• Bulletin of the Korean Chemical Society
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• v.31 no.8
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• pp.2399-2401
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• 2010

• Macromolecular Research
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• v.16 no.3
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• pp.238-246
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• 2008

A new strategy using protection-deprotection chemistry was used to prepare branched polymers using the ATRP method only. Among the several monomers with different protecting groups, vinyl benzyl t-butyloxy carbonate (VBt-BOC) and 4-methyl styrene (4-MeSt) could be polymerized successfully to form backbones using the ATRP method in a controlled fashion. The protected groups in the backbones were converted to alkyl bromides and used as initiating sites for branch formation. The benzyl t-butyloxy carbonate groups in the backbones containing VBt-BOC units were first deprotected to benzyl alcohol by trifluoroacetic acid, then converted to benzyl bromide by reacting them with triphenylphosphine/carbon tetrabromide. The benzyl bromide groups in the backbones containing 4-MeSt units could be generated by bromination of the methyl groups using N-bromosuccinimide/benzoyl peroxide. The structures of the prepared polymers were well-controlled, as evidenced by the controlled molecular weight as well as the narrow and unimodal molecular weight distribution.

• The Journal of Natural Sciences
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• v.7
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• pp.165-167
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• 1995

3'-Methylamino pyrimidine 3 was prepared from deoxy pyrimidine via the following 8 step reaction sequences; silyl protection, mesylation, cyclization, azide substitution, hydrogenation, t-Boc protection, methylation, and deprotection in 23% overall yield as a potential anti-AIDS agents.

• Bulletin of the Korean Chemical Society
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• v.34 no.1
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• pp.174-178
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• 2013

A highly reliable dealkylation protocol of alkyl aryl ethers, whose alkyl groups are longer than methyl group, has been developed. We report that various ethyl, n-propyl, and benzyl aryl ethers are successfully cleaved using an ionic liquid, 1-n-butyl-3-methylimidazolium bromide, [bmim][Br], under microwave irradiation. Despite many characteristics such as lower cost and less toxicity of the alkylating agents, and greater hydrophobicity of the products, longer alkyl ethers have been significantly less exploited than methyl ethers, probably due to more difficulty in the deprotection step. Since it has the same advantages as the demethylation method developed by this group including mild conditions, short reaction time, and small use of the ionic liquids, the dealkylation protocol can greatly encourage the broader use of longer alkyl groups in the protection of phenolic groups. As with our previous study of demethylation using [bmim][Br], the microwave irradiation is crucial for the deprotection of longer alkyl aryl ethers. Unlike the conventional heating, which causes either low conversion or decomposition, the microwave irradiation seems to more effectively provide energy to cleave the ether bonds and therefore suppresses the undesired reactions.

• Archives of Pharmacal Research
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• v.25 no.5
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• pp.585-589
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• 2002

Three hairpin polyamides were designed and synthesized by a haloform reaction and DCC/HOBt coupling reaction without amino protection and deprotection. Their anticancer activity were investigated with three kinds of cell lines-hepatic carcinoma, lung carcinoma and gastric carcinoma, and the values of $IC_{50}$ were at range of $10^{-7}~10^{-8}M$.

• Bulletin of the Korean Chemical Society
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• v.32 no.3
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• pp.1000-1006
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• 2011

The discovery of carbohydrate-based bioactive compounds has recently received considerable interest in the drug development. This paper stresses on the application of 1-methoxy-O-glucoside as the central scaffold, whereas salicylic pharmacophores were introduced with diverse spatial orientations probing into the structural preference of an enzymatic target, i.e. protein tyrosine phosphatase 1B (PTP1B). By employing regioselective protection and deprotection strategy, 2,6-, 3,4-, 4,6- and 2,3-di-O-propynyl 1-methoxy-O-glucosides were previously synthesized and then coupled with azido salicylate via click chemistry in forming the desired bidentate salicylic glucosides with high yields. The inhibitory assay of the obtained triazolyl derivatives leads to the identification of the 2,3-disubstituted salicylic 1-methoxy-O-glucoside as the structurally privileged PTP1B inhibitor among this bidentate compound series with micromole-ranged $IC_{50}$ value and reasonable selectivity over other homologous PTPs tested. In addition, docking simulation was conducted to propose a plausible binding mode of this authorized inhibitor with PTP1B. This research might furnish new insight toward the construction of structurally different bioactive compounds based on the monosaccharide scaffold.