• Bulletin of the Korean Chemical Society
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• v.5 no.6
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• pp.226-230
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• 1984

LIS's of cis and trans-methyl-2-phenylcyclopropanecarboxylate, cis and trans-t-butyl-2-phenylcyclopropanecarboxylate, cis and trans-N,N-dimethylcyclopropanecarboxamide, trans-2-phenylcyclopropyl methyl ketone and trans-2-phenylcyclopropyl t-butyl ketone have been studied. The LIS's hold the McConnell-Robertson relation and are mainly influenced by the steric effect. LIS's of trans isomers are larger than those of cis isomers. In trans isomers, the LIS's decrease in the following order: methyl ketone > methyl ester > N,N-dimethyl amide > t-butyl ketone${\sim}$t-butyl ester.

• Archives of Pharmacal Research
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• v.23 no.6
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• pp.564-567
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• 2000

The use of amino acid derivatives as building blocks in peptide synthesis is increasingly being recognized as a potential route for the development of pharmaceutical agents. Side chain protection of polyfunctional amino acids such as Ser, Thr, Tyr is viewed as being particularly important. Although these derivatives are commercially listed, they are expensive and not widely available. We describe here a practical large-scale synthesis of t-butyl introduced D-serine, one of the building blocks of zoladex, a peptide drug.

• Journal of the Korean Chemical Society
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• v.19 no.5
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• pp.367-374
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• 1975

Glycine residue in N-X-glycylphenylalanine methyl ester(X = trifluoroacetyl or acetyl) was converted into aspartic acid derivative by a photoalkylation reaction. The reaction was induced with 350 nm lamp using a combination of diacetyl/di-t-butyl peroxide (DBP) as the photoinitiator, and acetic anhydride as the alkylating agent. In the thermal reaction with DBP and acetic anhydride, the same alkylation reaction of the dipeptide was observed. From this thermal alkylation reaction the photoalkylation reaction is also thought to undergo via free radical mechanism.

• Korean Journal of Weed Science
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• v.17 no.2
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• pp.192-198
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• 1997

This experiment was carried out to determine selectivity of herbicide cyhalofop-butyl ester on enzyme activity, biosynthesis of fatty acid and protein between rice and Echinochloa crus-galli. Activity of the acetyl-CoA carboxylase(ACCase) was inhibited greater in E. crus-galli than in rice by the treatment of cyhalofop-butyl ester. The ACCase activity in E. crus-galli was observed with $I_{50}$ at 1-2ppm of cyhalofop-butyl ester, while in rice only at above 10ppm. Cyhalofop-butyl ester also inhibited the biosynthesis of fatty acid by 61% of palmitic acid, 54% of linoleic acid and 41% of linolenic acid in E. crux-galli. In contrast, no significant difference of fatty acid content was observed in rice at 5DAT as compared with the untreated control. Protein patterns of rice between the herbicide treatment and the untreated control were not significantly different, but in E. crus-galli, 3 protein spots were disappeared in between 29KD and 45KD.

• Archives of Pharmacal Research
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• v.28 no.10
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• pp.1111-1113
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• 2005

5-Aminolevulinic acid and its derivatives, which are known to affect the early diagnosis and treatment of cancer, have been synthesized. Simple methods for the synthesis of 5-aminole-vulinic acid (ALA), a precursor of porphyrins, have been developed in our laboratory for use in studies on the biosynthesis of porphyrins.

• YAKHAK HOEJI
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• v.50 no.5
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• pp.326-331
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• 2006

We designed and synthesized new benzylpiperidinyl ether derivatives as beta-amyloid aggregation inhibitors for the development of novel anti-Alzheimer's disease agents. As starting material, 4-hydroxypiperidine was used. For protection of the amine group in piperidine (2), di-tert-butyl dicarbonate was reacted with 4-hydroxypiperidine in the presence of triethylamine. For introduction of benzyl group, benzylbromide was treated with compound 2 in dioxane. After deprotection of Boc group on amine in compound 3, ester (5) was synthesized by addition of ethyl-4-chlorobutyrate. The alcohol 6 was synthesized by hydride reduction of 5 using $LiAlH_4$. To obtain final products (7-14), the alcohol 6 was condensed with each of substituted benzoic acids. To screen beta-amyloid aggregation inhibition of the products, thioflavinT assay was performed using $A{\beta}1-42\;at\;37^{\circ}C$ for 26 h incubation, in vitro. From the result of screening, compound 8, 9, 11 and 12 showed effective activity about $65{\sim}85\;{\mu}M\;as\;IC_{50}$ value. Among the prepared compounds, 4-[4-(benzyloxy)piperidino]butyl-4-chlorobenzoate (8) was the most effective inhibitor having $IC_{50}\;of\;65.4{\mu}M$.

• Journal of the Korean Chemical Society
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• v.48 no.2
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• pp.161-170
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• 2004

A series of ${\gamma}$-aminobutyric acid-derived, potent human cytosolic phospholipase A$_2$ inhibitors have been prepared from acyl cyanophosphoranes and amine derivatives in a convergent manner. The ${\alpha}$-keto amide functionalities in the inhibitors have been introduced as electrophilic fragments via direct coupling reactions between the labile ${\alpha},{\beta}$-diketo nitriles and ${\gamma}$-aminobutyric acid t-butyl ester derivatives at -78 $^{\circ}C$ in moderate to good yields.

• The Korean Journal of Pesticide Science
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• v.8 no.4
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• pp.258-264
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• 2004

The pyrazole family was discovered as effective insecticides/acaricides, and fenpyroximate and tebufenpyrad were introduced in the market. In this study, new series of pyrazole oxime ethers were designed and synthesized. The pyrazolone 1 was prepared by the condensation of ethyl acetoacetate with methylhydrazine, and then subsequently subjected to the Vilsmeier-Haack chloroformylation yielding 4-formyl-5-chloro-pyrazole 2. The nucleophilic aromatic substitution of 2 generally allowed the introduction of a wide range of heterocycles into the pyrazole ring. The resulting pyrazole aldehydes 3a-i were readily converted to the corresponding pyrazole oxime derivatives 4a-i, and subsequently to 5-substituted pyrazole oxime ether derivatives 6a-i. The screening assay results clearly show that the activities of 6d were comparable to those of fenpyroximate (6a) against BPH, DBM, and TSSM. It indicates that 6d has a potential to be developed as an insecticidal agent.

• Journal of Life Science
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• v.32 no.3
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• pp.210-221
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• 2022

This study investigated the mechanisms underlying the anti-cancer effects of non-steroidal anti-inflammatory drugs (NSAIDs) in human cancer cells in combination with either N-[N-(3, 5-difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester (DAPT), a γ-secretase inhibitor, or MHY2245, a new synthetic sirtuin 1 inhibitor. The results showed both DAPT and MHY2245 as novel chemosensitizers of human colon cancer KM12 and human hepatocellular carcinoma SNU475 cells to NSAIDs involving celecoxib and 2, 5-dimethyl celecoxib. The NSAID-induced cytotoxicity of these cells was significantly increased by DAPT and MHY2245 in a cyclooxygenase-2 independent manner. In addition, DAPT and MHY2245 reduced levels of p62, Notch1 intracellular domain, and multiple cancer stemness (CS)-related markers including Notch1, CD44, CD133, octamer-binding transcription factor 4, mutated p53 and c-Myc. However, the level of activating transcription factor 4 (ATF4) was enhanced, probably indicating the down-regulation of multiple CS-related markers by DAPT or MHY2245-mediated autophagy induction. Moreover, the NSAID-mediated reduction of p62/nuclear factor erythroid-derived 2-like 2 and CS-related marker proteins and the up-regulation of C/EBP homologous protein (CHOP)/ATF4 were accelerated by DAPT and MHY2245. As such, the combination of NSAID and either DAPT or MHY2245 resulted in higher cytotoxicity than NSAID alone by accelerating the down-regulation of multiple CS-related markers and PARP activation, indicating that both inhibitors promote NSAID-mediated autophagic cell death, possibly through the CHOP/ATF4 pathway. In conclusion, either combination strategy may be useful for the effective treatment of human cancer cells expressing CS-related markers.