Synthesis and cytotoxicity evaluation of highly functionalized pyranochromenes and pyranopyrans

被引：48

作者：

Emmadi, Narender Reddy ^{[1
]}

Atmakur, Krishnaiah ^{[1
]}

Chityal, Ganesh Kumar ^{[2
]}

Pombala, Sujitha ^{[2
]}

Nanubolu, Jagadeesh Babu ^{[3
]}

机构：

[1] Indian Inst Chem Technol, Crop Protect Chem Div, Hyderabad 500607, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Biol Chem Lab, Hyderabad 500607, Andhra Pradesh, India

[3] Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500607, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 23期

关键词：

4-Hydroxy chromenes; Ethyltrifluoro acetoacetate; Aromatic aldehydes; Tetrahydropyrano[3,2-c]chromenes; Dihydropyrano[3,2-b]pyrans; DERIVATIVES; 2-AMINO-2-CHROMENES; CHEMISTRY; CATALYST;

D O I：

10.1016/j.bmcl.2012.09.018

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of fluorinated tetrahydropyrano[3,2-c]chromenes and dihydropyrano[3,2-b]pyran derivatives have been synthesized and their in vitro cytotoxic activities have been determined in cervical cancer cell line (HeLa), human breast adenocarcinoma cell line (MDA-MB-231 and MCF-7) and human alveolar adenocarcinoma cell line (A549). Compounds 4g, 4k, 4p showed a very potent activity against MDA-MB-231, and 4c, 4p showed promising activity against MCF-7, while compounds 4c, 4g, 4p showed moderate activity against HeLa. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：7261 / 7264

页数：4

共 37 条

[1] Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media [J].

Abdolmohammadi, Shahrzad ;

Balalaie, Saeed .

TETRAHEDRON LETTERS, 2007, 48 (18) :3299-3303

[2] DABCO-catalyzed efficient synthesis of naphthopyran derivatives via one-pot three-component condensation reaction at room temperature [J].

Balalaie, Saeed ;

Ramezanpour, Sorour ;

Bararjanian, Morteza ;

Gross, Juergen H. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (07) :1078-1089

[3] Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media [J].

Ballini, R ;

Bosica, G ;

Conforti, ML ;

Maggi, R ;

Mazzacani, A ;

Righi, P ;

Sartori, G .

TETRAHEDRON, 2001, 57 (07) :1395-1398

[4]

BLOXHAM J, 1994, HETEROCYCLES, V38, P399

[5] Fluorinated heterocyclic compounds.: An effective strategy for the synthesis of fluorinated Z-oximes of 3-perfluoroalkyl-6-phenyl-2H-1,2,4-triazin5-ones via a ring-enlargement reaction of 3-benzoyl-5-perfluoroalkyl-1,2,4-oxadiazoles and hydrazine [J].

Buscemi, S ;

Pace, A ;

Piccionello, AP ;

Macaluso, G ;

Vivona, N ;

Spinelli, D ;

Giorgi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3288-3291

[6] RESOLUTION AND COMPARATIVE ANTI-HIV EVALUATION OF THE ENANTIOMERS OF CALANOLIDE-A AND CALANOLIDE-B [J].

CARDELLINA, JH ;

BOKESCH, HR ;

MCKEE, TC ;

BOYD, MR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (09) :1011-1014

[7]

Cravotto G, 2003, SYNTHESIS-STUTTGART, P1286

[8] The chemistry of coumarin derivatives.: XII.: A library of pyranocoumarin derivatives via a one-pot three-component hetero Diels-Alder reaction [J].

Cravotto, G ;

Nano, GM ;

Palmisano, G ;

Pilati, T ;

Tagliapietra, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (04) :965-971

[9]

Cravotto G, 2001, SYNTHESIS-STUTTGART, P49

[10] N,N′-Dioxide-nickel(II) complex catalyzed asymmetric Michael addition of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters [J].

Dong, Zhenhua ;

Feng, Juhua ;

Cao, Weidi ;

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

TETRAHEDRON LETTERS, 2011, 52 (27) :3433-3436

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