Synthesis of flavonoid analogues as scaffolds for natural product-based combinatorial libraries

Nianhuan Yao, Aiming Song, Xiaobing Wang, Seth Dixon, Kit Lam

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The design and synthesis of flavonoid analogues as combinatorial scaffolds is reported. Using commercially available materials, we synthesized chalcones with fluoro and carboxy groups. Nitration of these compounds generated highly functionalized flavonoid scaffolds with an o-fluoronitrobenzene template. Subsequent cyclizations of these chalcones resulted in the formation of several flavone and flavonone scaffolds. One of the flavonones was chosen as the scaffold to synthesize flavonoid derivatives on the solid phase. A series of flavonoid derivatives were obtained in high yields, which demonstrates that these highly functionalized scaffolds can be used in the synthesis of natural product-based combinatorial libraries for drug discovery.

Original languageEnglish (US)
Pages (from-to)668-676
Number of pages9
JournalJournal of Combinatorial Chemistry
Volume9
Issue number4
DOIs
StatePublished - Jul 2007

Fingerprint

Scaffold
Biological Products
Flavonoids
Scaffolds
Chalcones
Synthesis
Analogue
flavone
Derivatives
Nitration
Drug Discovery
Cyclization
Derivative
Template
Libraries
Series
Demonstrate

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

Cite this

Synthesis of flavonoid analogues as scaffolds for natural product-based combinatorial libraries. / Yao, Nianhuan; Song, Aiming; Wang, Xiaobing; Dixon, Seth; Lam, Kit.

In: Journal of Combinatorial Chemistry, Vol. 9, No. 4, 07.2007, p. 668-676.

Research output: Contribution to journalArticle

Yao, Nianhuan ; Song, Aiming ; Wang, Xiaobing ; Dixon, Seth ; Lam, Kit. / Synthesis of flavonoid analogues as scaffolds for natural product-based combinatorial libraries. In: Journal of Combinatorial Chemistry. 2007 ; Vol. 9, No. 4. pp. 668-676.
@article{b789c666de084672bd0524ee848b7097,
title = "Synthesis of flavonoid analogues as scaffolds for natural product-based combinatorial libraries",
abstract = "The design and synthesis of flavonoid analogues as combinatorial scaffolds is reported. Using commercially available materials, we synthesized chalcones with fluoro and carboxy groups. Nitration of these compounds generated highly functionalized flavonoid scaffolds with an o-fluoronitrobenzene template. Subsequent cyclizations of these chalcones resulted in the formation of several flavone and flavonone scaffolds. One of the flavonones was chosen as the scaffold to synthesize flavonoid derivatives on the solid phase. A series of flavonoid derivatives were obtained in high yields, which demonstrates that these highly functionalized scaffolds can be used in the synthesis of natural product-based combinatorial libraries for drug discovery.",
author = "Nianhuan Yao and Aiming Song and Xiaobing Wang and Seth Dixon and Kit Lam",
year = "2007",
month = "7",
doi = "10.1021/cc070009y",
language = "English (US)",
volume = "9",
pages = "668--676",
journal = "ACS Combinatorial Science",
issn = "2156-8952",
publisher = "American Chemical Society",
number = "4",

}

TY - JOUR

T1 - Synthesis of flavonoid analogues as scaffolds for natural product-based combinatorial libraries

AU - Yao, Nianhuan

AU - Song, Aiming

AU - Wang, Xiaobing

AU - Dixon, Seth

AU - Lam, Kit

PY - 2007/7

Y1 - 2007/7

N2 - The design and synthesis of flavonoid analogues as combinatorial scaffolds is reported. Using commercially available materials, we synthesized chalcones with fluoro and carboxy groups. Nitration of these compounds generated highly functionalized flavonoid scaffolds with an o-fluoronitrobenzene template. Subsequent cyclizations of these chalcones resulted in the formation of several flavone and flavonone scaffolds. One of the flavonones was chosen as the scaffold to synthesize flavonoid derivatives on the solid phase. A series of flavonoid derivatives were obtained in high yields, which demonstrates that these highly functionalized scaffolds can be used in the synthesis of natural product-based combinatorial libraries for drug discovery.

AB - The design and synthesis of flavonoid analogues as combinatorial scaffolds is reported. Using commercially available materials, we synthesized chalcones with fluoro and carboxy groups. Nitration of these compounds generated highly functionalized flavonoid scaffolds with an o-fluoronitrobenzene template. Subsequent cyclizations of these chalcones resulted in the formation of several flavone and flavonone scaffolds. One of the flavonones was chosen as the scaffold to synthesize flavonoid derivatives on the solid phase. A series of flavonoid derivatives were obtained in high yields, which demonstrates that these highly functionalized scaffolds can be used in the synthesis of natural product-based combinatorial libraries for drug discovery.

UR - http://www.scopus.com/inward/record.url?scp=34547232568&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34547232568&partnerID=8YFLogxK

U2 - 10.1021/cc070009y

DO - 10.1021/cc070009y

M3 - Article

VL - 9

SP - 668

EP - 676

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

SN - 2156-8952

IS - 4

ER -