1147-29-1

Basic information

• Product Name: columbianetin
• Synonyms: 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one;8-(1-hydroxy-1-methyl-ethyl)-8,9-dihydrofuro[2,3-h]chromen-2-one;8-(2-hydroxypropan-2-yl)-8,9-dihydrofuro[2,3-h]chromen-2-one
• CAS NO: 1147-29-1
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.25900
• Mol File: 1147-29-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 443oC at 760 mmHg
• Flash Point: 171.9oC
• Appearance: /
• Density: 1.334g/cm3
• Vapor Pressure: 1.25E-08mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: columbianetin(CAS DataBase Reference)
• NIST Chemistry Reference: columbianetin(1147-29-1)
• EPA Substance Registry System: columbianetin(1147-29-1)

Safety Data

• Hazardous Substances Data: 1147-29-1(Hazardous Substances Data)

Usage

Definition

ChEBI: The angular furanocoumarin analogue of the linear furanocoumarin marmesin.

Synthesis Reference(s)

Tetrahedron, 27, p. 4901, 1971 DOI: 10.1016/S0040-4020(01)98195-5

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

• 484-14-0 osthenol 
• 1351118-96-1 C₁₄H₁₄O₄ 
• 26079-33-4 2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-benzofuran-4-ol 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 27421-19-8 7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one 
• 27421-18-7 7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 484-12-8 osthole 

Relevant articles and documents

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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.

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.