66726-11-2Relevant articles and documents
Synthesis and in vitro cytotoxic activity of semisynthetic derivatives in the santonin series
Rossi,Ambrogi,Grandolini,Scarcia,Furlani
, p. 784 - 789 (1986)
The synthesis of two new santonin derivatives namely 3-oxo-6βH-11β-phenylselenoeudesm-1,4-dien-6,13-olide (13) and 3-oxo-6β-H-eudesm-1,4,11-trien-6,13-olide (14) is reported along with the results of a series of santonins tested for activity against the g
Design, synthesis and anticancer activity of Michael-type thiol adducts of α-santonin analogue with exocyclic methylene
Khazir, Jabeena,Riley, Darren L.,Chashoo, Gousia,Mir, Bilal Ahmad,Liles, David,Islam, Md. Ataul,Singh, Shashank K.,Vishwakarma, Ram A.,Pilcher, Lynne A.
, p. 769 - 779 (2015)
Abstract A series of Michael-type analogues were generated on the C-ring of α-santonin (α-methylene-γ-butyrolactone) upon reaction with various thiols. All the thiol adducts synthesized were evaluated for their anticancer activity against four human cance
REACTIONS AFFECTING THE γ-LACTONE RING OF α-SANTONIN
Adekenov, S. M.,Gafurov, N. M.
, p. 452 - 455 (1992)
The selective dehydrogenation of the eudesmanolide α-santonin and its alkylation with the introduction of an allyl fragment into its γ-lactone ring are described.It has been established that these reactions are regio- and stereoselective.The structures of
Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids
Liu, Jie,Flegel, Jana,Otte, Felix,Pahl, Axel,Sievers, Sonja,Strohmann, Carsten,Waldmann, Herbert
supporting information, p. 21384 - 21395 (2021/08/23)
We describe the synthesis and biological evaluation of a new natural product-inspired compound class obtained by combining the conceptually complementary pseudo-natural product (pseudo-NP) design strategy and a formal adaptation of the complexity-to-diversity ring distortion approach. Fragment-sized α-methylene-sesquiterpene lactones, whose scaffolds can formally be viewed as related to each other or are obtained by ring distortion, were combined with alkaloid-derived pyrrolidine fragments by means of highly selective stereocomplementary 1,3-dipolar cycloaddition reactions. The resulting pseudo-sesquiterpenoid alkaloids were found to be both chemically and biologically diverse, and their biological performance distinctly depends on both the structure of the sesquiterpene lactone-derived scaffolds and the stereochemistry of the pyrrolidine fragment. Biological investigation of the compound collection led to the discovery of a novel chemotype inhibiting Hedgehog-dependent osteoblast differentiation.
Preparation and Phytotoxicity Evaluation of 11,13-Dehydro seco-Guaianolides
Chinchilla, Nuria,Santana, Alejandro,Varela, Rosa M.,Fronczek, Frank R.,Molinillo, José M. G.,MacIás, Francisco A.
, p. 2501 - 2508 (2019/09/30)
11,13-Dehydro seco-guaianolides, a particular type of sesquiterpene lactones, were synthesized from the commercially available α-santonin (11) using a facile strategy involving a high-yielding photochemical reaction. Natural products 10 and 17 from Artemi
