Abstract
RA-III acetate was treated with Lawesson's reagent to afford [Tyr-3-Ψ(CS-NH)-Ala-4]RA-III acetate. Treatment of this product with Hg(OAc)2/Li2CO3 and then methanol gave an oxazole intermediate. Acid-catalyzed arylation of the methylene carbon atom on the oxazole ring and subsequent partial hydrolysis of the oxazole ring in the resultant compounds afforded RA-VII analogues having an aromatic amino acid at residue 2. [5-Fluoro-d-Trp-2]RA-VII showed IC50 values of 0.038 and 0.077 μM against the HL-60 and HCT-116 cell lines, respectively.
MeSH terms
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Amino Acids, Aromatic / chemical synthesis
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Amino Acids, Aromatic / chemistry
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Antineoplastic Agents* / chemical synthesis
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Antineoplastic Agents* / chemistry
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Antineoplastic Agents* / pharmacology
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Cell Proliferation / drug effects
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Drug Screening Assays, Antitumor
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HCT116 Cells
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HL-60 Cells
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Humans
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Molecular Structure
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Oligopeptides / chemical synthesis
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Oligopeptides / chemistry
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Peptides, Cyclic / chemical synthesis
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Peptides, Cyclic / chemistry
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Peptides, Cyclic / pharmacology
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Structure-Activity Relationship
Substances
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Antineoplastic Agents
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Amino Acids, Aromatic
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Oligopeptides
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Peptides, Cyclic