• Title/Summary/Keyword: Alkyl ester

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Synthesis of N-(Alkyl-N'-nitrosocarbamoyl)-amino Acid Ester Derivatives and their Anticancer Activity (N-(Alkyl-N'-nitrosocarbamoyl)-amino Acid Ester류의 合成 및 抗癌 作用 評價)

  • Kim, Jeong-Gyun;Park, Moon-Tae;Shin, Hong-Dae;Koh, Young-Sim;Yoon, Ung-Chan;Ryu, Sung-Ho;Moon, Kyung-Ho;Kim, Min-Sook
    • YAKHAK HOEJI
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    • v.28 no.4
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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.

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Synthesis of N-Aryl Phenylglycine Ο-Alkyl Esters and Its Substitution of Ester Moiety (N-Aryl Phenylglycine Ο-Alkyl Esters의 간편한 합성 및 에스테르 치환반응)

  • 박명숙;박해선
    • YAKHAK HOEJI
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    • v.47 no.5
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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.

MO Studies on the Electronic Structure and Reactivity of Glycinato, Glycine Ester Ligands (Glycinato 및 Glycine Ester 리간드의 전자구조와 반응성에 관한 분자궤도함수론적 연구)

  • Ja Hong Kim
    • Journal of the Korean Chemical Society
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    • v.24 no.1
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    • pp.15-19
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    • 1980
  • CNDO/2, EHT molecular orbital methods are used to investigate the electronic structure and reactivity of glycinato, glycine ester ligands. The results show that bidentate glycinato has a more stable structure, Gly-I with a $105.9^{\circ}$dihedral angle between ${\Delta}O_4C_3C_2$ and ${\Delta}C_3C_2N_1$ than Gly-Ⅱ. The electron inductive effects in the alkyl group substituted glycine ester ligands can also be derived from the calculation. According to the electron density, qN of ligands on the basis of CNDO/2 MO calculations, it is concluded that the stabilities are in the order of glycinato > Gly-Et-ester > Gly-i-Pr-ester > Gly-Me-ester.

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Conformational Characteristics of p-tert-Butylcalix[6]arene Mono-Alkyl Ester Derivatives

  • Yu, Hyo-Yeon;Seok, Da-Hyun;Chang, Suk-Kyu;Ahn, Sang-Doo;Chung, Kee-Choo
    • Journal of the Korean Magnetic Resonance Society
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    • v.14 no.2
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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.

The Synthesis of Urocanic Alkyl Ester and Photolysis (우로칸 알킬에스테르의 합노(合盧) 및 광학효과(光學效果))

  • No, Sueng-Ho;Lee, Hyang-Woo;Nam, Ki-Dae
    • Journal of the Korean Applied Science and Technology
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    • v.8 no.1
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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.

Scouring Effect of PAPE(Polyoxyethylene Alkyl Phosphoric Ester) on Cotton Fibres (면섬유에 대한 폴리옥시에틸렌 알킬 인산에스테르의 정련효과)

  • Ha, Youn-Shick;Kwak, Gyeong-Do;Chang, Yoon-Ho
    • Applied Chemistry for Engineering
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    • v.10 no.7
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    • pp.974-978
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    • 1999
  • This study was concerned with the scouring effect of anionic surfactants, PAPE(sodium polyoxyethylene alkyl phosphoric ester) for cotton fibres. Sodium polyoxyethylene(7) nonylphenyl phosphoric ester(CPB-1) and the sodium polyoxyethylene(7) tridecyl phosphoric ester(CPB-2) were synthesized by the phosphoric esterification reaction from NP-7(polyoxyethylene(7) nonylphenyl ether) and TDA-7(polyoxyethylene(7) tridecyl ether) as scouring agents. Defoaming ability, fibre wetting time and absorbency rate of scouring agents were investigated. Being compared with the conventional scouring agent(Ultravon GP; Ciba-guyge Co.), CPB-1 and CPB-2 showed a higher defoaming ability in the cotton scouring process at room temperature. And CPB-1 has a higher wetting effect than the agents, CPB-2 or GP in distilled water bath but CPB-2 showed more scouring effect in 1.2 wt % NaOH solution bath.

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Synthesis of 1,4-Dihydropyridine Carboxylic Acids (1,4-디하이드로피리딘 산류의 합성)

  • Suh, Jung-Jin;Hong, You-Hwa
    • YAKHAK HOEJI
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    • v.33 no.2
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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.

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Synthesis of 1N-alkyl-2-amino-3-ethoxycarbonyl-pyridino [2,3-f]indole-4,9-dione derivatives (I) (1N-알킬-2-아미노-3-에톡시카르보닐-피리디노 [2,3-f]인돌-4,9-디온 유도체의 합성 (I))

  • Suh, Myung-Eun;Shin, Sung-Hee
    • YAKHAK HOEJI
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    • v.41 no.5
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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.

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Synthesis and Anti-corrosion Properties of Succinic Acid Alkyl Half-Ester Derivatives (숙신산 알킬 하프-에스테르 유도체의 합성 및 해수에 대한 방청성능)

  • Baek, Seung-Yeob;Kim, Young-Wun;Chung, Keun-Wo;Yoo, Seung-Hyun
    • Applied Chemistry for Engineering
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    • v.22 no.4
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    • pp.367-375
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    • 2011
  • Succinic acid ester derivatives have been used as additives for the base oil of metal working fluids and pressure working oils. In this paper, a series of succinic acid alkyl half-esters were synthesized with over 97% yields by ring-opening reaction of succinic anhydride and fatty alcohol and were soluble in 100 N base oil within 1 wt% concentration. The structures and purities of ester derivatives were confirmed by $^1H-NMR$ and FT-IR spectrum and GC analysis. Anti-corrosion properties of the esters in sea water were evaluated through ASTM D665 method and weight loss method and compared to that of succinic alkyl esters without carboxylic acid group in the molecule. As the results, anti-corrosion properties of succinic acid alkyl half-esters with carboxylic acid group were better than those of succinic acid alkyl esters without carboxylic acid group. And, Anti-corrosion properties of the esters with a shorter alkyl chain of high concentration showed better performance than those with longer alkyl chain of low concentration. Inhibition efficiency % (IE%) of the esters was over 95% in the concentration of 80 ppm and corrosion rate (CR) was below 0.3 mm/year at the same concentration. Thus, the corrosion properties of succinic acid alkyl half-esters result from the carboxylic acid groups in molecules.

Effect of Polyoxyethylene Alkyl Esters on Permeation Enhancement and Impedance of Skin

  • Kim, Hee-Sun;Oh, Seaung-Youl
    • Biomolecules & Therapeutics
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    • v.19 no.1
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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.