• Title/Summary/Keyword: gamma-butyrolactone

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Stereoselective Halolactonization of$\alpha-Phenylsulfonyl-\gamma,\delta$-Unsaturated Amides

  • Lee, Jae-Wook;Jung, Jin-Hang;Oh, Dong-Young
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.842-845
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    • 1994
  • Iodine-induced lactonization of ${\alpha}$-Phenylsulfonyl-${\gamma},{\delta}$-Unsaturated Amides provided 2,4-trans-substitued ${\gamma}$-butyrolactones in high selectivity. NBS-or NCS-induced lactonization of N,N-dimethyl-2-(phenylsulfonyl)-4-pentenamide in DME-$H-2O(2:1 vol)$ gave 2-halo-4-(halomethyl)-2-(phenylsulfonyl)-${\gamma}$-butyrolactone.

Effect of Addition of Cosolvent γ-Butyrolactone on Morphology of Polysulfone Hollow Fiber Membranes (폴리설폰 중공사막 구조에 대한 조용매 γ-Butyrolactone 첨가 영향)

  • Yun, Sukbok;Lee, Yongtaek
    • Applied Chemistry for Engineering
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    • v.25 no.3
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    • pp.274-280
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    • 2014
  • Polysulfone (PSf) hollow fiber membranes were prepared via the nonsolvent induced phase separation technique. The cosolvent of ${\gamma}$-butyrolactone (GBL) was added to the polymer solution containing a mixture of PSf and N,N-dimethylacetamide (DMAc). Water was utilized as a precipitation nonsolvent. The morphology of prepared membranes was investigated using a field emission scanning electron microscopy. The fabricated membrane showed a typical asymmetric structure such as the dense layer on the porous support layer by the addition of GBL to the polymer solution. As the concentration of GBL increased, the asymmetric porous structure was shown to be more intensified. It was thought that the added GBL played a role of enhancing the liquid-liquid phase separation of the polymer solution, since the cosolvent of GBL might change the thermodynamic solubility parameter of the doping solution. Permeation properties through the prepared hollow fiber membranes were characterized by measuring the pure water flux and the solute rejection using $0.05{\mu}m$ polystyrene latex (PSL) beads. Experimental results revealed that the use of PEG as the internal coagulant enhanced the pure water flux up to 130 times compared to the use of EG while the rejection of the PSL beads decreased only 5%.

Synthesis and antitumor evaluation of $\alphamethylene-\gamma-butyrolactone-linked$ to 5-substituted uracil nucleic acid bases

  • Kim, Jack-C.;Kim, Ji-A;Kim, Si-Hwan;Park, Jin-Il;Kim, Seon-Hee;Park, Soon-Kyu;Park, Won-Woo
    • Archives of Pharmacal Research
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    • v.19 no.3
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    • pp.235-239
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    • 1996
  • Six, heretofore undescribed, $5^I-Methyl-5^I-(5-Substituted uracil-1-ylmethyl)-2^I-oxo-3^I-methylenetetrahydrofurans(F, Cl, Br, l, CH_3, H)(6a-f)$were synthesized and evaluated against three cell lines (FM-3A, P-388 and U-937). For the preparation of .alpha.-methylene-.gamma.-butyrolactone bearing 5-substituted uracils (6a-f), the effcient Reformatsky type reaction was employed which involves the treatment of ethyl .alpha.(bromomethyl) acrylate and zinc with the respective 5-substituted uracil-1-ylacetones (5a-f). The acetone derivatives (5a-f) were directly obtained by the respective alkylation reaction of 5-substituted uracils with chloroacetone in the presence of $K_{2}$$CO_{3}$(or NaH). These lactone compounds 6a-f exhibited moderate to significant activity in all of the three cell lines, and 6b, 6c and 6e showed significant antitumor activities (inhibitory concentrations ($IC_{50}$) ranged from 1.3-3.8 .mu.g/ml.

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Synthesis and Conformational Study of 2-Trityloxymethyltet­rahydrofurans as Key Intermediates for Antiviral Nucleosides

  • Choi Hye-Young;Kim Hee-Doo
    • Archives of Pharmacal Research
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    • v.28 no.1
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    • pp.16-21
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    • 2005
  • We wanted to elucidate the reason why the trityloxymethyl substituent in $\gamma$-trityloxymethyl-$\gamma$­butyrolactone takes a sterically unfavorable specific conformation, and so we synthesized 5-trityloxymethyldihydrofuran-3-one, 3-(trityloxymethyl)-4-butanolide and 2-trityloxymethyl- tetrahy­drofuran and we then analyzed their conformation by $^{1}H-NMR$ analysis.

Characteristics of Polyhydroxyalkanoates Synthesis by Ralstonia eutropha from Vegetable Oils (식물성 오일로부터 Ralstonia eutropha의 polyhydroxyalkanoates 합성 특성)

  • Park, Dae-Hoo;Kim, Beom-Soo
    • KSBB Journal
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    • v.25 no.3
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    • pp.239-243
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    • 2010
  • Six strains of Ralstonia eutropha were grown to investigate characteristics of polyhydroxyalkanoates (PHA) synthesis from vegetable oils or glycerol. Poly(3-hydroxybutyrate) homopolymer was formed using soybean oil, olive oil, or glycerol as carbon source, while poly(3-hydroxybutyrate-co-4-hydroxybutyrate) or poly(3-hydroxybutyrateco-3-hydroxyvalerate) copolymers were synthesized by co-feeding $\gamma$-butyrolactone or pentanoic acid, respectively. Optimum strain was determined as R. eutropha KCTC 2662 in terms of final cell concentration and PHA content. From 20 g/L of soybean oil (optimum substrate), cell concentration and PHA content at 72 h ranged 1.7~9.2 g/L and 70~92 wt%, respectively.

Mechanical Properties and Ionic Conductivities of Plasticized Gel Polymer Electrolyte Based on P(VdF-co-HFP) (가소화된 P(VdF-co-HFP)계 고분자 전해질의 기계적 성질 및 이온전도도)

  • 최종국;김성훈
    • Polymer(Korea)
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    • v.24 no.2
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    • pp.259-267
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    • 2000
  • Gel polymer electrolytes were prepared from poly(vinylidene fluoride-co-hexafluoro propylene)[P(VdF-co-HFP)] that had higher mechanical properties as well as higher dielectric constant ($\varepsilon$=8~13) than other polymeric matrix. Mechanical properties and ionic conductivities have been investigated as a function of blend ratio of electrolyte solution and polymer matrix. Ethylene carbonate (EC)/${\gamma}$-butyrolactone (${\gamma}$-BL) and lithium triflate (LiCF$_3$SO$_3$) were used as solvent and salt, respectively. The mechanical properties such as tensile strength, tensile modulus, compression modulus, and dynamic shear modulus were evaluated. The highest ionic conductivity was 1.09$\times$10$^{-3}$ S/cm for PVH40 containing 28.6 wt% of P(VdF-co-HFP) at $25^{\circ}C$. Tensile strength, tensile modulus and compression modulus were increased with P(VdF-co-HFP) content and abruptly changed between PVH70 and PVH80. Dynamic shear moduli showed a typical gel behavior and changed with shear strain.

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Synthesis and Biopharmaceutical Properties of Ceftezole Butyrolactone Ester, a Novel Prodrug of Ceftezole (세프테졸 부티로락톤 에스텔의 합성 및 생물약제학적 특성)

  • Lee, Jin-Hwan;Park, Jae-Young;Choi, Jun-Shik;Ko, Jae-Won
    • Journal of Pharmaceutical Investigation
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    • v.31 no.3
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    • pp.143-150
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    • 2001
  • Butyrolactone ester of ceftezole (CFZ-BL) was synthesized by esterification of ceftezole (CFZ) with ${\alpha}-bromo-{\gamma}-butyrolactone$. The synthesis was confirmed by spectroscopic analysis. CFZ-BL was more lipophilic than CFZ when the lipophilicity was assessed by partition coefficients between n-octanol and water at various pH. CFZ-BL itself did not show any microbiological activity in vitro, but serums taken after oral administration of CFZ-BL showed substaintial microbiological activity indicating that CFZ-BL is converted to microbiologically active metabolite, probably CFZ, in the body. The conversion was confirmed by in vitro incubation study, in which CFZ-BL was incubated in some body tissues of rabbit. Liver homogenate showed fastest conversion of CFZ-BL among the tissues tested (blood and intestine). Thus, CFZ-BL appeares to be rapidly metabolized in the liver to CFZ following oral administration. The metabolism process appears to be hydrolysis of the ester to CFZ, the parent drug of CFZ-BL. In vivo metabolism of CFZ-BL to CFZ was confirmed by analying CFZ by HPLC. CFZ concentration in the serum samples taken after oral administration of CFZ-BL were higher than those in the serum samples taken after oral administration of equivalent amount of CFZ. Oral bioavailability of CFZ-BL, a prodrug of CFZ, was 1.45-fold higher than that of CFZ in rabbits possibly due to enhanced lipophility and absorption of the prodrug.

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Antimicrobial Activities of Sesquiterpene Lactones Isolated from the Flower of Chrysanthemum coronarium L. (쑥갓의 꽃에서 분리한 sesquiterpene lactones의 항균활성)

  • Ha, Tae-Jung;Han, Hyo-Shim;Jang, Ki-Chang;Jang, Dae-Sik;Cho, Dong-Young;Yang, Min-Suk;Lee, Kyung-Dong
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.235-239
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    • 2003
  • Thirteen sesquiterpene lactones isolated from the flower of Chrysanthemum coronarium L., which has been widely cultivated in Korea as a vegetable for a long time, were investigated their antimicrobial activities against eight bacteria and five phytopathogenic fungi. The antimicrobial activities of dihydrochrysanolide (6) and 1-epi-dihydrochrysanolide (7) showed strong activities against all the bacteria such as Bacillus subtilis, Bacillus cereus, Staphylococcus aureus and Vibrio parahaemolyticus. Especially, Staphylococcus aureus was investigated that have very strong antibacterial activity to $1.56\;{\mu}g{\cdot}disc^{-1}$, respectively. Also, most of sesquiterpene lactones, which have ${\alpha}-methylene-{\gamma}-butyrolactone$ group, were exhibited strong activity to Gram(+) bacteria than Gram(-) bacteria. In the antifungal test, Rhizoctonia solani and Phytophthora capsici known as phytopathogenic fungi have exhibited all extensive activity about compounds that have ${\alpha}-methylene-{\gamma}-butyrolactone$ group.