114085-80-2

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 19523-08-1 1-(3,4,5-trimethoxyphenyl)pentan-1-ol 
• 1448644-06-1 2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborinane 
• 120-92-3 cyclopentanone 
• 3044-56-2 ethyl trimethoxybenzoyl acetate 
• 118-41-2 Eudesmic acid 

Downstream Products

• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 1202071-81-5 (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 114085-79-9 1-n-pentyl-3,4,5-trimethoxybenzene 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling of simple ketones via activation of unstrained carbon-carbon bonds

Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition.

Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

[3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn(OAc)3 mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 μM, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 μM. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin.

Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.

Propenone derivatives

The present invention relates to propenone derivatives represented by the following formula (I): STR1 wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR5 (wherein Y represents S or O; and R5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R2 and R3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R2 and R3 are combined to form substituted or unsubstituted methylene or ethylene; R4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.

A New Synthesis of 1-n-Alkyl-3,5-dimethoxybenzenes (Olivetol Dimethyl Ether and Homologs)

An efficient method is reported for the synthesis of 1-n-alkyl-3,5-dimethoxybenzenes, useful intermediates in the synthesis of cannabinoids, from the readily available and cheap 3,4,5-trimethoxybenzoic acid.The key step is the electron-transfer induced highly regioselective demethoxylation of 1-n-alkyl-3,4,5-trimethoxybenzenes.

Regioselective 4-Demethoxylation of 1-n-Alkyl-3,4,5-trimethoxybenzenes: a Key Step in the Synthesis of Olivetol and its Homologues

Selective removal of the 4-methoxy group in n-alkyl-3,4,5-trimethoxybenzenes was performed under electron-transfer conditions; a new synthesis of olivetol dimethyl ether is described.