Palladium-catalyzed cross-coupling reactions of estrone

被引：0

作者：

Langer, Peter ^{[1
]}

机构：

[1] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany

来源：

STEROIDS | 2025年 / 219卷

关键词：

Cross-coupling; Estrone; Palladium; Regioselectivity; Steroids; IN-VITRO; 13-ALPHA-ESTRONE DERIVATIVES; STRUCTURAL MODIFICATIONS; STEROIDS;

D O I：

10.1016/j.steroids.2025.109627

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：

Palladium catalyzed cross-coupling reactions of estrone allow for the synthesis of a variety of substituted steroids which are not readily available by other methods. Products include various alkynylated and arylated estrones and 13 alpha-estrones, 16-arylmethylidene-3-O-methylestrones and 16-alkynylmethylidene-3-O-methylestrones. Reactions usually proceed with excellent chemo- and regioselectivity and exhibit a broad functional group tolerance. In several cases, the estrone derivatives prepared proved to be active and selective inhibitors of alkaline phosphatases or exhibited considerable antiproliferative activities.

引用

页数：10

共 41 条

[1] Synthesis of leprapinic acid, calycine and analogues by sequential [3+2]cyclization/suzuki/lactonization" reactions [J].

Ahmed, Z ;

Albrecht, U ;

Langer, P .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (16) :3469-3474

[2] Investigation of the Antineoplastic Effects of 2-(4-Chlorophenyl)-13α-Estrone Sulfamate against the HPV16-Positive Human Invasive Cervical Carcinoma Cell Line SiHa [J].

Ali, Hazhmat ;

Traj, Peter ;

Szebeni, Gabor J. ;

Gemes, Nikolett ;

Resch, Vivien ;

Paragi, Gabor ;

Mernyak, Erzsebet ;

Minorics, Renata ;

Zupko, Istvan .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (07)

[3] Impact of estradiol structural modifications (18-methyl and/or 17-hydroxy inversion of configuration) on the in vitro and in vivo estrogenic activity [J].

Ayan, Diana ;

Roy, Jenny ;

Maltais, Rene ;

Poirier, Donald .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2011, 127 (3-5) :324-330

[4] Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors [J].

Bacsa, Ildiko ;

Jojart, Rebeka ;

Wolfling, Janos ;

Schneider, Gyula ;

Herman, Bianka Edina ;

Szecsi, Mihaly ;

Mernyak, Erzsebet .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :1303-1309

[5] Synthesis of A-ring halogenated 13α-estrone derivatives as potential 17β-HSD1 inhibitors [J].

Bacsa, Ildiko ;

Jojart, Rebeka ;

Schneider, Gyula ;

Woelfling, Janos ;

Maroti, Peter ;

Herman, Bianka Edina ;

Szecsi, Mihaly ;

Mernyak, Erzsebet .

STEROIDS, 2015, 104 :230-236

[6] Synthesis and in vitro investigation of potential antiproliferative monosaccharide-D-secoestrone bioconjugates [J].

Bodnar, Brigitta ;

Mernyak, Erzsebet ;

Szabo, Johanna ;

Woelfling, Janos ;

Schneider, Gyula ;

Zupko, Istvan ;

Kupihar, Zoltan ;

Kovacs, Lajos .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (09) :1938-1942

[7] Synthesis of Estrone Heterodimers and Evaluation of Their In Vitro Antiproliferative Activity [J].

Bozsity, Noemi ;

Nagy, Viktoria ;

Szabo, Johanna ;

Palhazi, Balazs ;

Kele, Zoltan ;

Resch, Vivien ;

Paragi, Gabor ;

Zupko, Istvan ;

Minorics, Renata ;

Mernyak, Erzsebet .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (08)

[8] Benzo-Annulated Steroids: Synthesis of Octahydro-indeno-phenanthrenes by Formal [3+3] Cyclocondensation Reaction with 1,3-Bis[(trimethylsilyl)oxy]buta-1,3-dienes [J].

Erben, Friedrich ;

Specowius, Verena ;

Woelfling, Janos ;

Schneider, Gyula ;

Langer, Peter .

HELVETICA CHIMICA ACTA, 2013, 96 (05) :924-930

[9]

Fedorova O.I., 1984, Chem. Nat. Comp., V20, P305, DOI [10.1007/BF00575753, DOI 10.1007/BF00575753]

[10]

GROEN MB, 1986, RECL TRAV CHIM PAY B, V105, P465

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