3804-70-4

Usage

Uses

Used in Pharmaceutical Applications:
Columbianetin is used as an anti-inflammatory agent, particularly for regulating mast cell-mediated allergic inflammatory responses. It has been shown to inhibit the expression of COX-2, a key enzyme involved in the production of prostaglandins, which are responsible for inflammation and pain.
Used in Research Applications:
As a chiral compound, Columbianetin is also used in research settings to study the effects of stereochemistry on biological activities and to develop new drugs with improved selectivity and efficacy.
Used in Columbianetin Inhibition Applications:
Columbianetin is used as a specific inhibitor for targeting COX-2, which can be beneficial in the development of novel therapeutic strategies for various inflammatory and pain-related conditions.

InChI:InChI=1/C14H14O4/c1-14(2,16)11-7-9-10(17-11)5-3-8-4-6-12(15)18-13(8)9/h3-6,11,16H,7H2,1-2H3

Upstream product

• 484-12-8 osthole 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 27421-18-7 7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one 
• 27421-19-8 7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 26079-33-4 2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-benzofuran-4-ol 
• 1351118-96-1 C₁₄H₁₄O₄ 
• 484-14-0 osthenol 
• 1269599-04-3 C₁₄H₁₄O₄ 
• 1196892-20-2 C₂₀H₂₈O₄Si 
• 1161258-85-0 7-(tert-butyldimethylsilyloxy)-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 
• 935426-58-7 C₁₅H₁₃F₃O₅S 
• 1161258-91-8 7-(2-(tert-butyldiphenylsilyl)ethoxy)-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 
• 1161258-88-3 8-(3-methylbut-2-en-1-yl)-7-triisopropylsilyloxy-2H-chromen-2-one 

Downstream Products

• 1196892-27-9 (S,E)-2-(2-oxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-yl)propan-2-yl 3-(4-(tert-butyldimethylsilyloxy)phenyl)acrylate 
• 3173-03-3 Columbianadin 

Relevant academic research and scientific papers

Angelmarin, a novel anti-cancer agent able to eliminate the tolerance of cancer cells to nutrient starvation

The CH2Cl2-soluble extract of Angelica pubescens was found to kill PANC-1 cancer cells preferentially under nutrition starvation at a concentration of 50 μg/ml, with virtually no cytotoxicity under nutrient-rich conditions. Further bioassay-guided fractionation and isolation led to the isolation of a novel compound named angelmarin as the primary compound responsible for the preferential cytotoxicity; the compound exhibited 100% preferential cytotoxicity against PANC-1 cells at a concentration of 0.01 μg/ml.

Design, synthesis and biological evaluation of novel osthole-based derivatives as potential neuroprotective agents

A total of 26 compounds based on osthole skeleton were designed, synthesized. Their cytoprotective abilities of antioxidation, anti-inflammation and Aβ42(Amyloid β-protein 42)-induced neurotoxicity were evaluated by MTT assays. Mechanism of the action of selected compounds were investigated by molecular docking. AlogP, logS and blood–brain barrier (BBB) permeability of all these compounds were simulated by admetSAR. Most of the compounds showed better antioxidative and anti-inflammatory activities compared with osthole, especially OST7 and OST17. The compound OST7 showed relative high activity in neuroprotection against H2O2 (45.7 ± 5.5%), oxygen glucose deprivation (64.6 ± 4.8%) and Aβ42 (61.4 ± 5.2%) at a low concentration of 10 μM. EC50 of selected compounds were measured in both H2O2 and OGD induced cytotoxicity models. Moreover, NO inhibiting ability of OST17(50.4 ± 7.1%) already surpassed the positive drug indomethacin. The structure activity relationship study indicated that introduction of piperazine group, tetrahydropyrrole group and aromatic amine group might be beneficial for enhancement of osthole neuroprotective properties. Molecular docking explained that the reason OST7 exhibited relatively stronger neuroprotection against Aβ because of the greater area of interactions between molecule and target protein. OST7 and OST17 both provided novel methods to investigate osthole as anti-AD drugs.

Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells

Coumarins are ubiquitous in higher plants and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of coumarin derivatives on tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in human hepatoma HepG2 cells. A series of coumarin derivatives were prepared and assessed for their cytoprotective effects. Among these, a caffeoyl acid-conjugated dihydropyranocoumarin derivative, caffeoyllomatin, efficiently protected against cell damage elicited by t-BHP. Our findings suggest that caffeoyllomatin appears to be a potent cytoprotective agent.

Accessing columbianetin-containing natural products via a domino on-water, in-water process

A domino on-water, in-water process has been developed for the rapid and efficient synthesis of (±)-columbianetin. This highlights the operational simplicity of on-water chemistry. The domino process forms the key step in the synthesis of the columbianetin-containing natural products (±)- columbianetin acetate, (±)-zosimin, (±)-libanorin and (±)-angelmarin.

Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC50 value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5- methoxypsoralen (35), 8-geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC50 values 25.0 μM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin

A five-step and protecting group free synthesis of (±)-columbianetin from cyclohexane-1,3-dione is reported. The former compound was converted into its p-hydroxycinnamate derivative, (±)-angelmarin, using Coster's esterification procedure. Efforts to modi

Asymmetric synthesis of 2-Substituted dihydrobenzofurans and 3-hydroxydihydrobenzopyrans through the enantioselective epoxidation of O-silyl-protected ortho-allylphenols

The Shi-type epoxidation of O-tert-butyldiphenylsilyl (TBDPS) protected o-allylphenols serves as an efficient strategy to construct the dihydrobenzofurans and dihydrobenzopyrans in up to 97% ee. This methodology led to the enantioselective synthesis of (+)-marmesin, (-)-(3′R)-decursinol, and (+)-lomatin.

Total synthesis of (+)-angelmarin

(Chemical Equation Presented) An efficient 8-step enantioselective total synthesis of (+)-angelmarin, starting from commercially available umbelliferone, has been achieved. Key reactions include olefin cross-metathesis and a Shi epoxidation-cyclization sequence.

Highly enantioselective synthesis of angelmarin

Angelmarin (1), a novel anti-cancer agent, was efficiently synthesized through a highly enantioselective epoxidation and a copper cyanide-mediated esterification of the hindered alcohol as the key steps in 53% overall yield.

Pharmaceutical Composition Useful as Acetylcholinesterase Inhibitors

A pharmaceutical composition useful as acetylcholinesterase inhibitors. The present invention relates to pharmaceutical composition comprising the naturally occurring compounds selected from (±) Marmesin, Columbianetin, Dihydroxanthyletin and substituted coumarin derivatives of 7-allyloxy coumarin, 7-benzyloxy coumarin, 7-methoxy coumarin, 7-acetyloxy coumarin, 4-methyl-7-hydroxy coumarin and 4-methyl-7-acetyloxy coumarin. The said compositions posses a high degree of acetylcholinesterase inhibitory (AChE) property.