• 제목/요약/키워드: Adducts

검색결과 270건 처리시간 0.018초

Synthesis of 3-Aryl-3-hydroxypyrrolidin-2-ones and 2-Benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione Derivatives from the Baylis-Hillman Adducts of Isatins

  • Kim, Seung Chan;Lee, Ka Young;Gowrisankar, Saravanan;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • 제27권8호
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    • pp.1133-1139
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    • 2006
  • We prepared 3-aryl-3-hydroxypyrrolidin-2-one and tricyclic 2-benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione derivatives starting from the Baylis-Hillman adducts of isatin derivatives.

New Water-soluble Cutting Fluids Additives Derived from the Thermal Reaction Products of Unsaturated Fatty Acids with Acrylic Acid and Maleic Anhydride

  • Watanabe, Shoji
    • 한국응용과학기술학회지
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    • 제20권4호
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    • pp.372-376
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    • 2003
  • Water-soluble cutting fluids are used for processing of aluminium materials. This short article describes properties of new additives of water-soluble cutting fluids for aluminium materials. Various Diels-Alder adducts of unsaturated fatty acids with acrylic acid of maleic anhydride were prepared by thermal reactions. Triethanolamine salts of Diels-Alder adducts of dehydrated castor oil fatty acids with acrylic acid or maleic anhydride showed excellent anti-corrosion property of aluminium materals. These thermal adducts showed anti-rust property for cast-iron chips, too.

Elucidation of Selectivity Difference in the Diels-Alder Reactions of 6,6-Disubstituted Cyclohexa-2,4-dienone

  • Jeong, Jun-Pyeong;Lee, Oh-Seuk;Yang, Ki-Yull
    • Bulletin of the Korean Chemical Society
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    • 제23권6호
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    • pp.829-837
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    • 2002
  • Recently it was reported that cycloaddition of 6,6-disubstituted cyclohexa-2,4-dienone, 1 with cyclopentadiene gave solely the adduct of type 1.while its reaction with 1,3-cyclohexadiene gave both Ⅱ and Ⅲ. Semiempirical MO calculations were done to elucidate the origin of the selectivity difference between the two dienes. Cycloaddition of 1 with cyclopentadiene is controlled thermodynamically to give only 1-diene adduct by ΔGvalues of 10.6-20.3 kcal/mol, while its reaction with 1,3-cyclohexadiene does not show 1-diene/1-dienophile selectivity due to similar stabilities of the two adducts. Thermodynamic parameters also show that 두애 adducts are more fabourably fromed in the cycloadditions of 1 with both cyclopentadiene and 1,3-cyclohexadiene, which coincides with experimental observations. Cope rearrangements of endo adducts are another avenue to convert between 1-diene and 1-dienophile.

Ginseng Prevents DNA-adduct Formation in Rat Hepatocytes in vitro Treated with DMBA

  • Kumar, Ashok
    • 고려인삼학회:학술대회논문집
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    • 고려인삼학회 1998년도 Advances in Ginseng Research - Proceedings of the 7th International Symposium on Ginseng -
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    • pp.263-269
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    • 1998
  • It is an established fact that most of the carcinogens implicate bay-region diol epoxides as the ultimate carcinogenic metabolites. These electrophiles react with nucleophilic sites in the cells to form abducts. It is the formation of carcinogenic-DNA adducts that is thought to initiate carcinogenesis. In our previous study we have reported chemopreventive property of Ginseng on 7,12-dimethylbenz (a)anthracene (DMBA) induced skin papillomagenesis in male Swiss albino mice. In this study we have examined the effect on formation of DMBA-DNA adducts in rat hepatocytes pretreated with ginseng. Primary cultures of rat hepatocytes were used. The cells wets treated with ginseng for 24 hrs and then with DMBA (iOn) for 18 hrs. Cells were then harvested, their DNA was isolated and analyzed by P)2 labelling. A significant reduction in the levels of DMBA-DNA adduces (adducts/108 nucleotides) was observed in all cultures pretreated with ginseng. The viability of cells was not affected by pre-treatment with ginseng. Our finding suggests that ginseng block or suppresses the events associated with chemical carcinogenesis by inhibiting metabolic activation of the carcinogens.

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Expedient One-Pot Synthesis of γ-hydroxybutenolides Starting from Baylis-Hillman Adducts: Lactonization, Isomerization, and Aerobic Oxidation of α-Methylene-γ-hydroxyester

  • Kim, Ko-Hoon;Lee, Hyun-Seung;Kim, Sung-Hwan;Lee, Ka-Young;Lee, Ji-Eun;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • 제30권5호
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    • pp.1012-1020
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    • 2009
  • We developed an efficient three-step synthetic protocol of $\gamma$-hydroxybutenolides starting from the Baylis-Hillman adducts: (i) bromination, (ii) Barbier reaction and (iii) one-pot $K_2CO_3$-mediated synthesis of $\gamma$-hydroxybutenolides. In addition, we showed the synthetic applicability of butenolides including self-dimerization, conjugate addition reaction, and alkylations.

An Efficient Synthesis of Phospha-Morita-Baylis-Hillman Adducts via Michaelis-Arbuzov Reaction of the DABCO Salt of Morita-Baylis-Hillman Bromide

  • Kim, Sung Hwan;Kim, Se Hee;Lee, Hyun Seung;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • 제34권1호
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    • pp.133-138
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    • 2013
  • An efficient synthesis of phospha-Morita-Baylis-Hillman adducts was carried out in good yields via the Michaelis-Arbuzov reaction of the DABCO salts of MBH bromides. Instead of a DABCO salt, a phosphonium salt could be effectively used for some substrates which showed some problems in the presence of DABCO.

Baylis-Hillman Reaction and Chemical Transformations of Baylis-Hillman Adducts

  • Lee, Ka-Young;Gowrisankar, Saravanan;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • 제26권10호
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    • pp.1481-1490
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    • 2005
  • Carbon-carbon single bond-forming reaction is the most useful and fundamental reaction in organic synthesis. Most of the basic carbon-carbon single bond-forming reactions, thus, developed in the past. In these respects, conceptually new C-C bond formation reaction can be highlighted. The Baylis-Hillman reaction was found at the early 1970’s. However, extensive studies on this highly potential reaction were started only before 15 years. This review has been written to shed more lights to the importance of Baylis-Hillman reaction. We have focused mainly on the reaction mechanism, conceptually related reactions, and chemical transformations of the Baylis-Hillman adducts.

7H-Dibenzo [c,g] carbazole과 Dibenz[a,j] acridine에 의한 DNA adduct의 32P-postlabeling 분석 (32P-postlabeling Analysis of 7H-Dibenzo [c,g] carbazole and Dibenz [a,j] acridine DNA Adduct in Mice)

  • 노재훈;문영한;데이비드 봐르쇼브스키;글렌 탈라스카
    • 한국산업보건학회지
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    • 제3권1호
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    • pp.14-21
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    • 1993
  • 7H-dibenzo[c,g]carbazole(DBC)과 dibenz[a, j]acridine(DBA) 및 이의 대사물 trans-DBA-1,2-dihydrodiol(DBA-1,2-DHD), trans-DBA-3,4-dihydrodiol(DBA-3,4-DHD), trans-DBA-5,6-dihydrodiol(DBA-5,6-DHD)]에 의한 DNA adduct형성을 알기 위해 Hsd:ISR 생쥐 피부에 이를 투여하고 용매 추출법으로 DNA를 분리하고 $^{32}P$-postlabeling법으로 DNA adduct를 분석하였다. DBC를 피부에 투여하여 DNA adduct가 국소작용 부위인 피부와 내장기관인 간, 폐 및 신장에 형성되어 DBC는 국소 및 전신 발암작용이 있음을 알 수 있었다. 또한 DNA adduct활성도가 간에서는 높고 피부, 폐, 신장에서는 상대적으로 낮아 DBC에 의한 발암의 주 표적 장기는 간임을 추측할 수 있었다. DBA, DBA-3,4-DHD 및 DBA-5,6-DHD 투여에 의해 두개의 adduct가 피부에서 관찰되었다. 대사 물질인 DBA-5,6-DHD에 의해 2개의 adduct가 형성되었으나 그 양상이 DBA 및 DBA-3,4-DHD와는 달랐으며 DBA-1,2-DHD에 의해서는 DNA adduct 형성이 관찰되지 않았다. 이상의 결과로 DBA는 국소발암작용이 있으며 활성 대사물인 DBA-3,4-DHD가 최종 발암원(ultimate carcinogen)이고 DBA-1,2-DHD는 무독화 대사물질로 추측된다.

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