Synthesis of novel 17-(5′-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro

被引：9

作者：

Schneider, Gyula ^{[1
]}

Goerbe, Tunas ^{[1
]}

Mernyak, Erzsebet ^{[1
]}

Woelfing, Janos ^{[1
]}

Holczbauer, Tamas ^{[2
]}

Czugler, Matyas ^{[2
]}

Sohar, Pal ^{[3
]}

Minorics, Renata ^{[4
]}

Zupko, Istvan ^{[4
]}

机构：

[1] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary

[2] Hungarian Acad Sci, Res Ctr Nat Sci, Inst Organ Chem, H-1025 Budapest, Hungary

[3] Eotvos Lorand Univ, Inst Chem, H-1117 Budapest, Hungary

[4] Univ Szeged, Dept Pharmacodynam & Biopharm, H-6720 Szeged, Hungary

来源：

STEROIDS | 2015年 / 98卷

基金：

匈牙利科学研究基金会;

关键词：

1,3-Dipolar cycloaddition; Iodotriazoles; Cytotoxic activity; X-ray analysis; ONE-POT REACTION; TERMINAL ALKYNES; STEROIDAL INHIBITORS; EFFICIENT SYNTHESIS; CLICK CHEMISTRY; ORGANIC AZIDES; DERIVATIVES; AGENTS; 1,2,3-TRIAZOLES; P450(17-ALPHA);

D O I：

10.1016/j.steroids.2015.02.018

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17 alpha- and 17 beta-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the classical CuAAC process was replaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-f and 11a-f) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-f and 11a-f), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by Cu! and ICI as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MDA-MB-231, MDA-MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring. (C) 2015 Elsevier Inc. All rights reserved.

引用

页码：153 / 165

页数：13

共 5 条

[1] Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro
Frank, Eva
Molnar, Judit
Zupko, Istvan
Kadar, Zalan
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STEROIDS, 2011, 76 (10-11) : 1141 - 1148
[2] Synthesis of novel 17-triazolyl-androst-5-en-3-ol epimers via Cu(I)-catalyzed azide-alkyne cycloaddition and their inhibitory effect on 17α-hydroxylase/C17,20-lyase
Kiss, Anita
Herman, Bianka Edina
Gorbe, Tamas
Mernyak, Erzsebet
Molnar, Barnabas
Wolfling, Janos
Szecsi, Mihaly
Schneider, Gyula
STEROIDS, 2018, 135 : 79 - 91
[3] Synthesis of pyrrol-pyridazyl-triazolyl-pyridines via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction
Yang, Wu
Fu, Leixia
Wu, Jie
Song, Chuanjun
SYNTHETIC COMMUNICATIONS, 2016, 46 (13) : 1118 - 1123
[4] A Peerless Aproach: Organophotoredox/Cu(I) Catalyzed, Regioselective, Visible Light Facilitated, Click Synthesis of 1,2,3-Triazoles via Azide-Alkyne [3+2] Cycloaddition
Mishra, Anu
Rai, Pratibha
Srivastava, Madhulika
Tripathi, Bhartendu Pati
Yadav, Snehlata
Singh, Jaya
Singh, Jagdamba
CATALYSIS LETTERS, 2017, 147 (10) : 2600 - 2611
[5] Application of PEG400 in the one-pot synthesis of 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines via SNAr and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition and preliminary evaluation of their anti-tumour activity
Rodrigues, Juliana M.
Calhelha, Ricardo C.
Ferreira, Isabel C. F. R.
Queiroz, Maria-Joao R. P.
TETRAHEDRON LETTERS, 2020, 61 (22)

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