THE DISSOCIATION OF HEXAARYLETHANES. XIII. HALOGEN SUBSTITUENTS<sup>1</sup>

Marvel, C. S.; Dietz, Frederick C.; Himel, Chester M.

doi:10.1021/jo01198a014

Cited by 5 publications

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“…Condensation of Ph 2 C(aryl or alkyl)OH (aryl = 4-(cyclohexyl)-Ph, 4-(Ph)-Ph, 4-( tert -Bu)-Ph, 4-( n -Bu)-Ph, 4-( i -Pr)-Ph, 4-( n -Pr)-Ph, 4-(CF 3 )-Ph, 4-(Et)-Ph, 4-(MeS)-Ph, 4-I-Ph, or alkyl = butan-2-yl, pentan-3-yl) 3 − 12 and 31 − 32 with l -cysteine ( 13 ) in the presence of BF 3 ·Et 2 O afforded target compounds 14 − 23 and 33 − 34 in 20−40% yield (Scheme ). , Starting alcohols 3 − 12 and 31 − 32 were prepared, according to the literature, in 49−95% yield by addition of phenylmagnesium bromide to the corresponding ester (data not shown). N , N -Dimethylation of STLC ( 1 ) was performed in the presence of formaldehyde and sodium triacetoxyborohydride to give 37 in 19% yield (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

“…(13) in the presence of BF 3 3 Et 2 O afforded target compounds 14-23 and 33-34 in 20-40% yield (Scheme 1). 18,19 Starting alcohols 3-12 and 31-32 were prepared, according to the literature, 20 in 49-95% yield by addition of phenylmagnesium bromide to the corresponding ester (data not shown). N,N-Dimethylation of STLC (1) was performed in the presence of formaldehyde and sodium triacetoxyborohydride to give 37 in 19% yield (Scheme 1).…”

Section: ' Introductionmentioning

confidence: 99%

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Structure−Activity Relationship and Multidrug Resistance Study of New S-trityl-l-Cysteine Derivatives As Inhibitors of Eg5

et al. 2011

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The mitotic spindle is a validated target for cancer chemotherapy. Drugs such as taxanes and vinca alkaloids specifically target microtubules and cause the mitotic spindle to collapse. However, toxicity and resistance are problems associated with these drugs. Thus, alternative approaches to inhibiting the mitotic spindle are being pursued. These include targeting Eg5, a human kinesin involved in the formation of the bipolar spindle. We previously identified S-trityl-L-cysteine (STLC) as a potent allosteric inhibitor of Eg5. Here, we report the synthesis of a new series of STLC-like compounds with in vitro inhibition in the low nanomolar range. We also performed a multidrug resistance study in cell lines overexpressing P-glycoprotein and showed that some of these inhibitors may have the potential to overcome susceptibility to this efflux pump. Finally, we performed molecular docking of the compounds and determined the structures of two Eg5-inhibitor complexes to explain the structure-activity relationship of these compounds.

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Section: Resultsmentioning

confidence: 99%