• 제목/요약/키워드: dihydro pyridine

검색결과 12건 처리시간 0.023초

Stereoselective Synthesis of L-Deoxyaltronojirimycin from L-Serine

  • Rengasamy, Rajesh;Curtis-Long, Marcus J.;Ryu, Hyung-Won;Oh, Kyeong-Yeol;Park, Ki-Hun
    • Bulletin of the Korean Chemical Society
    • /
    • 제30권7호
    • /
    • pp.1531-1534
    • /
    • 2009
  • (2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.

Evaluation of the inhibitive characteristics of 1,4-dihydropyridine derivatives for the corrosion of mild steel in 1M $H_2SO_4$

  • Sounthari, P.;Kiruthika, A.;Sai santhoshi, J.;Chitra, S.;Parameswari, K.;Selvaraj, A.
    • Corrosion Science and Technology
    • /
    • 제12권2호
    • /
    • pp.65-78
    • /
    • 2013
  • The present investigation deals with the corrosion inhibition of mild steel in 1M $H_2SO_4$ with 1, 4-dihydro pyridine and its derivatives prepared using microwave activation method. The synthesis of inhibitor was confirmed by IR spectra. The effect of 1, 4-dihydropyridine derivatives on the corrosion inhibition of mild steel in 1M $H_2SO_4$ was studied using weight loss and electrochemical polarization techniques. Influence of temperature (303-333K) and synergistic effect of halide ions ($I^-$, $Br^-$ and $Cl^-$) on the inhibition behaviour was also studied. Corrosion products on the metal surface were analyzed by scanning electron microscopy (SEM) and a possible mechanism of inhibition by the compounds is suggested. Thermodynamic parameters were calculated using weight loss data in order to elaborate the mechanism of corrosion inhibition. Polarization measurements revealed that the studied compounds acted as mixed type inhibitor but slightly anodic in nature. Electrochemical impedance measurements revealed that the compounds were adsorbed onto the carbon steel surface and the adsorption obeyed the Langmuir adsorption isotherm. The synergistic effect of halide ions on the IE increases with increase in concentration. The IE obtained from atomic absorption spectrophotometric studies was found to be in good agreement with that obtained from the conventional weight loss method. SEM revealed the information of a smooth, dense protective layer in presence of the inhibitors.

사철나무의 알칼로이드 성분 (Sesquiterpene Pyridine Alkaloids from Euonymus japonica)

  • 류재하;은진희;이소영;장준식;박만기;박정일;한용남;한병훈
    • 약학회지
    • /
    • 제41권5호
    • /
    • pp.554-558
    • /
    • 1997
  • Two alkaloidal components were isolated from the ether soluble part of the MeOH extract of the root bark of Euonymus japonica. Their structures were elucidated by the spe ctroscopic analylses as the sesquiterpene pyridine alkaloids derived from polyester sesquiterpenes which are characteristically detected in Celastraceae plants. These include macrocycle formed by two ester linkages between dihydro-${\beta}$-agarofuran nucleus and pyridinic dibasic acid(compound 1:evoninic acid, compound 2:wilfordic acid). The structure of compound $1[C_{47}H_{50}N_2O_{17},\;mp\;161{\sim}163^{circ}C$. $[{\alpha}]_D^{28}=+31.6^{\circ}$(c, 0.1 in EtOH)] was determined as novel structure named as euojaponine N, and compound $2[C_{48}H_{57}NO_{18},\;mp\;142{\sim}145^{circ}C,\;[{\alpha}_D^{27}=+27.0^{\circ}$(c, 0.1 in EtOH)] was identified as ebenifoline W-I reported from Maytenus ebenifolia.

  • PDF

Reducing Characteristics of Potassium Triethylborohydride

  • Yoon, Nung-Min;Yang H.S.;Hwang, Y.S.
    • Bulletin of the Korean Chemical Society
    • /
    • 제8권4호
    • /
    • pp.285-291
    • /
    • 1987
  • The approximate rates, stoichiometries and products of the reaction of potassium triethylborohydride $(KEt_3BH)$ with selected organic compounds containing representative functional groups under the standard condition $(0^{\circ}C,$ THF) were examined in order to explore the reducing characteristics of this reagent as a selective reducing agent. Primary alcohols, phenols and thiols evolve hydrogen rapidly whereas secondary and tertiary alcohols evolve very slowly. n-Hexylamine is inert to this reagent. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of noncamphor gives 3% exo- and 97% endo-norboneol. Anthraquinone is cleanly reduced to 9,10-dihydro-9,10-dihydroxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively but further reduction does not occur. Anhydrides utilize 2 equiv of hydride to give an equimolar mixture of acid and alcohol. Acid chlorides, esters and lactones are rapidly and quantitatively reduced to the corresponding alcohols. Epoxides are reduced at moderate rates with Markovnikov ring opening to give the more substituted alcohols. Primary amides liberate 1 equiv of hydrogen rapidly. Further reduction of caproamide is slow whereas benzamide is not reduced. Tertiary amides are reduced slowly. Benzonitrile utilizes 2 equiv of hydride in 3 h to go to the amine stage whereas capronitrile takes only 1 equiv. The reaction of nitro compounds undergo rapidly whereas azobenzene and azoxybenzene are reduced slowly. Cyclohexanone oxime rapidly evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine N-oxide and pyridine is reduced rapidly. Disulfides are rapidly reduced to the thiol stage whereas sulfoxide, sulfonic acid are practically inert to this reagent. Sulfones and cyclohexyl tosylate are slowly reduced. Octyl bromide is reduced rapidly but octyl chloride and cyclohexyl bromide are reduced slowly.

Antioxidant Activity of NADH and Its Analogue - An In Vitro Study

  • Olek, Robert Antoni;Ziolkowski, Wieslaw;Kaczor, Jan Jacek;Greci, Lucedio;Popinigis, Jerzy;Antosiewicz, Jedrzej
    • BMB Reports
    • /
    • 제37권4호
    • /
    • pp.416-421
    • /
    • 2004
  • The antioxidant activities of NADH and of its analogue, 1,4-dihydro-2,6-dimethyl-3,5-dicarbethoxy-pyridine ($PyH_2$), were evaluated in vitro. NADH was found to be oxidized by the peroxyl radical derived from 2,2-azobis-(2-amidinopropane) dihydrochloride (AAPH) decomposition, in a pH-dependent manner. Both NADH and $PyH_2$ inhibited the peroxidation of egg yolk lecithin (EYL) liposomes, although $PyH_2$ was more effective than NADH when 2,2'-azobis-4-methoxy-2,4-dimethyl-valeronitrile (methoxy-AMVN) was employed to induce EYL liposome peroxidation. The antioxidant activities of NADH and $PyH_2$ were also evaluated by measuring their influences on 1,3-diphenylisobenzofuran (DPBF) fluorescence decay in the presence of peroxyl radicals. NADH and $PyH_2$ were much more effective at inhibiting DPBF quenching in Triton X-100 micelles than in liposomes. These results indicate that NADH can inhibit lipid peroxidation despite being hydrophilic. Nevertheless, membrane penetration is an important factor and limits its antioxidant activity.

Influence of Bromocriptine on Release of Norepinephrine and Epinephrine Evoked by Cholinergic Stimulation from the Rat Adrenal Medulla

  • Lee, Seung-Il;Kang, Moo-Jin;Lim, Dong-Yoon
    • Biomolecules & Therapeutics
    • /
    • 제9권3호
    • /
    • pp.201-208
    • /
    • 2001
  • The present study was conducted to examine the effects of cholinergic stimulation and membrane depolarization on secretion of epinephrine (EP) and norepinephrine (NE) in the perfused model of the rat adrenal gland and to investigate the effect of bromocriptine on secretion of EP and NE evoked by these secreta-gogues. Acetylcholine (ACh, 5.32 mM), high $K^{+}$(56mM), 1.1-dimethyl-4-phenyl piperazinium iodide (DMPP, 100 $\mu$M for 2 min), (3-(m-cholro-phenyl-carbamoyl-oxy)-2butynyl trimethyl ammonium chloride (McN-A-343, 100 $\mu$M for 2 min), cyclopiazonic acid (10 $\mu$M for 4 min) and methyl-1,4-dihydro-2,6-dimethyl-3-nitro-4-(2-trifluoromethylphenyl) -pyridine-5-carboxylate (Bay-K-8644, 10 $\mu$M for 4 min) evoked a 1.3~5.3-fold greater secretion of EP than NE in the perfused rat adrenal gland. The perfusion of bromocriptine (1-10 $\mu$M) into an adrenal vein for 20 min produced relatively dose-dependent inhibition in secretion of EP and NE evoked by ACh, high $K^{+}$, DMPP, and McN-A-343. Moreover, under the presence of bromocriptine (1~10 $\mu$M), releasing responses of EP and NE evoked by cyclopiazonic acid and Bay-K-8644 were also greatly reduced. Taken together, these results suggest that cholinergic stimulation and membrane depolarization enhance more release of EP than NE in the perfumed rat adrenal medulla, and that bromocriptine inhibits the release of EP and NE evoked by stimulation of cholinergic receptors as well as by membrane depolarization. It seems that this inhibitory effect of bromocriptine is associated with inhibition of calcium channels through activation of dopaminergic D2-receptors located in the rat adrenomedullary chromaffin cells.lls.

  • PDF

Phytochemical Screening and Antibacterial Activity Coix lacryma-jobi Oil

  • Diningrat, Diky Setya;Risfandi, Marsal;Harahap, Novita Sari;Sari, Ayu Nirmala;Kusdianti, Kusdianti;Siregar, Henny Kharina
    • Journal of Plant Biotechnology
    • /
    • 제47권1호
    • /
    • pp.100-106
    • /
    • 2020
  • Coix lacryma-jobi (Hanjeli) is known to posses anti-microbial properties. Therefore, phytochemical compounds of C. lacryma-jobi have been studied to produce novel antimicrobial agents as treatments against antibiotic-resistant bacteria.The objective of this study was to determine the phytochemical composition and antibacterial activity of the C. lacryma-jobi oil against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The phytochemical composition of the oil was determined via gas chromatography mass spectrophotometry (GC-MS). Moreover, agar disk and agar well diffusion were employed to screen the antibacterial activity of the oil. An agar well diffusion test was implemented to determinate MIC's (minimum inhibitory concentrations). Dodecanoic acid, tetradecanoic acid, 2,3-dihydroxypropylester, 1,3-dioctanoin, N-methoxy-N-methyl-3,4-dihydro-2H-thiopyran6-carboxamide, propanamide, 5-Amino-1-(quinolin-8-yl)-1,2,3-triazole-4-carboxamide, and pyridine were identified in the C. lacryma-jobi oil. The MIC value of the oil was 0.031 g/L and the MBC of the oil was 0.125 g/L effective in all test bacteria. Dodecanoic acid displayed inhibitory activity against gram-positive and gram-negative bacteria. Therefore, our research demonstrated C. lacryma-jobi (Hanjeli) oil exhibited antibacterial activity against E. coli, S. aureus, and B. subtilis. These research suggest that C. lacryma-jobi root oil could be used for medicinal purposes; however clinical and in vivo tests must be performed to evaluate its potential as an antibacterial agent.

Reaction of Potassium 2-Thexyl-1,3,2-dioxaborinane Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Jin Soon Cha;Sung Eun Lee
    • Bulletin of the Korean Chemical Society
    • /
    • 제13권5호
    • /
    • pp.531-537
    • /
    • 1992
  • The approximate rates and stoichiometry of the reaction of excess potassium 2-thexyl-1,3,2-dioxaborinane hydride(KTDBNH) with 55 selected compounds containing representative functional groups under standardized conditions (tetrahydrofuran, TEX>$0^{\circ}C$, reagent : compound=4 : 1) was examined in order to define the characteristics of the reagent for selective reductions. Benzyl alcohol and phenol evolve hydrogen immediately. However, primary, secondary and tertiary alcohols evolve hydrogen slowly, and the rate of hydrogen evolution is in order of $1^{\circ}$> $2^{\circ}$> $3^{\circ}$. n-Hexylamine is inert toward the reagent, whereas the thiols examined evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to give the corresponding alcohols. Cinnamaldehyde is rapidly reduced to cinnamyl alcohol, and further reduction is slow under these conditions. The reaction with p-benzoquinone dose not show a clean reduction, but anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol. Carboxylic acids liberate hydrogen immediately, further reduction is very slow. Cyclic anhydrides slowly consume 2 equiv of hydride, corresponding to reduction to the caboxylic acid and alcohol stages. Acid chlorides, esters, and lactones are rapidly and quantitatively reduced to the corresponding carbinols. Epoxides consume 1 equiv hydride slowly. Primary amides evolve 1 equiv of hydrogen readily, but further reduction is slow. Tertiary amides are also reduced slowly. Both aliphatic and aromatic nitriles consume 1 equiv of hydride rapidly, but further hydride uptake is slow. Analysis of the reaction mixture with 2,4-dinitrophenylhydrazine yields 64% of caproaldehyde and 87% of benzaldehyde, respectively. 1-Nitropropane utilizes 2 equiv of hydride, one for hydrogen evolution and the other for reduction. Other nitrogen compounds examined are also reduced slowly. Cyclohexanone oxime undergoes slow reduction to N-cyclohexylhydroxyamine. Pyridine ring is slowly attacked. Disulfides examined are reduced readily to the correponding thiols with rapid evolution of 1 equiv hydrogen. Dimethyl sulfoxide is reduced slowly to dimethyl sulfide, whereas the reduction of diphenyl sulfone is very slow. Sulfonic acids only liberate hydrogen quantitatively without any reduction. Finally, cyclohexyl tosylate is inert to this reagent. Consequently, potassium 2-thexyl-1,3,2-dioxaborinane hydride, a monoalkyldialkoxyborohydride, shows a unique reducing characteristics. The reducing power of this reagent exists somewhere between trialkylborohydrides and trialkoxyborohydride. Therefore, the reagent should find a useful application in organic synthesis, especially in the field of selective reduction.

ALS 저해형 제초제 내성 고추품종 검정 (Assessment of ALS-Inhibiting Herbicides Tolerance in Pepper Cultivars)

  • 폰프롬 토사폰;변종영
    • 한국잡초학회지
    • /
    • 제17권3호
    • /
    • pp.325-333
    • /
    • 1997
  • ALS저해형 제초제 imazethapyr와 primisulfuron에 내성인 고추품종을 선발하기 위하여 42종 고추품종을 공시하여 고추의 약해, 초장, 생체중 및 건물중을 측정하여 품종 반응을 조사하였다. 1. 레드탑, 해피드라이, 골든 타워, 하교레 품종은 imazethapyr에 내성을, 코리아, 조양, 오리엔탈 글로리, 하남 품종은 감수성을 나타냈다. 레드혼, 조풍, 광복, 왕조는 primisulfuron에 내성을, 코리아, 다홍, 참조아, 풍천 품종은 감수성을 나타냈다. 2. Imazethapyr에 대한 $I_{50}$ 농도는 감수성 품종은 0.075kg/ha, 내성품종은 0.20kg/ha이며, primisulfuron의 경우, 감수성 품종은 0.065kg/ha, 내성품종은 0.16kg/ha이었다. 3. Imazethapyr 처리에 따른 $GR_{50}$을 감수성 품종에서 0.05kg/ha, 내쟁품종에서 0.20kg/ha이며 primisulfuron 처리의 경우 감수성 품종은 0.07kg/ha, 내성품종은 0.16kg/ha이었다. 4. 따라서 ALS저해형 제초제에 대한 내수성품종과 감수성 품종간 내성 정도는 imazethapyr에서 3~4배, primisulfuron에서는 2~3배 차이를 나타냈다.

  • PDF