Xanthenones: calixarenes-catalyzed syntheses, anticancer activity and QSAR studies

被引：33

作者：

da Silva, Daniel Leite ^{[1
]}

Terra, Bruna Silva ^{[1
]}

Lage, Mateus Ribeiro ^{[2
]}

Tasca Gois Ruiz, Ana Lucia ^{[3
]}

da Silva, Cameron Capeletti ^{[4
]}

de Carvalho, Joao Ernesto ^{[3
]}

de Mesquita Carneiro, Jose Walkimar ^{[2
]}

Martins, Felipe Terra ^{[4
]}

Fernades, Sergio Antonio ^{[5
]}

de Fatima, Angelo ^{[1
]}

机构：

[1] Univ Fed Minas Gerais, Dept Quim, Inst Ciencias Exatas, GEQOB, BR-31270901 Belo Horizonte, MG, Brazil

[2] Univ Fed Fluminense, Inst Quim, BR-24220900 Niteroi, RJ, Brazil

[3] Univ Estadual Campinas, Ctr Pluridisciplinar Pesquisas Quim Biol & Agr CP, BR-13081970 Paulinia, SP, Brazil

[4] Univ Fed Goias, Inst Quim, BR-74690900 Goiania, Go, Brazil

[5] Univ Fed Vicosa, Dept Quim, GQSB, BR-36570900 Vicosa, MG, Brazil

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 11期

关键词：

P-SULFONIC ACID; ORGANOCATALYSTS; EFFICIENT;

D O I：

10.1039/c4ob02611j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method is proposed for obtaining tetrahydrobenzo[a]xanthene-11-ones and tetrahydro-[1,3]-dioxolo[4,5-b]xanthen-9-ones. The method is based on the use of p-sulfonic acid calix[n]arenes as catalysts under solvent-free conditions. The antiproliferative activity of fifty-nine xanthenones against six human cancer cells was studied. The capacity of all compounds to inhibit cancer cell growth was dependent on the histological origin of the cells. QSAR studies indicate that among compounds derived from beta-naphthol the most efficient compounds against glioma (U251) and renal (NCI-H460) cancer cells are those having higher hydrogen bonding donor ability.

引用

页码：3280 / 3287

页数：8

共 37 条

[1] [Anonymous], SPART 06
[2] CHEMICAL ASPECTS OF SANTALIN AS A HISTOLOGICAL STAIN
BANERJEE, A
MUKHERJEE, AK
[J]. STAIN TECHNOLOGY, 1981, 56 (02): : 83 - 85
[3] Enlarging the size of calix[4]arene-crowns-6 to improve Cs+/K+ selectivity:: a theoretical and experimental study
Casnati, A
Della Ca', N
Sansone, F
Ugozzoli, F
Ungaro, R
[J]. TETRAHEDRON, 2004, 60 (36) : 7869 - 7876
[4] Timeline - Chemotherapy and the war on cancer
Chabner, BA
Roberts, TG
[J]. NATURE REVIEWS CANCER, 2005, 5 (01) : 65 - 72
[5] Free radical scavenging and antiproliferative properties of Biginelli adducts
da Silva, Daniel L.
Reis, Fabiano S.
Muniz, Dandara R.
Ruiz, Ana Lucia T. G.
de Carvalho, Joao E.
Sabino, Adao A.
Modolo, Luzia V.
de Fatima, Angelo
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (08) : 2645 - 2650
[6] p-Sulfonic acid calixarenes as efficient and reusable organocatalysts for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/-thiones
da Silva, Daniel L.
Fernandes, Sergio A.
Sabino, Adao A.
de Fatima, Angelo
[J]. TETRAHEDRON LETTERS, 2011, 52 (48) : 6328 - 6330
[7] de Fatima Angelo, 2009, Curr Drug Discov Technol, V6, P151
[8] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL
DEWAR, MJS
ZOEBISCH, EG
HEALY, EF
STEWART, JJP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3902 - 3909
[9] p-Sulfonic acid calix[n]arenes as homogeneous and recyclable organocatalysts for esterification reactions
Fernandes, Sergio Antonio
Natalino, Ricardo
Rodrigues, Poliana Aparecida
Jose da Silva, Gazolla Marcio
Jham, Gulab Newandram
[J]. TETRAHEDRON LETTERS, 2012, 53 (13) : 1630 - 1633
[10] CALIXARENES .4. THE SYNTHESIS, CHARACTERIZATION, AND PROPERTIES OF THE CALIXARENES FROM PARA-TERT-BUTYLPHENOL
GUTSCHE, CD
DHAWAN, B
NO, KH
MUTHUKRISHNAN, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) : 3782 - 3792

← 1 2 3 4 →