Synthesis and anti-metastatic effects of pregn-17(20)-en-3-amine derivatives

Potential of Steroidal Alkaloids in Cancer: Perspective Insight Into Structure–Activity Relationships

“…The activities of these C-16 carbonyl derivatives including 9a, 9g, 10a, and 10f were better than other two kinds of derivatives, which indicated that α, β -unsaturated fragment in ring D might be key for activities. It was worth noting that, except for 3-piperidin-1-yl derivatives, the activities of 3 β -substituted derivatives were better than 3 α -substituted derivatives among the derivatives without the substituted group on C-16 (5a-e, 5g vs 6a-e, 6g), but it did not appear the same phenomenon among C-16 carbonyl derivatives ( 13 ).…”

“…According to the results, Qin et al. speculated that the relative configuration of the 3 α -piperidine-1-group might be beneficial for some tumor migration targets, and the 3 α -piperidin-1-yl group was an effective functional group for the antimigration activity ( 13 ). Shaojie Huo et al.…”

“…Among pregn-17(20)-en-3-amine derivatives, the activities of 3a-piperidin-1-yl derivatives were better than those of 3b-piperidin1-yl derivatives (5f vs 6f, 7f vs 8f, and 9f vs 10f) (Figure S1). According to the results, Qin et al speculated that the relative configuration of the 3a-piperidine-1-group might be beneficial for some tumor migration targets, and the 3a-piperidin-1-yl group was an effective functional group for the antimigration activity (13). Shaojie Huo et al concluded structure-activity relationships by comparing hookerianine A (1) and epipachysamine D (4) that steroidal alkaloids with the phenylacetyl group instead of the benzoyl group at C-3 can enhance the cytotoxicity against SW480, SMMC-7721, PC3, and K562 human cells (Figure S1) (12).…”

Terminamines K–S, Antimetastatic Pregnane Alkaloids from the Whole Herb of Pachysandra terminalis

“…By comparing the 1D NMR spectra, it was considered that alkaloids 5 and 6 were stereoisomers at C-3 ( Table 2). Compared with literature reports [20], together with the 3-isomers of the pregnane alkaloid derivatives [17][18][19], the β-orientation of the 3-NH(Me) group in 5 could be assigned due to the chemical shift of C-3 (δ C 59.5), while the upfield shift of C-3 (δ C 54.9) leads to the assignment of a 3α-NH(Me) group in 6. Further analysis of the HSQC, HMBC, and ROESY NMR data was used to establish the structure of compounds 5 and 6 as 3β-methylamino-20α-senecioylamino-pregn-5-ene, and 3α-methylamino-20α-senecioylamino-pregn-5-ene, respectively (Figure 1).…”

“…However, there was no further chemical or spectral evidence for the identification of the relative configuration for C-3, except for the 1D-NMR data [8,13]. A series of 3-isomers of pregnane alkaloid derivatives were synthesized using the stereoselective Mitsunobu reaction [16] by this group [17][18][19]. The results suggested that the C-3 signal of 3β-dimethylamino derivatives appeared more downfield.…”