• Title/Summary/Keyword: Heterocyclic

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DFT/B3LYP Study to Investigate the Possible Ways for the Synthesize of Antioxidants with High Efficiency Based on Vitamin E

  • Najafi, Meysam;Najafi, Mohammad;Najafi, Houshang
    • Bulletin of the Korean Chemical Society
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    • v.33 no.10
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    • pp.3343-3348
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    • 2012
  • The possible ways for increasing the antioxidant properties of vitamin E have been investigated with density function theory. The effect of replacing three methyl groups of vitamin E with various substituents such as electron donating and electron withdrawing groups on the antioxidant properties of vitamin E were investigated. Also the effects of the reducing the number of atoms in the heterocyclic ring and replacing the oxygen heteroatom with other heteroatoms on the antioxidant properties of vitamin E were investigated. The novel structures that obtained from replacing methyl groups with substituents such as $NH_2$, OH, COOH and NHMe have greater antioxidant activity than vitamin E. Obtained results reveal that novel structure that obtained with replacing O with NH hetroatom would be a better antioxidant than vitamin E. The results reveal that reducing the number of atoms in the heterocyclic ring is a better way to synthesize novel antioxidants.

Three Component Solvent-free Synthesis of Chroman-2,4-dione-based Heterocyclic Ketene Aminal (HKA) Derivatives by "GAP" Chemistry

  • Yu, Fu-Chao;Hao, Xiao-Pan;Jiang, Xiu-Yang;Yan, Sheng-Jiao;Lin, Jun
    • Bulletin of the Korean Chemical Society
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    • v.35 no.6
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    • pp.1625-1632
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    • 2014
  • A concise and efficient one-pot synthesis of chroman-2,4-dione-based HKA derivatives by three component reaction of HKAs, triethoxymethane and 4-hydroxycoumarin derivatives under solvent-free and catalyst-free conditions is described. This protocol has many advantages, in that the GAP (Group-Assistant-Purification) chemistry process is involved in this method. As a result, the experimenter can avoid cumbersome process steps such as traditional chromatography and recrystallization purifications. The desired products can be easily obtained by washing the crude products with 95% EtOH.

Elucidation of Anti-Tumor Initiator and Promoter Derived from Seaweed-4: Desmutagenic Principles of Ecklonia stolonifera Extracts against Carcinogenic Heterocyclic Amines (해조류 중의 Anti-Tumor Initiator 및 Promoter의 해석-4: 발암성 Heterocyclic Amine에 대한 곰피 추출물 중의 돌연변이원성 억제인자)

  • 김선봉;박영범;안종관;유승재;박덕천;김인수;박영호
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.27 no.3
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    • pp.537-542
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    • 1998
  • The present study was performed to elucidate desmutagenic principles from Ecklonia stolonifera extracts against 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine(PhIP) and 2-amino-3,8-dime-thylimidazo[4,5-f]duinoxaline(MeIQx) with Salmonella/mammalian-microsome mutagenicity test. Alginate, phenols, chlorophyll and carotenoids from Ecklonia stolonifera were extracted and their desmutagenicities were assayed. Alginate hydroysates showed desmutagenic activities against PhIP and MeIQx at high level dose. Phenol fractions and bromophenol showed desmutagenic activity of about MeIQx at high level dose. Phenol fractions and bromophenol showed desmutagenic activity of about 90% per 0.5mg against PhIP and MeIQx. Chlorophyllin among chlorophyll derivatives exhibited remarkable desmutagenic activities of 92.9% and 82.7% at 20uM against PhIP and MeIQx, respectively. Carotenoids, such as lutein and $\alpha$-cryptoxanthin isolated from Ecklonia stolonifera exerted also high desmutagenic activity. Major desmutagenic substances from Ecklonia stolonifera are considered to be chlorophyllin, phenols, lutein, $\alpha$-cryptoxanthin and low molecular alginates.

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A Synthesis of Sulfonyl Urea Derivatives in Aqueous Media (수용액에서 술포닐 우레아 유도체들의 합성)

  • Lee, Chun-Soo;Yoon, Mu-Hong;Choe, Seok-Burn;Rho, Seung-Baik
    • Applied Chemistry for Engineering
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    • v.3 no.1
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    • pp.100-110
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    • 1992
  • Arylsulfonyl urea derivatives can be easily prepared in good yield by treating amines with arylsulfonyl carbamates in aqueous solution : 1) N-Arylsulfonyl-N'-aryl urea derivatives, 2) N-Arylsulfony-N'-alkyl urea derivatives, 3) N-Arylsulfonyl-N'- heterocyclic urea derivatives. The proposed reaction mechanisms for preparing arylsulfonyl ureas involve formation of an ion-pair conformation by initial acid-base reaction, then formation of a so-called tetrahedral intermediate by nucleophilic addition, followed by an acid-catalyzed elimination of an alkoxide ion and loss of a proton.

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LASER FLASH PHOTOLYSIS STUDY ON THE PHOTOCYCLIZATION OF N-(O-HALOBENZYL) IMIDAZOLE

  • Park, Yong-Tae;Hwang, Young-Sun;Song, Woong Song;Kim, Dongho
    • Journal of Photoscience
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    • v.3 no.2
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    • pp.91-93
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    • 1996
  • In connection with our interest on the photochemical properties of heteroaryl halides, which are currently the subject of heterocyclic ring formation and haloarene degradation, we have studied the photochemistry of the haloarene linked to N-heteroarene compounds. Imidazo[5,1-a]isoindole was synthesized from N-(ochlorobenzyl)imidazole or N-(o-bromobenzyl) imidazole in acidic aqueous solution or acetonitrile via the intramolgcular photocyclization (Table 1). This type of reaction provides the synthetic methods for 5- and 6-membered polyheteroatomic heterocyclic ring compounds. However, the reaction mechanism for the intramolecular photocyclization of haloarene tethered heteroarenes has not yet been established. Grimshaw et al. suggested a mechanism for homolyric carbonhalogen bond fission assisted by radical complexation to explain their results in the photocyclization of 5-(2-chlorophenyl)-1,3-diphenylpyrazole. They also reported the detection of acyclohexadienyl intermediate involved in the above reaction. Park et al. reported several transient 'intermediates involved in the laser flash photolysis of N-(o-halobenzyl) pyridinium and N-benzyl-2-halopyridinium salts. Thus we performed the laser flash photolysis study on the photocyclization reaction of N-(o-chlorobenzyl) imidazole to identify the intermediate species involved in the reaction. Here, we report on the preliminary results in the photocyclization reaction of N-(o-halobenzyl)imidazole through the detection of reaction intermediates.

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Ring Flipping of Seven-membered and Eight-membered Dithienodisila-heterocycles

  • Lee, In-Sook;Kwak, Young-Woo;Ghosh, Manikkumer;Ohshita, Joji;Choi, Cheol-Ho
    • Bulletin of the Korean Chemical Society
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    • v.29 no.2
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    • pp.377-380
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    • 2008
  • Ground state structures and ring flipping transition states of eight- and seven-membered silicon containing heterocyclic compounds such as dithienodisilacyclooctatriene and oxadithienodisilacycloheptadiene derivatives, respectively have theoretically been investigated. Although the bithienylene moiety of the derivatives does not change the ground state structures, they significantly increase the ring flipping barrier by 13-17 kcal/mol in the case of the eight-membered rings (2, 3, and 4) in comparison with that of silicon containing heterocyclic compound 6, chosen as a model. The same moiety increases the flipping barrier of seven-membered ring (5) is only slightly (3.3 kcal/mol) in comparison with that of model compound 7. Hence, it has been concluded that not only the existing ring strain of eight-membered ring but also the bithienylene moiety collectively increases the ring flipping barrier so as to prevent such conformational changes explaining anomalous NMR behaviour of dithienodisilacyclooctatriene derivatives (2-4). In contrast, the effect of substituents R1 and R2 at the olefinic carbons of the eight-membered ring on the flipping barrier turned out to be mild.

A Selective Oxidation of Tetraline by Chromium (VI) Compounds (I) (Cr (VI) 촉매에 의한 Tetraline 의 선택적 산화반응 (I))

  • Sun-Kun Bae;Sang-Bong Lee;Dae-Chul Park;Kyu-Wan Lee
    • Journal of the Korean Chemical Society
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    • v.33 no.1
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    • pp.106-112
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    • 1989
  • Liquid phase oxidation of tetralin with clean air were carried out utilizing complexes composed of various heterocyclic base and CrO$_3$ in N,N-dialkylamides. In the CrO$_3$-N,N-dialkylacetamide complex catalyzed oxidations of tetralin at 90$^{\circ}$C, the maximum conversion of tetralin to the products and selectivity of ${\alpha}$-tetralone were 35.2% and 96.1%, respectively. Under this condition, however, negligible amount of ${\alpha}$-tetralol was determined.

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Antimicrobial Activity of Garlic Heated under Different Conditions, Time of Heating, and pH

  • Kim, Eun-Hee;Kang, Seung-Sik;Kang, Dong-Hee;Kyung, Kyu-Hang
    • Food Science and Biotechnology
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    • v.18 no.3
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    • pp.771-775
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    • 2009
  • Antimicrobial activity of garlic (pH 6.0) heated at $120^{\circ}C$ reached its maximum at 45 min of heating and maintained the level for the rest of heating time (300 min) when tested against Candida utilis ATCC42416. The principal antimicrobial compound was allyl alcohol (AA), a highly volatile compound without sulfur in its molecule. The concentration of AA in heated garlic gradually increased to over 2,000 ppm for the first 90 min and stayed at the level without appreciable changes in spite of further heating. Other antimicrobial compounds secondary to AA were lowly volatile sulfur compounds including diallyl polysulfides (diallyl trisulfide, diallyl tetrasulfide, and diallyl pentasulfide) and heterocyclic sulfur compounds (4-methyl-1,2,3-trithiolane, 5-methyl-1,2,3,4-tetrathiane, and 6-methyl-1,2,3,4,5-pentathiepane). When the pH of the garlic extract was lowered before heating, considerably more secondary antimicrobial sulfur compounds were formed and the antimicrobial activity was stronger than the pH unadjusted garlic. Lowly volatile sulfur compounds contributed a significant part of antimicrobial activity of heated garlic only during the early period (45-120 min) of heating regardless of pH treatment.