97465-82-2

Upstream product

• 458-35-5 coniferal alcohol 
• 33050-60-1 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one 
• 109792-90-7 (7S,8R)-4,9′-di-β-D-glucopyranosyloxydehydrodiconiferyl alcohol 
• 184046-40-0 (7'E)-(7S,8R)-4-hydroxy-3,5'-dimethoxy-4',7-epoxy-8,3'-neolig-7'-en-9,9'-diyil diacetate 
• 3929-47-3 3-(3,4-dimethoxyphenyl)-1-propanol 
• 90-05-1 2-methoxy-phenol 
• 215227-91-1 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2S,3R)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester 
• 215227-86-4 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2S,3R)-7-methoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 215227-96-6 (E)-3-[(2S,3R)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3'-methoxy-4'-methoxymethoxyphenyl)-1-benzo[b]furan-5-yl]-2-propenal 
• 118799-85-2 (E)-3-[(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl]-2-propenal 
• 208341-82-6 (S)-2-{[(2S,3S)-5-[(E)-2-((S)-1-Ethoxycarbonyl-ethylcarbamoyl)-vinyl]-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-2,3-dihydro-benzofuran-3-carbonyl]-amino}-propionic acid ethyl ester 
• 180579-78-6 trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid 
• 208341-80-4 (E)-N-(feruloyl)-L-alanine ethyl ester 

Downstream Products

• 118916-57-7 (E)-3-[2-(4-Hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo[b]furan-5-yl]-2-propenal 
• 215228-14-1 hierochin B 
• 14049-57-1 2α,3β-7-O-methylcedrusin 
• 168751-78-8 dihydrodehydrodiconiferyl alcohol triacetate 
• 5234-70-8 tetrahydrodehydrodiconiferyl alcohol 

Relevant academic research and scientific papers

Chemical constituents of Brazilian propolis and their cytotoxic activities

The EtOAc-soluble fraction of the MeOH extract of propalia afforded a new prenylated chromane derivative, 3-hydroxy-2,2-dimethyl-8-prenylchromane- 6-propenoic acid (1), along with 22 known compounds, 2-23. Of the known compounds, 4, 7, 12-19, and 22 were isolated for the first time from propolis, and the absolute configuration of 23 was established as (2S,3R). Investigation suggested that Baccharis spp. are a significant source of tropical Brazilian propalia, in addition to Clusia minor, Clusia major, and Araucaria heterophylla. All the compounds were tested for their cytotoxicity toward human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Among these compounds, 9 and 19-21 showed potent cytotoxicity, having ED50 values equal to or less than 10 μg/mL.

(±)-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.

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

Low molecular weight lignin suppresses activation of NF-κB and HIV-1 promoter

Human immunodeficiency virus type 1 (HIV-1) is a cytopathic retrovirus and the primary etiological agent of acquired immunodeficiency syndrome (AIDS) and related disorders. In cells chronically infected with HIV-1, nuclear factor-κB (NF-κB) activation by external stimuli such as tumor necrosis factor α (TNFα) augments replication of HIV-1. NF-κB involves in many diseases such as inflammation, cancer, and Crohn's disease. In this paper, we exhibit that (i) HIV-1gene expression was inhibited by lignin, (ii) fraction of small molecular mass in HBS lignin (less than 0.5 kDa) had stronger inhibitory effects than large molecular mass (more than 1.3 kDa), (iii) lignin also inhibited activation of NF-κB induced by TNFα, (iv) among six lignin dimer-like compounds, compound 6 containing β-5 bond has more potent inhibitory activity than compounds 1, 2, 3, 4 and 5, which contain β-1, β-O-4, 5-5, or β-β structural units. These results suggested that small molecules of lignin inhibit HIV-1 replication through suppression of HIV-1 transcription from LTR including activation via NF-κB. Low molecular lignin may be a beneficial material or drug leads as a new class for AIDS and NF-κB-related diseases.

Asymmetric biomimetic oxidations of phenols using oxazolidines as chiral auxiliaries: The enantioselective synthesis of (+)- and (-)-dehydrodiconiferyl alcohol

Stereoselective bimolecular radical coupling reactions of phenylpropenoid phenols are described. Evans's 2-oxazolidinone 11a-d derivatives of ferulic acid were prepared and oxidized to give dimeric benzofuran neolignan structures 12-13a-d in 40-50% overal

Stereoselective synthesis of the neolignan, (+ )-dehydrodiconiferyl alcohol.

A stereo controlled synthesis of the biologically active neolignan, (+)-dehydrodiconiferyl alcohol (1) was achieved. This synthetic method was also efficient for preparing its enantiomer and other derivatives with biological activity.

Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of dehydrodiconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA)

Stereoselective bimolecular radical coupling of enantiopure phenylpropenoidic phenols are described, starting from enantiopure amidic derivatives of ferulic acid. The latter were prepared from ferulic acid by reaction with (S)-alanine or Oppolzer camphor sultam. The oxidation step was performed both enzymatically (HRP/H2O2) and chemically (Ag2O). The observed enantioselectivity in the oxidation step encompasses the range 65-84% and is consistent with the conformational analysis of the quinone methide intermediates at the PM3 level.

Synthesis and structural elucidation of xanthonolignoids: Trans-(±)- kielcorin B and trans-(±)-isokielcorin B

This paper reports the synthesis and characterization of two isomeric xanthonolignoids - trans-(±)-kielcorin B and trans-(±)isokielcorin B. The synthetic approach is based on the oxidative coupling of 2,3-dihydroxy-4- methoxyxanthone with coniferyl alcohol in the presence of silver carbonate. The structural elucidation of these compounds was achieved by extensive NMR studies: 1H and 13C NMR spectra, homonuclear correlation spectroscopy (COSY, COSYLR), heteronuclear correlation spectroscopy (HETCOR), nuclear Overhauser effect (NOE) and one-dimensional selective INEPT. The NMR spectroscopic techniques used in this study led to an unambiguous characterisation of trans-(±)-kielcorin B and trans-(±)-isokielcorin B, which includes the assignment of all proton and carbon resonances and the establishment of the substituents orientation and protons configurational relationship on their 1,4-dioxane ring.

Enantioselective synthesis of a benzofuranic neolignan by oxidative coupling

The first stereoselective free radical coupling of a phenylpropenoidic phenolic compound is reported. The oxidation of a chiral ferulic acid amide to give dimeric benzofuranic neolignan is performed enzymatically using horseradish peroxidase as the catalyst. Enantiomeric excess in a biologically active compound with phenylcoumaran skeleton (β-5 dimer) is thus obtained.

On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton

Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI2 inducer (2), dehydrodiconiferyl alcohol-4-β-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methylcedrusin (5) have been unambiguously established.