Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

doi:10.1002/chem.202000617

Review

. 2020 Sep 4;26(50):11349-11390.

doi: 10.1002/chem.202000617. Epub 2020 Jul 9.

Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Haibo Mei¹, Jianlin Han¹, Sarah White², Daniel J Graham², Kunisuke Izawa³, Tatsunori Sato³, Santos Fustero⁴, Nicholas A Meanwell⁵, Vadim A Soloshonok^{6

7}

Affiliations

¹ Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P.R. China.
² Oakwood Chemical, Inc., 730 Columbia Hwy. N, Estill, SC, 29918, USA.
³ Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
⁴ Departamento de Química Orgánica, Universidad de Valencia, 46100, Burjassot, Valencia, Spain.
⁵ Department of Small Molecule Drug Discovery, Bristol-Myers Squibb Research and Development, P.O. Box 4000, Princeton, NJ, 08543-4000, USA.
⁶ Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain.
⁷ IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013, Bilbao, Spain.

PMID: 32359086
DOI: 10.1002/chem.202000617

Review

Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Haibo Mei et al. Chemistry. 2020.

. 2020 Sep 4;26(50):11349-11390.

doi: 10.1002/chem.202000617. Epub 2020 Jul 9.

Authors

Haibo Mei¹, Jianlin Han¹, Sarah White², Daniel J Graham², Kunisuke Izawa³, Tatsunori Sato³, Santos Fustero⁴, Nicholas A Meanwell⁵, Vadim A Soloshonok^{6

7}

Affiliations

¹ Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P.R. China.
² Oakwood Chemical, Inc., 730 Columbia Hwy. N, Estill, SC, 29918, USA.
³ Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
⁴ Departamento de Química Orgánica, Universidad de Valencia, 46100, Burjassot, Valencia, Spain.
⁵ Department of Small Molecule Drug Discovery, Bristol-Myers Squibb Research and Development, P.O. Box 4000, Princeton, NJ, 08543-4000, USA.
⁶ Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain.
⁷ IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013, Bilbao, Spain.

PMID: 32359086
DOI: 10.1002/chem.202000617

Abstract

Structural analysis of modern pharmaceutical practices allows for the identification of two rapidly growing trends: the introduction of tailor-made amino acids and the exploitation of fluorinated motifs. Curiously, the former represents one of the most ubiquitous classes of naturally occurring compounds, whereas the latter is the most xenobiotic and comprised virtually entirely of man-made derivatives. Herein, 39 selected compounds, featuring both of these traits in the same molecule, are profiled. The total synthesis, source of the corresponding amino acids and fluorinated residues, and medicinal chemistry aspects and biological properties of the molecules are discussed.

Keywords: amino acids; cancer; drug discovery; fluorine substitution; fluorine-containing drugs.

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References

1. None
1. Asymmetric Synthesis and Application of alpha-Amino Acids, ACS Symposium Series #1009 (Eds.: V. A. Soloshonok, K. Izawa), Oxford University Press, Oxford, 2009;
1. M. A. T. Blaskovich, J. Med. Chem. 2016, 59, 10807-10836;
1. A. Henninot, J. C. Collins, J. M. Nuss, J. Med. Chem. 2018, 61, 1382-1414;
1. D. R. W. Hodgson, J. M. Sanderson, Chem. Soc. Rev. 2004, 33, 422-430;

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21761132021/National Natural Science Foundation of China

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[1] None

[2] None

[3] Asymmetric Synthesis and Application of alpha-Amino Acids, ACS Symposium Series #1009 (Eds.: V. A. Soloshonok, K. Izawa), Oxford University Press, Oxford, 2009;

[4] Asymmetric Synthesis and Application of alpha-Amino Acids, ACS Symposium Series #1009 (Eds.: V. A. Soloshonok, K. Izawa), Oxford University Press, Oxford, 2009;

[5] M. A. T. Blaskovich, J. Med. Chem. 2016, 59, 10807-10836;

[6] M. A. T. Blaskovich, J. Med. Chem. 2016, 59, 10807-10836;

[7] A. Henninot, J. C. Collins, J. M. Nuss, J. Med. Chem. 2018, 61, 1382-1414;

[8] A. Henninot, J. C. Collins, J. M. Nuss, J. Med. Chem. 2018, 61, 1382-1414;

[9] D. R. W. Hodgson, J. M. Sanderson, Chem. Soc. Rev. 2004, 33, 422-430;

[10] D. R. W. Hodgson, J. M. Sanderson, Chem. Soc. Rev. 2004, 33, 422-430;

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Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

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Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

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