Synthesis of 3-Hydroxy-3-cyclobutene-1,2-dione Based Amino Acids

Campbell, Eric F.; Park, Anna K.; Kinney, William A.; Fengl, R. W.; Liebeskind, L. S.

doi:10.1021/jo00110a060

Cited by 19 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further building on this idea, the group at Wyeth developed methods to convert squarates into amino acid isosteres of glycine, alanine and g-aminobutyric acid. 42 This work has since been expanded by Shinada, Ohfune et al to generate analogues of a wider range of amino acids for incorporation into a program to synthesise bioactive peptides (Fig. 24).…”

Section: Squaramides As Isosteric Replacements For Carboxylic Acids A...mentioning

confidence: 99%

Squaramides: physical properties, synthesis and applications

2011

View full text Add to dashboard Cite

Squaramides are remarkable four-membered ring systems derived from squaric acid that are able to form up to four hydrogen bonds. A high affinity for hydrogen bonding is driven through a concomitant increase in aromaticity of the ring. This hydrogen bonding and aromatic switching, in combination with structural rigidity, have been exploited in many of the applications of squaramides. Substituted squaramides can be accessed via modular synthesis under relatively mild or aqueous conditions, making them ideal units for bioconjugation and supramolecular chemistry. In this tutorial review the fundamental electronic and structural properties of squaramides are explored to rationalise the geometry, conformation, reactivity and biological activity.

show abstract

Section: Squaramides As Isosteric Replacements For Carboxylic Acids A...mentioning

confidence: 99%

Squaramides: physical properties, synthesis and applications

2011

View full text Add to dashboard Cite

show abstract

“…The reaction between K and Nu N 1-H or Nu C 1-H nucleophiles produces the corresponding semisquaric acid chlorides L [41] and M [42][43][44][45], respectively. The subsequent acidic hydrolysis furnishes semisquaraines H and I [46][47][48][49], which could then be converted to squaraines following established protocols (Scheme 1).…”

Section: Crown Ether-containing Squaraine Sensorsmentioning

confidence: 99%

Squaraine-Based Optical Sensors: Designer Toolbox for Exploring Ionic and Molecular Recognitions

Dzyuba

2021

Chemosensors

View full text Add to dashboard Cite

Small molecule-based chromogenic and fluorogenic probes play an indispensable role in many sensing applications. Ideal optical chemosensors should provide selectivity and sensitivity towards a variety of analytes. Synthetic accessibility and attractive photophysical properties have made squaraine dyes an enticing platform for the development of chemosensors. This review highlights the versatility of modular assemblies of squaraine-based chemosensors and chemodosimeters that take advantage of the availability of various structurally and functionally diverse recognition motifs, as well as utilizing additional recognition capabilities due to the unique structural features of the squaraine ring.

show abstract

“…As such, considerable effort has been placed in advancing bioisosteres of the carboxylic acid moiety. Predominately, these surrogates aim to mimic the acidity and hydrophilic properties of the parent acid, and include such groups as acyl sulfonamides, tetrazoles, hydroxamic acids, and sulfonylureas. , Squaric acid has found some use in this regard, owing to its high acidity. − Squaramides substituted with both amines and hydroxy groups have similarly been used for the generation of novel drug leads, primarily in amino acid and peptidomimetic drug discovery (see Section ).…”

Section: Squaramides As Bioisosteresmentioning

confidence: 99%

Squaramides as Bioisosteres in Contemporary Drug Design

Agnew‐Francis

Williams

2020

Chem. Rev.

View full text Add to dashboard Cite

Squaramides represent a class of vinylogous amides that are derived from the squarate oxocarbon dianion. While they have been known since the 1950s, squaramides have only recently emerged (in the last 10–20 years) as particularly useful chemical entities in a variety of applications. They have found particular use as bioisosteric replacements of several heteroatomic functional groups, notably ureas, thioureas, guanidines, and cyanoguanidines, owing in part to their similar capacity toward hydrogen bonding and ability to reliably engender defined conformations in drug ligands. This Review aims to provide a comprehensive overview of the deployment of squaramides as bioisosteres within the drug design landscape. Their utility in this space is further rationalized through an examination of the physicochemical properties of squaramides in contrast to other functional groups. In addition, we consider the deployment of related cyclic oxocarbanion derivatives as potential bioisosteric replacements of ureas and related functional groups.

show abstract

Synthesis of 3-Hydroxy-3-cyclobutene-1,2-dione Based Amino Acids

Cited by 19 publications

References 0 publications

Squaramides: physical properties, synthesis and applications

Squaramides: physical properties, synthesis and applications

Squaraine-Based Optical Sensors: Designer Toolbox for Exploring Ionic and Molecular Recognitions

Squaramides as Bioisosteres in Contemporary Drug Design

Contact Info

Product

Resources

About