Evaluation of the pharmacophoric motif of the caged Garcinia xanthones

Oraphin Chantarasriwong; Woo Cheal Cho; Ayse Batova; Warinthorn Chavasiri; Curtis Moore; Arnold L. Rheingold; Emmanuel A. Theodorakis

doi:10.1039/b913496d

Evaluation of the pharmacophoric motif of the caged Garcinia xanthones

Oraphin Chantarasriwong, Woo Cheal Cho, Ayse Batova, Warinthorn Chavasiri, Curtis Moore, Arnold L. Rheingold, Emmanuel A. Theodorakis

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

54 Scopus citations

Abstract

The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garcinia xanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols that, together with a Claisen/Diels-Alder reaction cascade, provides rapid and efficient access to various caged analogues. Evaluation of the growth inhibitory activity of these compounds leads to the conclusion that the intact ABC ring system containing the C-ring caged structure is essential to the bioactivity. Studies with cluvenone (7) also showed that these compounds induce apoptosis and exhibit significant cytotoxicity in multidrug-resistant leukemia cells. As such, the caged Garcinia xanthone motif represents a new and potent pharmacophore.

Original language	English (US)
Pages (from-to)	4886-4894
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	7
Issue number	23
DOIs	https://doi.org/10.1039/b913496d
State	Published - 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/b913496d

Cite this

@article{ff88f7f22f024e7fac6a8ac4590c401c,

title = "Evaluation of the pharmacophoric motif of the caged Garcinia xanthones",

abstract = "The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garcinia xanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols that, together with a Claisen/Diels-Alder reaction cascade, provides rapid and efficient access to various caged analogues. Evaluation of the growth inhibitory activity of these compounds leads to the conclusion that the intact ABC ring system containing the C-ring caged structure is essential to the bioactivity. Studies with cluvenone (7) also showed that these compounds induce apoptosis and exhibit significant cytotoxicity in multidrug-resistant leukemia cells. As such, the caged Garcinia xanthone motif represents a new and potent pharmacophore.",

author = "Oraphin Chantarasriwong and Cho, {Woo Cheal} and Ayse Batova and Warinthorn Chavasiri and Curtis Moore and Rheingold, {Arnold L.} and Theodorakis, {Emmanuel A.}",

year = "2009",

doi = "10.1039/b913496d",

language = "English (US)",

volume = "7",

pages = "4886--4894",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "23",

}

TY - JOUR

T1 - Evaluation of the pharmacophoric motif of the caged Garcinia xanthones

AU - Chantarasriwong, Oraphin

AU - Cho, Woo Cheal

AU - Batova, Ayse

AU - Chavasiri, Warinthorn

AU - Moore, Curtis

AU - Rheingold, Arnold L.

AU - Theodorakis, Emmanuel A.

PY - 2009

Y1 - 2009

N2 - The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garcinia xanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols that, together with a Claisen/Diels-Alder reaction cascade, provides rapid and efficient access to various caged analogues. Evaluation of the growth inhibitory activity of these compounds leads to the conclusion that the intact ABC ring system containing the C-ring caged structure is essential to the bioactivity. Studies with cluvenone (7) also showed that these compounds induce apoptosis and exhibit significant cytotoxicity in multidrug-resistant leukemia cells. As such, the caged Garcinia xanthone motif represents a new and potent pharmacophore.

AB - The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garcinia xanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols that, together with a Claisen/Diels-Alder reaction cascade, provides rapid and efficient access to various caged analogues. Evaluation of the growth inhibitory activity of these compounds leads to the conclusion that the intact ABC ring system containing the C-ring caged structure is essential to the bioactivity. Studies with cluvenone (7) also showed that these compounds induce apoptosis and exhibit significant cytotoxicity in multidrug-resistant leukemia cells. As such, the caged Garcinia xanthone motif represents a new and potent pharmacophore.

UR - http://www.scopus.com/inward/record.url?scp=72449141611&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=72449141611&partnerID=8YFLogxK

U2 - 10.1039/b913496d

DO - 10.1039/b913496d

M3 - Article

C2 - 19907779

AN - SCOPUS:72449141611

SN - 1477-0520

VL - 7

SP - 4886

EP - 4894

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 23

ER -

Evaluation of the pharmacophoric motif of the caged Garcinia xanthones

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this