• Title/Summary/Keyword: Acyl chlorides

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Synthesis of Hydroxylactams and Esters Derived from Thalidomide and Their Antitumor Activities

  • Sun, Guanglong;Liu, Xiangchao;Zhou, Heng;Liu, Zenglu;Mao, Zhenmin
    • Bulletin of the Korean Chemical Society
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    • v.35 no.5
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    • pp.1337-1342
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    • 2014
  • A novel and convenient route for the synthesis of a series of thalidomide derivatives is described. Compound 2 was cyclized with different amines under alkaline condition to obtain 4-nitro substituted phthalimidines 3a-d. Hydroxylactams 4a-d were produced via bromination and hydroxylation. Different acyl chlorides were reacted with hydroxylactams to provide the desired esters 5a-d. All compounds were evaluated by MTT assay for their inhibitory activities against HCT-116, MG-63, MCF-7, HUVEC and HMVEC cell lines in vitro. Most of them showed no obvious cytotoxic effect on normal human cells, compounds 4a-d, $5a_2$, $5a_4$, $5a_5$, $5b_2$, $5c_2$ and $5d_2$ exhibited potent antitumor activities, among which compounds $5a_2$ and $5b_2$ were more effective than 5-FU.

Preparation of Bonded Cellulose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phases by Using Three Bifunctional Reagents

  • Zhang, Yi Jun;Huang, Mingxian;Zhang, Yuping;Ryoo, Jae Jeong
    • Bulletin of the Korean Chemical Society
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    • v.34 no.9
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    • pp.2623-2628
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    • 2013
  • Three di-acyl chlolide reagents, adipoyl chloride, terephthaloyl chloride and isophthaloyl chloride, were used as spacer reagents to prepare bonded type of three cellulose (3,5-dimethylphenyl)carbamate (CDMPC) chiral stationary phases (CSPs). The CDMPC CSPs were prepared using these three acid chlorides as spacer agents at the 6-position of the primary hydroxyl group on the glucose unit of cellulose regioselectively. The chiral recognition ability of the prepared CSPs for five racemates was evaluated by normal-phase high-performance liquid chromatography (HPLC) with the following mobile phases: hexane/isopropanol (IPA), hexane/IPA/tetrahydrofuran (THF) and hexane/IPA/chloroform. The result showed that these prepared CSPs can be used in THF and chloroform solutions and the chiral recognition abilities of the CSPs were improved depending on the eluents and chiral samples.

Ester Derivatives from Tannase-treated Prunioside A and Their Anti-inflammatory Activities

  • Jun, Chang-Soo;Yoo, Myung-Ja;Lee, Woo-Yiel;Kwak, Kyung-Chell;Bae, Moon-Sung;Hwang, Woo-Taek;Son, Dong-Hwan;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • v.28 no.1
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    • pp.73-76
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    • 2007
  • Prunioside A, isolated from the methanol extract of Spiraea prunifolia var. Simpliciflora's root, is composed of coumaroyl, monoterpene-type, and glucosyl units. The esterase activity of tannase was used to remove the p-coumaroyl and glucopyranosyl groups. The enzymatically hydrolyzed compound was reacted with various acyl chlorides to synthesize its ester derivatives, which showed the inhibitory effects on NO production in murine machrophage?like RAW 264.7 cells stimulated with lipopolysaccharide and interferon-γ.

Synthesis of Several Diester Group-Containing Calix[4]arenes

  • 남계준;양용식;전종철;최용국
    • Bulletin of the Korean Chemical Society
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    • v.17 no.6
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    • pp.502-506
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    • 1996
  • Several ester group-containing calix[4]arenes were synthesized by the reaction of calix[4]arene and various acyl chlorides. Two or four ethyl succinyl units could be introduced into the calix[4]arene lower rim depending on the reaction conditions. But the mixture of three and four ethyl malonyl substituted calix[4]arenes were obtained and only three ethyl oxalyl units were introduced at the lower rim of calix[4]arene. Interestingly when calix[4]arene was treated with ethyl oxalyl chloride in the presence of aluminum chloride, two ethyl oxalyl units were introduced at the upper rim of calix[4]arene. The conformation of those ester-containing calix[4]arenes was presented based on the 1H and 13C NMR spectra.

Membrane Performance and Chemical Instability of 1,3,5-Benzenetricarbonyl Trichloride (1,3,5-Benzenetricarbonyl Trichloride의 화학적 불안정성과 분리막 성능)

  • Park, Chul Ho;Kim, Chan-soo;Sim, Joonmok;Park, Hyun-Seol;Joe, Yun-Haeng
    • Membrane Journal
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    • v.30 no.3
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    • pp.200-204
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    • 2020
  • 1,3,5-benzenetricarbonyl trichloride is a chemical substance in which three acyl chlorides are located at 1,3,5 position in the benzene ring, and is an important chemical for the area where the good physical and chemical properties are required through high degree of crosslinking. In particular, it is possible to form a three-dimensional structure having a certain pore size, it is used in various separation and purification fields. However, the high reactivity of acyl chloride has the advantage of a fast reaction rate, which means that it is difficult to control chemically to have a certain performance in other aspects. Therefore, in this study, we observed how the chemical change of 1,3,5-benzenetricarbonyl trichloride affected the membrane performance.

Selective Reduction with Lithium Borohydride. Reaction of Lithium Borohydride with Selected Organic Compounds Containing Representative Functional Groups (수소화붕소리튬에 의한 선택환원. 수소화붕소리튬과 대표적 유기화합물과의 반응)

  • Nung Min Yoon;Jin Soon Cha
    • Journal of the Korean Chemical Society
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    • v.21 no.2
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    • pp.108-120
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    • 1977
  • The approximate rates and stoichiometries of the reaction of lithium borohydride, with fifty two selected organic compounds containing representative functional groups under the standard condition (tetrahydrofuran, $0^{\circ}$), were studied.Among the active hydrogen compounds,primary alcohols and compounds containing an acidic proton liberated hydrogen relatively fast, but secondary and tertiary alcohols very sluggishly. All the carbonyl compounds examined were reduced rapidly within one hour. Especially, among the ${\alpha}{\beta}$-unsaturated carbonyl compounds tested, the aldehydes consumed one hydride cleanly, however the cyclic ketones consumed more than one hydride even at $-20^{\circ}$. Carboxylic acids were reduced very slowly, showing about 60% reduction in 6 days at $25^{\circ}$, however acyl chlorides reduced immediately within 30 minutes. On the other hand, the reductions of cyclic anhydrides proceeded moderately to the hydroxy acid stage, however the further reductions were very slow. Aromatic and aliphatic esters, with exception of the relatively moderate reduction of acetate, were reduced very slowly, however lactones were reduced at a moderate rate. Epoxides reacted slowly, but amides and nitriles as well as the nitro compounds were all inert to this reagent. And cyclohexanone oxime and phenyl isocyanate were reduced very sluggishly. Last of all, all sulfur compounds studied were inert to this hydride.

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Reducing Characteristics of Potassium Tri-sec-butylborohydride

  • Yoon, Nung-Min;Hwang, Young-Soo;Yang, Ho-Seok
    • Bulletin of the Korean Chemical Society
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    • v.10 no.4
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    • pp.382-388
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    • 1989
  • The approximate rates and stoichiometry of the reaction of excess potassium tri-sec-butylborohydride ($K_s-Bu_3BH$) with selected organic compounds containing representative functional groups were determined under the standard conditions (0$^{\circ}C$, THF) in order to define the characteristics of the reagent for selective reductions. Primary alcohols evolve hydrogen in 1 h, but secondary and tertiary alcohols and amines are inert to this reagent. On the other hand, phenols and thiols evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of norcamphor gives 99.3% endo- and 0.7% exo-isomer of norboneols. The reagent rapidly reduces cinnamaldehyde to the cinamyl alcohol stage and shows no further uptake of hydride. p-Benzoquinone takes up one hydride rapidly with 0.32 equiv hydrogen evolution and anthraquinone is cleanly reduced to the 9,10-dihydoxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively, however further reduction does not occur. Anhydrides utilize 2 equiv of hydride and acyl chlorides are reduced to the corresponding alcohols rapidly. Lactones are reduced to the diol stage rapidly, whereas esters are reduced moderately (3-6 h). Terminal epoxides are rapidly reduced to the more substituted alcohols, but internal epoxides are reduced slowly. Primary and tertiary amides are inert to this reagent and nitriles are reduced very slowly. 1-Nitropropane evolves hydrogen rapidly without reduction and nitrobenzene is reduced to the azoxybenzene stage, whereas azobenzene and azoxybenzene are inert. Cyclohexanone oxime evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine and quinoline are reduced slowly, however pyridine N-oxide takes up 1.5 equiv of hydride in 1 hr. Disulfides are rapidly reduced to the thiol stage, whereas sulfide, sulfoxide, sulfonic acid and sulfone are practically inert to this reagent. Primary alkyl bromide and iodide are reduced rapidly, but primary alkyl chloride, cyclohexyl bromide and cyclohexyl tosylate are reduced slowly.