• Title/Summary/Keyword: Heterocyclic

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Rhodium(I) Complexes of 1,1$^\prime$-Bis(diphenylphosphino)-ferrocene as Efficient Catalysts in Regioselective Hydrogenation of Polynuclear Heteroaromatic Compounds

  • Kim, Tae-Jeong;Lee, Kyu-Chul
    • Bulletin of the Korean Chemical Society
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    • v.10 no.3
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    • pp.279-282
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    • 1989
  • Two rhodium(I) complexes of the types [Rh(BPPF)(NBD)]$ClO_4$ (10) and [Rh(BPPF)$Cl]_2$ (11) (BPPF = 1,1'-bis(diphenylphosphino)-ferrocene) have been prepared and investigated as catalysts for the regioselective hydrogenation of polynuclear heteroaromatic nitrogen and sulfur compounds such as quinoline (1), acridine (2), phenanthridine (3), 7,8-benzoquinoline (4), benzothiophene (5), isoquinoline (6), indole (7), pyridine (8), and thiophene (9). Both complexes 10 and 11, except for the cases of indole (7) and mononuclear heteroaromatics 8-9, are very efficient in the selective reduction under quite mild hydrogenation conditions to give the corresponding saturated nitrogen and sulfur heterocyclic analogues of 1-6 in fast conversion rates and in excellent yields. Relative rate studies revealed that the reduction depends significantly on the steric and electronic effects of the substrates. Of the two complexes 10-11, the dimeric species 11 gives faster reaction rates in all cases studied.

A Comparative Study of the DFT and MP2 Methods Molecular Structure of Diphosphadithiatetrazocine

  • Jeong, Gyu Seong;Lee, Deok Hwan
    • Bulletin of the Korean Chemical Society
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    • v.21 no.3
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    • pp.300-304
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    • 2000
  • The B3LYP method based on the density functional theory(DFT) is shown to be much better than the ab initio MP2 method for structural determination of diphosphadithiatetrazocine systems having transannular S--S bonding. The presence of bonding between the two sulfur atoms across the cyclic ring is theoretically confirmed in the case of the neutral diphosphadithiatetrazocine. The S--S dobding disappears in the ionized species. The planarity of the dicationic heterocyclic ring system turns out to be closely associated with the $\pi-electron$ delocalization over the entire ring as well as the N-S-N bonds, which become stiffened upon ionizaiton. In the case of dianionic species, the chair-boat and chair conformers are nearly degenerate and far more stable than the crown conformer.

Cycloplatinated Complexes of Thiosemicarbazones. Synthesis and Crystal Structure of [$Ph_2PC_6H_4CHNNC(S)NHCH_3PtCl$]

  • 유동원;강상욱;고재정;최문근
    • Bulletin of the Korean Chemical Society
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    • v.18 no.3
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    • pp.305-310
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    • 1997
  • The synthesis and characterization of the platinum heterocyclic carboxaldehyde thiosemicarbazone complexes [NC5H4CRNNC(S)NHR'PtCl] (R=H, R'=CH3(1); R=CH3, R'=CH3(2); R=CH3, R=H(3)) and diphenylphosphinophenyl carboxaldehyde thiosemicarbazone complexes [Ph2PC6H4CHNNC(S)NHRPtCl] (R=CH3(5); R=iC3H7(6); R=Ph(7)) are described. Compounds 1-3 were prepared by reaction of Pt(SEt2)2Cl2 with 2-acetylpyridine-4-alkylthiosemicarbazone in the presence of NEt3. Compounds 5-7 were prepared using Pt(SEt2)2Cl2 in toluene with diphenylphosphinophenyl carboxaldehyde alkylthiosemicarbazone. The compounds have been characterized by microanalysis, NMR (1H, 13C, 31P) spectroscopy, and single-crystal X-ray diffraction. X-ray single crystal diffraction analysis reveals that compound 5 is a mononuclear platinum compound with P,N,S-coordination mode.

Synthesis and Characterization of New Group 13 Complexes of 2-Acetylpyridine-S-methyldithiocarbazate. Single-Crystal Structure of Me₂Ga[$NC_5H_4C$(CH₃)NNC(S)SMe] and Me₂In[$NC_5H_5C$(CH₃)NNC(S)SMe]

  • 백철기;강상욱;이채호;이영행;고재정
    • Bulletin of the Korean Chemical Society
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    • v.18 no.3
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    • pp.311-316
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    • 1997
  • The synthesis and characterization of the mononuclear group 13 heterocyclic carboxaldehyde methyldithiocarbazate complexes Me2M[NC5H4CRNNC(S)SCH3] (M=Al, R=H(1); M=Ga, R=H(2); M=Al, R=CH3(3); M-Ga, R=CH3(4); M=In, R=CH3(5)) are described. Compounds 1-5 were prepared by the reaction of MMe3 (M=Al, Ga, In) with 2-formy or 2-acetylpyridine-S-methyldithiocarbazate in toluene. These compounds 1-5 have been characterized by microanalysis, NMR (1H, 13C) spectroscopy, mass spectra, and single-crystal X-ray diffraction. X-ray single-crystal diffraction analyses reveal that 4-5 are mononuclear metal compounds with coordination number of 5 and N,N,S coordination mode.

Synthesis and biological evaluation of 4,7-benzimidazolediones that inhibit vascular smooth muscle cell proliferation

  • Ryu, Chung-Kyu;Chae, Mi-Jin;Han, Ja-Young;Jung, Ok-Jai;Hong, Sung-Yu;Chung, Kwang-Hoe;Choi, Ik-Hwa
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.182.2-182.2
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    • 2003
  • The abnormal proliferation and migration of vascular smooth muscle cell (SMC) play an important role in the pathology of coronary artery atherosclerosis and restenosis. Platelet-derived growth factor (PDGF) is one of the most potent promoters of the proliferation and migration of the SMC. The heterocyclic quinones represent an important class of biologically active molecules. However, the inhibitory activity of quinone classes on the proliferation of the SMC has not been reported. (omitted)

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Activated Nitrites in Heterocyclic Synthesis: Syntheses of Thiazole, Pyrazole and 4H-l,4-Benzothiazine Derivatives

  • El-Taweel, Fathy Mohamed Abdel-Aziz;Hadi-Mashaly, Mohamed-Abdel;Ali-Elagamey, Abdel-Ghani
    • Archives of Pharmacal Research
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    • v.13 no.3
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    • pp.261-264
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    • 1990
  • 4-Arylazo-3-phenyl-5-aminopyrazoles (5a, b) and substituted hydroxythiazoles 8a, b were synthesized from the reaction of 4a, b with hydrazine hydrate and mercaptoacetic acid respectively. Compounds 5a, b and 8a, b were also obtained from coupling of 2a, b with 6 and 7, respectively. 4H-1, 4-Benzothiazine 11 was prepared from 1 and 10. The resaction of the diazonium salts 2a-c with diethyl 3-amino-2-cyanopenet-2-en-1, 5-dicarboxylate 12 was also reported.

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Development of Functional Seasoning Agents from Skipjack Processing By-product with Commercial Proteases 2. Flavor Compounds in Powdered Skipjack Hydrolysate (참치 가공부산물로부터 단백질 분해효소를 이용한 기능성 천연조미료 제재의 개발 2. 분말 참치 가수분해물의 향미성분)

  • 김은정;차용준
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.25 no.4
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    • pp.617-626
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    • 1996
  • Nitrogenous compounds in hydrolysate of skipjack processing by-product(SPB) was increased 6.4 times in amount comparing that of raw SPB. The major compounds in hydrolysate were anserine, histidine, leucine, hydroxyproline, arginine, phenylalanine and taurine, and composed 56.25% of total nitrogenous compounds. In fatty acid composition, the highest amount was saturated fatty acids in both samples. Polyunsaturated fatty acids such as $C_{20:5}$ and $C_{22:6}$ were increased after hydrolysis. A total of 99 volatile compounds was detected in raw and hydrolysate of SPB by vacuum simultaneous steam distillation-solvent extraction/gas chromatography/mass chromatorgraphy. Of these, 75 compounds were identified in raw SPB, while 72 compounds were identified in hydorlysate of SPB. There compounds were composed mainly of 28 aldehydes, 20 ketones, 19 alcohols, 5 nitrogen containing compounds, 5 aromatic hydrocarbons, 4 furans and 12 miscellaneous compounds. Levels of aldehydes and aromatic hydrocarbons decreased after hydrolysis, whereas heterocyclic compounds such as pyrazies, furans increased.

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Desmutagenic Effects of Maillard Reaction Products against Mutagenic Heterocyclic Amines (변이원성 Heterocyclic Amine에 대한 Maillard 반응생성물의 변이원성 억제효과)

  • KIM Seon-Bong;PARK Yeung-Ho;HAYASE Fumitaka;KATO Hiromichi
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.19 no.2
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    • pp.127-135
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    • 1986
  • Each molecular weight (Mw) fraction of melanoidins prepared from a D-glucose and glycine system, i. e., Mw below 1,000, Mw between 1,000 to 5,000 and Mw above 5,000 and nondialyzable and ozone-treated melanoidins were reacted with heat-induced mutagens such as Trp-P-1, Trp-P-2, Glu-P-1, Glu-P-2 and IQ at $37^{\circ}C$ for 30 min. The inhibitory effects of the melanoidins on the mutagens increased with increasing molecular weight. The reducing ability ana antioxidative activity of melanoidins also increased in proportion to the increase in molecular weight, whereas the mutagenic inhibitory effect decreased on reduction of the melanoidins with sodium borohydride. It was also observed that a part of Trp-P-1 was adsorbed to melanoidin molecules. On modification of amino groups of these mutagens with carbonyl compounds derived through the Maillard reaction such as diacetyl and glyceraldehyde, their mutagenic activities were remarkably suppressed. Accordingly, it is speculated that the mutagenic inhibitory action of melanoidins is due to their reducing ability and antioxidative activity, and electrostatic binding and carbonyl groups of the melanoidin molecules.

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Characteristics of Flame Retardent and Mothproof Conservation of Microwave Heated wood (마이크로파 가열 목재의 방염·방충 복합 보존처리 특성)

  • Kim, Chong-Gun;Park, Cheul-Woo;Yoon, Tae-Ho;Lim, Nam-Gi
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.3
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    • pp.234-246
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    • 2013
  • It was found that test piece heated rapidly by 3 kW microwave for 5 minutes satisfies the targeted temperature and the percentage of moisture content, and the highest rate of weight increase is obtained in case of 120 minute immersion in the mixture of phosphates and heterocyclic compounds, from the result of such analysis as: kiln drying schedule, flame retardent by flammability test, insect resistance by termites, and permeability of combined penetrant for the wood after assigning multifunctional finish by immersing conifer structural frame, which is used for the frame work of wooden house and indoor/outdoor finishing in flame retardant and insect repellent materials mixture with the remaining heat of microwave. In addition, after a test of flame retardent treated item, it was identified that every mixture of phosphates corresponds with the standards of flame retardent, and upon investigation of moritality of 7 days after putting termites, it was showed that test piece immersed in the mixture of phosphates and heterocyclic compounds has the best characteristics, showing over 96% of high moritality. From the analysis of inward permeability of combined penetrant for the wood, it was decided that excellent performance in the flame retardent and insect resistance of the wood revealed due to full penetration of combined penetrant as it was found that combined penetrant penetrated through the whole inner cells of the wood.

Antimicrobial Assessment of Some Heterocyclic Compounds Utilizing Ethyl 1-Aminotetrazole-5-carboxylate (Ethyl 1-Aminotetrazole-5-carboxylate로부터 유도된 헤테로고리 화합물들의 항균 활성 시험)

  • Taha, Mamdouh A. M.;El-Badry, Susan M.
    • Journal of the Korean Chemical Society
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    • v.54 no.4
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    • pp.414-418
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    • 2010
  • Ethyl 1-aminotetrazole-5-carboxylate (1) reacted with hydrazine hydrate to give the corresponding aminohydrazide 2. Cyclization of 2 by carbon disulfide yielded 1,3,4-oxadiazole-5-thiol structure 3. Reaction of 3 with either chloroacetone or ethyl chloroacetate furnished S-acyl 1,3,4-oxadiazole derivatives 4 and 5, respectively. Also compound 3 reacted with hydrazine hydrate afforded 4-amino-1,2,4-triazole-5-thiol derivative 6. 6-Methyl-1,3,4-triazolo[3,4-b]-1,3,4-thiadiazole structure 7 was synthesized by reaction of aminothiol 6 with glacial acetic acid. Diazotization of 1 with sodium nitrite in presence of hydrochloric acid yielding the diazonium salt which on treating with hippuric acid, oxazolone derivative 8 was obtained. Furthermore, tetrazolo[5,1-f]-1,2,4-triazine 9 was constructed via cyclization of aminoester 1 with formamide. Compound 9 reacted with carbon disulfide to furnish 8-thione derivative 10 which reacting with chloroacetone, ethyl chloroacetate, and hydrazine hydrate, the corresponding chemical structures 11, 12, and 13 were synthesized. 1,2,4-Triazolo[4,3-d]tetrazolo[5,1-f]-1,2,4-triazines 14 and 15 were resulted by treating of compound 13 with triethyl orthoformate, and glacial acetic acid, respectively. The structures of the newly synthesized products were elucidated according to elemental analyses and spectroscopic evidences. Some of the representative members of the prepared compounds were screened for antimicrobial activity.