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Kwon, S.J.,Gil, M.G.,Kim, D.Y. Pergamon Press ; Elsevier Science Ltd 2017 Tetrahedron letters: the international organ for t Vol.58 No.16
A visible light mediated photocatalytic oxidative coupling reaction of N-phenyl tetrahydroisoquinoline with β-keto acids has been developed. This approach provides a mild and operationally simple access to the synthesis of C1-acylmethylated tetrahydroisoquinolines.
Ki-Churl Chang,Young-Jin Kang,Young-Soo Lee,Won-Seog Chong,Hye-Sook Yun-Choi,Duck-Hyong Lee,Jae-Chun Ryu 대한생리학회-대한약리학회 1998 The Korean Journal of Physiology & Pharmacology Vol.9 No.5
<P> Tetrahydroisoquinoline (THI) alkaloids can be considered as cyclized derivatives of simple phenylethylamines, and many of them, especially with 6,7-disubstitution, demonstrate relatively high affinity for catecholamines. Two -OH groups at 6 and 7 positions are supposed to be essential to exert -receptor activities. However, it is not clear whether -OH at 6,7 substitution of THIs also shows -adrenoceptor activities. In the present study, we investigated whether -OH or -OCH<SUB>3</SUB> substitutions of 6,7 position of THIs differently affect the <SUB>1</SUB>-adrenoceptor affinity. We synthesized two 1-naphthylmethyl THI alkaloids, 1--naphthylmethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline HBr (YS 51) and 1--naphthylmethyl-6, 7-dimethoxy-1,2,3,4-tetrahydroisoquinoline HCl (YS 55), and their pharmacological actions on <SUB>1</SUB>-adrenoceptor were compared. YS 51 and YS 55, concentration-dependently relaxed endothelium-denuded rat thoracic aorta precontracted with phenylephrine (PE, 0.1 ㄍM) in which pEC<SUB>50</SUB> were 5.890.21 and 5.930.19, respectively. Propranolol (30 nM) did not affect the relaxation-response curves to YS 51 and YS 55. Concentration-response curves to PE were shifted to right by the pretreatment with YS 51 or YS 55. The pA<SUB>2</SUB> values of YS 51 and YS 55 showed 6.050.24 and 5.880.16, respectively. Both probes relaxed KCl (65.4 mM)-contracted aorta and inhibited CaCl<SUB>2</SUB>-induced contraction of PE-stimulated endothelium- denuded rat thoracic aorta in Ca<SUP>2</SUP>-free solutions. In isolated guinea pig papillary muscle, 1 and 10 ㄍM YS 51 increased contractile force about 4- and 8- fold over the control, respectively, along with the concentration-dependent increment of cytosolic Ca<SUP>2</SUP> ions. While, 10 ㄍM YS 55 reduced the contractile force about 50 % over the control and lowered the cytosolic Ca<SUP>2</SUP> level, in rat brain homogenates, YS 51 and YS 55 displaced [<SUP>3</SUP>H]prazosin binding competitively with K<I>i</I> 0.15 and 0.12 ㄍM, respectively. However, both probes were ineffective on [<SUP>3</SUP>H]nitrendipine binding. Therefore, it is concluded that two synthetic naphthylmethyl-THI alkaloids have considerable affinity to <SUB>1</SUB>-adrenenoceptors in rat aorta and brain.
Ju, Sung-Min,Kim, Kun-Jung,Lee, Jong-Gil,Lee, Chai-Ho,Han, Dong-Min,Yun, Young-Gab,Hong, Gi-Yun,An, Won-Gun,Jeon, Byung-Hun The Physiological Society of Korean Medicine and T 2005 동의생리병리학회지 Vol.19 No.3
The tetrahydroisoquinolines included potent cytotoxic agents that showed antitumor activity,antimicrobial activity, and other biological properties. We studied the effect of CDST, 1-Chloromethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-sulfonic acid amide, a newly synthesized anti-cancer agent. The cytotoxic activity of CDST in HL-60 cells was increased in a dose-dependent manner. CDST, tetrahydroisoquinolines derivative, was cytotoxic to HL-60 cells, with IC50 of $80{\mu}g/ml$. Treatment of CDST to HL-60 cells showed the fragmentation of DNA in a dose- and time dependent manner, suggesting that thesecells underwent apoptosis. Treatment of HL-60 cells with CDST was induced in a dose- and time-dependent activation of caspase-3, caspase-8 and proteolytic cleavage of poly(ADP-ribose) polymerase. In caspase activity assay, caspase-3 and -8 was activated after 12 h and 6 h posttreatment, respectively. CDST also caused the release of cytochrome c from mitochondria into the cytosol. CDST-induced cytochrome c release was mediated by caspase-8-dependent cleavage of Bid and Bax translocation. These results suggest that caspase-8 induced Bid cleavage and Bax translocation, caused mitochondrial cytochrome c release, and induce caspase-3 activationduring CDST-induced apoptosis in HL-60 cells.
Lee, A.,Choi, H.J.,Jin, K.B.,Hyun, M.H. Elsevier 2011 Journal of chromatography A Vol.1218 No.26
A liquid chromatographic chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied for the first time to the resolution of biologically important 1-aryl-1,2,3,4-tetrahydroisoquinolines. The unusual resolution of cyclic secondary amino compounds on a chiral crown ether-based CSP was quite successful with the use of a mixture of methanol-acetonitrile-triethylamine at a ratio of 30/70/0.5 (v/v/v) as a mobile phase. From the chromatographic behaviours for the resolution of seven 1-aryl-1,2,3,4-tetrahydroisoquinolines, the steric bulkiness of the 1-phenyl ring at the chiral center of analytes was concluded to play an important role in the chiral recognition.
Lee, Sang Gyu,Sin, Seunghui,Kim, Seungyeon,Kim, Sung-Gon Elsevier 2018 Tetrahedron letters: the international organ for t Vol.59 No.15
<P><B>Abstract</B></P> <P>A Lewis acid-catalyzed Friedel-Crafts/Michael cascade reaction between <I>N</I>-dialkyl-3-vinylanilines and <I>N</I>-tosylaziridines has been developed for the stereoselective synthesis of tetrahydroisoquinolines (THIQs). The reaction using Gd(OTf)<SUB>3</SUB> as the Lewis acid catalyst was tolerant to the various <I>N</I>-dialkyl-3-vinylaniline and <I>N</I>-tosylaziridine substrates and provided access to 28 new, highly functionalized THIQs in typically high yields with moderate- to- excellent diastereoselectivities.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Concise synthesis of 1,3,4-trisubstituted tetrahydroisoquinolines (THIQs) is developed. </LI> <LI> The method involves Friedel-Crafts/Michael cascade reaction of <I>N</I>-dialkyl-3-vinylanilines with <I>N</I>-tosylaziridines. </LI> <LI> Gd(OTf)<SUB>3</SUB> is used as the Lewis acid catalyst. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
양정은,정재경,Yang, Jung-Eun,Jung, Jae-Kyung 대한약학회 2009 약학회지 Vol.53 No.3
Synthetic studies directed toward an asymmetric total synthesis of calycotomine, an representative tetrahydroisoquinoline, are described. The application of N-tert-butane sulfinyl chiral auxiliary to the Pictet-Spengler type reaction for the efficient synthesis of tetrahydroisoquinoline skeleton has been also investigated.
Won-Seog Chong,Young-Soo Lee,Young-Jin Kang,Duck-Hyung Lee,Jae-Chun Ryu,Hye Sook Yun-Choi,Ki-Churl Chang 대한생리학회-대한약리학회 1998 The Korean Journal of Physiology & Pharmacology Vol.2 No.3
<P> Tetrahydroisoquinoline (THI) alkaloids can be considered as cyclized derivatives of simple phenylethylamines. Many of them, especially with 6,7-disubstitution, demonstrate a relatively high affinity for catecholamines. Present study examines the pharmacological action of limited series of THI, using rats isolated atria and aorta. In addition, a [<SUP>3</SUP>H] prazosin displacement binding study with THI compounds was performed, using rat brain homogenates to investigate whether these probes have -adrenoceptor affinity. We also compared the vascular relaxation potency of these probes with dobutamine. YS 49, YS 51, higenamine and dobutamine, concentration-dependently, relaxed endothelium-denuded rat thoracic aorta precontracted with phenylephrine (PE, 0.1 ㄍM) in which pEC<SUB>50</SUB> were 5.56⁑0.32 and 5.55⁑0.21, 5.99⁑1.16 and 5.57⁑0.34, respectively. These probes except higenamine also relaxed KCl (65.4 mM)-contracted aorta. In isolated rat atria, all THIs and dobutamine increased heart rate and contractile force. In the presence of propranolol, the concentration response curves of YS 49 and YS 51 shifted to the right and resulted in pA<SUB>2</SUB> values of 8.07⁑0.84 and 7.93⁑0.11, respectively. The slope of each compound was not deviated from unity, indicating that these chemicals are highly competitive at the cardiac -adrenoceptors. YS 49, YS 51, and higenamine showed -adrenoceptor affinity in rat brain, in which the dissociation constant (K<SUB>i</SUB>) was 2.75, 2.81, and 1.02 ㄍM, respectively. It is concluded, therefore, that THI alkaloids have weak affinity to <SUB>1</SUB>-adrenoceptors in rat aorta and brain, respectively, while these probes show relatively high affinity for cardiac -adrenoceptors. Thus, these chemicals may be useful in the treatment of congestive heart failure.
Jung-Eun Yang,인진경,Mi-Sung Lee,곽재환,이희순,이수재,강한영,서영거,정재경 대한화학회 2007 Bulletin of the Korean Chemical Society Vol.28 No.8
An efficient Pictet-Spengler type reaction of N,O-acetal TMS ethers for the practical synthesis of 1-substituted tetrahydroquinolines, medicinally important alkaloids, has been accomplished. To demonstrate the versatility of this novel procedure, the total synthesis of calycotomine, a representative 1-hydroxymethyl substituted tetrahydroisoquinoline, is also described.