New protein farnesyltransferase inhibitors in the 3-arylthiophene 2-carboxylic acid series: diversification of the aryl moiety by solid-phase synthesis

Solid phase synthesis methodology on a benzhydrylamine resin was used for the synthesis of three analogues of vasopressin with the non-coded amino acid, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), in the position 2 ([Tic2, Lys8]VP (I)) and in the position 3 ([Tic3, Lys8]VP (II)). The analogue containing only one Tic in place of both aromatic residues was also isolated (des-Tyr2-[Tic3, Lys8]VP (III)). The biological activities of all analogues were negligible.

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Solid-phase synthesis of peptides containing the spin-labeled 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid (TOAC)

Journal of Peptide Research ◽

10.1034/j.1399-3011.2001.00940.x ◽

2001 ◽

Vol 58 (5) ◽

pp. 424-432 ◽

Cited By ~ 33

Author(s):

L. Martin ◽

C. Vita ◽

A. Ivancich ◽

F. Formaggio ◽

C. Toniolo

Keyword(s):

Carboxylic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Phase Synthesis

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Dihydropyran-2-carboxylic acid, a novel bifunctional linker for the solid-phase synthesis of peptides containing a C-terminal alcohol

Chemical Communications ◽

10.1039/a707934f ◽

1998 ◽

pp. 649-650 ◽

Cited By ~ 14

Author(s):

Hsing-Pang Hsieh ◽

Ying-Ta Wu ◽

Shui-Tein Chen

Keyword(s):

Carboxylic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Phase Synthesis

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ChemInform Abstract: Dihydropyran-2-carboxylic Acid, a Novel Bifunctional Linker for the Solid-Phase Synthesis of Peptides Containing a C-Terminal Alcohol.

ChemInform ◽

10.1002/chin.199830219 ◽

2010 ◽

Vol 29 (30) ◽

pp. no-no

Author(s):

H.-P. HSIEH ◽

Y.-T. WU ◽

S.-T. CHEN ◽

K.-T. WANG

Keyword(s):

Carboxylic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Phase Synthesis

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Solid-Phase Synthesis of C-Terminal Peptide Libraries for Studying the Specificity of Enzymatic Protein Farnesyltransferase

Peptides Across the Pacific: The Proceedings of the Twenty-Third American and the Sixth International Peptide Symposium ◽

10.17952/23aps.2013.102 ◽

2013 ◽

Author(s):

Yen-Chih Wang ◽

Mark D. Distefano

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Peptide Libraries ◽

Phase Synthesis ◽

Protein Farnesyltransferase

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Combinatorial synthesis of heterocycles: Solid phase synthesis of 2-arylquinoline-4-carboxylic acid derivatives

Tetrahedron Letters ◽

10.1016/s0040-4039(96)02456-2 ◽

1997 ◽

Vol 38 (6) ◽

pp. 907-910 ◽

Cited By ~ 39

Author(s):

Ariamala Gopalsamy ◽

Peter V. Pallai

Keyword(s):

Carboxylic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Combinatorial Synthesis ◽

Phase Synthesis

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Strategies for the Synthesis of Hydroxamic Acids

Current Organic Synthesis ◽

10.2174/1570179414666170614123508 ◽

2018 ◽

Vol 15 (2) ◽

pp. 154-165 ◽

Cited By ~ 3

Author(s):

Ankit Ganeshpurkar ◽

Devendra Kumar ◽

Sushil K. Singh

Keyword(s):

Cardiovascular Diseases ◽

Carboxylic Acid ◽

Organic Compounds ◽

Acid Chloride ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Allergic Diseases ◽

Hydroxamic Acids ◽

Phase Synthesis ◽

Major Class

Background: Hydroxamic acids are a major class of organic compounds. They have a wide variety of pharmacological actions in targeting cancers, cardiovascular diseases, HIV, Alzheimer's disease, Malaria, Allergic diseases. Objective: The present review focuses on the chemistry of conventional and non-conventional routes for the synthesis of hydroxamic acids reported till date. Conclusion: The hydroxamic acids are conventionally synthesized via carboxylic acid and their acid chloride derivatives. However, some other functional groups i.e. aldehyde, amine, amide and alcohol can also be converted to hydroxamate with ease. The solid phase synthesis techniques are also gaining importance for the synthesis of hydroxamic acids and these pathways have opened a wide arena for the synthesis of diverse and complex hydroxamic acids.

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