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${\beta},\;{\beta}$-Dichlorostyrene 유도체의 Cysteine 및 Thioglycolic Acid에 대한 친핵성 첨가반응의 반응속도론적 연구
김태린,류정열,하덕찬,Tae-Rin Kim,Jong-Yol Ryu,Duk-Chan Ha 대한화학회 1988 대한화학회지 Vol.32 No.3
${\beta},\;{\beta}$-Dichlorostyrene 유도체(p-H, p-Cl, $p-CH_3,\;및\;p-OCH_3$)에 대한 thioglycolic acid 및 cysteine의 친핵성 첨가반응속도를 자외선 분광분석법으로 측정하여 pH에 따르는 반응속도상수의 변화, 일반염기(general base) 및 치환기 효과등으로 부터 넓은 pH범위에서 실험치와 잘 일치하는 반응속도식을 구하였고, 실험사실에 잘 맞는 반응 메카니즘을 제안하였다. 즉 pH 9.0 이상에서의 반응속도는 sulfide anion이 pH $9.0{\sim}7.0$에서는 thioglycolic acid 및 cysteine의 중성분자와 그의 anion들이 경쟁적으로 첨가되며 pH 7.0 이하에서는 thioglycolic acid 및 cysteine의 중성분자만이 첨가됨을 알았다. The rate constants for the nucleophilic addition reactions of thioglycolic acid and cysteine to ${\beta},\;{\beta}$-dichlorostyrene derivatives(p-H, p-Cl, $p-CH_3,\;and\;p-OCH_3$) were photochemically determined at various pH and a rate equation which can be applied over a wide pH range was obtained. On the bases of rate equation, general base catalysis and substituent effect, the plausible addition reaction mechanism was proposed: Above pH 9.0, the reaction was initiated by the addition of sulfide anion, and in the range of pH 7.0 to 9.0, the neutral molecules and it's anions attacked to the double bond, competitively. However, below pH 7.0, only the neutral molecules of thioglycolic acid or cysteine added to the carbon-carbon double bond.
Synthesis and Evaluation of Benzoquinolinone Derivatives as SARS-CoV 3CL Protease Inhibitors
Tae-Young Ahn,Chih-Jung Kuo,Hun-Ge Liu,하덕찬,Po-Huang Liang,Young-Sik Jung 대한화학회 2010 Bulletin of the Korean Chemical Society Vol.31 No.1
For the discovery of new antivirals against Severe Acute Respiratory Syndrome-coronavirus (SARS-CoV), we prepared and evaluated several benzoquinoline compounds as its 3C-like protease (3CLpro) inhibitors. Based on the computer modeling study that each of the two rigid benzoquinolinone and N-phenoltetrazole moieties of the compound 1 is bound to the S1 and S2 sites, respectively, of the SARS protease by forming H-bonds and hydrophobic interactions, we designed and synthesized alkylated benzoquinolines at both the sites of the hydroxyl groups. We found that the compound 2a showed five times higher inhibiting activity against the 3CLpro compared to the compound 1.