A Novel Approach in Drug Discovery: Synthesis of Estrone–Talaromycin Natural Product Hybrids

Tietze, Lutz F.; Schneider, Gyula; Wölfling, János; Fecher, Anja; Nöbel, Thomas; Petersen, Sönke; Schuberth, Ingrid; Wulff, Christian

doi:10.1002/1521-3765(20001016)6:20<3755::aid-chem3755>3.3.co;2-c

Cited by 15 publications

(18 citation statements)

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“…Exocyclic enol ethers have been used to prepare spiroacetals by cycloadditions, [3][4][5][6][7][8] or through acid-induced cyclisation of alcohols. [9][10][11][12][13] Such enol ethers have been metathesis, 22 Baeyer-Villiger oxidation of cyclic ketones 23 and by oxidation of sugars, 24 as well as by methods which would be appropriate for preparation of acyclic esters.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of spiroacetals using functionalised titanium carbenoids

Main

Rahman

Hartley

2008

Tetrahedron Letters

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Section: Methodsmentioning

confidence: 99%

Synthesis of spiroacetals using functionalised titanium carbenoids

Main

Rahman

Hartley

2008

Tetrahedron Letters

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“…37 The unnatural 13α derivatives, with C/D cis ring annelation, are of stereochemical and biological interest. The 13α-estrone, 3-methyl (37) and 3-benzyl ethers (38) have been converted into their epimers (39, 40) and D-seco derivatives (41, 42) in the above-mentioned way (Scheme 9). OEt 2 /NaI, respectively (Scheme 10).…”

Section: Methodsmentioning

confidence: 99%

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Wölfling¹

2007

ChemInform

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Both naturally occurring and synthetic D-homologs of compounds with a sterane skeleton exhibit diverse biological activity. The main sources of isolation are plants and marine organisms. The synthetic D-homosteroids are potential leads for drug discovery. This review focuses on steroids with a six-membered carbocyclic ring D and related compounds, the isolation or syntheses of which were reported between the mid-1990s and mid-2006.

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“…The glycoalkaloids solasonine and tomatine, extracted from different plant species, have demonstrated to exert strong antiproliferative effects on various human cancer cell lines of diverse origins [4,5], while the synthetic spiro-type hybrid of estrone and talaromycin B has also been reported to exhibit cytotoxic activity [6,7]. In general, the spiro functionality, in which two rings are connected through merely one carbon atom, is a recurring structural motif in a number of natural products with noteworthy biological activities [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel steroidal 16-spiroisoxazolines by 1,3-dipolar cycloaddition, and an evaluation of their antiproliferative activities in vitro

et al. 2014

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Efficient synthesis of novel 16-spiroisoxazolines in the androst-5-ene series was carried out by 1,3-dipolar cycloadditions of different aryl nitrile oxides to 3β-acetoxy-16-methylene-androst-5-en-17-one. During the intermolecular ring closures, the attack of the O terminus of the nitrile oxide dipole from the α side on C-16 predominated for steric reasons permitting the reactions to occur in a regio-and stereoselective manner. The minor isomers in which the angular methyl group on C-13 and the O atom of the isoxazoline heteroring were in the β, β-cis orientation were obtained in a yield of only ∼10 %. Moreover, the conversions were influenced to a certain extent by the substituents on the aromatic moiety of the 1,3-dipoles. The stereostructures of the related diastereomers were confirmed by 2D NMR methods. Deacetylation of the primarily formed main products resulted in the corresponding 3β-OH analogs, which were further reduced to furnish 3β, 17β-diols. All of the synthetized compounds were subjected to in vitro pharmacological studies in order to investigate their antiproliferative

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A Novel Approach in Drug Discovery: Synthesis of Estrone–Talaromycin Natural Product Hybrids

Cited by 15 publications

References 0 publications

Synthesis of spiroacetals using functionalised titanium carbenoids

Synthesis of spiroacetals using functionalised titanium carbenoids

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Synthesis of novel steroidal 16-spiroisoxazolines by 1,3-dipolar cycloaddition, and an evaluation of their antiproliferative activities in vitro

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