288617-58-3

Upstream product

• 288617-57-2 (E)-4-{4-[2-(N-Ethoxycarbonyl-N-methylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol 
• 97151-02-5 (E)-(+/-)-alpha-Hydroxytamoxifen 
• 501-53-1 benzyl chloroformate 
• 162070-61-3 alpha-Hydroxy-N-desmethyltamoxifen 

Downstream Products

• 743458-11-9 (2-{4-[(E)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1,2-diphenyl-but-1-enyl]-phenoxy}-ethyl)-methyl-carbamic acid benzyl ester 
• 743458-14-2 9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-{(E)-1-methyl-3-[4-(2-methylamino-ethoxy)-phenyl]-2,3-diphenyl-allylamino}-1,9-dihydro-purin-6-one 
• 743458-12-0 {2-[4-((E)-3-Amino-1,2-diphenyl-but-1-enyl)-phenoxy]-ethyl}-methyl-carbamic acid benzyl ester 
• 288617-59-4 (E)-2-Acetoxy-4-{4-[2-(N-benzyloxycarbonyl-N-methylamino)ethoxy]phenyl}-3,4-diphenyl-3-butene 

Relevant academic research and scientific papers

Synthesis of oligodeoxynucleotides containing a single diastereoisomer of α-(N2-2′-deoxyguanosinyl)-N-desmethyltamoxifen

A phosphoramidite chemical synthesis of oligodeoxynucleotides containing a diastereoisomer of (E)-α-(N2-deoxyguanosinyl)-N- desmethyltamoxifen, a major tamoxifen (TAM)-derived DNA adduct in animal and women treated with TAM, was described. The

Identification of tamoxifen-DNA adducts induced by α-acetoxy-N-desmethyltamoxifen

Treatment with tamoxifen increased the risk of endometrial cancers in breast cancer patients and women participating in the chemoprevention study. In our laboratory, tamoxifen-DNA adducts, including α-(N2-deoxyguanosinyl)tamoxifen (dG-N2-TAM), were detected in the endometrium of women taking tamoxifen [Shibutani, S., et al. (1999) Chem. Res. Toxicol. 12, 646-653]. On the basis of recent animal studies, deoxyguanosinyl-N-desmethyltamoxifen (dG-N-desmethylTAM) adducts are also suspected to be formed in the liver. In the study presented here, we synthesized α-acetoxy-N-desmethyltamoxifen as a model activated metabolite of N-desmethyltamoxifen. The overall yield of α-acetoxy-N-desmethyltamoxifen from α-hydroxy-tamoxifen was approximately 42%. α-Acetoxy-N-desmethyltamoxifen was highly reactive to 2'-deoxyguanosine, as was similarly observed for tamoxifen α-sulfate. The two reaction products were identified as a mixture of epimers of the trans form or cis form of α-(N2-deoxyguanosinyl)-N-desmethyltamoxifen (dG-N2-N-desmethylTAM) by mass and proton magnetic resonance spectroscopy. In addition, the trans and cis forms of dG 3'-monophosphate-N2-N-desmethylTAM were prepared as standard markers for 32P-postlabeling/HPLC analysis. Using this technique, dG-N2-N-desmethylTAM adducts were detected in calf thymus DNA reacted with α-acetoxy-N-desmethyltamoxifen.