65563-75-9

Usage

Molecular structure

2,5a-dimethyl-9-methylideneoctahydro-2H-oxireno[4,4a]naphtho[2,3-b]furan-8(9H)-one has a complex molecular structure, which includes a three-membered cyclic ether ring (oxirene) and a naphtho-furan ring system.

Type of compound

It is a type of oxirene, which is a class of organic compounds containing a three-membered cyclic ether ring.

Presence of multiple groups

The compound contains multiple methyl (CH3) and methylidene (CH2) groups, which contribute to its chemical and physical properties.

Naphtho-furan ring system

The presence of a naphtho-furan ring system in the compound adds to its complexity and potential applications.

Unique chemical and physical properties

Due to the presence of various groups and ring systems, the compound exhibits unique chemical and physical properties that may make it useful in various applications.

Potential applications

The compound may be useful in fields such as pharmaceutical or material science research, owing to its unique properties.

Complex structure analysis

The compound's complex structure requires careful handling and detailed analysis to fully understand its behavior and potential uses.

Upstream product

• 546-43-0 alantolactone 

Relevant academic research and scientific papers

Sesquiterpene lactone nitrogen methyl piperazine derivative and salt thereof, and application thereof in medicine preparation

The invention relates to sesquiterpene lactone nitrogen methyl piperazine derivatives and pharmaceutically acceptable salts thereof, and applications thereof in medicine preparation. The invention concretely relates to compounds represented by formulas (I), (II), (III) and (IV), and pharmaceutically acceptable salts thereof, as well as the applications of the compounds shown in formulas (I), (II), (III) and (IV) and pharmaceutically acceptable salts and compositions thereof for preparing anti-cancer or auxiliary anti-cancer drugs.

Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones

Abstract—: Derivatives of sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative properties of the conjugates have been examined on tumor and pseudonormal cell lines. The cytotoxicity of the conjugates is lower than that of parent lactones; however, in some cases, as with the conjugates of alantolactone with artemisiten, it remains moderate in all tumor cell lines tested.

Synthesis and discovery of a drug candidate for treatment of idiopathic pulmonary fibrosis through inhibition of TGF-β1 pathway

In this study, anti-IPF lead compounds 42 and 44, derived from natural sesquiterpene lactones Isoalantolactone and alantolactone, were discovered by screening from a high-throughput TGF-β1 reporter luciferase assay. Notably, they could reduce the myofibroblast activation and extracellular matrix deposition both in vitro and in vivo. Additionally, compounds 42 and 44 could significantly attenuate bleomycin-induced pulmonary fibrosis in mice. Further validation of pharmacokinetics study and toxicity evaluation indicated that compound 44 might be a promising anti-IPF drug candidate.

Alantolactone derivative and application of derivative salt to preparation of drugs for treating inflammatory bowel diseases

The invention provides an alantolactone derivative and an application of derivative salt to preparation of drugs for treating inflammatory bowel diseases. The alantolactone derivative is as shown in a formula (I-II) or (I-III). According to the alantolactone derivative, acid forming the salt is inorganic acid or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boracic acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulfurous acid, the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-acid, oxalic acid, methanesulfonic acid, valeric acid, oleic acid, lauric acid, p-toluene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycollic acid, thioglycollic acid, glycine, sarcosine, sulfonic acid, nicotinic acid, picoline acid, isonicotinic acid and benzoic acid or substituted benzoic acid.

Application of alantolactone derivative and salt thereof in preparing drug for treating thyroiditis

The invention relates to application of an alantolactone derivative and salt thereof in preparing a drug for treating thyroiditis, and provides application of the alantolactone derivative as the formula (I-II) or the formula (I-III) and the salt thereof in preparing the drug for treating thyroiditis. Acid for forming the salt is inorganic or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boracic acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulphurous acid, and the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-lactic acid, oxalic acid, methanesulfonic acid, pentanoic acid, oleic acid, lauric acid, p-methylbenzene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycollic acid, mercaptan acid, glycine, sarcosine, sulfonic acid, nicotinic acid, methylpyridine, isonicotinic acid, benzoic acid and substituted benzoic acid.

Alantolactone derivative and salts thereof

The invention provides an alantolactone derivative shown as formula (I). The acid for salt forming is inorganic acid or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boric acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulfurous acid, and the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-acid, oxalic acid, methanesulfonic acid, pentanoic acid, oleic acid, lauric acid, p-toluene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycollic acid, mercaptan acid, glycine, sarcosine, sulfonic acid, nicotinic acid, methylpyridine acid, isonicotinic acid, benzoic acid or substituted benzoic acid.

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.

Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults

An Aedes aegypti larval toxicity bioassay was performed on compounds representing many classes of natural compounds including polyacetylenes, phytosterols, flavonoids, sesquiterpenoids, and triterpenoids. Among these compounds, two eudesmanolides, alantol

Acidic isomerization of alantolactone derivatives

A series of derivatives of the natural sesquiterpene lactones alantolactone (1) and isoalantolactone (2) was prepared. The α-methylene-γ- lactone moiety was retained in the structures of these for further modifications using reactions that affected exclusively the nonconjugated double bonds of the decalin ring.

Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa

In a bioassay guided search for antimycobacterial compounds from higher plants, the root extracts of Elecampane (Inula helenium L.; Asteraceae) and Sweet Coneflower (Rudbeckia subtomentosa Pursh.; Asteraceae) were chemically investigated for their active constituents. Chromatographic fractions of root extracts of I. helenium, which exhibited significant activity against Mycobacterium tuberculosis, provided the known eudesmanolides alantolactone, isoalantolactone, and 11αH,13-dihydroisoalantolactone. Peracid epoxidation of alantolactone and isoalantolactone provided 5α-epoxyalantolactone and 4(15)α-epoxyisoalantolactone, respectively and oxidation of alantolactone with OsO4 gave 11,13-dihydroxyalantolactone. Active fractions from R. subtomentosa contained the known alloalantolactone and 3- oxoalloalantolactone. The structures of the above compounds were established by spectroscopic methods including 1D and 2D NMR techniques as well as spectral comparison with previously reported data. The molecular structure of 5α-epoxyalantolactone was determined by single crystal X-ray diffraction. Eleven natural and semisynthetic eudesmanolides were tested in a radiorespirometric bioassay for activity against M. tuberculosis. 5α- Epoxyalantolactone and encelin from Montanoa speciosa showed minimum inhibitory concentrations (MICs) of 8 and 16 μg ml-1, respectively. Alantolactone, isoalantolactone and its 4α,15-epoxide, 1,2-dehydro-3-epi- isotelekin and alloalantolactone gave MICs of 32 μg ml-1. All other compounds showed MIC values of 128 μg ml-1 or higher.