Synthesis and characterization of a fluorescent steroid dimer linked through C-19 by a 1,4-Bis(phenylethynyl)phenylene fragment

Vazquez‐Chavez, Josué; Aguilar‐Granda, Andrés; Iglesias-Arteaga, Martı́n A.

doi:10.1016/j.steroids.2022.109098

Cited by 2 publications

(2 citation statements)

References 34 publications

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“…We have recently described the synthesis and photophysical properties of the dimers 2 [4] and 3 [5] in which the steroid cores are bridged by a 1,4‐bis(phenylethynyl)phenylene fluorescent fragment (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a highly fluorescent benzofuran dimer derived from estradiol

Santiago‐Sampedro,

Mayorquín‐Torres,

Aguilar‐Granda

et al. 2024

Journal of Heterocyclic Chem

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Pd‐catalyzed cyclization of a fluorescent dimer in which two cores of the potent estrogenic estradiol are bridged by the 1,4‐diethynil benzene moiety led to a steroid dimer bearing the 1,4‐di(benzofuran‐2‐yl)benzene. The obtained compound showed an intense blue fluorescence characterized by a broad emission band between 350 and 550 nm, with four maxima at 384, 403, 435, and 456 nm. The benzofuran dimer showed an 18‐fold increased quantum yield compared with that of its synthetic precursor.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a highly fluorescent benzofuran dimer derived from estradiol

Santiago‐Sampedro,

Mayorquín‐Torres,

Aguilar‐Granda

et al. 2024

Journal of Heterocyclic Chem

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“…The study on dimerization and oligomerization of the cholic acid skeleton as an architectural building block was particularly intensive [17][18][19]. Various methods of synthesis of steroid dimers with linear [20] or cyclic [21] structures, e.g., Sonogashira coupling, Yamaguchi esterification, Wurtz reaction, ring closing metathesis, etc., were employed [22]. In the last decades, the interesting chemical, biological, and physical properties of the growing number of steroid dimers synthesized or isolated from living organisms have triggered Molecules 2023, 28, 7068 2 of 14 increased activity in this field.…”

Section: Introductionmentioning

confidence: 99%

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

Tomkiel,

Majewski,

Siergiejczyk

et al. 2023

Molecules

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The reactions of sterols (androst-5-en-3β-ol-17-one, diosgenin, and cholesterol) and their tosylates with hydroquinone aimed at the synthesis of O,O-1,4-phenylene-linked steroid dimers were studied. The reaction course strongly depended on the conditions used. The study has shown that the major reaction products are the elimination products and unusual steroid dimers resulting from the nucleophilic attack of the hydroquinone C2 carbon atom on the steroid C3 position, followed by an intramolecular addition to the C5–C6 double bond. A different reaction course was observed when montmorillonite K10 was used as a catalyst. The reaction of androst-5-en-3β-ol-17-one under the promotion of this catalyst afforded the O,O-1,4-phenylene-linked steroid dimer in addition to the disteroidal ether. The formation of the latter compound was suppressed by using 3-tosylate as a substrate instead of the free sterol. The reactions of androst-5-en-3β-ol-17-one tosylate and cholesteryl tosylate with hydroquinone catalyzed by montmorillonite K10 carried out under optimized conditions afforded the desired dimers in 31% and 67% yield, respectively.

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Synthesis and characterization of a fluorescent steroid dimer linked through C-19 by a 1,4-Bis(phenylethynyl)phenylene fragment

Cited by 2 publications

References 34 publications

Synthesis and characterization of a highly fluorescent benzofuran dimer derived from estradiol

Synthesis and characterization of a highly fluorescent benzofuran dimer derived from estradiol

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

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