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Suh, Young-Ger,Lim, Changjin,Sim, Jaehoon,Lee, Jae Kyun,Surh, Young-Joon,Paek, Seung-Mann American Chemical Society 2017 Journal of organic chemistry Vol.82 No.3
<P>A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-fi-carboline intermediate and an unprecedented tandem Reformatsky aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.</P>
Synthesis of cis-disubstitude cyclohexane synthesis of cis-1-ethenyl-2-hydroxymethyl-cyclohexane
Suh, Young-Ger,Kim, Soon-Ai,Cho, Youn-Sang The Pharmaceutical Society of Korea 1990 Archives of Pharmacal Research Vol.13 No.2
The efficient synthetic routes to cis-1-ethenyl-2-hydroxymethyl-cyclohexane, an useful synthetic intermediate, have been described. Access to the cis-disubstituted cyclo hexane is gained through the Clasen rearrangment and selective DHP protection of diol respectively.
Suh, Young-Ger,Jang, Jaebong,Yun, Hwayoung,Han, Sae Mi,Shin, Dongyun,Jung, Jae-Kyung,Jung, Jong-Wha American Chemical Society 2011 ORGANIC LETTERS Vol.13 No.21
<P>A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the <I>N</I>-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate <I>N</I>-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a β-amino acid has been achieved by applying this method.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2011/orlef7.2011.13.issue-21/ol202573s/production/images/medium/ol-2011-02573s_0002.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol202573s'>ACS Electronic Supporting Info</A></P>
A stereo-controlled access to functionalized macrolactams <i>via</i> an aza-Claisen rearrangement
Suh, Young-Ger,Lee, Yong-Sil,Kim, Seok-Ho,Jung, Jae-Kyung,Yun, Hwayoung,Jang, Jaebong,Kim, Nam-Jung,Jung, Jong-Wha The Royal Society of Chemistry 2012 Organic & biomolecular chemistry Vol.10 No.3
<p>A novel and stereo-controlled method for the preparation of functionalized macrolactams was developed. The process involves stereoselective enol ether formation, followed by an azacyclic ring expansion <I>via</I> an aza-Claisen rearrangement. Herewith, we describe a systematic investigation of an aza-Claisen rearrangement-induced ring expansion of azacycles prepared by appending <I>E</I>/<I>Z</I>-enol ethers to the medium-sized lactams as well as the stereochemical outcome. In addition, the strategy was successfully applied to the total synthesis of fluvirucinine A<SUB>1</SUB> and 3-<I>epi</I>-fluvirucinine A<SUB>1</SUB>. This method offers an attractive alternative to the intramolecular amide–aldol reaction for the elaboration of β-alkoxy-α-substituted motifs.</p> <P>Graphic Abstract</P><P>A novel and stereo-controlled method that offers an attractive alternative to the intramolecular amide–aldol reaction for the elaboration of β-alkoxy-α-substituted motifs has been developed. <img src='http://pubs.rsc.org/ej/OB/2011/c1ob06733h/c1ob06733h-ga.gif'> </P>
Development of 20㎾ Energy Storage System for Smart Green Town
Young-Ger Seo,Jeong-Min Lee,In-Young Suh 전력전자학회 2011 ICPE(ISPE)논문집 Vol.2011 No.5
The main purpose of this paper is to introduce the development and structure of 20㎾ Energy Storage System (ESS). The basis of the capacity selection of 20㎾ ESS, which will be installed in ‘Se-hwa sanatorium’, is introduced. The Smart Green Town is defined and its structure is also introduced in this paper. The possibility of success with this system will be verified as an ESS through the simulated results of the grid-connected mode and the stand-alone mode.
Suh, Young-Ger 이화여자대학교 세포신호전달연구센터 2007 고사리 세포신호전달 심포지움 Vol. No.9
Since capsaicin was found as an excellent TRPV1 receptor agonist, considerable efforts toward the development of novel agonist-based analgesics have been continued. However, the small therapeutic window between the analgesic effect and the excitatory side effects precluded development of the agonists as a systemic agent. Thus recent studies on TRPV1 agonists or antagonists have focused on separating the excitatory effects of capsaicin analogs from the antinociceptive properties of these molecules. Recently, we have looked for non-vanilloid TRPV1 antagonists by developing ideal vanilloid equivalents, which might provide the perfect analgesic effects without the side effects caused by TRPV1 receptor agonists. During the course of our work on TRPV1 antagonists, we have developed a new class of potent and selective TRPV1 antagonists based on the endogenous activators. These synthetic ligands act as potent inhibitors of Ca^(2+) uptake with best IC_(50) values compared to the reported TRPV1 antagonists up to date. Moreover, series of our novel VR1 antagonists are devoid of the important shortcomings of agonists, such as hypothermia and pungency. In particular, preclinical trials of the analogs, which showed excellent in vitro activities, have shown promising results for therapeutic uses without any particular problems. Ultimately, these analogs are anticipated to be therapeutically important and conceptually new analgesic. Type 2 diabetes is a metabolic disorder and characterized by insulin resistance, hyperglycemia, hyperinsulinimia, leading to complete depletion of insulin in the latter stages. As members of the nuclear hormone receptor super family of ligand-activated transcription factors, the PPARs(Peroxisome Proliferator-activated Receptors) exert a role in regulating various cellular processes including the storage and catabolism of fats and carbohydrates. PPARγ among three PPAR isotypes is predominantly expressed in adipose tissue and its activation induces adipocyte differentiation, lipid uptake and amelioration of insulin resistance. PPARα has been known to regulate lipid homeostasis via control of fatty acid catabolism. Considering the significantly increased risk of a complication related with lipid catabolism among patients with type 2 diabetes, it has been postulated that PPAR α/γ dual agonist might present outstanding agents for the treatment of type 2 diabetes and dyslipidemia. Based on the natural products and chemical library, we have developed potent PPAR α/γ dual agonists, which exhibited excellent EC_(50S) in the human cell-based assay. In particular, SD-0052 and SD-0076 showed more potent activity in blood glucose lowering effects(41.7 and 60.1%, respectively at 3mg/Kg) compared to the currently known PPAR α/γ dual agonist. The binding modes and the rationale for our drug design of both TRPV1 antagonists and PPAR α/γ dual agonists as well as their structure-activity relationship will be also discussed.
Suh, Jinyoung,Kim, Do-Hee,Kim, Eun-Hee,Park, Sin-Aye,Park, Jong-Min,Jang, Jeong-Hoon,Kim, Su-Jung,Na, Hye-Kyung,Kim, Nam-Doo,Kim, Nam-Jung,Suh, Young Ger,Surh, Young-Joon Elsevier 2018 Cancer letters Vol.424 No.-
<P><B>Abstract</B></P> <P>15-Deoxy-Δ<SUP>12,14</SUP>-prostaglandin J<SUB>2</SUB> (15d-PGJ<SUB>2</SUB>), one of the terminal products of cyclooxygenase-2-catalized arachidonic acid metabolism, has been shown to stimulate breast cancer cell proliferation and migration through Akt activation, but the underlying mechanisms remain poorly understood. In the present study, we investigated the effects of 15d-PGJ<SUB>2</SUB> on the activity of PTEN, the inhibitor of the phosphoinositide 3-kinase (PI3K)-Akt axis, in human breast cancer (MCF-7) cells. Since the α,β-unsaturated carbonyl moiety in the cyclopentenone ring of 15d-PGJ<SUB>2</SUB> is electrophilic, we hypothesized that 15d-PGJ<SUB>2</SUB>-induced Akt phosphorylation might result from the covalent modification and subsequent inactivation of PTEN that has several critical cysteine residues. When treated to MCF-7 cells, 15d-PGJ<SUB>2</SUB> bound to PTEN, and this was abolished in the presence of the thiol-reducing agent dithiothreitol. A mass spectrometric analysis by using recombinant and endogenous PTEN protein revealed that the cysteine 136 residue (Cys<SUP>136</SUP>) of PTEN is covalently modified upon treatment with 15d-PGJ<SUB>2</SUB>. Notably, the ability of 15d-PGJ<SUB>2</SUB> to covalently bind to PTEN as well as to induce Akt phosphorylation was abolished in the cells expressing a mutant form of PTEN in which Cys<SUP>136</SUP> was replaced by serine (C136S-PTEN). The present study demonstrates for the first time that electrophilic 15d-PGJ<SUB>2</SUB> directly binds to cysteine 136 of PTEN and provides new insight into PTEN loss in cancer progression associated with chronic inflammation. These observations suggest that 15d-PGJ<SUB>2</SUB> can undergo nucleophilic addition to PTEN, presumably at Cys<SUP>136</SUP>, thereby inactivating this tumor suppressor protein with concomitant Akt activation.</P> <P><B>Highlights</B></P> <P> <UL> <LI> PTEN is inactivated through covalent modification by 15-deoxy-Δ<SUP>12,14</SUP>-prostaglandin J<SUB>2</SUB> in breast cancer MCF-7 cells. </LI> <LI> 15-Deoxy-Δ<SUP>12,14</SUP>-prostaglandin J<SUB>2</SUB> directly binds to the cysteine 136 residue of the recombinant PTEN. </LI> <LI> PTEN interaction with 15-deoxy-Δ<SUP>12,14</SUP>-prostaglandin J<SUB>2</SUB> stimulates Akt phosphorylation. </LI> <LI> 15-Deoxy-Δ<SUP>12,14</SUP>-prostaglandin J<SUB>2</SUB> stimulates growth of MDA-MB-231 cells when inoculated to the athymic nude mice. </LI> </UL> </P>