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Sterically Constrained and Encumbered : An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core. / Golubev, Pavel; Krasavin, Mikhail.

In: European Journal of Organic Chemistry, Vol. 2017, No. 13, 03.04.2017, p. 1740-1744.

Research output: Contribution to journal › Article › peer-review

Harvard

Golubev, P & Krasavin, M 2017, 'Sterically Constrained and Encumbered: An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core', European Journal of Organic Chemistry, vol. 2017, no. 13, pp. 1740-1744. https://doi.org/10.1002/ejoc.201700152

APA

Golubev, P., & Krasavin, M. (2017). Sterically Constrained and Encumbered: An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core. European Journal of Organic Chemistry, 2017(13), 1740-1744. https://doi.org/10.1002/ejoc.201700152

Vancouver

Golubev P, Krasavin M. Sterically Constrained and Encumbered: An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core. European Journal of Organic Chemistry. 2017 Apr 3;2017(13):1740-1744. https://doi.org/10.1002/ejoc.201700152

Author

Golubev, Pavel ; Krasavin, Mikhail. / Sterically Constrained and Encumbered : An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 13. pp. 1740-1744.

BibTeX

@article{c5abec7d70f24e1385ac537dc7a958a4,
title = "Sterically Constrained and Encumbered: An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core",
abstract = "The combination of two privileged motifs, that is, indoline and the constrained peptidomimetic piperazine-2,5-dione, within one tricyclic structure resulted in a scaffold that is abundant in nature but surprisingly scarce in the domain of synthetic bioactive molecules. Utilizing the power of the isocyanide-based Joulli{\'e}–Ugi reaction followed by postcondensation cyclization, we synthesized such compounds with four elements of diversity in good yields from readily available precursors. The compounds are constrained peptidomimetics distinctly encumbered in a steric sense and have a pronounced three-dimensional character, which is a highly desirable feature in modern drug design.",
keywords = "Molecular diversity, Multicomponent reactions, Nitrogen heterocycles, Peptidomimetics, Polycycles",
author = "Pavel Golubev and Mikhail Krasavin",
year = "2017",
month = apr,
day = "3",
doi = "10.1002/ejoc.201700152",
language = "English",
volume = "2017",
pages = "1740--1744",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "13",

}

RIS

TY - JOUR

T1 - Sterically Constrained and Encumbered

T2 - An Approach to the Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core

AU - Golubev, Pavel

AU - Krasavin, Mikhail

PY - 2017/4/3

Y1 - 2017/4/3

N2 - The combination of two privileged motifs, that is, indoline and the constrained peptidomimetic piperazine-2,5-dione, within one tricyclic structure resulted in a scaffold that is abundant in nature but surprisingly scarce in the domain of synthetic bioactive molecules. Utilizing the power of the isocyanide-based Joullié–Ugi reaction followed by postcondensation cyclization, we synthesized such compounds with four elements of diversity in good yields from readily available precursors. The compounds are constrained peptidomimetics distinctly encumbered in a steric sense and have a pronounced three-dimensional character, which is a highly desirable feature in modern drug design.

AB - The combination of two privileged motifs, that is, indoline and the constrained peptidomimetic piperazine-2,5-dione, within one tricyclic structure resulted in a scaffold that is abundant in nature but surprisingly scarce in the domain of synthetic bioactive molecules. Utilizing the power of the isocyanide-based Joullié–Ugi reaction followed by postcondensation cyclization, we synthesized such compounds with four elements of diversity in good yields from readily available precursors. The compounds are constrained peptidomimetics distinctly encumbered in a steric sense and have a pronounced three-dimensional character, which is a highly desirable feature in modern drug design.

KW - Molecular diversity

KW - Multicomponent reactions

KW - Nitrogen heterocycles

KW - Peptidomimetics

KW - Polycycles

UR - http://www.scopus.com/inward/record.url?scp=85017125473&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201700152

DO - 10.1002/ejoc.201700152

M3 - Article

AN - SCOPUS:85017125473

VL - 2017

SP - 1740

EP - 1744

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 13

ER -

ID: 34634156