68370-47-8

Usage

Uses

Used in Pharmaceutical Industry:
(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one is used as a pharmaceutical agent for the inhibition of resistant acute leukemic cells. It selectively targets cancer stem and progenitor cells, making it a promising candidate for cancer treatment.
Used in Drug Delivery Systems:
(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one can be used in drug delivery systems to improve the efficacy and bioavailability of pharmaceutical agents. Its unique chemical properties may allow for the development of novel drug delivery methods, enhancing the therapeutic outcomes of various treatments.
Used in Chemical Research:
(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one can be utilized in chemical research for the development of new compounds and materials. Its complex structure and unique properties make it an interesting subject for further investigation and potential applications in various fields.

InChI:InChI=1/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1

Upstream product

• 67-56-1 methanol 
• 503551-53-9 parthenolide 
• 1403357-80-1 11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride 
• 1403357-81-2 11βH,13-dihydro-13-dimethylaminomicheliolide 

Relevant academic research and scientific papers

Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids

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.

Design, synthesis and in vivo anticancer activity of novel parthenolide and micheliolide derivatives as NF-κB and STAT3 inhibitors

Parthenolide and micheliolide have attracted great attention in anticancer research due to their unique activities. In this study, thirteen parthenolide derivatives and twenty-three micheliolide derivatives were synthesized. Most synthesized compounds showed higher cytotoxicity than parthenolide or micheliolide. The in vivo anticancer activity of several representative compounds was evaluated in mice. One micheliolide derivative, 9-oxomicheliolide (43), showed promising in vivo antitumor activity compared with clinical drugs cyclophosphamide or temozolomide. Compound 43 was particularly effective against glioblastoma, with its tumor inhibition rate in mice comparable to the drug temozolomide. The discovery of compound 43 also demonstrates the feasibility of developing anticancer micheliolide derivatives by modification at C-9 position. Anticancer mechanism studies revealed that 9-oxomicheliolide exhibited inhibition effect against NF-κB and STAT3 signaling pathways, as well as induction effects of cell apoptosis. It is postulated that 9-oxomicheliolide is likely to be a modulator of the immune system, which regulates the anticancer immune responses.

Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome

Parthenolide (PTL) can target NLRP3 inflammasome to treat inflammation and its related disease, but its cytotoxicity limits further development as an anti-inflammatory drug. A series of PTL analogs and their Michael-type adducts were designed and synthesi

Chamomile lactone derivative as well as preparation method and application thereof (by machine translation)

The invention relates to the technical field of organic synthesis, in particular to a small white chrysanthemum lactone derivative and a preparation method and application thereof. To the invention, small white chrysanthemum is used as the original main raw material, 11 small white chrysanthemum lactone derivatives are synthesized through a series of chemical reactions, and the derivatives have certain anti-proliferative activity on glioblastoma cells. The invention also proves that the deuterated derivative DMAPAPAPAPAPT-D6 can significantly induce accumulation of active oxygen of glioblastoma cells, thereby leading DNA damage in glioblastoma cells. Furthermore, DMAPAPAPAPAPT-D6 promotes exogenous apoptosis mediated by the death receptor of caspase, indicating DNA damage induced by DMAPAPAPAPAPT-D6 inducible glioblastoma apoptosis. , ROS accumulation caused by DMAPAPAPAPAPT-D6 treatment leads DNA damage and death receptor-mediated apoptosis, which indicates that DMAPAPAPAPAPT-D6 with novel ingredients has therapeutic potential for treating glioblastoma and can be applied to preparation of drugs for treating glioblastoma. (by machine translation)

Micheliolide derivative, pharmaceutical composition as well as preparation method and application thereof

The invention discloses a new type micheliolide derivative (the formulas of the derivative are shown as formula I and II, and the formulas are shown in the description) or salt, a preparation method,a pharmaceutical composition and application thereof, pa

Acid-induced rearrangement of epoxygermacranolides: Synthesis of furanoheliangolides and cadinanes from nobilin

The acid-induced rearrangement of three epoxyderivatives of nobilin 1, the most abundant sesquiterpene lactone in Anthemis nobilis flowers, was investigated. From the 1, 10-epoxyderivative 2, furanoheliangolide 5 was obtained, while the 4, 5-epoxy group o

Sesquiterpene lactone compound and its derivatives use in the preparation of medicament

The invention relates to a sesquiterpene lactone compound and uses of a derivative thereof in preparation of drugs, belongs to the technical field of the drugs, specially relates to the uses of a formula (I) compound in preparation of the drugs, and particularly relates to the uses of a formula (I) compound in preparation of the drugs for treatment of rheumatoid arthritis and treatment of cancer through inhibition of cancer stem cells.

USES OF SESQUITERPENE LACTONE COMPOUNDS AND THEIR DERIVATIVES IN DRUGS PREPARATION

The present invention relates to the uses of sesquiterpene lactone compounds and their derivatives in preparing drugs. It belongs to the field of drug technology, specifically relates to the uses of the compounds of Formula (I) in preparing the drugs, especially the uses in preparing the drugs to treat rheumatoid arthritis and treat cancers through inhibiting cancer stem cells.

Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-κB activation and MCP-1 and TGF-β1 expression in rat mesangial cells

Diabetic nephropathy (DN) is one of the most common and serious chronic complications of diabetes mellitus, however, no efficient clinical drugs exist for the treatment of DN. We selected and synthesized several sesquiterpene lactones (SLs), and then used the MTT assay to detect rat mesangial cells (MCs) proliferation, ELISA to measure the expression level of monocyte chemoattractant protein-1 (MCP-1), transforming growth factor beta (TGF-β1) and fibronectin(FN), real-time fluorescent quantitative PCR analysis to measure the MCP-1 and TGF-β1 gene expression, western blot to detect the level of IκBα protein and EMSA to measure the activation of nuclear factor kappa B (NF-κB). We discovered that SLs, including parthenolide (PTL), micheliolide (MCL), arglabin, and isoalantolactone (IAL), as well as several synthetic analogs of these molecules, could effectively attenuate the high glucose-stimulated activation of NF-κB, the degradation of IκBα, and the expression of MCP-1, TGF-β1 and FN in rat mesangial cells (MCs). These findings suggest that SLs and their derivatives have potential as candidate drugs for the treatment of DN.

Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells

Small molecules that can selectively target cancer stem cells (CSCs) remain rare currently and exhibit no common structural features. Here we report a series of guaianolide sesquiterpene lactones (GSLs) and their derivatives that can selectively eradicate