Construction of a family of biphenyl combinatorial libraries: Structure-activity studies utilizing libraries of mixtures

Neustadt, Bernard R.; Smith, Elizabeth M.; Lindo, Neil; Nechuta, Terry; Bronnenkant, Alan; Wu, Arthur S. H.; Armstrong, Lydia; Kumar, Chandra

doi:10.1016/s0960-894x(98)00433-8

Cited by 25 publications

(18 citation statements)

References 10 publications

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“…Within this context, the synthesis of so-called 'privileged structures' 1 is of considerable interest, because such structures combine drug-like properties with the ability to address various biological targets, depending on their substitution pattern. Examples include the synthesis of benzodiazepines, 2 benzopyrans, 3 biphenyls, 4 phenyl piperazines, 5 and spiro-piperidines. 6 In the course of our ongoing efforts directed towards the synthesis of novel scaffolds for medicinal chemistry purposes, we were interested in the diversification of the 1H-pyrazolo [3,4-b]pyridine scaffold, another example of a 'privileged structure'.…”

Section: Introductionmentioning

confidence: 99%

Use of 3-(trifluoromethyl)-1H-pyrazolo-[3,4-b]pyridine as a versatile building block

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Use of 3-(trifluoromethyl)-1H-pyrazolo-[3,4-b]pyridine as a versatile building block

et al. 2015

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“…Abc 2K is a derivative of the nanometer-long amino acid 4’-amino-[1,1’-biphenyl]-4-carboxylic acid, with two propyloxyammonium side chains for water solubility. Abc 2K is linear (180°), m -Abc 2K creates a 120° angle, and o -Abc 2K creates a 60° angle 7. In this paper, we report the syntheses of Fmoc-protected derivatives Fmoc- m -Abc 2K(Boc) -OH ( 1a ) and Fmoc- o -Abc 2K(Boc) -OH ( 1b ) and the application of these derivatives to the synthesis of nanometer-scale water-soluble macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Nanometer-Scale Water-Soluble Macrocycles from Nanometer-Sized Amino Acids

Gothard

Nowick

2009

J. Org. Chem.

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This paper introduces the unnatural amino acids m-Abc2K and o-Abc2K as nanometersized building blocks for the creation of water-soluble macrocycles with well-defined shapes. m-Abc2K and o-Abc2K are homologues of the nanometer-sized amino acid Abc2K, which we recently introduced for the synthesis of water-soluble molecular rods of precise length. [J. Am. Chem. Soc. 2007, 129, 7272]. Abc2K is linear (180°), m-Abc2K creates a 120° angle, and o-Abc2K creates a 60° angle. m-Abc2K and o-Abc2K are derivatives of 3’-amino-[1,1’-biphenyl]-4-carboxylic acid and 2’-amino-[1,1’-biphenyl]-4-carboxylic acid, with two propyloxyammonium side chains for water solubility. m-Abc2K and o-Abc2K are prepared as Fmoc-protected derivatives Fmoc-m-Abc2K(Boc)-OH (1a) and Fmoc-o-Abc2K(Boc)-OH (1b). These derivatives can be used alone or in conjunction with Fmoc-Abc2K(Boc)-OH (1c) as ordinary amino acids in Fmoc-based solid-phase peptide synthesis. Building blocks 1a–c were used to synthesize macrocyclic “triangles” 9a–c, “parallelograms” 10a,b, and hexagonal “rings” 11a–d. The macrocycles range from a trimer to a dodecamer, with ring sizes from 24 to 114 atoms, and are 1–4 nm in size. Molecular modeling studies suggest that all the macrocycles except 10b should have well-defined triangle, parallelogram, and ring shapes if all of the amide linkages are trans and the ortho-alkoxy substituents are intramolecularly hydrogen bonded to the amide NH groups. The macrocycles have good water solubility and are readily characterized by standard analytical techniques, such as RP-HPLC, ESI-MS, and NMR spectroscopy. 1H and 13C NMR studies suggest that the macrocycles adopt conformations with all trans-amide linkages in CD3OD, that the “triangles” and “parallelograms” maintain these conformations in D2O, and that the “rings” collapse to form conformations with cis-amide linkages in D2O.

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“…10 Moreover, the presence of a carboxylic function, mimicking the aspartic acid residue in the original binding motif, is a fundamental feature to create a ionic interaction with the metal cation in the receptor active site. 11 We envisaged 3-bromo-5,6-dihydropyridin-2-one 12 as a scaffold that could be converted into a potential a v b 3 integrin ligand introducing a carboxylic acid and a guanidinic appendage (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of enantiomerically pure αvβ3 integrin ligands based on a 5,6-dihydropyridin-2-one scaffold

Benfatti

Cardillo

Fabbroni

et al. 2006

Tetrahedron: Asymmetry

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Construction of a family of biphenyl combinatorial libraries: Structure-activity studies utilizing libraries of mixtures

Cited by 25 publications

References 10 publications

Use of 3-(trifluoromethyl)-1H-pyrazolo-[3,4-b]pyridine as a versatile building block

Use of 3-(trifluoromethyl)-1H-pyrazolo-[3,4-b]pyridine as a versatile building block

Nanometer-Scale Water-Soluble Macrocycles from Nanometer-Sized Amino Acids

Synthesis of enantiomerically pure αvβ3 integrin ligands based on a 5,6-dihydropyridin-2-one scaffold

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