Design and synthesis of novel D-ring fused steroidal heterocycles

•Steroidal dehydroepiandrosterone[17,16-d]-2-amino thiazole were synthesized in quantitive yields under mild conditions.•Aldehydes reacted with steroidal dehydroepiandrosterone[17,16-d]-2-amino thiazole to give the Steroidal imines.•Steroidal D-ring fused with heterocycles were obtained with a moder...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Steroids 2013-12, Vol.78 (12-13), p.1200-1208
Hauptverfasser: Zhang, Bao-Le, Zhang, En, Pang, Lu-Ping, Song, Li-Xing, Li, Ya-Fei, Yu, Bin, Liu, Hong-Min
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:•Steroidal dehydroepiandrosterone[17,16-d]-2-amino thiazole were synthesized in quantitive yields under mild conditions.•Aldehydes reacted with steroidal dehydroepiandrosterone[17,16-d]-2-amino thiazole to give the Steroidal imines.•Steroidal D-ring fused with heterocycles were obtained with a moderate to good yields. Using dehydroepiandrosterone as the starting material, we have synthesized a series of steroid analogs possessing a D-ring fused with heterocycles which are pyridine, imidazo [2,1-b]thiazoles or substituted thiazole imines. All the final structures are first reported and identified by NMR and MS spectroscopys, the yields of these products are moderate to good and the reaction conditions are mild. The cytotoxicity of the synthesized compounds against EC-109(human esophageal carcinoma), EC-9706(human esophageal carcinoma), MGC-803(human gastric carcinoma) were investigated.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2013.07.006