• Biomolecules & Therapeutics
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• 제25권2호
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• pp.122-129
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• 2017

A diversity of synthetic cathinones has flooded the recreational drug marketplace worldwide. This variety is often a response to legal control actions for one specific compound (e.g. methcathinone) which has resulted in the emergence of closely related replacement. Based on recent trends, the nitrogen atom is one of the sites in the cathinone molecule being explored by designer type modifications. In this study, we designed and synthesized two new synthetic cathinones, (1) ${\alpha}-piperidinopropiophenone$ (PIPP) and (2) ${\alpha}-piperidinopentiothiophenone$ (PIVT), which have piperidine ring substituent on their nitrogen atom. Thereafter, we evaluated whether these two compounds have an abuse potential through the conditioned place preference (CPP) in mice and self-administration (SA) in rats. We also investigated whether the substances can induce locomotor sensitization in mice following 7 days daily injection and challenge. qRT-PCR analyses were conducted to determine their effects on dopamine-related genes in the striatum. PIPP (10 and 30 mg/kg) induced CPP in mice, but not PIVT. However, both synthetic cathinones were not self-administered by the rats and did not induce locomotor sensitization in mice. qRT-PCR analyses showed that PIPP, but not PIVT, reduced dopamine transporter gene expression in the striatum. These data indicate that PIPP, but not PIVT, has rewarding effects, which may be attributed to its ability to affect dopamine transporter gene expression. Altogether, this study suggests that PIPP may have abuse potential. Careful monitoring of this type of cathinone and related drugs are advocated.

• Bulletin of the Korean Chemical Society
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• 제24권4호
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• pp.494-498
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• 2003

The transition from aromatics to heteroaromatics is very attractive since it provides an extremely large structural variety, the chemical functionality as well as the possibilities for electronic tuning of the fullerene properties. A synthesis of heterofullerenes in macroscopic quantities is unknown however the spectrometric detection of $C_{59}B$ has been reported. The electronic structures of $C_{(60-2x)}(BN)_x$ systems, isoelectronic with $C_{60}$ have been explored by Extended Hukel, AM1 and ab initio methods. The polyhedral assembly energy are 7.7 kcal greater than $C_{60}$ when one B-N unit is substituted with C-C unit. The assembly energies are getting bigger if more B-N unit is introduced. We focus on HOMO-LUMO energy gap and the stability effects in $C_{(60-2x)}(BN)_x$ with different compositions of $(BN)_x$ moiety. The bonding properties of the substituent atoms were investigated in detail.

• 대한화학회지
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• 제51권2호
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• pp.115-124
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• 2007

α, β-불포화 케톤 유도체를 실리카-황산 촉매 하에서 비용매 교차 알돌 응축 반응법을 이용하여 합성하였다. 합성 수율은 90% 이상이었으며, 사용된 촉매는 회수 가능하였다. 합성돤 화합물들의 물리화학적인 특성은 IR, NMR, Mass 등의 분광학적 분석 방법을 이용하여 결정하였다. 케톤 생성물에 미치는 치환기 효과는 측정된 분광 데이터와 Hammet 치환기 상수간의 상관관계로 표현되는 다중 상관계수 방정식에 의하여 잘 설명될 수 있었다.

• Bulletin of the Korean Chemical Society
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• 제32권4호
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• pp.1143-1145
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• 2011

The synthesis of novel iminecalix[4]arenes and further modification thereafter is described using a synthetic strategy. The reaction of the benzaldehyde derivatives with tetraamine functions on the calix[4]arene easily afforded the pure compounds in 92.4-95.7% yields, regardless of the effect of the substituents on the benzaldehyde derivatives. These compounds were stable under the conditions to obtain their analogue dialkylated in the narrow rim, with 83.2-89.9% yields. Characterization of the newly synthesized iminecalix[4]arene derivatives by spectroscopic methods revealed that all compounds are in the cone conformations.

• 한국응용과학기술학회지
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• 제11권1호
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• pp.27-31
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• 1994

The rate constants of hydrolysis of ${\alpha}$-phenly-N-iso-propylnitrone and its derivatives have been determined by UV spectrophotometry at $25^{\circ}C$ and a rate equation which can be applied over a wide pH range was obtained. On the basis of rate equations derived and judging from the hydrolysis products obtained and general base and substituent effects, plausible mechanism of hydrolysis in various pH range have been proposed. Below pH 4.5, the hydrolysis was initiated by the protonation and followed by the addition of water to ${\alpha}$-carbon. Above pH 10.0, the hydrolysis was proceeded by the addition of hydroxide ion to ${\alpha}$-carbon. In the range of $4.5{\sim}10.0$, the addition of water to nitrone was rate controlling step.

• Bulletin of the Korean Chemical Society
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• 제32권9호
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• pp.3355-3360
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• 2011

The nucleophilic substitution reactions of 1,2-phenylene phosphorochloridate (1) with substituted anilines ($XC_6H_4NH_2$) and deuterated anilines ($XC_6H_4ND_2$) are investigated kinetically in acetonitrile at $-15.0^{\circ}C$. The studied substrate of 1,2-phenylene phosphorochloridate is cyclic five-membered ring of phosphorus ester, and the anilinolysis rate of 1 is much faster than its acyclic analogue (4: ethyl phenyl chlorophosphate) because of extremely small magnitude of the entropy of activation of 1 compared to 4. The Hammett and Bronsted plots exhibit biphasic concave upwards for substituent X variations in the nucleophiles with a break point at X = 3-Me. The values of deuterium kinetic isotope effects (DKIEs; $k_H/k_D$) change from secondary inverse ($k_H/k_D$ < 1) with the strongly basic anilines to primary normal ($k_H/k_D$ > 1) with the weakly basic anilines. The secondary inverse with the strongly basic anilines and primary normal DKIEs with the weakly basic anilines are rationalized by the transition state (TS) variation from a predominant backside attack to a predominant frontside attack, in which the reaction mechanism is a concerted $S_N2$ pathway. The primary normal DKIEs are substantiated by a hydrogen bonded, four-center-type TS.

• 한국전기전자재료학회논문지
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• 제14권2호
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• pp.145-151
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• 2001

In this study, blue light emiting, soluble PPV copolymers were synthesized by Witting reaction and characterized. ITO/copolymer/Ca and ITO/copolymer/A1 structured light emitting diodes(LED) were fabricated and their I-V characteristics were examined. Copolymers showed $\pi$-$\pi$ transition in UV-Vis./NIR spectra. The PL and abosorption spectrum showed the symmetric vibration modes with mirror images which means that copolymers are highly aligned. By introducing aliphatic hydrocarbon group on polymer main chain, the solubility of copolymers was improved and no significant effects of substituent were observed. The band offset of copolymers are well suited as light emitting material for LED application than monomer or oligomer does. THe band offset of copolymers is ∼3eV in PL spectrum and the threshold voltages of ITO/copolymer/Ca and ITO/copolymer/Al structured LED 3V, 12V respectively. In the case of ITO/copolymer/Ca LED, it is believed that the amount of electrons and holes is well balanced and the recombination of opposite charges occurs easily because the work functions of Ca and Al electrodes are 2.9 and 4.3eV respectively and the difference in barrier height between polymer and electrode was small.

• 대한화학회지
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• 제30권2호
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• pp.159-165
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• 1986

몇가지 알킬화피리딘(2, 3 and 4-methyl and ethylpyridine)의 해리상수의 온도 및 압력 의존성을 알아 보았으며 해리상수는 전도도법을 이용하여 측정했다. 이들 치환피리딘의 해리는 온도가 높아지면 증가하고 압력이 높으면 감소함을 알았다. 또 이들 해리상수 값에서 해리반응의 열역학적 성질을 계산하여 해리반응의 여러가지 성질을 알아 보았으며 알킬화피리딘의 특이성을 알 수 있었다.

• 대한화학회지
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• 제31권5호
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• pp.395-399
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• 1987

루신의 해리상수를 전도도법을 이용하여 온도(15 to 40$^{\circ}$C)와 압력(1~2,500bar)을 변화시키면서 측정했다. 루신의 두가지 해리상수는 온도가 높아지면 모두 증가하였다. 그러나 압력이 높아지면 첫째 해리상수는 증가하였으나 둘째 해리상수는 낮은 온도에서는 감소하고 높은 온도에서는 증가했다. 이들 해리상수를 이용하여 해리반응의 열역학적 성질들을 계산하고 이들 성질로부터 해리반응의 특성을 알아보았다.

• Bulletin of the Korean Chemical Society
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• 제24권2호
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• pp.205-208
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• 2003

Laser-induced Raman spectroscopy has been utilized to demonstrate its feasibility for studying the kinetics of imine formation in chloroform solvent. The imine formation, by the nucleophilic addition of primary amine to the carbonyl group of ketone, has been monitored at ten minute intervals for eight hours. The intensity of the C=O stretching mode at 1684 $cm^{-1}$ was measured to determine the rate constant of the reaction. In order to correct the sample-to-sample fluctuations in Raman peak area, this peak was normalized to the C-Cl bending peak at 666 $cm^{-1}$. By the peak area change during the course of reaction, the second order rates at three different temperatures have been determined. The substituent effects on the π conjugations of imine product have also been investigated. On the basis of Raman frequency shifts, the delocalization properties of the aromatic system modified by substitution of a hydrogen atom with -Cl and $-CH_3O$ groups could be clearly understood.