15658-10-3

Upstream product

• 19438-10-9 methyl 3-hydroxybenzoate 
• 591-51-5 phenyllithium 
• 108-86-1 bromobenzene 

Downstream Products

• 168007-26-9 C₂₀H₁₈O₂ 
• 1004999-67-0 C₃₈H₃₀O₃ 
• 1357108-06-5 (2R)-2-amino-3-(((3-hydroxyphenyl)(diphenyl)methyl)sulfanyl)propanoic acid 
• 111500-13-1 3-Hydroxy-trityl 
• 108368-64-5 3-(α-chloro-benzhydryl)-phenol 
• 86137-90-8 Octanedioic acid bis-[3-(chloro-diphenyl-methyl)-phenyl] ester 
• 84868-54-2 (3-hydroxyphenyl)diphenylmethane 

Relevant academic research and scientific papers

Triphenylbutanamines: Kinesin spindle protein inhibitors with in vivo antitumor activity

The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-l-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit Kiapp ≥ 10 nM and GI50 ≈ 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

Chemistry of photogenerated α-phenyl-substituted o-, m-, and p-quinone methides from phenol derivatives in aqueous solution

The enhanced photochemical reactivity of o-substituted phenols in its propensity to give o-quinone methide (o-QM) intermediates via excited state intramolecular proton transfer (ESIPT) was uncovered by Keith Yates as part of his now classic studies of photohydration of aromatic alkenes, alkynes, and related compounds. Photogeneration of QMs and the study of their chemistry along with potential biological applications are the focus of many groups. In this work, photochemical precursors to o-, m-, and p-QMs based on substituted phenols (hydroxybenzyl alcohols) and related compounds have been studied in aqueous solution as a function of pH and water content. The focus will be on QMs that are stabilized by an a-phenyl substituent, which enhances quantum yields for their formation, with the resulting QMs having longer lifetimes and easier to detect. Noteworthy is that all QM isomers can. be photogenerated with the o and m isomers being the most efficient, consistent with the Zimmerman "ortho-meta" effect. m-QMs have formal non-Kekule structures, and although they can be routinely photogenerated, are found to be most reactive. One m-QM was found, to undergo a photocondensation reaction at high pH giving rise to m-substituted oligomers. The mechanism, of QM formation in aqueous solution is believed to involve singlet excited phenols that undergo adiabatic deprotonation to give the corresponding photoexcited phenolate ion, which subsequently expels the hydroxide ion (photodehydroxylation). A pathway involving direct loss of water for the o-isomers is also possible in organic solvents.