• 약학회지
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• 제34권6호
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• pp.422-428
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• 1990

2,3-Dibromo-1,4-naphthoquinone was reacted with p-aminobenzoic acid, 2-aminopyridine, 2-amino-4-metylpyridine, m-nitroaniline, sulfathiazol, p-chloroaniline, phenetidine and 2-bromo-3-(N-arylamino)-1,4-naphthoquinones($1{\sim}8$). 2,3-Epoxy-2,3-dihydro-1,4-naphthoquinone was also reacted with p-amonobenzoic acid, p-toluidine, p-chloroaniline, m-chloroaniline, m-nitroaniline, p-phenetidine, N,N-dimethyl-1,4-pheylenediamine as a ring opening and dehydogenation to form 2-hydroxy-3-(N-arylamino)-naphthoquinones ($9{\sim}16$) in good yield. These new compounds($1{\sim}16$) are expected to have a biological activities such as anticoagulant and cytotoxic.

• Bulletin of the Korean Chemical Society
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• 제34권6호
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• pp.1619-1620
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• 2013

• 약학회지
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• 제36권2호
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• pp.110-114
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• 1992

In order to evaluate the antimicrobial effect of 2, 3-substituted-1, 4-naphthoquinone derivatives, we newly synthesized several 2-chloro, 2-bromo and 2-hydroxy-1, 4-naphthoquinones and subjected to antibacterial and antifungal activities, in vitro, against Escherichia coli NIHJ, Staphylococcus aureus ATCC6538p, Candida albicans 10231, Aspergillus niger 1231 and Tricophyton mentagrophytes 6085. Among these derivatives 3, 9, 18 and 23 showed the potent antibacterial activities. 18, 23 and 28 have the antifungal activities. However, these compounds have no significant hemolytic activity at concentrations higher than that required for showing the antibacterial and antifungal activities.

• 약학회지
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• 제44권2호
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• pp.141-148
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• 2000

A new synthetic method of 6-(1-oxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones was developed, 2-formyl-1,4,5,8-tetramethoxynaphthalene was oxidized to form 6-formyl-5,8-dimethoxy-1,4-naphthoquinone(DMNQ). This was selectively reduced and benzylated to produce 6-formyl-5,8-dimethoxy-1,4-dibenzyloxynaphthalene, to which various alkylmagnesium halide were added, followed by debenzylation and oxidation in sequence, yielding 6-(1-hydroxyalkyl)-DMNQ derivatives. 6-(1-hydroxyalkyl)-5,8-diethoxy-1,4-naphthalene (DENQ) derivatives were synthesized by similar procedure. 1'-OH of the naphthoquinone derivatives was acylated with various alkanoic acids to give 6-(1-acyloxyalkyl)-DMNQ or DENQ derivatives. TOPO-I inhibitory activity and cytotoxicity of DENQs were less potent than that of DMNQs. Among the DMNQ and DENQ analogues, the ones with alkyl group being heptyl were most potent in TOPO-I inhibition $IC_{50}$/; 30.1, 36.4 $\mu$M). DUNQ derivatives with a longer side chain exhibited a weaker cytotoxicity. A correlation between size of the alkyl side chain and cytotoxicity was not observed for DENQ derivatives. Acylation of 1'-hydroxyl group, in general, decreased both TOPO-I inhibitory activity and cytotoxicity T/C (%) values of the DENQ derivatives on S-180 intraperitoneal tumor were larger than those of DMNQ derivatives. Among the compounds synthesized,6-(1-hydroxyheptyl)-DENQ and 6-(1-hex-anoyloxyoctyl)-DMNQ showed the highest T/C values of 183% and 182%, respectively.

• Natural Product Sciences
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• 제15권1호
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• pp.22-26
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• 2009

Phytochemical investigation of the roots of Echiochilon fruticosum resulted in the isolation of two naphthoquinone derivatives. Compound 1 was identified as anhydroalkanin while compound 2 was identified as a new derivative 5-hydroxy 8-methoxy 2-(4-methylpent-1,3-dienyl) naphthalene-1,4-dione named as echiochiloquinone. In addition, caffeic acid 3, caffeic acid methyl ester 4 were isolated. The structures were determined by physical, chemical and spectral methods. The anti-inflammatory activity of the root extracts and compound 2 was evaluated utilizing both cotton pellet-induced and carragenin-induced rat paw edema. The ulcerogenic effect was also studied.

• Applied Biological Chemistry
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• 제39권1호
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• pp.89-94
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• 1996

한방에서 종기, 치질, 위암 및 염증의 치료목적으로 사용되어온 당느릅나무 (Ulmus davidiana Planch) 근피의 메탄을 추출물로부터 sesquiterpene o-naphthoquinone류 화합물 세가지를 분리 정제하였다. 이들의 구조를 UV-vis, IR, EIMS, HR-EIMS 및 여러 가지 NMR 스펙트럼, 특히 새로운 기법인 pulse field gradient (PFG)-HMQC 및 HMBC 스펙트럼의 분석에 의하여 결정하였다. 그 결과 이들은 2,3-dihydro-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione, 3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione 및 2,3-dihydro-4-hydroxy-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione으로 동정 되었으며, 각각 mansonone E, F 및 H로 밝혀졌다. 이 화합물들은 당느릅나무에서는 처음 분리되었으며, 특히 mansonone H는 아프리카 열대식물인 Mansonia altissima Chev 및 Helicters angustifolia에서 분리된 후 자연계에서 처음으로 분리되었다. 문헌에 잘못 보고된 mansonone E 와 F의 C-3a, C-6a 및 C-9b의 세 사급탄소의 chemical shift를 최신 PFG-NMR기법에 의하여 동정하여 교정하였다.

• The Korean Journal of Physiology and Pharmacology
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• 제21권6호
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• pp.687-694
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• 2017

Plumbagin, a hydroxy 1,4-naphthoquinone compound from plant metabolites, exhibits anticancer, antibacterial, and antifungal activities via modulating various signaling molecules. However, its effects on vascular functions are rarely studied except in pulmonary and coronary arteries where NADPH oxidase (NOX) inhibition was suggested as a mechanism. Here we investigate the effects of plumbagin on the contractility of skeletal artery (deep femoral artery, DFA), mesenteric artery (MA) and renal artery (RA) in rats. Although plumbagin alone had no effect on the isometric tone of DFA, $1{\mu}M$ phenylephrine (PhE)-induced partial contraction was largely augmented by plumbagin (${\Delta}T_{Plum}$, 125% of 80 mM KCl-induced contraction at $1{\mu}M$). With relatively higher concentrations (>$5{\mu}M$), plumbagin induced a transient contraction followed by tonic relaxation of DFA. Similar biphasic augmentation of the PhE-induced contraction was observed in MA and RA. VAS2870 and GKT137831, specific NOX4 inhibitors, neither mimicked nor inhibited ${\Delta}T_{Plum}$ in DFA. Also, pretreatment with tiron or catalase did not affect ${\Delta}T_{Plum}$ of DFA. Under the inhibition of PhE-contraction with L-type $Ca^{2+}$ channel blocker (nifedipine, $1{\mu}M$), plumbagin still induced tonic contraction, suggesting $Ca^{2+}$-sensitization mechanism of smooth muscle. Although ${\Delta}T_{Plum}$ was consistently observed under pretreatment with Rho A-kinase inhibitor (Y27632, $1{\mu}M$), a PKC inhibitor (GF 109203X, $10{\mu}M$) largely suppressed ${\Delta}T_{Plum}$. Taken together, it is suggested that plumbagin facilitates the PKC activation in the presence of vasoactive agonists in skeletal arteries. The biphasic contractile effects on the systemic arteries should be considered in the pharmacological studies of plumbagin and 1,4-naphthoquinones.