• 약학회지
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• 제28권4호
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• pp.197-206
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• 1984

The derivatives of N-(alkylcarbamoyl) amino acid methyl ester, N-(2-chloroethylcarbamoyl)-glycine methyl ester (7a), -valine methyl ester (8a), -phenylalanine methyl ester (9a), N-(N'-methylcarbamoyl)-glycine methyl ester (7b), -valine methyl ester (8b), and-phenylalanine methyl ester (9b), were prepared by reacting the corresponding free amino acid methyl ester (glycine-, valine-, phenylalanine-methyl ester) with isocyanate (R-N=C=O${\cdot};R=Cl-CH_2-CH_2-or\; CH_3-)$. The prepared N-(alkylcarbamoyl) amino acid methyl esters (7,8,9) were treated with $NaNO_2$/98% HCOOH in order to obtain their nitrosoated products, N-(alkyl-N'-nitrosocarbmoyl)amino acid methyl ester. The compound (7,8,9) gave N-(2-chloroethyl-N'-nitrosocarbamoyl)-valine methyl ester (14a),-phenylalanine methyl ester (15a), N-(N'-alkyl-N'-nitrosocarbamoyl)-glycine methyl ester (13b),-valine methyl ester. (14b), and-phenylalanine methyl ester (15b) respectively under the nitrosoation. On the other hand, N-(2-chloroethylcarbamoyl) glycine methyl ester produced N-(2-chloroethylcarbamoyl)-N-nitrosoglycine methyl ester (13a). The inhibitory activity of the prepared N-(alkylcarbamoyl) amino acid methyl ester (7,8,9) and N-(alkyl-N'-nitrosocarbamoyl) amino acid methyl ester (13,14,15) towards the growth of L1210 murine leukemia cells were examined. Among them the compound (14a) and (15a) exhibit excellent activity having $ED_{50}\; to\;be\;1.5{\mu}g/ml\;and\;3.0{\mu}g/ml respectively.

• 약학회지
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• 제47권5호
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• pp.276-282
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• 2003

For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through esterification, bromination, C-N bond formation from commercially available phenylacetic acids. An efficient and practical reaction condition for esters 2a∼c was that the starting materials 1a∼c were refluxed in absolute methanol for 3 hours with catalytic concentrated hydrosulfuric acid. In addition, bromines 3a∼c were formated for 3h in dichloromethane at rt with N-bromosuccinimide. Bromines 3a∼c were also converted to 4a∼i through substitution of arylamines during refluxing for 24 hours in ethanol with triethylamine. Interestingly, ethyl esters 5a∼c were formed via transesterification reaction when the p-sulfamylanilino group was used as a nucleophile in ethanol solvent.

• 대한화학회지
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• 제24권1호
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• pp.15-19
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• 1980

Glycinato 및 glycine ester 리간드의 전자구조와 반응성을 조사하기 위하여 CNDO/2와 EHT 분자궤도함수법을 적용하였다. 두자리 배위자로 작용하는 glycinato 리간드의 구조는 탄소에서 질소쪽으로 가는 결합이 ${\Delta}O_4C_3C_2$ 와 ${\Delta}O_3C_2N_1$ 평면에서 $105^{\circ}9'$의 dihedral angle을 가지는 Gly-I 구조가 Gly Ⅱ 구조보다 안정함을 알았으며, glycine ester 리간드에 대한 에너지 성분 분석 결과로서 alkyl가 치환에 따른 전자효과를 볼 수 있었다. CNDO/2 MO 계산으로 얻은 전자밀도 $q_N$값으로부터 리간드의 안정도 순위는 Glycinato>Gly-Et-Ester>Gly-i-Pr-ester>Gly-Me-ester 순으로 나타났다.

• 한국자기공명학회논문지
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• 제14권2호
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• pp.144-153
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• 2010

Conformational properties of several mono-alkyl ester derivatives of p-tert-butylcalix[6]arene depending on temperatures have been investigated by solution NMR spectroscopy. It is found out that all derivatives can adopt a cone-like conformation around room temperature, while the conformational characteristics at high temperatures seem to be quite different each other.

• 한국응용과학기술학회지
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• 제8권1호
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• pp.45-49
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• 1991

The synthesis of urocanic acid which was started D-fructose, and its alkyl esters, urocanic ethyl ester and urocanic isobutyl ester, were prepared by esterificated. Urocanic ethyl ester and urocanic isobutyl ester were insoluble in water and soluble most organic solvents (ethanol, benzene, toluene, pyridine, THF, DMF) which adds to their practical applicability, and absorb ultraviolet light of greater wavelength than the free acid and there by are more effective for shielding sensitive materials, including the humanbody, from the chemically most effective portion of the solar ultraviolet spectrum.

• 공업화학
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• 제10권7호
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• pp.974-978
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• 1999

면섬유에 대한 정련제로서 NP-7(polyoxyethylene(7) nonylphenyl ether) 및 TDA-7((polyoxyethylene(7) tridecyl ether)을 인산에스테르화 반응시켜 PAPE(sodium polyoxyethylene alkyl phosphoric ester)형 음이온 계면활성제인 sodium polyoxyethylene(7) nonylphenyl phosphoric ester(CPB-1)와 sodium polyoxyethylene(7) tridecyl phosphoric ester(CPB-2)를 각각 합성하였다. 합성한 CPB-1과 CPB-2를 기존의 상용제품인 Ultravon GP(GP)와 각 기능별로 성능을 비교하였다. 그 결과 상온 및 $100^{\circ}C$에서의 억포 및 파포력이 CPB-2>CPB-1>GP의 순으로 CPB-2의 기포가 가장 적었고, 또한 가장 빨리 파포되어졌다. 증류수에서의 침윤효과는 CPB-1>GP>CPB-2의 순으로 나타났으나, 실제 일반 정련에서 많이 사용하는 1.2 wt % NaOH 수용액에서의 침윤효과는 전반적으로 CPB-2가 가장 우수한 것으로 나타났다. 섬유가공시의 정련조건인 알카리 상태에서의 안정성은 $CPB-2{\geq}CPB-1$>GP의 순으로 나타났으며, 재흡수력 실험결과 CPB-2>CPB-1>GP의 순으로 CPB-2의 정련력이 가장 우수한 것으로 나타났다.

• 약학회지
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• 제33권2호
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• pp.80-86
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• 1989

2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl 5-(2'-phenylsulfinyl) ethyl ester (10) or 2,6-Dimethyl-4-(2' or 3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-alkyl 5-(2-methylsulfonyl) ethyl ester (14a, b, c) were hydrolyzed by treatment with NaOH in aqueous EtOH solution to give 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (4b), 2,6-Dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (4c) and 2,6-Dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monoisopropyl ester (4d) in 80 -90% yield. By the same procedure, 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-bis (2'-methylsulfonyl) ethyl ester (15) gave 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid (4e) in 96% yield.

• 약학회지
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• 제41권5호
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• pp.575-581
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• 1997

The 6,7-dichlorquinoline-5,8-dione was reacted with ${alpha}$-cyanoacetic acid ethyl ester in ammonia solution to yield 6-(${alpha}$-cyano-${alpha}$-ethoxycarbonyhnethyl)-7-chloroquinoline- 5,8-dione (compound I). When this compound was reacted with some alkyl amines (methylamine, ethylamine, isopropylamine, etc) 2-amino-3-ethoxycarbonyl-N-alkyl-pyridino[2,3-f]indole-4,9-diones (compounds II a-e) were obtained.

• 공업화학
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• 제22권4호
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• pp.367-375
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• 2011

숙신산 에스테르 유도체는 방청성능 및 윤활성능이 우수하여 금속가공유 및 유압작동유 등의 첨가제로 많이 사용되고 있다. 본 연구에서는 광유계 윤활기유의 방청제로 사용하기 위하여 알킬 무수 숙신산과 여러 가지 지방 알콜과의 개환반응을 행하여 카르복실 그룹과 에스테르 그룹을 동시에 함유하는 숙신산 알킬 하프-에스테르 유도체를 97% 이상의 수율로 합성하였으며 1 중량% 농도범위에서 광유계 오일에 잘 용해되었다. 합성 유도체는 $^1H-NMR$ 및 FT-IR 스펙트럼으로 구조를 확인하였으며, GC 분석을 통하여 화합물의 순도를 확인하였다. 또한, 합성 유도체의 해수에 대한 방청성능을 ASTM D665 표준방법과 무게 중량법으로 평가하여 카르복실산 그룹을 함유하지 않는 숙신산 알킬 에스테르 유도체와 비교하였다. 방청성능 평가 결과, 합성 유도체의 농도가 증가하고 분자 내에 포함된 알킬기의 사슬이 짧을수록 상대적으로 방청성능이 우수하였으며 비교물질인 숙신산 알킬 에스테르 유도체는 방청성능을 전혀 나타내지 않았다. 무게 중량법으로 평가한 80 중량ppm 농도를 첨가한 오일의 방청효율 % (IE%)는 알킬기의 사슬이 짧을수록 높은 값을 나타내어 최고 95% 이상이었다. 또한, 발청속도(Corrosion rate, CR)는 알킬기의 사슬이 짧을수록 낮은 값을 나타내어 80 중량ppm에서 최고 0.3 mm/year 이하를 나타내었다. 즉, 숙신산 알킬 하프-에스테르 유도체의 해수에 대한 방청성능은 분자 내에 함유되어 있는 카르복실산 그룹으로 인하여 나타나는 것으로 판단되었다.

• Biomolecules & Therapeutics
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• 제19권1호
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• pp.109-117
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• 2011

In this work, we have investigated the effect of polyoxyethylene alkyl ester nonionic surfactants on percutaneous permeation enhancement of a model drug, ketoprofen. We also investigated the mechanism involved in the enhancement using impedance and solubility measurement. Three groups of nonionic surfactants with different ethylene oxide content were studied. The permeation results showed that all surfactants enhanced the percutaneous absorption, irrespective of the molecular weight. The permeation results from PEG-45 monostearate (PEGMS45) were rather unexpected. Impedance and solubility results indicate that the mechanism involved in the enhancement of permeation by PEG-10 monooleate (PEGMO10) and PEGMS45 is rather different. The results from PEGMS45 suggest that it could be a potential candidate as a skin penetration enhancer with high molecular weight, which may poses less skin irritation and systemic side effect than the smaller surfactant molecules. Overall, this work provided some useful information on percutaneous transport enhancement and the mechanistic insights involved in skin permeation for these nonionic surfactants.