Estrone formate: a novel type of irreversible inhibitor of human steroid sulfatase

Schreiner, Erwin; Billich, Andreas

doi:10.1016/j.bmcl.2004.07.013

Cited by 15 publications

(5 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These preparations of aminoacyl steroidal esters require several days for completion 102,103 and in most cases proof of enantiopurity was not provided. In addition, phenolic steroids were prepared (i) by the active ester method, 107 or (ii) using acetic anhydride 108 alone or together with (a) pyridine over basic alumina under microwave irradiation, 109 (b) catalytic amounts of niobium(V) chloride, 110 (c) catalytic amounts of magnesium perchlorate 111 or (d) other catalysts. 107 Drawbacks for such transformations, however, include lack of generality, problems in scale up and interference with other functional groups.…”

Section: Steroid Esters Of A-amino Acidsmentioning

confidence: 99%

“…In addition, phenolic steroids were prepared (i) by the active ester method, 107 or (ii) using acetic anhydride 108 alone or together with (a) pyridine over basic alumina under microwave irradiation, 109 (b) catalytic amounts of niobium(V) chloride, 110 (c) catalytic amounts of magnesium perchlorate 111 or (d) other catalysts. 107 Drawbacks for such transformations, however, include lack of generality, problems in scale up and interference with other functional groups. 110,111 Benzotriazole methodology offers an advantage for the synthesis of O-(protected a-aminoacyl)steroids since it uses shorter reaction times of ca.…”

Section: Steroid Esters Of A-amino Acidsmentioning

confidence: 99%

“…(c) catalytic amounts of magnesium perchlorate 111 or (d) other catalysts 107. Drawbacks for such transformations, however, include lack of generality, problems in scale up and interference with other functional groups 110,111.…”

mentioning

confidence: 98%

See 2 more Smart Citations

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Katritzky¹,

Angrish²,

Todadze³

2009

Synlett

View full text Add to dashboard Cite

N-(Protected a-aminoacyl)benzotriazoles are efficient intermediates for N-and O-aminoacylation. These intermediates enable fast preparations of biologically relevant peptides and peptide conjugates in high yields and purity, under mild reaction conditions, with full retention of the original chirality. The developed methodology allows simple solution-and solid-phase preparative techniques to generate complex peptides and peptide conjugates and serves as a platform for generating diverse medicinal chemistry building block libraries involving amino acid and heterocyclic moieties crucial for drug development.

show abstract

Section: Steroid Esters Of A-amino Acidsmentioning

confidence: 99%

Section: Steroid Esters Of A-amino Acidsmentioning

confidence: 99%

See 1 more Smart Citation

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Katritzky¹,

Angrish²,

Todadze³

2009

Synlett

View full text Add to dashboard Cite

show abstract

“…1). 1 Cefamandole nafate is a clinical wide-spectrum antibiotic of cephalosporin with a formyl protected cefamandole sodium salt. Formylated estrone is an inhibitor of human steroid sulfatase.…”

mentioning

confidence: 99%

“…Notably, product 5 is a known inhibitor of human steroid sulfatase. 1 The synthesis of 5 can be scaled up using 4 mmol estrone to give 5 in 0.8 g, 67% yield. This gram scale synthesis of a biologically active compound shows the practicability of this difluorocarbene-mediated formylation method.…”

mentioning

confidence: 99%

Direct formylation of phenols using difluorocarbene as a safe CO surrogate

Feng

Zhang

2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Oxydiazomethylation of Alkenes via Photoredox Catalysis

Zeng,

Zheng,

Shen

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

α‐Diazoesters belong to significantly important carbenoid precursors in synthetic chemistry. Diazomethylation‐based difunctionalization of alkenes is highly valuable but remain nontrivial. Herein, we reported a general and modular approach for the direct 1,2‐oxydiazomethylation of alkenes through visible‐light photoredox catalysis. This process exploits photocatalyzed strategy to convert alkenes to γ‐formyloxyl‐α‐diazoesters using α‐diazo iodonium salts as carbyne precursors, featuring wide substrate tolerance and broad late‐stage diversiﬁcations. Mechanistic studies suggest that the formation of γ‐carbocation‐tethered α‐diazoesters plays a crucial role in trapping DMF and H2O to allow for this transformation.

show abstract

Estrone formate: a novel type of irreversible inhibitor of human steroid sulfatase

Cited by 15 publications

References 20 publications

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Direct formylation of phenols using difluorocarbene as a safe CO surrogate

Oxydiazomethylation of Alkenes via Photoredox Catalysis

Contact Info

Product

Resources

About