14794-71-9

Usage

InChI:InChI=1/C17H20O4/c1-8-7-14(20-11(4)18)10(3)15-12(8)5-6-13-9(2)17(19)21-16(13)15/h7,9,13,16H,5-6H2,1-4H3

Upstream product

• 108-24-7 acetic anhydride 
• 438-50-6 (+/-)-α-Desmotroposantonin 
• 438-50-6 (+/-)-β-Desmotroposantonin 
• 858438-41-2 2-(7-hydroxy-5,8-dimethyl-1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid 
• 481-06-1 santonin 

Downstream Products

• 13743-90-3 (-)-α-desmotroposantonin methyl ether 
• 1426436-56-7 C₂₅H₂₆N₄O₄ 
• 1426436-55-6 C₂₅H₂₅N₃O₄ 
• 1426436-51-2 C₂₅H₂₄F₃N₃O₃ 
• 1426436-50-1 C₂₅H₂₅BrFN₃O₄ 
• 1426436-49-8 C₂₆H₂₈BrN₃O₄ 
• 1426436-48-7 C₂₇H₃₀ClN₃O₄ 
• 1426436-47-6 C₂₄H₂₂BrF₂N₃O₃ 
• 1426436-46-5 C₂₄H₂₂BrFIN₃O₃ 
• 1426436-44-3 C₂₅H₂₆IN₃O₃ 
• 1426436-43-2 C₂₄H₂₄IN₃O₃ 
• 1426436-42-1 C₂₄H₂₄BrN₃O₃ 

Relevant academic research and scientific papers

Sesquiterpene Lactones Potentiate Olaparib-Induced DNA Damage in p53 Wildtype Cancer Cells

Despite notable advances in utilising PARP inhibitor monotherapy, many cancers are not PARP inhibitor-sensitive or develop treatment resistance. In this work, we show that the two structurally-related sesquiterpene lactones, a 2-bromobenzyloxy derivative

Rational drug design and synthesis of new α-Santonin derivatives as potential COX-2 inhibitors

Sesquiterpene compounds are widely known for their numerous pharmacological activities. Herein the focus of the authors was on α-Santonin, a sesquiterpene lactone from the Artemisia genus: the aim was to determine whether α-Santonin could be considered in the treatment of inflammation and pain. To this purpose, a small series of derivatives was designed and screened in silico against the enzyme COX-2 along with the parent compound. Drug-likeness parameters were also assessed. The compounds were eventually synthesized, and few were tested to determine their efficacy in the inhibition of COX-2 activity and expression. Overall, compound A2 was the only one with a detectable inhibitory potential of COX-2 activity whilst two of its ether derivatives demonstrated improved ability in the inhibition of COX-2 expression.

T- and B-cell immunosuppressive activity of novel α-santonin analogs with humoral and cellular immune response in Balb/c mice

In continuation of our endeavours to synthesize immunosuppressive agents from α-santonin, we report herein the design and synthesis of a new series of α-santonin derived O-aryl/aliphatic ether, ester and amide analogs and the evaluation of their immunosuppressive activities. The in vitro studies led to several analogs with significant immunosuppressive effects by inhibiting ConA and LPS stimulated T- and B-cell proliferation in a dose dependent manner. The more significant compounds 4d, 4e, 4f, 4h, 6a and 6b displayed potent inhibitory activity on the mitogen-induced T- and B-cell proliferation in comparison to α-santonin 1. Compound 4e displayed stupendous in vitro immunosuppressive effects with ～80% suppression of B and ～75% suppression of T lymphocyte proliferation, respectively. The in vivo investigation on BALB/c mice revealed that non-cytotoxic compound 4e suppresses both humoral and cellular immunity.

Synthesis of α-santonin derivatives for diminutive effect on T and B-cell proliferation and their structure activity relationships

A new library of 20 compounds from α-santonin was synthesized and tested against Con-A induced T-cell proliferation and LPS-induced B-cell proliferation via MTT assay. The study resulted in the identification of potent immunosuppressant molecules, which w

Diminutive effect on T and B-cell proliferation of non-cytotoxic α-santonin derived 1,2,3-triazoles: A report

α-Santonin derived new series of 1,2,3-triazoles synthesized through Azide-Alkyne Huisgen 1,3-dipolar cycloaddition reaction between substituted aryl azide and a propargylated α-desmotrosantonin were bio-evaluated for their diminutive effect on ConA induced T-cell and LPS induced B-cell proliferation. Interestingly, most of the synthesized compounds showed better immunosuppressant activity than α-santonin. Triazole derivatives 9, 10, 17, 18, 29, and 30 displayed significant diminutive effect on cell proliferation. Compounds 12 and 13 were found selective against ConA T-cell proliferation exhibiting >90% inhibition at 1 × 10-6 M concentration. The present study resulted in identification of several triazole derivatives as effective immunosuppressive agents.

Kinetics and Mechanism of the Acid-induced Rearrangements of α-Santonin, 6-epi-α-Santonin, and Related Compounds

The well known rearrangements of α-santonin (2) to α-desmotroposantonin (3) in aqueous sulphuric acid, and to its acetate in acetic anhydride, have been reinvestigated.No evidence was found for the formation of isomeric products apart from the known β-desmotroposantonin (4).Kinetic and basicity measurements, allied to the use of acidity functions, allow the conclusion that, in >45percent H2SO4, α-santonin (2) rearranges slowly to trans-desmotroposantonin, which rapidly epimerises to (3).In more dilute acid there is evidence of a change in mechanism.The cation of 6-epi-α-santonin (5) rearranges about 1 000 times faster than those of α-santonin and a number of analogues, including the lactone-free analogue (6).This is attributed to a favourable interaction between the lactone ring of (5) and the dienone ring over which it can be closely folded.