• Title/Summary/Keyword: amine derivatives

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Novel Synthesis of 8-tert-Butyl-6,7-Dihydro-5-Methyl-8H-Pyrrolo[3,2-e]-s-Triazolo-[1,5-a] Pyrimidine (Bumepidil), a New Cardiovascular Agent (관상혈관 확장제인 8-tert-Butyl-6, 7-Dihydro-5-Methyl-8H-Pyrrolo[3,2-e]-s-Triazolo-[1,5-a] Pyrimidine (Bumepidil)의 합성)

  • 서명은;김혜경;김중협
    • YAKHAK HOEJI
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    • v.31 no.5
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    • pp.338-342
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    • 1987
  • 8-tert-Butyl-6,7-dihydro-5-methyl-8H-pyrrolo [3,2-e]-s-triazolo [1,5-a] pyrimidine (Bumepidil), one of the s-triazolo [1,5-a] pyrimidine derivatives, has been recently found to be the most promising potential coronary vasodilator and antihypertensive agent. In this report, a new synthetic approach for Bumepidil, via direct N-amination of amino pyrimidine intermediate, was studied and found to be useful method. The novel synthetic method comprise the following steps, acylation of $\gamma$-butyrolactone, condensation with guanidine, direct N-amination, cyclization, chlorination, and finally cyclization using tert-butyl amine.

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Synthesis of Alginate-derived Polymeric Surfactants (알지네이트계 고분자 계면활성제의 합성)

  • 강현아
    • KSBB Journal
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    • v.15 no.4
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    • pp.375-379
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    • 2000
  • Alginate derivatives possessing various lengths of alkyl amine (C8, C12, C16) chain were prepared by oxidation followed by reductive amination of alginate and the products were characterized by spectral analysis. The surface tension critical micelle concentration (c. m. c) and solubility of a hydrophobic compound azobenzene were examined. Series of synthesized alginate-derived polymeric surfactants(APSs) reduced the surface tension. The dissolving capacity of APSs toward azobenzene was about half that of SDS. In order to investigate the capacity of metal adsorption Co and Pb were selected as a representative metal. The overall removal efficiency of APSs were high compared with that of alginate at pH 3.5 and 7 respectively. Major mechanism of the heavy metal removal is the complex of metal with carboxyl group.

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Reaction Conditions and Mechanism of Electrolytic Reduction of Nitrobenzene (니트로벤젠의 전해환원 반응 조건과 메카니즘)

  • Chon Jung Kyoon;Paik Woon Kie
    • Journal of the Korean Chemical Society
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    • v.21 no.6
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    • pp.404-412
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    • 1977
  • Electrochemical reduction of nitrobenzene (${\phi}NO_2$) and its derivatives on Pb electrode was studied by means of galvanostatic measurements and coulometric electrolysis in ethanol-water solvent. In acidic solutions phenylhydroxyl amine and aniline ethanol-water solvent. In acidic solutions phenylhydroxyl amine and aniline were produced while nitrosobenzene and coupled products such as azo-and hydrazobenzene were produced in basic solutions. Nitrosobenzene (${\phi}NO$) was not found to be an intermediate in the reduction reactions of ${\phi}NO_2$ in acidic solutions. No direct coupling between ${\phi}NO\;and\;{\phi}NHOH$ was observed to occur in the electrolyte solutions used. Mechanisms of the production of phenylhydroxylamine and nitrosobenzene are deduced from Tafel slope, pH dependence and reaction order with respect to nitrobenzene. Mechanism for the reduction of substituted nitrobenzenes seems to be identical to that of nitrobenzene.

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A new efficient route for synthesis of R,R- and S,S-hexamethylpropyleneamine oxime for labeling with technetium-99m

  • Vinay Kumar Banka;Young Ju Kim;Yun-Sang Lee;Jae Min Jeong
    • Journal of Radiopharmaceuticals and Molecular Probes
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    • v.6 no.2
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    • pp.75-91
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    • 2020
  • [99mTc]Tc-Hexamethylpropylene amine oxime (HMPAO) is currently used as a regional cerebral blood flow imaging agent for single photon emission computed tomography (SPECT). The HMPAO ligand exists in two isomeric forms: d,l and meso showing different properties in vivo. Later studies indicated that brain uptake patterns of 99mTc-complexes formed from separated enantiomers differed. Separation of enantiomers is difficult by fractional crystallizations method. Usually, the substance is obtained in low chemical yield in a time-consuming procedure. Furthermore, the final product still contains some impurity. So we have developed new efficient route for synthesis of R,R- and S,S-HMPAO enantiomeric compounds in 6-steps. Nucleophilic substitution (SN2) reactions of 2,2-dimethylpropane-1,3-diamine either with S- (1a) or R-methyl2-chloropropanoate (1b) were performed to produce compounds R,R- (2a) or S,S-isomer (2b) derivatives protected with benzylchloroformate (Cbz), respectively. And then Weinreb amide and methylation reaction using Grignard reagent, oxime formation with ketone group and deprotectiion of Cbz group by hydrogenolysis gave S,S- (7a) or R,R-HMPAO (7b), respectively. Entaniomeric compounds were synthesied with high yield and purity without any undesired product. The 7a or 7b kits containing 10 ㎍ SnCl2-2H2O were labeled with 99mTc with high radiolabeling yield (90%).

Binding Properties of Anthryl Derivatives to Synthetic Polynucleotide and the Role of Guanine Amine Group in the Energy Transfer (안트라센 유도체-합성DNA의 결합형태와 에너지전달과정에서 구아닌 염기의 아민기의 역할)

  • Cho, Chang-Beom;Son, Gwan-Su;Han, Sung-Wook;Jung, Maeng-Jun;Chong, Hyun-Suk;Lee, Gil-Jun
    • Journal of the Korean Chemical Society
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    • v.44 no.1
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    • pp.45-51
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    • 2000
  • The binding mode of anthryl derivatives to synthetic polynucleotides were investigated by various spectroscopic methods. The spectroscopic properties of anthracence with metbylamine and methylethylenediamine side chains, complexed with $poly[d(A-T)_2]$ and $poly[d(G-C)_2]$, can be summarized as a red-shift, with a strong hypochromism in the absortion spectrum, similar induced CD spectra, and a strong negative LD spectrum with an $LD^r$ magnitude comparable to the DNA absorption region. These observations indicate that anthracene moiety is intercalated between the nucleo-bases of $poly[d(A-T)_2]$ and $poly[d(G-C)_2]$. The side chains did not alter the spectroscopic properties, demonstrating that the binding mode was not affected by them. A strong energy transfer was observed from poly[d(A-T),] and $poly[d(I-C)_2]$ but not from $poly[d(G-C)_2]$, as reported by Kumar et al. (J. Am. Chem. Soc.(1993) 115, 8547). Since the binding mode is the same for all the polynucleotides, the amine group of the guanine base, which protrudes into the minor groove of $poly[d(G-C)_2]$, is concluded to disrupt the energy transfer.

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Synthesis, Fastness and Spectral Properties of Some New Azo Pyrazole and Pyrazolotriazole Derivatives (Pyrazole과 Pyrazolotriazole 유도체의 합성 및 특성 연구)

  • Rizk, Hala F.;El-Badawi, Mahmoud A.;Ibrahim, Seham A.;El-Borai, Mohamed A.
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.737-743
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    • 2010
  • Coupling of 5-amino-1,3-diaryl-pyrazoles 1a-c with diazonium salts of different aryl amines gave a series of novel 1,3-diaryl-5-amino-4-arylazopyrazoles 3a-l. Such compounds could be also obtained by reaction of 5-amino-1,3-diaryl-4-nitroso- 1H-pyrazoles 2a-c with different aryl amines in alkaline medium. Oxidation of azo derivatives 3a-l with cupric acetate, in dimethyl formamide and stream of air, gave 2,4,6-triaryl-2,4-dihydropyrazolo [4,3-d]-1,2,3-triazoles 4a-l. and the fluorescence properties of the cyclic triazoles were studied. Diazotization of 5-amino-1,3-diaryl-1H-pyrazoles 1a-c by sodium nitrite in ortho-phosphoric acid followed by coupling with some aryl amines gave o-aminoazo compounds 5a-f. Cyclisation of compounds 5a-f in pyridine and cupric acetate gave the corresponding triazoles 6a-f. The coupling of compounds 6a-f with different aryl diazonium salts gave compounds 7a-j. The synthesized dyes were applied to polyesters as disperse dyes and the fastness properties were evaluated.

Current Researches on the Protection of Exterior Wood from Weathering (목재의 기상열화 방지에 관한 최근의 연구 동향)

  • Kim, Yeong-Suk
    • Journal of the Korean Wood Science and Technology
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    • v.46 no.5
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    • pp.449-470
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    • 2018
  • A review of research trends on wood surface protection for exterior use obtained the following conclusions: It has been reported that inorganic compounds such as chrome and copper used as wood preservatives can protect wood from weathering. It has been shown that precoating with hydrophobic substances such as wax and oil, UV absorbers, and HALS (Hindered Amine Light Stabilizers) enhances weathering resistance on the surface of ACQ-treated wood. Opaque coatings of paint/stains and semitransparent stains on the surface of preservative treated wood can increase the synergistic effects on prevention of weathering deterioration. Also the need for repainting periodically for the protection of the preservative treated wood surface has also been suggested. ZnO or $TiO_2$ of fine particles, metal ions such as Co, Cr, Fe, Mn, Ni and Ti, and UV absorbers such as tris-resorcinol triazine derivatives, triazine and benzotriazole were introduced as additives for preventing UV in the transparent coating on wood. Several reports showed that chemical modification such as methylation, acetylation, or alkylations have made some increases the effects of preventing weathering with the increasing weight gain of chemical formulas. In heat-treated wood, there were various contradictory reports on the resistance of weathering, and there were some other reports emphasizing the necessity of painting with UV resistance, which leads to the necessity of more advanced studies.

Characteristics of Histamine Forming Bacteria from Tuna Fish Waste in Korea (국내 참치 부산물 내 히스타민 생성 주요 세균의 특성 구명)

  • Bang, Min-Woo;Chung, Chang-Dae;Kim, Seon-Ho;Chang, Moon-Baek;Lee, Sung-Sil;Lee, Sang-Suk
    • Journal of Life Science
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    • v.19 no.2
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    • pp.277-283
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    • 2009
  • Biogenic amines are generally formed through the decarboxylation of specific free amino acids by exogenous decarboxylases released by microbial species associated with the fish products and fermented feeds. This study was conducted to investigate the properties of e tuna waste regarding the control of degradation of biogenic amines (histamine, tyramine, tryptamine, putrescine, and cadaverine) that might be related with the anti-nutritional factor of the tuna waste that is used for manufacturing domestic fish meal. The values of pH and the salt content were 6.51, 3.35% in tuna waste and 5.58 and 5.83% in tuna fish meal, respectively. The strains and dominant bacteria tested in the tuna waste sample were 9.20, 9.29, 5.67, 7.82 and 7.58 log CFU/g of total bacteria, aerobic plate count (APC), total coliform (TC), Lactobacillus spp. and Bacillus spp., respectively. The main histamine forming-bacteria (HFB) in tuna waste were detected by silica gel thin-layer chromatography (TLC) and 7 histamine-forming bacterial species were isolated among microbes grown in selective medium. The histamine concentration was determined by detection of fluorescence of ο-phthaldialdehyde (OPA) derivatives using HPLC and the date were used to reconfirm the identities of the amine-producing bacteria. The 15 histamine- forming bacteria strains grown in trypicase soy broth (TSB) supplemented with 1% L-histidine (TSBH) were identified as Lactococcus(L.) lactis subsp. lactis, Klebsiella pneummonlae, L. garvieae 36, Vibrio olivaceus, Hafnia alvei and L. garvieae which were main dominant amine - producing strains, and Morganella morganii identified by 16S ribosomal RNA (rRNA) sequencing with PCR amplification. A Phylogenetic tree generated from the 16S rRNA sequencing data showed different phyletic lines that could be readily classified as biogenic amine forming gram-positive and negative bacteria.

Effect of Amino Acids and Organic Nitrogen Sources on Cyclosporin A Fermentation by Tolypocladium inflatum (Tolypocladium inflatum을 이용한 Cyclosporin A 발효에서 아미노산과 유기질소원의 영향)

  • Kim, Jeong-Keun;Lee, Byung-Kyu;Chang, Seog-Won;Park, Yong-Deok;Rho, Yong-Taek
    • Microbiology and Biotechnology Letters
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    • v.37 no.2
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    • pp.140-146
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    • 2009
  • Cyclosporin, an immunosuppressant, is a representative group of biologically active secondary metabolites produced by the fungus Tolypocladium inflatum. The amount and ratio of cyclosporin derivatives in the culture broth are an important factors for the production of cyclosporin A and the purification in the industrial process. Therefore, we studied the effect of amino acids and complex organic nitrogen sources using Tolypocladium inflatum mutants on the productivity of cyclosporin A and the ratio of cyclosporin derivatives. Overproducing mutant YHC-004 having seven times higher productivity than mother strain's could be obtained through the artificial mutation by UV irradiation. The concentration and kind of organic nitrogens and amino acids shows the profound effect on the productivity of cyclosporin A and ratio of cyclosporin derivatives. As a result, it was possible to raise the productivity and the ratio of cyclosporin A up to 3,430 mg/L and 93% respectively, but on the other hand the other cyclosporin derivatives decreased less than 2% in the culture broth.

Preparation of Trifluoroacetyl Chitosan Derivatives with Antiviral Activity (항바이러스 활성을 갖는 Trifluoroacetyl Chitosan 유도체의 제조)

  • Kim, Chun-Ho;Shin, Cha-Gyun;Shin, Kye-Sook;Son, Tae-il
    • Applied Chemistry for Engineering
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    • v.10 no.4
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    • pp.599-602
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    • 1999
  • Chitosan was depolymerized by using nitrous acid. In order to synthesize new fluorinated chitosan oligomer(FCO) derivative, free amine groups of resulting low molucular weight chitosan oligomers were reacted with trifluoroacetic anhydride. The structure changes in the samples were conformed by using FT-IR, $^{1}H\;NMR$, $^{13}C\;NMR$ and $^{19}F\{^{1}H\}NMR$. Antiviral activity of FCO was studied by measuring DAN amounts of the replication viruses at 36 hr after the cells were infected with the viral solution containing FCO of various concentrations. The viral replications in the cells infected with the viral solution containing FCO were proportionally decreased with the FCO does, compared to those of the control groups, indicating that FCO efficiently inhibits viral infection. In particular, viral replication was decreased to 40% in the 1% FCO-treated cells.

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