• Journal of the Society of Cosmetic Scientists of Korea
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• v.31 no.1 s.49
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• pp.91-96
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• 2005

Holographic quantitative structure-toxicity relationships (HQSTR) of alkyl-3,4-dihydroxybenzoate (A) and N-alkyl-3,4-dihydroxybenzamide (B) derivatives were analyzed and discussed. The HQSTR model X for the skin sensitivity showed the best predictability based on the cross-validated $r^2_{cv}.$ ($q^2 = 0.744$), non cross-validated, and conventional coefficient ($r^2_{ncv}.$=0.978). The relationships between melanogenesis inhibitory activities and skin sensitization of compounds have a tendency to a reciprocal proportion. Therefore, the more higher melanogenesis inhibitory activities of compounds were, the more lower skin sensitization of compounds became. The side chain, C1 ${\~}$ C3 part of R1-substituents in (A) and (B) did not exhibit any contribution to skin sensitization. Particularly, it is reveals that the skin sensitization of ester (A) were slightly lower (A < B) than that of amide (B) and melanogenesis Inhibitory activities of (A) were slightly higher (A > B) than that of (B). It is founded that the alkyl-3,4-dihydroxybenzoate derivatives (A) were an ideal compound as an ingredient of whitening agents.

• YAKHAK HOEJI
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• v.20 no.1
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• pp.19-26
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• 1976

Sixteen compounds of 2-aminobenzothiazole derivatives were synthesized from alkyl ($C_{1-5}$) p-aminosalicylate by thiocyanation reaction. The NMR spectra of synthesized compounds showed that they were actually mixture of 5-hydroxy-6-alk-oxycarbonyl-2-aminobenzothiazole [alkoxy=methoxy(Ia), ethoxy (IIa), n-propoxy (IIIa), iso-propoxy (IVa), n-butoxy (Va), iso-butoxy (VIa), n-amoxy (VIIa), iso-amoxy(VIIIa)] and 7-(1b), ethoxy(IIb), n-propoxy(IIIb), iso-propoxy(IVb), n-butoxy(Vb), iso-butpxy (VIb), n-amoxy (VIIb), iso-amoxy (VIIIb)]. The mixtures of two isomeric benzothiazole were separated by two isomers varied with the kind of alkyl chain in alkyl p-aminosalicylate. These compounds were subjected to the test for antimicrobial activities using Staphylococcus aureus and Escherichia coli by tube dilutioin method. The seven compounds, Ia, IIa, IIIa, VIa, IIIb, IVb and Vb showed inhibition of the growth of S. aureus at the concentration of 10${\mu}$g/ml. As to the growth of E. coli, IVb, VIb, VIIb, and VIIIb were observed inhibition at the concentration of 1${\mu}$g/ml. Ia, IIa, IIIa, VIIa, Va, VIIIa, and IIb exhibited potential antimicrobial activities against showed inhibition of the growth of E.coli at the concentration of 100${\mu}$/ml.

• Bulletin of the Korean Chemical Society
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• v.17 no.4
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• pp.362-365
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• 1996

Carbonyl compounds 1, alkyl- and arylaldehydes and alkyl, aryl, benzylic, and cyclic ketones were converted to the corresponding 1,3-dioxolanes 2 and 1,3-dioxanes 4 with ethylene glycol and 2,2-dimethyl-1,3-propanediol in the presence of 1-3 mol% of 1-(p-substituted)benzyl-1,1-dimethyl-2-(p-substituted)-benzoyl hydrazinium hexafluoroantimonates 3 in high yields.

• Bulletin of the Korean Chemical Society
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• v.19 no.9
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• pp.947-951
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• 1998

$K_2NiF_4$-type layered compounds of the ($C_nH_{2n+1}NH_3)_2SnCl_4$ (n=2, 4, 6, 8, and 10) system have been synthesized from a stoichiometric mixture of $SnCl_2$ and alkyl ammonium salt using a low temperature solution technique under the inert atmosphere condition. Their crystal structures are assigned to the orthorhombic system by X-ray powder diffraction analysis. The a and b cell parameters show small changes. However, the c parameter is varied significantly according to the increment of alkyl chains of the organic layer which is located between inorganic layers in the compounds. The conformational phase transitions of the compounds are studied by the DSC in the temperature range of 300 to 500 K. FT-IR and Raman spectra are analyzed in the ranges of 1300 to 4000 cm-1 and of 50 to 360 $cm^{-1}$ with Ar-laser (λ=514.5 nm) excitation, respectively. Photoluminescence phenomena are observed for some compounds. The bond-length of Sn-Cl is determined by the EXAFS spectroscopic analysis.

• YAKHAK HOEJI
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• v.48 no.5
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• pp.272-277
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• 2004

The 2-amino-l-phenylpropanols 4∼7 were reacted with isothiocyanates to afford the 20 thioureido MAPP derivatives 8a∼11e, which were tested their cytotoxic activity by MTT assay. The cytotoxicity of alkylthioureido compounds were increased and decreased by alkyl chain length from $C_{8}$ to $C_{14}$ and of phenylthioureido compounds showed poor activity. The compounds (8b, 8c, 9b, 9c, l0b, 10c, 11b, 11c) with $C_{10}$ and $C_{12}$ alkyl chains gave stronger activity than reference compound B13. The $IC_{50}$/ of compound 8c was 1.05$\mu$M and 3 times stronger activity than B13. The stereochemistry of synthesized compounds affected very little to cytotoxic activity.

• The Korean Journal of Pesticide Science
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• v.2 no.1
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• pp.12-17
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• 1998

Salicylic acid and 3-hydroxy benzoic acid are nitrated and esterified with some alcohols. Five phosphate and six carbamate compounds of alkyl-5-nitrosalicylate and alkyl-3-hydroxy-4-nitrobenzoate are synthesized by reacting alkyl-5-nitrosalicylate and alkyl-3-hydroxy-4-nitrobenzoate with diethyl-chlorophosphate and methyl isocyanate. As the bioassay results of synthesized compounds on five insects and six pathogens, the brown planthopper (BPH, Nilaparvata lugens) mortality of O-(2-carbomethoxy-4-nitrophenyl) O,O-diethylphosphate and O-(2-nitro-5-carbo methoxyphenyl) O,O-diethylphosphate was 96%, while four compounds including O-(2-carbo-(2-chloroethoxy)-4-nitrophenyl) O,O-diethylphosphate showed more than 95% of fungicidal activity on rice blast.

• Archives of Pharmacal Research
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• v.29 no.9
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• pp.728-734
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• 2006

A series of 7-hydroxy-4-oxo-4H-chromene- (3a - h) and 7-hydroxychroman-2-carboxylic acid N-alkyl amides (4a - g) were synthesized and their antioxidant activities were evaluated. While compounds 3a - h were less active, compounds 4a - g exhibited more potent inhibition of lipid peroxidation initiated by $Fe^{2+}$ and ascorbic acid in rat brain homogenates. Among them, 7-hydroxychroman-2-carboxylic acid N-alkylamides (4e - g) bearing nonyl, decyl, and undecyl side chain exhibited 3 times more potent inhibition than trolox (1).

• Mass Spectrometry Letters
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• v.6 no.3
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• pp.65-70
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• 2015

N-Alkyl/benzyl substituted isatin derivatives are intermediates and synthetic precursors for the preparation of biological active heterocycles. N-alkyl/benzyl isatins have showed various biological activities, such as cytotoxicity, antiviral, caspase inhibition, cannabinoid receptor 2 agonists for the treatment of neuropathic pain, etc. In this study, N-alkyl/benzyl isatin derivatives were synthesized from isatin and alkyl/benzyl halides in presence of K₂CO₃ in DMF and excellent to quantitative yields (~95%) were obtained. Isatins and benzyl-isatins were condensed with fluorescein hydrazide to form fluorescein hydrazone. All the compounds were subjected to their fragmentation behavior study using LC/MSⁿ. N-Alkyl substituted isatin derivatives fragmented at nitrogen-carbon (N-C) bond, hence gave daughter ion as [RN+H]⁺. Whereas, N-benzyl substituted isatin derivatives fragmented at carbon-carbon (C-C) bond of alkyl chain which linked with nitrogen molecules, therefore gave N-methyl fragments [RNCH₂]⁺. This study demonstrated that, isatin moiety present in a small/large molecule or in a matrix of reaction mixture with/without N-alkyl/benzyl substituents can be identified by mass spectroscopic fragmentation behavior study.

• Proceedings of the Korean Society of Dyers and Finishers Conference
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• 2008.10a
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• pp.77-78
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• 2008

Affinity between alkyl substituted super hydrophobic dyes and polypropylene fiber has been analyzed by using the molecular descriptor as a method to predict chemical and physical characteristics of compounds. Hydrophobicity of synthesized dyes calculated by LogP which is one of molecular descriptors was increased continuously as the length of alkyl substituents increased.

• Journal of the Korean Chemical Society
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• v.15 no.5
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• pp.275-280
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• 1971

Six previously unreported N-acylated-DL-1-amino alkyl phosphonic acids were prepared; N-Acetyl-DL-1-amino-3-methyl butyl phosphonic acidN-Benzoyl-DL-1-amino-2-methyl propyl phosphonic acidN-Benzoyl-DL-1-amino-3-methyl butyl phosphonic acidN-Benzoyl-DL-1-amino-2-methyl butyl phosphonic acidN-Acetyl-DL-1-amino-2-methyl propyl phosphonic acidN-Acetyl-DL-1-amino-2-methyl butyl phosphonic acidThe first four compounds were characterized, and the last two compounds were obtained in the crude oil state. The above three DL-1-amino-alkyl phosphonic acid were synthesized from iso-valeric acid, iso-caproic acid and ${\beta}$-methyl valeric acid using Hell-Volhard-Zelinsky reaction, the condensation reaction with triethyl-phosphite and the modified Curtius Reaction. Iso-caproic acid and ${\beta$-methyl valeric acid were prepared by the conventional methods.