10079-74-0

Usage

Uses

Used in Organic Synthesis:
1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol is utilized as a building block in organic synthesis for the creation of various biologically active molecules. Its unique structure allows for the development of compounds with diverse applications in different fields.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol is used as a key component in the synthesis of pharmaceuticals. Its potential antioxidant and anti-inflammatory properties make it a promising candidate for the development of new drugs to address various health conditions.
Used in Cancer Treatment:
1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol has been studied for its potential role in cancer treatment, particularly due to its cytotoxic effects on cancer cells. This makes 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol a valuable asset in the ongoing research and development of novel cancer therapies.
Used in Pharmaceutical Development:
Given its wide range of potential applications, 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol is a significant compound in the field of pharmaceutical development. Its properties and reactivity make it a versatile building block for creating new and improved medications.
Used in Materials Science:
1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol's unique structure and properties also make it a candidate for use in materials science, where it could potentially be employed in the development of new materials with specific characteristics or applications.

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 70277-75-7 lithium acetylide 
• 4301-14-8 acetylenemagnesium bromide 
• 1187388-06-2 4-hydroxy-4-(3,4,5-trimethoxyphenyl)but-2-ynoic acid 
• 1066-54-2 trimethylsilylacetylene 
• 65032-27-1 ethynylmagnesium chloride 
• 75-20-7 calcium carbide 
• 1066-26-8 sodium acetylide 

Downstream Products

• 912677-66-8 1,4-bis-(3,4,5-trimethoxy-phenyl)-but-2-yne-1,4-diol 
• 1235527-56-6 ethyl 2-(4-(hydroxy(3,4,5-trimethoxyphenyl)methyl)-1H-1,2,3-triazol-1-yl)acetate 
• 1235527-60-2 (1H-1,2,3-triazol-4-yl)(3,4,5-trimethoxyphenyl)methanol 
• 1235527-84-0 3-(2-((4-(hydroxy(3,4,5-trimethoxyphenyl)methyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-oll 
• 1235527-94-2 3-(4-((4-(hydroxy(3,4,5-trimethoxyphenyl)methyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol 
• 1235527-57-7 (1-benzyl-1H-1,2,3-triazol-4-yl)(3,4,5-trimethoxyphenyl)methanol 
• 1235527-89-5 3-(3-((4-(hydroxy(3,4,5-trimethoxyphenyl)methyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-oll 
• 1612873-43-4 benzyl (E)-1-(3,4,5-trimethoxyphenyl)-3-(dimethyl(phenyl)silyl)allylcarbamate 
• 1612873-29-6 (E)-1-(3,4,5-trimethoxyphenyl)-3-(dimethyl(phenyl)silyl)prop-2-en-1-ol 
• 71277-13-9 3,4,5-trimethoxycinnamaldehyde 

Relevant academic research and scientific papers

Lipase/Oxovanadium Co-Catalyzed Dynamic Kinetic Resolution of Propargyl Alcohols: Competition between Racemization and Rearrangement

Quantitative conversion of racemic propargyl alcohols into optically active propargyl esters with up to 99% ee has been achieved by lipase/oxovanadium co-catalyzed dynamic kinetic resolution, which combines the lipase-catalyzed enantioselective esterification of the racemic substrates and the in situ racemization of the remaining enantiomers. The success is owed to our discovery of a magic solvent, (trifluoromethyl)benzene, that accelerated the racemization while sufficiently suppressing the common oxovanadium-catalyzed rearrangement of propargyl alcohols to irreversibly produce enals.

A bifunctional ligand enables efficient gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids

Terminal allylic alcohols are important motifs in natural products, and also key intermediates/precursors in numerous novel reaction transformations. In this study, enabled by a bifunctional ligand featuring a basic amino group, a gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids has been first established, and efficiently affords various terminal aryl-substituted allylic alcohols with moderate to high yields under mild conditions.

Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry

Steganacin and podophyllotoxin are two naturally occurring lignans first isolated from plant sources, which share the capability to disrupt tubulin assembly. Although not strictly essential for its activity, the lactone ring on both structures represents

Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling

Ball milling of calcium carbide (CaC2) enables the reaction of its ethynyl moiety with organic electrophiles. This was realized simply by co-milling CaC2 with organic substrates in a sealed jar without the need for an additive or a catalyst. Various ketones including those bearing α-hydrogens were ethynylated in good yields at short reaction times. Aryl halides are also amenable substrates for this protocol as they furnish aryl ethynes through a benzyne intermediate. This method offers a practical and cheap alternative to the established procedures for introducing ethynyl functionalities.

Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition

A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).

2,4,6-TRIALKOXYSTRYL ARYL SULFONES, SULFONAMIDES AND CARBOXAMIDES, AND METHODS OF PREPARATION AND USE

Compounds according to Formula (I) are provided and salts thereof, wherein R1, R2, R33, R4, R5, R6, R13, A, X and Y are as defined herein. Methods for preparing compounds of Form

2-Arylaminobenzothiazole-arylpropenone conjugates as tubulin polymerization inhibitors

A new series of 2-arylaminobenzothiazole-arylpropenone conjugates 5-6(a-r) was designed, synthesized and investigated for their cytotoxic potency against the various human cancer cell lines. Most of these conjugates exhibited cytotoxic activity and inhibi

Design and Synthesis of Aminostilbene-Arylpropenones as Tubulin Polymerization Inhibitors

A series of aminostilbene - arylpropenones were designed and synthesized by Michael addition and were investigated for their cytotoxic activity against various human cancer cell lines. Some of the investigated compounds exhibited significant antiproliferative activity against a panel of 60 human cancer cell lines of the US National Cancer Institute, with 50% growth inhibition (GI50) values in the range from 50 value of 50) values ranging from 0.011 to 8.56μM. A cell cycle assay revealed that these compounds arrested the G2/M phase of the cell cycle. Two compounds exhibited strong inhibitory effects on tubulin assembly with IC50 values of 0.71 and 0.79μM. Moreover, dot-blot analysis of cyclinB1 demonstrated that some of the congeners strongly induced cyclinB1 protein levels. Molecular docking studies indicated that these compounds occupy the colchicine binding site of tubulin.

Regioselective solvent-dependent benzannulation of conjugated enynes

The transformation of enynes under cobalt-catalysis leads to symmetrical benzannulation products in dichloromethane. In tetrahydrofuran the cobalt-catalysed reactions afforded the unprecedented unsymmetrical benzannulation products in moderate to good yields and good regioselectivities. In addition, cyclotrimerisation of the alkyne subunit can be realised when electron-deficient enynes are applied in the cobalt-catalysed transformations to generate 1,2,4-trivinylbenzene derivatives using tetrahydrofuran as solvent.

(Z)-1-Aryl-3-arylamino-2-propen-1-ones, highly active stimulators of tubulin polymerization: Synthesis, structure-activity relationship (SAR), tubulin polymerization, and cell growth inhibition studies

Tubulin, the major structural component of microtubules, is a target for the development of anticancer agents. A series of (Z)-1-aryl-3-arylamino-2- propen-1-one (10) were synthesized and evaluated for antiproliferative activity in cell-based assay. The most active compound (Z)-1-(2-bromo-3,4,5- trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)prop-2-en-1-one (10ae) was tested in 20 tumor cell lines including multidrug resistant phenotype and was found to induce apoptosis in all these cell lines with similar GI50 values. Flow cytometry studies showed that 10ae arrested the cells in G2/M phase of cell cycle. In addition to G2/M block, these compounds caused microtubule stabilization like paclitaxel and induced apoptosis via activation of the caspase family. The observations made in this investigation demonstrate that (Z)-1-Aryl-3-arylamino-2-propen-1-one (10) represents a new class of microtubule-stabilizing agents.