2890-85-9Relevant academic research and scientific papers
Synthesis of D-Ring Annulated Pyridosteroids from β-Formyl Enamides and Their Biological Evaluations
Nongthombam, Geetmani Singh,Borah, Kasmika,Muinao, Thingreila,Silla, Yumnam,Pal, Mintu,Deka Boruah, Hari Prasanna,Boruah, Romesh Chandra
supporting information, p. 11 - 27 (2019/01/11)
Herein, we report the synthesis of a novel class of substituted androst[17,16-b]pyridines (pyridosteroids) from the reaction of β-formyl enamides with alkynes in high yields. The optimized reaction protocol was extended to acyclic and cyclic β-formyl enamides to afford nonsteroidal pyridines. Cell survival assay of all compounds were carried against prostate cancer PC-3 cells wherein 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine showed the highest cytotoxic activity. Phase contrast microscopy and flow cytometry studies exhibited marked morphological features characteristic of apoptosis in 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine and abiraterone treated PC-3 cells. The treatment of 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine induces G2/M phase cell cycle arrest in prostate cancer PC-3 cells. Enhancement of apoptotic inductions of PC-3 cells by 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine and abiraterone through the activation of caspases-6, -7, and -8 pathways were supported by qRT-PCR. In silico study of the compound 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine showed stable and promising interaction with the key caspase proteins. Our studies revealed that the pyridosteroid 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine, bearing pyridine-2,3-dicarbethoxy pharmacophore, facilitated initiation of caspase-8 and activates downstream effectors caspase-6 and caspase-7 and thereby triggering apoptosis of PC-3 cancer cells.
Ruthenium-catalyzed hydrovinylation of N-acetylenamines leading to amines with a quaternary carbon center
Wang, Qiu-Shi,Xie, Jian-Hua,Li, Wei,Zhu, Shou-Fei,Wang, Li-Xin,Zhou, Qi-Lin
supporting information; experimental part, p. 3388 - 3391 (2011/08/21)
A catalytic hydrovinylation of N-acetylenamines with ethylene is reported. This new hydrovinylation reaction is catalyzed by a ruthenium hydride complex, RuHCl(CO)(PCy3)2, providing a series of N-acetylamines with a quaternary carbon center with up to 99% yield.
PREPARATION OF CHIRAL AMIDES AND AMINES
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Page/Page column 23, (2009/06/27)
This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.
Heterogeneously catalyzed asymmetric hydrogenation of α-arylenamides over immobilized RhBPE and RhDUPHOS complexes
Crosman, Adrian,Hoelderich, Wolfgang F.
experimental part, p. 229 - 237 (2009/10/16)
Optically active α-1-arylalkylamine derivatives were successfully synthesized through heterogeneous asymmetric hydrogenation of α-arylenamides over immobilized RhBPE and RhDUPHOS complexes on aluminum-containing M41S and SBA-15 type materials. The heterog
An efficient synthesis of enamides from ketones
Hang, Zhao,Vandenbossche, Charles P.,Koenig, Stefan G.,Singh, Surendra P.,Bakale, Roger P.
, p. 505 - 507 (2008/09/19)
A new synthesis of enamides from ketones is disclosed that involves a phosphine-mediated reductive acylation of oximes. The resulting enamides are isolated in good yields (up to 89%) and excellent purity, permitting a subsequent hydrogenation to access en
The Direct Synthesis of Secondary Amides from Aldehydes; A Novel General Redox Procedure Mediated by Iodotrichlorosilane (ITCS)
Elmorsy, Saad S.,Badawy, Doria S.,Nour, Mohamed A.,Kandeel, Ezzat M.
, p. 417 - 421 (2007/10/02)
A unique, general redox process for the preparation of secondary amides by the interaction, of aldehydes with nitriles in the presence of two equivalents of iodotrichlorosilane (ITCS) is described and possible pathways are discussed. - Keywords: Iodotrichlorosilane, Aldehydes, Nitriles, sec-Amides
