkaloids from the Marine Sponge Monanchora pulchra Show Cytotoxic Properties and Prevent EGF-Induced Neoplastic Transformation in Vitro.

Authors:  Sergey A Dyshlovoy; Kseniya M Tabakmakher; Jessica Hauschild; Regina K Shchekaleva; Katharina Otte; Alla G Guzii; Tatyana N Makarieva; Ekaterina K Kudryashova; Sergey N Fedorov; Larisa K Shubina; Carsten Bokemeyer; Friedemann Honecker; Valentin A Stonik; Gunhild von Amsberg
Journal:  Mar Drugs       Date:  2016-07-15       Impact factor: 5.118
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