Molecular diversity in cyclization of Ugi-products leading to the synthesis of 2,5-diketopiperazines: computational study

Molecular diversity in cyclization of Ugi-products leading to the synthesis of... & Morteza Shiri mshiri@alzahra.ac.ir & Majid M. Heravi mmh1331@yahoo.com Department of Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa 123 2120 V. Zadsirjan et al. Keywords Ugi reaction  Aroylacrylic acids  Base catalysis  Intramolecular Michael addition  2,5-Diketopiperazines  Molecular diversity  Density functional theory  Quantum theory of atoms in molecules  Polarized continuum model Antibacterial and antifungal activities Introduction The 2,5-Diketopiperazines (2,5-DKPs), cyclodipeptides can be prepared by the reaction of two a-amino acids. They are found in nature, and are usually created from the degradation of polypeptides found in beverages and processed food. They are present in various bacteria, fungi, mammals and the plant kingdom. For example, 2,5-DKPs abound in the structure of numerous natural products such as okaramine N [1], dysamide B [2], FR106969 [3] and citreoindole [4] (Fig. 1). Due to the ability of 2,5-diketopiperazines to bind to a number of receptors, they can be considered as attractive scaffolds in drug discovery. In these small heterocyclic molecules, it is possible to have a number of stereocenters to create diverse structures. Several reviews on the synthesis of natural products containing http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Molecular diversity in cyclization of Ugi-products leading to the synthesis of 2,5-diketopiperazines: computational study

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Publisher
Springer Netherlands
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2750-1
Publisher site
See Article on Publisher Site

Abstract

& Morteza Shiri mshiri@alzahra.ac.ir & Majid M. Heravi mmh1331@yahoo.com Department of Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa 123 2120 V. Zadsirjan et al. Keywords Ugi reaction  Aroylacrylic acids  Base catalysis  Intramolecular Michael addition  2,5-Diketopiperazines  Molecular diversity  Density functional theory  Quantum theory of atoms in molecules  Polarized continuum model Antibacterial and antifungal activities Introduction The 2,5-Diketopiperazines (2,5-DKPs), cyclodipeptides can be prepared by the reaction of two a-amino acids. They are found in nature, and are usually created from the degradation of polypeptides found in beverages and processed food. They are present in various bacteria, fungi, mammals and the plant kingdom. For example, 2,5-DKPs abound in the structure of numerous natural products such as okaramine N [1], dysamide B [2], FR106969 [3] and citreoindole [4] (Fig. 1). Due to the ability of 2,5-diketopiperazines to bind to a number of receptors, they can be considered as attractive scaffolds in drug discovery. In these small heterocyclic molecules, it is possible to have a number of stereocenters to create diverse structures. Several reviews on the synthesis of natural products containing

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 11, 2016

References

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