ChemInform Abstract: Tailor-Made α-Amino Acids in the Pharmaceutical Industry: Synthetic Approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA)

The reaction of 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) with each of sarcosine and (±)-pipecolinic acid afforded the corresponding N-(4- oxoquinolin-7-yl)-α-amino acids 8 and 9. Reductive lactamization of the latter with sodium dithionite gave hexahydropyrido[2,3- f ]quinoxaline (10) and octahydrodipyrido[1,2-a : 2,3- f ]quinoxaline (11) derivatives, respectively. Compounds 8 - 11 and their homologs 1 - 6, accessible from (S)-proline, (2S, 4R)-4-hydroxyproline and (S)-tetrahydroisoquinoline-3-carboxylic acid exhibit good to excellent antibacterial activities against E. coli and S. aureus.

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Enzymatic resolution of (±)-5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2009.07.025 ◽

2009 ◽

Vol 20 (16) ◽

pp. 1940-1947 ◽

Cited By ~ 5

Author(s):

Giuseppe Cremonesi ◽

Piero Dalla Croce ◽

Alessandra Forni ◽

Maddalena Gallanti ◽

Raffaella Gandolfi ◽

...

Keyword(s):

Amino Acids ◽

Carboxylic Acid ◽

Ethyl Ester ◽

Acid Ethyl Ester ◽

Enzymatic Resolution

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Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives

Angewandte Chemie International Edition ◽

10.1002/anie.201710915 ◽

2018 ◽

Vol 57 (8) ◽

pp. 2233-2237 ◽

Cited By ~ 34

Author(s):

Bin Hu ◽

Li Deng

Keyword(s):

Amino Acids ◽

Carboxylic Acid ◽

Asymmetric Synthesis ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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Cyclodextrin Multicomponent Complexes: Pharmaceutical Applications

Pharmaceutics ◽

10.3390/pharmaceutics13071099 ◽

2021 ◽

Vol 13 (7) ◽

pp. 1099

Author(s):

Virginia Aiassa ◽

Claudia Garnero ◽

Marcela R. Longhi ◽

Ariana Zoppi

Keyword(s):

Amino Acids ◽

Pharmaceutical Industry ◽

Drug Effects ◽

Water Soluble ◽

Therapeutic Drug ◽

Water Soluble Polymers ◽

Soluble Polymers ◽

Pharmaceutical Applications ◽

Auxiliary Substance ◽

Acids And Bases

Cyclodextrins (CDs) are naturally available water-soluble cyclic oligosaccharides widely used as carriers in the pharmaceutical industry for their ability to modulate several properties of drugs through the formation of drug–CD complexes. The addition of an auxiliary substance when forming multicomponent complexes is an adequate strategy to enhance complexation efficiency and to facilitate the therapeutic applicability of different drugs. This review discusses multicomponent complexation using amino acids; organic acids and bases; and water-soluble polymers as auxiliary excipients. Special attention is given to improved properties by including information on the solubility, dissolution, permeation, stability and bioavailability of several relevant drugs. In addition, the use of multicomponent CD complexes to enhance therapeutic drug effects is summarized.

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