25533-65-7

Upstream product

• 3943-97-3 methyl 4-hydroxycinnamate 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 94405-68-2 6-[(2S,3S)-2-(4-Methoxy-phenyl)-3-pentafluorophenyloxycarbonyl-2,3-dihydro-benzofuran-5-yl]-8-oxo-1,5,9,13-tetraaza-cycloheptadecane-1-carboxylic acid tert-butyl ester; compound with acetic acid 
• 94405-66-0 6-[(2S,3S)-2-(4-Methoxy-phenyl)-3-pentafluorophenyloxycarbonyl-2,3-dihydro-benzofuran-5-yl]-8-oxo-1,5,9,13-tetraaza-cycloheptadecane-1,13-dicarboxylic acid 1-tert-butyl ester 13-(2,2,2-trichloro-ethyl) ester 
• 94405-64-8 2-[(2S,3S)-3-Methoxycarbonyl-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-4-oxo-3,4,6,7,9,10,11,12,14,15-decahydro-2H,5H-1,4a,8,13-tetraaza-benzocyclotridecene-8,13-dicarboxylic acid 13-tert-butyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 94405-65-9 6-[(2S,3S)-3-Methoxycarbonyl-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-8-oxo-1,5,9,13-tetraaza-cycloheptadecane-1,13-dicarboxylic acid 1-tert-butyl ester 13-(2,2,2-trichloro-ethyl) ester 
• 94405-69-3 C₃₄H₄₆N₄O₆ 
• 64366-67-2 (+/-)-O-methylorantine 
• 94405-75-1 (2S,3S)-5-(2-Amino-2-methoxycarbonyl-ethyl)-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester 
• 94405-63-7 (2S,3S)-5-(1-Amino-2-methoxycarbonyl-ethyl)-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester 
• 94405-60-4 (2S,3S)-5-((E)-2-Methoxycarbonyl-vinyl)-2-(4-methoxy-phenyl)-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization

A series of 19 related dihydrobenzofuran lignans and benzofurans was obtained by a biomimetic reaction sequence involving oxidative dimerization of p-coumaric, caffeic, or ferulic acid methyl esters, followed by derivatization reactions. All compounds were evaluated for potential anticancer activity in an in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Leukemia and breast cancer cell lines were relatively more sensitive to these agents than were the other cell lines. Compounds 2c and 2d, but especially 2b (methyl (E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3- methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate), the dimerization product of caffeic acid methyl ester, containing a 3',4'-dihydroxyphenyl moiety and a hydroxyl group in position 7 of the dihydrobenzofuran ring, showed promising activity. The average GI50 value (the molar drug concentration required for 50% growth inhibition) of 2b was 0.3 μM. Against three breast cancer cell lines, 2b had a GI50 value of 3-side chain, reduction of the methoxycarbonyl functionalities to primary alcohols, or oxidation of the dihydrobenzofuran ring to a benzofuran system resulted in a decrease or loss of cytotoxic activity. Compound 2b inhibited mitosis at micromolar concentrations in cell culture through a relatively weak interaction at the colchicine binding site of tubulin. In vitro it inhibited tubulin polymerization by 50% at a concentration of 13 ± 1 μM. The 2R,3R-enantiomer of 2b was twice as active as the racemic mixture, while the 2S,3S- enantiomer had minimal activity as an inhibitor of tubulin polymerization. These dihydrobenzofuran lignans (2-phenyl- dihydrobenzofuran derivatives) constitute a new group of antimitotic and potential antitumor agents that inhibit tubulin polymerization.

PHENOLIC DIHYDROBENZOFURANE DERIVATIVES, MEDICAL AND COSMETIC PREPARATIONS CONTAINING THESE DERIVATIVES, AND USE THEREOF

The invention relates to novel dihydrobenzofurane derivatives and their use as cosmetics and medicaments. These compounds possess antibacterial, anti-inflammatory and antioxidative properties. The invention relates also to compositions, preferably antibac

(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis

Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.

Detailed 1H and 13C NMR spectral data assignment for two dihydrobenzofuran neolignans

In this work we present a complete proton (1H) and carbon 13(13C) nuclear magnetic resonance (NMR) spectral analysis of two synthetic dihydrofuran neolignans (±)-trans-dehydrodicoumarate dimethyl ester and (±)-trans-dehydrodiferulate

The Relative Configuration of Grossamide and Hordatines

The phenyl group at C-7 of grossamide (1) was determined by PMR spectra to be situated in a trans relationship to the carbonyl group at C-8.It was elucidated that the hordatines (3a, 4a) also have a trans configuration.