Synthesis and biological evaluation of new jasplakinolide (jaspamide) analogs

Ghosh, Arun K.; Dawson, Zachary L.; Moon, Deuk Kyu; Bai, Ruoli; Hamel, Ernest

doi:10.1016/j.bmcl.2010.07.023

Cited by 12 publications

(8 citation statements)

References 32 publications

(13 reference statements)

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“…This synthesis enabled us to probe the importance of various substituents, improve potency, and reduce complexity. As shown in Figure 16, two less complex jasplakinolide analogs have shown comparable potency (IC 50 ) to jasplakinolide, when assayed against CA46 Burkitt lymphoma human cell lines 63. Analog 88 (IC 50 = 20 nM) allowed us to replace the metabolically susceptible phenolic OH with OMe.…”

Section: Introductionmentioning

confidence: 99%

Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine

Ghosh

2010

J. Org. Chem.

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In this perspective article, I outline my group's research involving the chemical syntheses of medicinally important natural products, exploration of their bioactivity, and development of new asymmetric carbon-carbon bond forming reactions. The article also highlights our approach to molecular design and synthesis of conceptually novel inhibitors against target proteins involved in the pathogenesis human diseases, including AIDS and Alzheimer's disease.

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Section: Introductionmentioning

confidence: 99%

Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine

Ghosh

2010

J. Org. Chem.

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“…It is interesting to note that in compound 14j the phenolic OH group is substituted by a methoxy group while the C(2) atom is no longer asymmetric [36]. …”

Section: Cyclic Peptides With Fragments Of β 3 -Arylamino Acidsmentioning

confidence: 99%

“…Synthetic analogs of jaspamide 14d-g [35] Quite recently eight new derivatives of jasplakinolide 14h-o were synthesized [36]. All the obtained compounds were assessed for their effect on the growth of cell lines of human Burkitt's lymphoma (CA46) and cytotoxicity.…”

Section: Cyclic Peptides With Fragments Of β 3 -Arylamino Acidsmentioning

confidence: 99%

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Biologically active cyclic polypeptides with fragments of β-amino acid derivatives isolated from marine organisms (review)

Romanova

Tallo

Rybalko

et al. 2011

Chem Heterocycl Comp

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Published data on the structure, stereochemistry, and biological activity of natural cyclic polypeptides containing fragments of β-amino acids are reviewed, and an attempt is made to relate the structure to the biological activity.According to available estimates [1], there are more β-amino acids in the nature than the 22 proteinogenic α-amino acids that take part in ribosomal protein synthesis. The β-amino acids exist either as such or as fragments of the molecules of natural compounds with various degrees of complexity [2] and most often as linear or cyclic peptides that are, in all probability, formed by such microorganisms as bacteria and fungi as a result of non-ribosomal protein synthesis [3].Before 1996 nothing was known about the structure of the simplest β-peptides in the crystal and in solution. Today there are numerous papers and reviews on natural, semisynthetic, and fully synthetic β-peptides, the most comprehensive of which are the papers [4][5][6]. For this reason we will not dwell on these aspects here.The aim of our review is to classify published data on the structure, stereochemistry, and biological activity and also to study the structure-activity relationship of cyclic β-peptides, which have shown greater resistance to the action of enzymes than their linear analogs and α-peptides and therefore exhibit biological selectivity.

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“…For the assembly of the amino acid head, we adopted an auxiliarybased protocol developed for the synthesis of (R)-(+)β -phenylalanine by Davis et al [27,28], which has also been applied by Ghosh et al for the synthesis of jasplakinolide and derivatives [29,30].…”

Section: Synthesismentioning

confidence: 99%

Enantioselective Synthesis and Photoreactivity of a Diazirinyl-substituted (R)-β-Phenylalanine

Schäckermann

Lindel

2014

Zeitschrift Für Naturforschung B

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The first enantioselective synthesis of a photoreactive (R)-β -phenylalanine is described. In the key step, m-diazirinyl-substituted benzaldehyde is converted to a chiral sulfinimine in a Ti(OEt) 4mediated reaction, followed by diastereoselective enolate addition. The absolute configuration of photo (R)-β -phenylalanine was confirmed by Mosher analysis. The photo amino acid proved to be thermally stable under standard laboratory conditions. Irradiation in toluene afforded cycloheptatriene/norcaradiene valence tautomers, together with carbene benzylation. Quantumchemical calculations indicate a small triplet-singlet gap.

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Synthesis and biological evaluation of new jasplakinolide (jaspamide) analogs

Cited by 12 publications

References 32 publications

Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine

Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine

Biologically active cyclic polypeptides with fragments of β-amino acid derivatives isolated from marine organisms (review)

Enantioselective Synthesis and Photoreactivity of a Diazirinyl-substituted (R)-β-Phenylalanine

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