Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: tert-Butyl (2-(bromomethyl)phenyl)carbamate, is researched, Molecular C12H16BrNO2, CAS is 166329-43-7, about Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine: Replacement of the Ribose Moiety by Substituted Benzyl Groups.Quality Control of tert-Butyl (2-(bromomethyl)phenyl)carbamate.
4-Nitrobenzylthioinosine (NBTI, 1) is a well-known inhibitor for the nucleoside transport protein ENT1. However, its highly polar nature is unfavorable for oral absorption and/or penetration into the CNS. In the search for compounds with lower polarity than NBTI we replaced its ribose moiety by substituted benzyl groups. Halogen, hydroxyl, (trifluoro)methyl(-oxy), nitro, and amine functionalities were among the substituents at the benzyl group. In general, substitution of the benzyl group resulted in a lower affinity for ENT1. Only 2-hydroxyl substitution showed a higher affinity. Most likely this is the result of hydrogen bonding. Substitution at the 2-position of the benzyl group with aryl groups was also addressed. Compared to parent compound carrying a 2-phenylbenzyl group, all synthesized analogs gave higher affinities. Introduction of fluoro, trifluoromethyl, methoxy, and hydroxyl groups at the Ph group clearly showed that addition to the 4-position was preferable. Despite the highly different character of a ribose and a benzyl group, Ki values in the low nanomolar range were obtained for the benzyl-substituted derivatives Compound LUF5919, and compound LUF5929, displayed the highest affinity (Ki = 39 nM for both compounds), having a polar surface area of 101 Å2 and 85 Å2, resp.
The article 《Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine: Replacement of the Ribose Moiety by Substituted Benzyl Groups》 also mentions many details about this compound(166329-43-7)Quality Control of tert-Butyl (2-(bromomethyl)phenyl)carbamate, you can pay attention to it, because details determine success or failure
Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts