115237-06-4

Upstream product

• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 6751-75-3 2-bromoresorcinol 
• 100-39-0 benzyl bromide 

Downstream Products

• 57303-99-8 7,8-Dihydroxybenzo[a]pyrene 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 63323-30-8 (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 65199-11-3 benzo[a]pyren-7,8-dione 
• 13345-26-1 7-hydroxy benzopyrene 

Relevant academic research and scientific papers

Facile and divergent optimization of chromazonarol enabled the identification of simplified drimane meroterpenoids as novel pharmaceutical leads

The diversity of drimane hydroquinones was significantly expanded by the facile construction of (+)-chromazonarol relevant natural products, isomers, and analogues for the discovery of new pharmaceutical leads. The structure-activity relationship of (+)-c

KV3 MODULATORS

A compound of formula (I) and related aspects.

NOVEL COMPOUNDS

A compound of formula (I): (Formula (I)) and related aspects.

Enantiopure Chiral Concave 1,10-Phenanthrolines

Chiral information has been introduced into concave 1,10-phenanthrolines of different ring sizes by using a 2,7-disubstituted naphthalene bridgehead, which causes axial chirality. A tetraphenolic 2-(dihydroxynaphthyl)-9-(dihydroxyphenyl)-1,10-phenanthroline was synthesized as a key intermediate. Two strategies were followed to obtain the bimacrocyclic chiral concave 1,10-phenanthrolines: quadruple Williamson ether synthesis or alkenylation of the OH groups and subsequent ring-closing metathesis followed by hydrogenation. The overall yields of bimacrocyles 19 were 10 to 17 % starting from the respective Suzuki coupling of the substituted arenes 11 and 13 to 2,9-dichloro-1,10-phenanthroline (5). Racemic mixtures of the three concave 1,10-phenanthrolines 19 were separated by using chiral high-performance liquid chromatography (HPLC) techniques, and their absolute stereochemistry was assigned by comparison of simulated and experimental circular dichroism (CD) spectra. The enantiopure concave 1,10-phenanthrolines were used as ligands in a copper-catalysed cyclopropanation, and their selectivity was determined by chiral gas chromatography (GC).

Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene

Polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BaP), are ubiquitous environmental contaminants that are implicated in causing lung cancer. BaP is a component of tobacco smoke that is transformed enzymatically to active forms that interact with DNA. We reported previously development of a sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the complete set of its 13C4-labelled oxidized metabolites needed as internal standards They include the metabolites not involved in carcinogenesis (Group A) and the metabolites implicated in initiation of cancer (Group B). The synthetic approach is novel, entailing use of Pd-catalyzed Suzuki, Sonogashira, and Hartwig cross-coupling reactions combined with PtCl2-catalyzed cyclization of acetylenic compounds. This synthetic method requires fewer steps, employs milder conditions, and product isolation is simpler than conventional methods of PAH synthesis. The syntheses of 13C4-BaP and 13C4-BaP-8-ol each require only four steps, and the 13C-atoms are all introduced in a single step. 13C4-BaP-8-ol serves as the synthetic precursor of all the oxidized metabolites of 13C-BaP implicated in initiation of cancer. The isotopic purities of the synthetic 13C 4-BaP metabolites were estimated to be ≥99.9%.