Cyclic derivatives of 3,3-diphenylalanine (Dip) (II), novel α-amino acids for peptides of biological interest

Beylin, Vladimir G.; Chen, Huai G.; Dunbar, James B.; Goel, O. P.; Harter, William G.; Marlatt, M.; Topliss, John G.

doi:10.1016/s0040-4039(00)77463-6

Cited by 21 publications

(7 citation statements)

References 11 publications

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“…5 H -Dibenzo[ a , d ]cycloheptene-5-acetic Acid (5d). Compound 5d was synthesized via the method described in ref . Tacky yellow solid, yield = 70%.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P₃ Position

et al. 1997

J. Med. Chem.

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As part of an effort to prepare efficacious and orally bioavailable analogs of the previously reported thrombin inhibitors 1a, b, we have synthesized a series of compounds that utilize 3,3-disubstituted propionic acid derivatives as P3 ligands. By removing the N-terminal amino group, the general oral bioavailability of this class of compounds was enhanced without excessively increasing the lipophilicity of the compounds. The overall properties of the molecules could be drastically altered depending on the nature of the groups substituted onto the 3-position of the P3 propionic acid moiety. A number of the compounds exhibited good oral bioavailability in rats and dogs, and numerous compounds were efficacious in a rat FeCl3-induced model of arterial thrombosis. Compound 7, the 3,3-diphenylpropionic acid derivative, showed the best overall profile of in vivo and in vitro activity. Molecular modeling studies suggest that these compounds bind in the thrombin active site in a manner essentially identical to that previously reported for compound 1a.

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“…5 H -Dibenzo[ a , d ]cycloheptene-5-acetic Acid (5d). Compound 5d was synthesized via the method described in ref . Tacky yellow solid, yield = 70%.…”

Section: Methodsmentioning

confidence: 99%

“…The requisite 3,3-disubstituted propionic acids were obtained commercially ( 5a ), synthesized via literature methods ( 5b , 5c , 5d , 5f ), or synthesized via routes developed in our laboratories (Table ). The saturated bridged tricyclic 5e was synthesized by reduction of the corresponding unsaturated compound 5d .…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P₃ Position

et al. 1997

J. Med. Chem.

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“…Reaction of the chiral potassium enolate of 31 with trisyl azide gave, after hydrolysis of the chiral auxiliary, product 32. 41,42 This reaction sequence was used for the synthesis of many unusual amino acids including diphthamide, 43 phosphotyrosine, 44 -methylphenylalanine, 45 and ethynyltyrosine. 46 In 1998, Ahn and co-workers showed that this azidation reaction could be performed on chiral sultam auxiliaries.…”

Section: Electrophilic Azidation Using Evans' Chiral Auxiliarymentioning

confidence: 99%

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

Moreira¹,

Noden²,

Taylor³

2020

Synthesis

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Azido acids are important synthons for the synthesis of complex peptides. As a protecting group, the azide moiety is atom-efficient, easy to install and can be reduced in the presence of many other protecting groups, making it ideal for the synthesis of branched and/or cyclic peptides. α-Azido acids are less bulky than urethane-protected counterparts and react more effectively in coupling reactions of difficult-to-form peptide and ester bonds. Azido acids can also be used to form azoles on complex intermediates. This review covers the synthesis of azido acids and their application to the total synthesis of complex peptide natural products.1 Introduction2 Synthesis of α-Azido Acids2.1 From α-Amino Acids or Esters2.2 Via α-Substitution2.3 Via Electrophilic Azidation2.4 Via Condensation of N-2-Azidoacetyl-4-Phenylthiazolidin- 2-Thi one Enolates with Aldehydes and Acetals2.5 Synthesis of α,β-Unsaturated α-Azido Acids and Esters3 Synthesis of β-Azido Acids3.1 Preparation of Azidoalanine and 3-Azido-2-aminobutanoic Acids3.2 General Approaches to Preparing β-Azido Acids Other Than Azi doalanine and AABA4 Azido Acids in Total Synthesis4.1 α-Azido Acids4.2 β-Azido Acids and Azido Acids Containing an Azide on the Side Chain5 Conclusions

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“…After removal of the chiral auxiliary with LiOH/H202, the azido acid was hydrogenated over Pd/C (Fig. 19) (Evans et al, 1989(Evans et al, , 1990aChen et al, 1992;Beylin et al, 1993;Lundquist and Dix, 1998).…”

Section: Electrophilic Arninationmentioning

confidence: 99%

How to build optically active?-amino acids

Calmès

Daunis

1999

Amino Acids

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Cyclic derivatives of 3,3-diphenylalanine (Dip) (II), novel α-amino acids for peptides of biological interest

Cited by 21 publications

References 11 publications

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P₃ Position

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P₃ Position

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

How to build optically active?-amino acids

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Cyclic derivatives of 3,3-diphenylalanine (Dip) (II), novel α-amino acids for peptides of biological interest

Cited by 21 publications

References 11 publications

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P3 Position

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P3 Position

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

How to build optically active?-amino acids

Contact Info

Product

Resources

About

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P₃ Position

Synthesis of a Series of Potent and Orally Bioavailable Thrombin Inhibitors That Utilize 3,3-Disubstituted Propionic Acid Derivatives in the P₃ Position