Cyclic tailor-made amino acids in the design of modern pharmaceuticals

被引：47

作者：

Liu, Jiang ^{[1
]}

Han, Jianlin ^{[1
]}

Izawa, Kunisuke ^{[2
]}

Sato, Tatsunori ^{[2
]}

White, Sarah ^{[3
]}

Meanwell, Nicholas A. ^{[4
]}

Soloshonok, Vadim A. ^{[5
,6
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Nanjing 210037, Jiangsu, Peoples R China

[2] Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan

[3] Oakwood Chem Inc, 730 Columbia Hwy N, Estill, SC 29918 USA

[4] Bristol Myers Squibb Res & Early Dev, Dept Small Mol Drug Discovery, POB 4000, Princeton, NJ 08543 USA

[5] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

[6] Basque Fdn Sci, IKERBASQUE, Maria Diaz Haro 3,Plaza Bizkaia, Bilbao 48013, Spain

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2020年 / 208卷

基金：

中国国家自然科学基金;

关键词：

Cyclic amino acids; Tailor-made amino acids; Drug design; Pharmaceuticals and medicinal formulations; DIPEPTIDYL-PEPTIDASE-IV; MICHAEL ADDITION-REACTIONS; GLUCAGON-LIKE PEPTIDE-1; OREXIN RECEPTOR ANTAGONISTS; SCALE ASYMMETRIC-SYNTHESIS; HCV PROTEASE INHIBITOR; POLY(ADP-RIBOSE) POLYMERASE PARP; DIELS-ALDER REACTION; SELF-DISPROPORTIONATION; NI(II) COMPLEXES;

D O I：

10.1016/j.ejmech.2020.112736

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Tailor-made AAs are indispensable components of modern medicinal chemistry and are becoming increasingly prominent in new drugs. In fact, about 30% of small-molecule pharmaceuticals contain residues of tailor-made AAs or structurally related diamines and amino-alcohols. Cyclic tailor-made AAs present a particular value to rational structural design by virtue of their local conformational constraints and are widely used in lead optimization programs. The present review article highlights 34 compounds, all of which are derived from cyclic AAs, representing recently-approved, small-molecule pharmaceuticals as well as promising drug candidates currently in various phases of clinical study. For each compound, the discussion includes the discovery, therapeutic profile and optimized synthesis, with a focus on the preparation of cyclic tailor-made AA as the principal structural feature. The present review article is intended to serve as a reference source for organic, medicinal and process chemists along with other professionals working in the fields of drug design and pharmaceutical discovery. (c) 2020 Elsevier Masson SAS. All rights reserved.

引用

页数：74

共 344 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
AbdelMagid, AF
Carson, KG
Harris, BD
Maryanoff, CA
Shah, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
[2] Abele S., 2015, European Patent Application, Patent No. [EP 2883876A1, 2883876]
[3] DIASTEREOSELECTIVE AZA-DIELS-ALDER REACTION - USE OF 1-PHENYLETHYLIMINE OF ALKYL GLYOXYLATE FOR SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS
ABRAHAM, H
STELLA, L
[J]. TETRAHEDRON, 1992, 48 (44) : 9707 - 9718
[4] Inhibition of dipeptidyl peptidase-4 reduces glycemia, sustains insulin levels, and reduces glucagon levels in type 2 diabetes
Ahrén, B
Landin-Olsson, M
Jansson, PA
Svensson, M
Holmes, D
Schweizer, A
[J]. JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 2004, 89 (05) : 2078 - 2084
[5] Allian A., 2017, US pat, Patent No. [WO2017066775, 2017066775, WO2017066775A1]
[6] Alvaro G., 2009, Pyridine Derivatives Used to Treat Orexin Related Disorders, Patent No. [WO2009124956A1., 2009124956]
[7] Alvaro G., 2007, PCT Int. Appl., Patent No. [WO 2007042239, 2007042239]
[8] Alvaro G., 2010, p6R, Patent No. [WO 2010/063663A1, 2010063663]
[9] Pharmacokinetics of novel dipeptide ester prodrugs of acyclovir after oral administration: Intestinal absorption and liver metabolism
Anand, BS
Katragadda, S
Mitra, AK
[J]. JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2004, 311 (02) : 659 - 667
[10] Orexin Receptor Antagonists: Historical Perspectives and Future Opportunities
Andrews, Stephen P.
Aves, Sarah J.
Christopher, John A.
Nonoo, Rebecca
[J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (29) : 3438 - 3469

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