14001-37-7Relevant articles and documents
Solvent-induced dichotomy in the oxidation mechanism of alkyl aromatic selenoethers
Fechete, Ioana,Jouikov, Viatcheslav
, p. 634 - 640 (2014)
Changing solvent polarity (considered in terms of dielectric permittivity ? is an easy experimental way for tuning the reactivity of electrogenerated cation radicals of alkyl aromatic selenoethers. First-order cleavage of SeC3 bond is favored in polar media, whereas bimolecular cation radical disproportionation becomes the main reaction in low-polar solvents. The key element of this dichotomy is the dielectric adjustment of specific transannular interactions between Se and CO group in the cation radicals. A series of alkyl arylselenides with pending carboxy or acetamido substituents was studied by cyclic voltammetry, IR spectroscopy and DFT calculation in binary solvents covering the span of polarity 8 2Se 2.
A convenient preparation of N-acyl-1-aza-1,3-diene from β-formylenamide and its utility in inverse electron demand Diels-Alder reactions
Boruah, Romesh C.,Ahmed, Shahadat,Sharma, Utpal,Sandhu, Jagir S.
, p. 922 - 925 (2000)
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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
, 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.
Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid
Zhang, Minmin,Yu, Shuowen,Hu, Fangzhi,Liao, Yijun,Liao, Lihua,Xu, Xiaoying,Yuan, Weicheng,Zhang, Xiaomei
, p. 8757 - 8760 (2016/07/15)
Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.
