• Title/Summary/Keyword: 3'-Ethenyl

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Synthesis of an Intermediate for Carbaprostacyclin: Stereoselective Synthesis of 1-Alkoxy-3-benzenesulfonyl-3-cyano-4-ethenyl cyclopentane (카바프로스타싸이클린 중간체의 합성 : 1-Alkoxy-3-benzenesulfonyl-3-cyano-4-ethenyl cyclopentane의 입체선택적 합성)

  • 서영거;정재경;구본암;최영기;조윤상
    • YAKHAK HOEJI
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    • v.39 no.1
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    • pp.41-47
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    • 1995
  • An efficient and stereoselective synthetic route to the trisubstituted hydroxy cyclopentane as an useful synthetic intermediate for carbaprostacyclin is described. Pd(0)-mediated intramolecular alkylation of allylic carbonate has been employed as a key reaction.

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Highly Efficient Synthesis of Conformationally Fixed Bicyclo[3.1.0]hexyl Nucleosides with an Ethenyl Group at C3'-Position as Potential Antiviral Agents

  • Kim, Seong Jin;Woo, Youngwoo;Park, Ah-Young;Kim, Hye Rim;Son, Sujin;Yun, Hwi Young;Chun, Pusoon;Moon, Hyung Ryong
    • Bulletin of the Korean Chemical Society
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    • v.35 no.9
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    • pp.2649-2654
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    • 2014
  • Synthesis of north-5'-methylbicyclo[3.1.0]hexyl adenine and hypoxanthine nucleosides with an ethenyl group at C3' position was successfully achieved by a highly facile method. Methylbicyclo[3.1.0]hexanone (${\pm}$)-7 with three contiguous chiral centers and its epimer (${\pm}$)-6 was remarkably simply constructed only by four steps involving a carbenoid insertion reaction in the presence of rhodium (II) acetate dimer as a metal catalyst, giving a correct relative stereochemistry of the generated three chiral centers. Due to steric hindrance from the concave face of the bicyclo[3.1.0]hexanone system, a Grignard reaction of (${\pm}$)-7 with ethenylmagnesium bromide showed exclusive diastereoselectivity towards the b-face. The Grignard reaction chemoselectively proceeded without reacting with ester functionality. Coupling reaction of glycosyl donor (${\pm}$)-11 with 6-chloropurine nucleobase afforded only the desired $N^9$-alkylated nucleoside without the formation of $N^7$-regioisomer. By the conventional method, 6-chloro group was converted into 6-amino and 6-hydroxy groups to give the desired adenine and hypoxanthine bicyclo[3.1.0]hexyl carbanucleosides with 3'-ethenyl group, respectively.

Radical Scavenging Hydroxyphenyl Ethanoic Acid Derivatives from a Marine-Derived Fungus

  • Li Xifeng;Kim Se-Kwon;Kang Jung-Sook;Choi Hong-Dae;Son Byeng-Wha
    • Journal of Microbiology and Biotechnology
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    • v.16 no.4
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    • pp.637-638
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    • 2006
  • Bioassay-guided fractionation of an organic extract of the culture broth from an unidentified marine-derived fungus led to the isolation of a new metabolite, N-[2-(4-hydroxyphenyl) acetyl]formamide (1), along with four known polyketides, 4-hydroxyphenyl acetamide (2), 4-hydroxyphenyl acetic acid (3), 3,4-dihydroxyphenyl acetic acid (4), and N-[2-(4-hydroxyphenyl)ethenyl]formamide (5). The structures of 1-5 were elucidated by spectral data analyses. Among them, compounds 1, 4, and 5 exhibited significant radical scavenging activity against 1, 1-diphenyl-2-picrylhydrazyl (DPPH) with $IC_{50}$ values of 8.4, 11.9, and $0.2{\mu}M$, respectively.

Platelet Anti-aggregating Activities of Higenamine Analogs (Higenamine 유도체들의 혈소판응집 억제작용)

  • 윤혜숙;백승환;이종란
    • YAKHAK HOEJI
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    • v.30 no.5
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    • pp.245-252
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    • 1986
  • Various structural analogs of higenamine, 1-(4'-hydroxylbenzyl)-6,7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline, were synthesized and their inhibitory activities against platelet aggregation induced by either arachidonic acid, ADP or collagen. Among the twenty-five compounds tested, inhibitory activity is favored by the 3, 4-dihydroisoquinoline system with the methyl bridge between the two aromatic rings replaced by either ethyl or ethenyl group. N-Methyl quaternization decreased the inhibitory activities. * 이논문의 내용중 편집상의 오류가 있습니다. 그에대한 정오표는 v.31, n.1의 45p.에 있습니다.

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Structural Study on an Permethyl Ether of a New Polyphenolic Compound Isolated from Panax ginseng (인삼으로부터 분리된 새로운 Polyphenal 성분의 Permethyl ether 의 구조에 관한 연구)

  • Wi, Jae-Jun;Park, Jong-Dae;Kim, Man-Uk
    • Journal of Ginseng Research
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    • v.14 no.1
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    • pp.27-29
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    • 1990
  • A Polyphenolic Compound was isolated from ethyl acetate fraction of Panax ginseng. And the chemical structure of its permethyl ether was suggested as 6-[2(3,4-dimethoxyphenyl)ethenyl]-5-(3,4-dimethoxyphenyl)2,8,10-trimethoxybenzo[a] xanthen-9-one by spectroscopic and chemical degradative evidences.

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Studies on Asymmetric Synthesis of Carbaprostacyclin and Its Structural Analogs

  • 서영거;정재경;구본암;조윤상
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1994.04a
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    • pp.215-215
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    • 1994
  • PGI$_2$ 안정한 구조를 갖는 carbaprostacyclin 및 그 structural analog들을 입체 선택적으로 합성하고, 혈관 순환 개선제로 발전시키고자 중요한 합성 중간체이며 광학활성을 갖는 5-ethenyl-3-hydroxy cyclopentane carboxylate를 합성하였다. 반응의 핵심 단계는 butyrolactone moiety를 갖는 allylic carbonate를 Pd(0)촉매하에서 환화시킨 후, 정교한desulfonation에 이온 lactone의 개열 단계를포함한다.

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Changes in Fructosazines and Major Volatile Components of Burley Leaf Tobacco Extracts by Heat Treatment (버어리잎담배 추출물의 열처리에 의한 화학성분 변화)

  • 이재곤;곽재진;장희진;김옥찬
    • Journal of the Korean Society of Tobacco Science
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    • v.19 no.2
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    • pp.151-158
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    • 1997
  • Burley leaf tobacco extracts has been heated at loot for 2 hours and changes in non-volatile fructosazines and volatile components were investigated. Major changes for the heat treatment with corn syrup of burley leaf tobacco extracts were as follows, increases in the contents of 2,5-deoxyfructosazine and 2,5-fructosazine that is produce for the heating reaction of sugar and ammonia, production of pyraEine compounds, such as 2,6-dimethyl pyrazine,2,4-dimethyl pyrazine, ethrnyl pyrazine, methylethyl pyraxine, trimethyl pyrazine, 2-ethenyl-5-methyl pyrazine, 2-acetyl parazine and 2-acetyl-3-methyl pyrazine, increases in the content of furfuryl alcohol derived from sugar degrad ation, production of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one derived from thermal degradation of Amadori compounds.

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Chemical Constituents of Fermented Noni (Morinda citrifolia) Juice Exudates and Their Biological Activity

  • Youn, Ui Joung;Chang, Leng Chee
    • Natural Product Sciences
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    • v.23 no.1
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    • pp.16-20
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    • 2017
  • In a continuing study of the fermented noni (Morinda citrifolia) juice exudates, five compounds, heptanyl $2-O-{\beta}-{\small{D}}-xylofuranosyl-(1{\rightarrow}6)-{\beta}-{\small{D}}-glucopyranoside$ (1), n-butyl ${\beta}-{\small{D}}-glucopyranoside$ (2), (1S)-(3-ethenyl-phenyl)-1,2-ethanediol (3), (2S)-2-hydroxybutanedioic acid (4), and daucosterol (5) were isolated from the buthanol partition of the extract. The structures of the isolates were identified by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with the published values. Among the isolates, compounds 1 - 3 were isolated for the first time from the plant species. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production and tumor necrosis factor alpha ($TNF-{\alpha}$)-induced $NF-{\kappa}B$ activity, and quinonone reductase-1 (QR1)-inducing effect.

Volatile Compounds and Ultrastructure of Petal Epidermal Cells According to Scent Intensity in Rosa hybrida (장미꽃의 향기정도에 따른 주요성분 및 꽃잎 세포의 미세구조)

  • Lee, Young-Soon;Lee, Yun-Hae;Lim, Seung-Hee;Park, Gun-Hwan;Choi, Sunk-Young;Hong, Hae-Jung;Ko, Jeong-Ae
    • Horticultural Science & Technology
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    • v.31 no.5
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    • pp.590-597
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    • 2013
  • Principle component and emission localization of volatile compounds were investigated according to scent intensity of rose flower. Scent intensity in cultivars and bred-line of Rosa hybrida was divided into three levels; light ('Feel Lip', 'Venus Berry'), medium ('GR07-135'), strong ('Honey Blue'). The major volatile compounds were different depending on the cultivars and selected line; 3,5-dimethoxytoluene (DMT), benzene, 1,3,5-trimethoxy ('Feel Lip'), megastigma-4,6(Z),8(E)-triene ('Venus Berry'), DMT, benzene,1-ethenyl-4-methoxyand, phenylethylalcohol ('GR07-135') and germacrene-D, DMT ('Honey Blue'). The adaxial epidermal cells were conical papillate shape, whereas the abaxial epidermal cells were flat shape. The adaxial epidermal cells of 3 cultivars and 1 selected line were surrounded by thick cell wall and covered by waxy cuticle of 2 cultivars and 1 selected line (except 'Honey Blue'). The adaxial epidermal cells contained starches in 'Feel Lip', osmiophlic droplets in 'Venus Berry', starchs, plastids, vacuoles in 'GR07-135' and plastoglobules, plastids, vacuoles in 'Honey Blue'. Based on these results, it appears that plastids and vacuoles in adaxial epidermal cells with conical papillate shape are associated production and emission of volatile compounds in scent R. hybrida.

Novel 4,7-Dithien-2-yl-2,1,3-benzothiadiazole-based Conjugated Copolymers with Cyano Group in Vinylene Unit for Photovoltaic Applications

  • Kim, Jin-Woo;Heo, Mi-Hee;Jin, Young-Eup;Kim, Jae-Hong;Shim, Joo-Young;Song, Su-Hee;Kim, Il;Kim, Jin-Young;Suh, Hong-Suk
    • Bulletin of the Korean Chemical Society
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    • v.33 no.2
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    • pp.629-635
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    • 2012
  • Two novel conjugated copolymers utilizing 4,7-dithien-2-yl-2,1,3-benzothiadiazole (DTBT) coupled with cyano (-CN) substituted vinylene, as the electron deficient moeity, have been synthesized and evaluated in bulk heterojunction solar cell. The electron deficient moeity was coupled with carbazole and fluorene unit by Knoevenagel condition to provide poly(bis-2,7-((Z)-1-cyano-2-(5-(7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl)-2-thienyl)ethenyl)-alt-9-(1-octylnonyl)-9H-carbazol-2-yl-2-butenenitrile) (PCVCNDTBT) and poly(bis-2,7-((Z)-1-cyano-2-(5-(7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl)-2-thienyl)ethenyl)-alt-9,9-dihexyl-9H-fluoren-2-yl) (PFVCNDTBT). The optical band gaps of PCVCNDTBT (1.74 eV) and PFVCNDTBT (1.80 eV) are lower than those of PCDTBT (1.88 eV) and PFVDTBT (2.13 eV), which is advantageous to provide better coverage of the solar spectrum in the longer wavelength region. The high $V_{oc}$ value of the PSC of PCVCNDTBT (~0.91 V) is attributed to its lower HOMO energy level ( 5.6 eV) as compared to PCDTBT ( 5.5 eV). Bulk heterojunction solar cells based on the blends of the polymers with [6,6]phenyl-$C_{61}$-butyric acid methyl ester ($PC_{61}BM$) gave power conversion efficiencies of 0.76% for PCVCNDTBT under AM 1.5, 100 mW/$cm^2$.