Design of a New Class of Orally Active Fibrinogen Receptor Antagonists

Klein, Scott I.; Molino, Bruce F.; Czekaj, Mark; Gardner, Charles J.; Chu, Valeria; Brown, Karen; Sabatino, Ralph D.; Bostwick, Jeffrey S.; Kasiewski, Charles; Bentley, Ross; Windisch, Vincent; Perrone, Mark H.; Dunwiddie, Christopher T.; Leadley, Robert J.

doi:10.1021/jm9801096

Cited by 19 publications

(17 citation statements)

References 36 publications

(42 reference statements)

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“…Melting points are uncorrected. The Boc‐protection of piperidine‐4‐carboxylic acid ( A ) and 1‐(2‐bromoethoxy)‐2‐(2‐methoxyethoxy)ethane were performed based on literature procedures …”

Section: Methodsmentioning

confidence: 99%

Far‐Red‐ to NIR‐Emitting Adamantyl‐Functionalized Squaraine Dye: J‐Aggregation, Dissociation, and Cell Imaging

Liu

Zhang

et al. 2018

Eur J Org Chem

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Squaraine dyes AM‐1′ and AM‐1 bearing adamantyl termini were synthesized and spectroscopically characterized. AM‐1′ exhibited intense absorption and sharp emission in the far‐red to near‐infrared (NIR) spectral region. The degenerate two‐photon absorption (2PA) spectrum of AM‐1′ was obtained over a broad spectral range with a maximum cross section of ca. 360 GM. In aqueous solutions, AM‐1′ displayed a strong tendency for J‐aggregation and the reference AM‐1 exhibited entirely different aggregation behavior. We conclude that both the terminal pendant groups and substituents adjacent to the squaraine core play important roles in determining the aggregation behaviors and optical properties of the resultant squaraine dyes. Further an AM‐1′/β‐cyclodextrin complex dramatically suppressed squaraine π–π stacking and dissociated the J‐aggregate. Fluorescence microscopy imaging of HCT 116 cells incubated with the complex was accomplished, suggesting the potential application of this complex in fluorescence bioimaging.

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Section: Methodsmentioning

confidence: 99%

Far‐Red‐ to NIR‐Emitting Adamantyl‐Functionalized Squaraine Dye: J‐Aggregation, Dissociation, and Cell Imaging

Liu

Zhang

et al. 2018

Eur J Org Chem

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“…86 These compounds are crucial as anti-inflammatory, 87 antiproliferative, 88 antithrombotic, 89 General routes from N-protected amino acids to their Nsubstituted amides involve the activation of the carboxylic acid function. Isolated active intermediates can be used such as N-protected aminoacyl chlorides 97 or fluorides.…”

Section: Heterocyclic Aminesmentioning

confidence: 99%

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Katritzky¹,

Angrish²,

Todadze³

2009

Synlett

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N-(Protected a-aminoacyl)benzotriazoles are efficient intermediates for N-and O-aminoacylation. These intermediates enable fast preparations of biologically relevant peptides and peptide conjugates in high yields and purity, under mild reaction conditions, with full retention of the original chirality. The developed methodology allows simple solution-and solid-phase preparative techniques to generate complex peptides and peptide conjugates and serves as a platform for generating diverse medicinal chemistry building block libraries involving amino acid and heterocyclic moieties crucial for drug development.

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“…The utility of the anthracene construct system has been demonstrated by analysis after each step in the synthesis of the fibrinogen antagonist 7 [46] (Scheme 2). Using the construct 5, it possible to readily establish conversions during each chemical transformation.…”

Section: Uv Chromophore-containing Analytical Constructsmentioning

confidence: 99%