• Title/Summary/Keyword: Benzylamine

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Kinetics and Mechanism of the Aminolysis of O-Methyl S-Aryl Thiocarbonates in Acetonitrile

  • Oh, Hyuck-Keun
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1539-1542
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    • 2011
  • The aminolysis of O-methyl S-aryl thiocarbonates with benzylamines are studied in acetonitrile at -45.0$^{\circ}C$. The ${\beta}_X$(${\beta}_{nuc}$) values are in the range 0.62-0.80 with a negative cross-interaction constant, ${\rho}_{XZ}$ = -0.42, which are interpreted to indicate a concerted mechanism. The kinetic isotope effects involving deuterated benzylamine nucleophiles ($XC_6H_4CH_2ND_2$) are large, $k_H/k_D$ = 1.29-1.75, suggesting that the N-H(D) bond is partially broken in the transition state by forming a hydrogen-bonded four-center cyclic structure. The concerted mechanism is enforced by the strong push provided by the MeO group which enhances the nucleofugalities of both benzylamine and arenethiolate from the putative zwitterionic tetrahedral intermediate.

Kinetic Isotope Effects Involving Deuterated Benzylamine Nucleophiles

  • Lee, Ik-Choon;Koh, Han-Joong;Sohn, Dong-Sook;Lee, Byung-Choon
    • Bulletin of the Korean Chemical Society
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    • v.12 no.1
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    • pp.101-103
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    • 1991
  • The kinetic isotope effects (KIE) are determined for the reactions of benzyl benzenesulfonates (BBS), ethyl benzenesulfonates (EBS) and phenacyl benzensulfonates (PAB) with deuterated benzylamine nucleophiles. The inverse secondary ${\alpha}$-deuterium KIE observed were somewhat smaller than those for the corresponding reactions with aniline nucleophiles. The primary $KIE_s$ obtained with PAB were slightly greater than those for the corresponding reactions with anilines, which suggested that the inverse secondary KIE is decreased due to a relatively earlier transition state for bond-making with little change in the hydrogen bonding strength to the carbonyl oxygen.

Synthesis of 2-phenylimino-1,3-thiazoline hydrochloride salts (2-Phenylimino-1,3-thiazoline 염산염 유도체의 합성)

  • Hahn, Hoh-Gyu;Nam, Kee-Dal;Shin, Sun-Ho;Mah, He-Duck
    • The Korean Journal of Pesticide Science
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    • v.5 no.2
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    • pp.13-17
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    • 2001
  • A synthesis of new 2-phenylimino-1,3-thiazolines 2 for the purpose of development of new agrochemical fuugicide was described. Reaction of chlorine with diketene followed by treatment of benzylamine without isolation of intermediate 8a gave ${\gamma}-chloro-{\beta}-keto$ benzylamide 10a. Thioureas 4 obtained from the reaction of methyl isothiocyanate with aniline derivatives were subjected to 10a in acetone solution to afford the corresponding 2-phenylimino-1,3-thiazoline hydrochloric acid salts 2 through unisolable inltermediates 11 and 12. The plausible reaction mechanism including nucleophilic attack of sulfur assisted neighboring nitrogen lone pair electron on phenyl of thiourea 4 was discussed.

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Effects of Some Monoterpenes on Rat Brain Monoamine Oxidase (수종 모노테르펜계 화합물이 랫드 뇌의 monoamine oxidase활성에 미치는 영향)

  • 문창규;임종석;유충규
    • Journal of Food Hygiene and Safety
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    • v.10 no.4
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    • pp.279-282
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    • 1995
  • Eight natural or semistynthesized monoterpenes were examined for their effects in rat brain monoamine oxidase(MAO) using benzylamine as substrate. Thujone and 3-carene were found to have the inhibition effects on rat brain MAQ activity, 38% and 95% inhibition at 103M respectively. The kinetic study on 3-carene, the most potent inhibitive type. But (+) pulegon and (-) isopulegon was found to activate MAO slightly.

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Kinetics and Mechanism of the Reactions of S-Phenyl Dithiobenzoates with Benzylamines in Acetonitrile

  • 오혁근;신철호;이익춘
    • Bulletin of the Korean Chemical Society
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    • v.16 no.7
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    • pp.657-661
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    • 1995
  • Kinetic studies are carried out on the reaction of S-phenyl dithiobenzoates with benzylamines in acetonitrile at 30.0 ℃. Small magnitude of ρX (βX) as well as ρZ (βZ) obtained suggests rate-limiting nucleophilic attack of the thiocarbonyl carbon. This is supported by the unusually small magnitude of ρXY and ρYZ, albeit their signs do not agree with those expected. Moreover, the inverse secondary kinetic isotope effects (kH/kD<1.0) involving deuterated benzylamine nucleophiles are also in line with the proposed mechanism.

Anti-stress and Promoting Effect of the Fruit of Morus alba (상심자(Morus alba)의 운동능력 향상과 스트레스 개선효과)

  • Hwang, Keum-Hee
    • Korean Journal of Food Science and Technology
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    • v.37 no.1
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    • pp.95-102
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    • 2005
  • Effects of Morus alba fruit extracts on monoamine oxidase (MAO) activity were examined in rats during and after physical exercise. Oral administration of M. alba extract (0.3 g/kg body weight) significantly increased brain MAO-A activity but decreased liver MAO-B activity when they were measured using serotonin and benzylamine as substrates. Type of physical exercises had significant effect on MAO activity. Brain MAO-A activity markedly decreased with physical activity-related stress compared to normal group, whereas Liver MAO-B activity increased up to 60 min after exercise. Lactate dehydrogenase (LDH) activity and lactate concentration in blood, clinical indices of physical exercise activities, were also determined for correlation to MAO activities. MAO-A activity of rats subjected to oral administration of M. alba extract and physical exercise increased whereas MAO-B and LDH activities, and lactate level decreased, All indices eventually recovered normal levels, These results suggest M. alba may increase capability of physical activities by modulating MAO activities during exercise.

The Inhibitory Activity on Monoamine Oxidase of the Fruit of Morus alba (상심자의 모노아민산화효소 저해활성)

  • Hwang, keum-Hee;Song, Im
    • Korean Journal of Pharmacognosy
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    • v.34 no.2 s.133
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    • pp.185-189
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    • 2003
  • We examined the inhibitory activities against monoamine oxidase (MAO) of Morus alba in vitro and in vivo methods. Methanolic extract of M. alba showed significantly inhibitory activities on MAO-A and MAO-B that were prepared from rat brain and liver in vitro. The inhibitory activities were measured by serotonin and benzylamine as substrates, respectively. MAO-A and MAO-B activities were potently inhibited by ethylacetate extracts of M. alba in vitro tests. Those activities in vivo tests have different tendency each other. MAO-A activity was increased by the oral administration of methanolic extract of M. Alba, while, MAO-B activity was decreased. Consequently, we can suggest that M. alba may have the effects on the inhibitory activities against MAO both in vitro and in vivo.

The Influence of Sodium Fluoride on the Release of Catecholamine from Perfused Organs and Monoamine Oxidase Activity (Fluoride가 적출장기(摘出臟器)의 Catecholamine 유리(遊離) 및 Monoamine Oxidase 활성도(活性度)에 미치는 영향(影響))

  • Cheon, Yun-Sook;Kim, Sung-Sook;Lee, Kyung-Hee;Shin, Kyung-Chul
    • The Korean Journal of Pharmacology
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    • v.8 no.2
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    • pp.41-47
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    • 1972
  • Fluorides were supposed to exert a stimulatory action on the catecholamine release. In this study, the authors attempted to investigate the action of sodium fluoride on the catecholamine release from the isolated perfused cow adrenal gland and rat heart. And also the inhibitory effect of sodium fluoride on the monoamine oxidase activity in rat heart and liver mitochondria was investigated. The monoamine oxidase activity was measured by the conversion of benzylamine to benzaldehyde. The results obtained were follows; 1. Sodium fluoride stimulated the release of catecholamine from the isolated perfused cow adrenal gland and rat heart. 2. Sodium fluoride inhibited the rat heart and liver mitochondrial monoamine oxidase activity.

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Inhibitory Activity on Monoamine Oxidase of Prunella vulgaris (하고초의 Monoamine Oxidase 저해활성)

  • Hwang, Keum-Hee
    • Korean Journal of Pharmacognosy
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    • v.37 no.3
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    • pp.157-161
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    • 2006
  • We examined the inhibitory activities against monoamine oxidase (MAO) of Prunella vulgaris in vitro and in vivo methods. Methanolic extract of P. vulgaris showed significantly Inhibitorγ activities on MAO-A and MAO-B that were prepared from rat brain and liver in vitro. The inhibitory activities were measured by serotonin and benzylamine as substrates, respectively. MAO-A and MAO-B activities were potently inhibited by ethylacetate extracts of P. vulgaris in vitro tests. It was observed that those activities in vivo tests have different tendency each other. MAO-A activity was increased by the oral administration of methanolic extract of P. vulgaris while MAO-B activity was decreased. Consequently, we suggest that P. vulgaris may have the effects on the inhibitory activities against MAO both in vitro and in vivo.