41744-29-0

Upstream product

• 917-54-4 methyllithium 
• 489422-95-9 3-bromo-2-(3,4-dimethoxyphenyl)-5-(prop-1-enyl)benzo[b]furan 
• 186581-53-3 diazomethane 
• 41744-28-9 eupomatenoid-5 
• 489422-89-1 3,5-dibromo-2-(3,4-dimethoxyphenyl)benzo[b]furan 
• 2859-78-1 4-Bromoveratrole 
• 568593-05-5 2,3,5-tribromo-2,3-dihydrobenzofuran 
• 64150-67-0 2,3,5-tribromobenzofuran 
• 99660-97-6 dibromo-3,5 benzofuranne 
• 23145-07-5 5-bromobenzofuran 
• 86253-64-7 2-(1-bromoethyl)-4-(1-bromopropyl)phenyl 3,4-dimethoxybenzoate 

Relevant academic research and scientific papers

Activity of neolignans isolated from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck against Trypanosoma cruzi

The in vitro antiproliferative effects of 4 neolignans purified from the ethyl-acetate extract from leaves of Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck against Trypanosoma cruzi were investigated. These isolated compounds were identified through spectral analyses of UV, EI-MS, 1H-, 13C-NMR, H-H COSY, gNOE, HETCOR, and HMBC. The compounds eupomatenoid-5, eupomatenoid-6, and conocarpan showed considerable activity against epimastigote forms of T. cruzi, with 50% inhibition concentrations (IC50) of 7.0, 7.5, and 8.0 μg/ml respectively. After methylation, these compounds showed a lessened inhibitory activity to the growth of the protozoan, suggesting that loss of the hydroxyl group from their molecules reduces the activity. The compound eupomatenoid-3 showed lower activity than the hexane fraction. Eupomatenoid-5 was significantly more active than benznidazole, the antiparasitic drug of choice for treatment of Chagas' disease. The crude extract, hexane fraction, and eupomatenoid-5 caused no lysis in sheep blood at concentrations which inhibit the growth of epimastigote forms. The compound eupomatenoid-5 showed low cytotoxic effects against Vero cells. These results provide new perspectives on the development of novel drugs obtained from natural products with trypanocidal activity. However, the extracts and active compound isolated from P. regnellii var. pallescens should be further studied in animal models for in vivo efficacy.

Regioselective C-C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans. Total syntheses of eupomatenoids 3, 4, 5, 6, and 15

Regioselective C-C-bond formation reactions at 2,3-dibromobenzofuran (1) and 2,3,5-tribromobenzofuran (6) were studied. Pd-catalyzed Sonogashira and Negishi cross-coupling occurred with perfect regioselectivity at carbon atom C-2 to provide 2-substituted 3-bromobenzofurans (12, 14) and 3,5-dibromobenzofurans (17, 18) in 50-91% yield. A regioselective displacement of the bromine substituents in 3,5-dibromobenzofurans 18 was achieved by a halogen-metal exchange reaction at carbon atom C-3 and by a Nicatalyzed Kumada cross-coupling at C-5. The methodology was applied to the synthesis of eupomatenoids 3, 4, 5, 6, and 15 (5). The synthesis of these compounds was achieved in overall yields of up to 60%.

Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions

Six different eupomatenoids (1a-c, 1f-h) were prepared from 2,3,5-tribromobenzofuran (2) in a concise and high-yielding synthetic sequence. The overall yields vary between 29 and 60% over four to six steps. Key to the success of the syntheses is the high

Natural Benzofuranes. Synthesis of Eupomatenoids-1, -3, -4, -5, -6, -7, and -13

A group of eupomatenoids, natural lignans possessing 2-aryl-3-methyl-5-propenylbenzofuran structures have been synthesized by short pathways which include the intramolecular Wittig reaction of an o-bromoethylaryl benzoate ester as a key step.