76638-09-0Relevant articles and documents
Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives
Zhu, Longqing,Li, Junfang,Fan, Xiaohong,Hu, Xiaoling,Chen, Jinhong,Liu, Yonghong,Hao, Xiangyong,Shi, Tao,Wang, Zhen,Zhao, Quanyi
, (2021/04/29)
Marine natural products derived from special or extreme environment provide an important source for the development of anti-tumor drugs due to their special skeletons and functional groups. In this study, based on our previous work on the total synthesis and structure revision of the novel marine natural product Chrysamide B, a group of its derivatives were designed, synthesized, and subsequently of which the anti-cancer activity, structure-activity relationships and cellular mechanism were explored for the first time. Compared with Chrysamide B, better anti-cancer performance of some derivatives against five human cancer cell lines (SGC-7901, MGC-803, HepG2, HCT-116, MCF-7) was observed, especially for compound b-9 on MGC-803 and SGC-7901 cells with the IC 50 values of 7.88 ± 0.81 and 10.08 ± 1.08 μM, respectively. Subsequently, cellular mechanism study suggested that compound b-9 treatment could inhibit the cellular proliferation, reduce the migration and invasion ability of cells, and induce mitochondrial-dependent apoptosis in gastric cancer MGC-803 and SGC-7901 cells. Furthermore, the mitochondrial-dependent apoptosis induced by compound b-9 is related with the JAK2/STAT3/Bcl-2 signaling pathway. To conclude, our results offer a new structure for the discovery of anti-tumor lead compounds from marine natural products.
The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide
Lifchits, Olga,Mahlau, Manuel,Reisinger, Corinna M.,Lee, Anna,Fares, Christophe,Polyak, Iakov,Gopakumar, Gopinadhanpillai,Thiel, Walter,List, Benjamin
supporting information, p. 6677 - 6693 (2013/06/05)
Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.
Catalytic generation of activated carboxylates: Direct, stereoselective synthesis β-hydroxyesters from epoxyaldehydes
Chow, Kenneth Yu-Kin,Bode, Jeffrey W.
, p. 8126 - 8127 (2007/10/03)
The catalytic generation of activated carboxylates from epoxyaldehydes enables the direct, stereoselective synthesis of β-hydroxyesters under mild, convenient reaction conditions. In addition to providing a new method for the synthesis of anti-aldol adducts, this chemistry unveils a mechanistically viable solution to the catalytic, waste-free synthesis of esters. Copyright
A divergent approach to the myriaporones and tedanolide: Enantioselective preparation of the common intermediate
Taylor, Richard E.,Ciavarri, Jeffrey P.,Hearn, Brian R.
, p. 9361 - 9364 (2007/10/03)
The tedanolide and myriaporone classes of natural products represent interesting targets for synthesis because of their structural similarity and biological activity. The asymmetric preparation of a potential common intermediate in the total synthesis of each of these targets is presented. The key step, a Zr-mediated allylation, allows for the efficient preparation of the hydroxypropionate structural unit.
Stereospecific rearrangements of optically active 2-aryl-3-ethenyloxiranes to give optically active β-ethenylbenzeneethanols: Benzyl vs. allyl cations and an efficient synthesis of (s)-ibuprofen
Jung, Michael E.,Anderson, Karen L.
, p. 2605 - 2608 (2007/10/03)
Rearrangements of aryl- and ethenyl-substituted oxiranes proceed well in the presence of triethylsilane and BF3 to give optically active alcohols, which we have used for a synthesis of (S)-ibuprofen 1. We have also shown that a vinyl group migrates to a benzylic cation faster than a phenyl group migrates to an allyl cation.
EPOXIDATION OF 2-ALKYL-3-PHENYLPROPENALS WITH HYDROGEN PEROXIDE IN AN ALKALINE MEDIUM
Revinskii, I. F.,Tishchenko, I. G.,Burd', V. N.
, p. 961 - 964 (2007/10/02)
The epoxidation of E-2-methyl-, E-2-ethyl-, and E-2-propyl-3-phenylpropenals with hydrogen peroxide in an alkaline medium leads to the formation of a mixture of cis and trans isomers of the respective oxiranes.Analogous oxidation of the E and Z forms of 2
ASYMMETRIC HALOLACTONISATION REACTION-4 ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE α,β-EPOXYALDEHYDES FROM α,β-UNSATURATED ACIDS
Hayashi, M.,Terashima, S.,Koga, K.
, p. 2797 - 2803 (2007/10/02)
The bromolactones (5) stereoselectively produced by the asymmetric bromolactonisation of (S)-N-(α,β-unsaturated)acylprolines (3), were elaborated to highly optically active 2(R),3(S)-epoxyaldehydes (8) (84-98percent ee) by successive epoxide formation and reductive cleavage of the proline moiety.The overall process constitutes a highly efficient asymmetric synthesis of 8 from α,β-unsaturated acids (1).
A highly efficient asymmetric synthesis of optically active α,β-epoxyaldehydes from α,β-unsaturated acids
Terashima, Shiro,Hayashi, Masaji,Koga, Kenji
, p. 2733 - 2736 (2007/10/02)
The bromolactones(3) prepared from α,β-unsaturated acids(1) were converted to optically active α,β-epoxyaldehydes(2(R),3(S)-6)(84-98% ee) by successive epoxide formation and reductive cleavage of the proline moiety. The overall process constitutes a highly efficient asymmetric synthesis of 2(R),3(S)-6 from 1.
