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REVIEW : Progress in the studies on tryptanthrin, an alkaloid of history
( Yurngdong Jahng ) 영남대학교 약품개발연구소 2013 영남대학교 약품개발연구소 연구업적집 Vol.23 No.0
Tryptanthrin, an indoloquinazoline alkaloid, was first obtained by sublimation of natural indigo and later isolated from the culture of fungus Candida lipolytica and a variety of other natural sources.Tryptanthrin showed a variety of intriguing biological properties such as antibacterial, antifungal, antiprotozoal, and antiparasitic activities, inhibitory activities against COX-2, 5-LOX, NO synthase and PGE(2) expression, as well as cytotoxic and antitumor activities. Present review covers recent studieson the natural sources, biological activities and mechanisms of their actions, synthesis, structure-activity relationship, and metabolism of tryptanthrin.
Synthesis of 5-azapentacene by Ffiedlander reaction and its properties
( Yurngdong Jahang ),( Moinul Karim ) 영남대학교 약품개발연구소 2016 영남대학교 약품개발연구소 연구업적집 Vol.26 No.-
The Friedlander reaction of cyclohexanone with 3-aminoanthracene-2-carbaldehyde afforded corre-sponding 1,2,3,4-tetrahydronaphtho[2.3-b]acridine in 79%. which was also prepared by reduction of the alternative Friedlander adduct 1,2,3,4-tetrahydronaphthoI2,3-b]acridine-7,12-dione, in 56% yield. De-hydrogenation of 1,2,3,4-tetrahydronaphtho[2,3-b]acridine led to naphtha[2.3-b)acridine (5-azapentacene). 1,2,3,4-Tetrahydro-5-azapentacene and 5-azapentacene are somewhat unstable in solu-tion while these compounds keep their identity in solid state a little longer period of time under inert gas in the refrigerator. The decomposition rate of 1,2,3,4-tetrahydro-5-azapentacene was determined by UV absorption spectra to afford a rate constant, 3.92x10-3 S-l (R~0.982) while 5-azapentacene was too unstable to determine the decomposition rate constant.
( Yurngdong Jahng ),( Dong Hyeon Kim ),( Moinul Karim ),( Yang Lu ) 영남대학교 약품개발연구소 2015 영남대학교 약품개발연구소 연구업적집 Vol.25 No.-
A series of dihydroxytryptanthrins was prepared by the reaction of a suitably substituted isatoic anahydride and isatin as possible metabolites of tryptanthrin. A high-performance liquid charomatography analysis of the synthetic compounds confirmed thar 8,9-dihydroxytryptanthrin is the metabolite isolated from rat liver cytosolic metabolites. Although try ptanthrin shows strong cytotoxicity anainst human cancer cell lines, none of the hydroxylated tryptanthrins exhibit any significant cytotoxicity anainst selected human cancer cell lines up to 50μM.
Synthesis and Properties of 2,2′-Di(heteroaryl)-9,9′-spirobifluorenes
Jahng, Yurngdong,Rahman, A. F. M. Motiur The Chemical Society of Japan 2010 Bulletin of the Chemical Society of Japan Vol.83 No.6
<P>A series of 2,2′-di(heteroaryl)-9,9′-spirobifluorenes were prepared by employing Friedländer reaction of 2,2′-diacetyl-9,9′-spirodifluorene with a series of <I>ortho</I>-aminoarenecarbaldehydes. The compound 2,2′-di(benzo[<I>b</I>]-1,10-phenanthrolin-2-yl)-9,9′-spirofluorene (<B>4e</B>) showed a green light emission at 500 nm upon the excitation of the absorption at 374 nm while 2,2′-di(benzo[<I>h</I>]quinolin-2-yl)-9,9′-spirofluorene (<B>4c</B>), 2,2′-di(1,10-phenanthrolin-2-yl)-9,9′-spirofluorene (<B>4d</B>), 2-(benzo[<I>h</I>]quinolin-2-yl)-2′-(benzo[<I>b</I>]-1,10-phenanthrolin-2-yl)-9,9′-spirofluorene (<B>4g</B>), and 2-(1,10-phenanthrolin-2-yl)-2′-(benzo[<I>b</I>]-1,10-phenanthrolin-2-yl)-9,9′-spirofluorene (<B>4h</B>) showed emissions at 413, 465, 442, and 442 nm upon excitation of the absorption at 370, 362, 370, and 363 nm, respectively, thus having potential for OLED applications.</P>
Synthesis and Biological Activity of Conformationally Controlled 2-PAM Derivatives
Jahng, Yurngdong,Park, Jae Gyu,Yu, Jung Whey,Kim, Sun Young,Kim, Taean,Yang, Jae Ho 영남대학교 약품개발연구소 2000 영남대학교 약품개발연구소 연구업적집 Vol.10 No.-
A series of conformationally controlled 2-PAM derivatives were prepared from 2-acetylpyridine and 2,3-pyrido[b]cycloalkenones in two steps and their reactivities towards parathion poisoned AChE were evaluated. The most planar 2,3-pyrido[b]cyclohexanone oxime methiodide showed an activity comparable to 2-PAM implying E-syn is that the most active comformation of 2-PAM in the biological system.
Synthesis and Properties of Luotonin A Homologues and Their Aza-analogues
Jahng, Yurngdong,Seok Lee, Eung,Gyu Park, Jae,Ill Kim, Seung Japan Institute of Heterocyclic Chemistry 2006 Heterocycles Vol.68 No.1
<P>A series of new 3,2'-polymethylene-2-(quinol-2-yl)-4(3H)-quinazolinones and their aza-analogues were prepared as a homologous series of luotonin A. Their inhibitory activities against topoisomerase and cytotoxicities against selected cancer cell lines were evaluated to show that luotonin A and its aza-analogue were shown significant cytotoxicity. Conformational study revealed that trimethylene-bridged systems were rigid at room temperature with activation energies for interconversion of 15.7 and 14.6 kcal/mol for 3,2'-trimethylene-2-(quinol-2-yl)-4(3H)-quinazolinone and its aza-anlogue, respectively.</P>