• 제목/요약/키워드: Aldol

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Acetonylidene americanin A, An artefact isolated from phytolacca americana

  • Woo, Won-Sick;Kang, Sam-Sik;Otto-Seligmann;Wagner, Hildebert
    • Archives of Pharmacal Research
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    • 제5권1호
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    • pp.1-5
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    • 1982
  • From the seeds of Phytolacca americana, acentonylidene americanin. A was isolated and its structure elucidated mainly by spectroscopic methods. This compound is not a genuine constituent but formed in the tissue on heating with acetone.

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An Efficient and Concise Synthesis of Biologically Interesting Natural Flemichapparin A, Flemingin A, Flemingin D, and Their Non-natural Analogues

  • Lee, Yong-Rok;Xia, Likai
    • Bulletin of the Korean Chemical Society
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    • 제28권9호
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    • pp.1579-1584
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    • 2007
  • The efficient and concise synthesis of natural and non-natural pyranochalcones was achieved from readily available 2,4,5-trihydroxyacetophenone. The key steps in the synthetic strategy were ethylenediamine diacetate-catalyzed benzopyran formation and aldol reactions.

새로운 항암성 제리쿠드라닌 E 유도체의 합성 및 항암활성 (Synthesis and Antitumor Activity of Novel Gericudranin E Derivatives)

  • 박재호;박경란;호현순;김희두;표명윤
    • 약학회지
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    • 제43권5호
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    • pp.559-565
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    • 1999
  • The two gericudranin E derivatives, GER-I & II, were synthesized and evaluated their antitumour activities for the elucidation of structure-activity relationship. 2,4,6-Trihydroxyacetophenone was converted to target molecules GER-I and GER-B in 5 steps via sequential protection, aldol condensation, Michael type-cyclization, regioselective C-benzylation. The cellular growth inhibition of compounds GER-I and GER-II were investigated against P388, L1210, K562, HCT-15, SK-HepG-1, MCF-7 as cancer cell lines and mouse splenocytes as a normal cell by MTT assay.

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Asymmetric synthesis of (2S, 3R, 4E) 5-Aryl-4-pentene-1,3-diol-2-aminoueras

  • Im, C.U.;Kim, Y.H.;Jyung, M.L.;Lim, C.B.
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.237.1-237.1
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    • 2003
  • (2S 3R. 4E) 5-Aryl-4-pentene-1,3-diol-2-aminoueras had been synthesized for their cytotoxic activity. Pinene was oxidized with KMnO4 to give 2-hydroxy-3-pinanone. which treated with ethyl glycinate to yield iminoglycinate and then reacted with aldehyde derivatives and titanium enolate to afford 3-hydroxy aldol compounds. (omitted)

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Synthesis of Renewable Jet Fuel Precursors from C-C Bond Condensation of Furfural and Ethyl Levulinate in Water

  • Cai, Chiliu;Liu, Qiying;Tan, Jin;Wang, Tiejun;Zhang, Qi;Ma, Longlong
    • Korean Chemical Engineering Research
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    • 제54권4호
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    • pp.519-526
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    • 2016
  • Biomass derived jet fuel is proven as a potential alternative for the currently used fossil oriented energy. The efficient production of jet fuel precursor with special molecular structure is prerequisite in producing biomass derived jet fuel. We synthesized a new jet fuel precursor containing branched $C_{15}$ framework by aldol condensation of furfural (FA) and ethyl levulinate (EL), where the latter of two could be easily produced from lignocellulose by acid catalyzed processes. The highest yield of 56% for target jet fuel precursor could be obtained at the optimal reaction condition (molar ratio of FA/EL of 2, 323 K, 50 min) by using KOH as catalyst. The chemical structure of $C_{15}$ precursor was specified as (3E, 5E)-6-(furan-2-yl)-3-(furan-2-ylmethylene)-4-oxohex-5-enoic acid ($F_2E$). For stabilization, this yellowish solid precursor was hydrogenated at low temperature to obtain C=C bonds saturated product, and the chemical structure was proposed as 4-oxo-6-(tetrahydrofuran-2-yl)-3-(tetrahydrofuran-2-yl)-methyl hexanoic acid ($H-F_2E$). The successful synthesis of the new jet fuel precursors showed the significance that branched jet fuel could be potentially produced from biomass derived FA and EL via fewer steps.

Concise Total Synthesis of Biologically Interesting Prenylated Chalcone Natural Products: 4'-O-Methylxanthohumol, Xanthohumol E, and Sericone

  • Lee, Yong-Rok;Li, Xin;Lee, Seung-Woo;Yong, Chul-Soon;Hwang, Ma-Ro;Lyoo, Won-Seok
    • Bulletin of the Korean Chemical Society
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    • 제29권6호
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    • pp.1205-1210
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    • 2008
  • A new and efficient synthetic approach is reported for biologically interesting prenylated chalcones, 4'-Omethylxanthohumol (3), xanthohumol E (4), and sericone (5) from 2,4,6-trihydroxyacetophenone. The strategies involve the introduction of a prenyl group onto an aryl ring, benzopyran formation, and basecatalyzed aldol reactions.

Threonine의 생물공학적 생산 (Biotechnology for the Production of Threonine Production)

  • 김경자
    • 약학회지
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    • 제34권6호
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    • pp.447-456
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    • 1990
  • Various methods are available for the production of L-threonine. The microbial production of L-threonine has been achieved by breeding L-threonine analog-resistant auxotrophic mutants of various bacteria. The enzymatic production of L-threonine has been demonstrated by use of threonine metabolic enzymes such as threonine deaminase, threonine aldolase, or threonine dehydrogenase complex. Threonine synthesis from glycine and ethanol seems to be catalyzed by the enzymes Methanol dehydrogenase(MDH) and Serine hydroxymethyltransferase(SHMT), which was also found to catalyze the aldol condensation of glycine with acetaldehyde. The improved production of L-threonine has been achieved by amplifying the genes for the L-threonine biosynthetic enzymes using recombinant DNA techniques.

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Studies on the Nuclear Magnetic Resonance Spectra of (E)-1-Aryl-3-(2- and 3-thienyl)-2-propenones and Unique Observation of 4J and 5J Coupling in Their 1H-1H COSY

  • HanLee, In-Sook;Jeon, Hyun-Ju;Lee, Chang-Kiu
    • Bulletin of the Korean Chemical Society
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    • 제32권2호
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    • pp.687-692
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    • 2011
  • $^1H$ and $^{13}C$ NMR spectra of series of (E)-1-aryl-(2- and 3-thienyl)-2-propenones, that are aldol condensation products between 2- and 3-thiophenecarbaldehydes and m- and p-substituted acetophenones, were examined to make complete assignments of the chemical shifts. Long range couplings, $^4J$ and $^5J$, are observed in the $^1H-^1H$ COSY of both 2- and 3-thienyl compounds, which makes the elucidation of the conformation in solution possible. In contrast, the 2-furyl analogue shows the long range coupling phenomena, but the 3-furyl and phenyl analogues do not show similar phenomena.

A Study on the Synthesis of Nortropinone Derivatives

  • Jung, Dai-II;Park, Chil-Sung;Choi, Hak-Ki;Kim, Dong-Hee;Lee, Do-Hun;Jung, Il-Soo;Park, Yu-Mi;Choi, Soon-Kyu
    • Journal of Life Science
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    • 제9권1호
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    • pp.81-83
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    • 1999
  • 2,4-Disubstituted nortropinone derivatives anticipated anticonvulsant activity were respectively synthesized by the reaction of N-substituted nortropinones, ethanol, 5N-NaOH and benzaldehyde ({TEX}$R_{1}${/TEX}CHO)

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항암제로서의 (${\pm}$) -3-데옥시제리쿠드라닌 A의 설계 및 합성 (Design and Synthesis of (${\pm}$) -3-Deoxygericudranin A as an Antitumour Agent)

  • 최윤정;심필종;김희두
    • 약학회지
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    • 제41권1호
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    • pp.14-17
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    • 1997
  • (${\pm}$)-3-Deoxygericudranin A was designed and synthesized for the development of novel antitumour agent and for the elucidation of the effect of 3-hydroxyl group in gericudranin A on antitumour activity. 2,4.6-Trihydroxyacetophenone was converted to 3-deoxygericudranin A in 5 steps via sequential protection, aldol condensation, Michael tvpe-cyclization, regioselective, C-benzylation and deprotection.

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