• 제목/요약/키워드: 1,2-naphthoquinone

검색결과 112건 처리시간 0.03초

항응고성의 2-Chloro-3-(N-Arylamino)-1,4-Naphthoquinone 유도체 합성 (Synthesis of Anticoagulant 2-Chloro-3-(N-Arylamino)-1,4-Naphthoquinones)

  • 유충규
    • 약학회지
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    • 제32권4호
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    • pp.245-250
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    • 1988
  • Naphthoquinone derivatives have been found to be anticoagulant. In this report, several new 2-chloro-3-(N-arylamino)-naphthoquinone derivatives were synthesized in oder to develope mild anticoagulant. 2, 3-dichloro-1, 4-naphthoquinone was reacted with p-aminobenzoic acid, m-aminobenzoic acid, toluidine, m-nitroaniline, sulfanilamide, sulfathiazole, sulfaguanidine, phenetidine, 2-aminopyrimidine and 3-amino-5-methylisoxazole in EtOH or AcOH afford 2-chloro-3-(p-carboxy anilino)-naphthoquinone (1), 2-chloro-3-(m-carboxyanilino)-naphthoquinone (2),2-chloro-3-(toluidino)-naphthoquinone (3),2-chloro-3-(m-nitroanilino)-naphthoquinone (4), 2-chloro-3-(4-sulfanilanilino)-naphthoquinone (5), 2-chloro-3-(4-sulfathiazolino)-naphthoquinone (6),2-chloro-3-(4-sulfaguanidino)-naphthoquinone (7),2-chlro-3-(phenetidino)-naphthoquinone (8), 2-chloro-3-(pyrimidine-2-amino)-naphthoquinone (9) and 2-chloro-3-(5-methylisoxazole-3-amino)-naphthoquinone (10) in good yield.

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가래나무 뿌리껍질의 휘발성 화합물 (Volatile Compounds from Root Shell of Juglans mandshurica)

  • 권동주;김진규;배영수
    • 한국산림과학회지
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    • 제97권3호
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    • pp.199-203
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    • 2008
  • 가래나무 뿌리껍질에서 단리한 4종의 휘발성 성분을 GC-MS를 이용하여 화학구조를 규명하였다. 각 성분들의 fragment pattern은 NIST와 Wiely 6 스펙트럼과 비교하여 aliphatic alcohol인 3-ethyl-2-methyl-1-pentene-3-ol과 naphthoquinone 유도체인 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone (juglone) 및 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin)임을 확인하였다. 정량분석 결과 1,4-naphthoquinone $54.4{\mu}g/g$, 5-hydroxy-1,4-naphthoquinone $21.3{\mu}g/g$, 5-hydroxy-2-methyl-1,4-naphthoquinone $17.1{\mu}g/g$의 함량을 나타냈으며, 1,4-naphthoquinone과 5-hydroxy-1,4-naphthoquinone은 가래나무 뿌리껍질의 주요 휘발성 성분이었다.

벤조-[f]-인돌-4, 9-디온 유도체의 합성 (Synthesis of -4,9-Dione Derivatives)

  • 이지영;서명은
    • 약학회지
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    • 제34권1호
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    • pp.15-21
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    • 1990
  • -4,9-dione derivatives were prepared from $2-chloro-3-({\alpha}-accetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. $2-Chloro-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ was reacted with amines to give $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ derivatives. Subsequent treatment of $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ with sodium ethoxide gave -4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium ${\alpha}-cyano$ ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl--4,9-dione was obtained. However, with sodium diethyl malonate, not -4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.

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Antibacterial Activities of Persimmon Roots-derived Materials and 1,4-Naphthoquinone's Derivatives against Intestinal Bacteria

  • Kim, Hyung-Wook;Lee, Chi-Hoon;Lee, Hoi-Seon
    • Food Science and Biotechnology
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    • 제18권3호
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    • pp.755-760
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    • 2009
  • The growth-inhibiting activities of persimmon roots-derived materials against intestinal bacteria were evaluated and compared with that of 1,4-naphthoquinone as a positive control. The active constituent isolated from persimmon roots was characterized as 5-hydroxy-2-methyl-1,4-naphthoquinone using various spectroscopic analyses. Treatment with 1,4-naphthoquinone at a dose of 1.0 mg/disc strongly inhibited the growth of 6 intestinal bacteria. Furthermore, when the structure-activity relationships of 1,4-naphthoquinone's derivatives were evaluated, 5-hydroxy-2-methyl-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone were found to strongly inhibit the growth of Clostridium difficile, Clostridium perfringens, and Escherichia coli without adversely affecting the growth of Bifidobacterium adolescentis, Bifidobacterium longum, and Lactobacillus acidophilus. Additionally, 2-hydroxy-1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone strongly inhibited the growth of C. difficile and C. perfringens, but did not inhibit the growth of E. coli. Taken together, these results indicate that persimmon roots-derived materials and some of 1,4-naphthoquinone's derivatives could be useful preventive agents against diseases caused by harmful intestinal bacteria.

A Facile Preparation of Red Aminoquinones by Direct Irradiation of 1,4-BenzoQuinone and Naphthoquinones in Diethylamine

  • Kim, Sung Sik;Mah, Yoon Jung;Park, Sang Kyu
    • Journal of Photoscience
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    • 제11권2호
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    • pp.61-63
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    • 2004
  • Some quinones such as 1,4-benzoquinone 2, 1,4-naphthoquinone 3 and 1,2-naphthoquinone 4 dissolved in diethylamine were irradiated with 300 nm UV light to afford red aminoquinones 6, 7, and 9 as the major products. Irradiation of a solution of a primary product, i.e., 2,5-bis(diethylamino)-1,4-benzoquinone 6 in benzene gave 2,5-bis (ethylamino)-1,4-benzoquinone 10 in 80% yield, along with an oxazoline 11 in 19% yield via photochemical deethylation. A solution of 2-diethylamino-1,4-naphthoquinone 7 in benzene was also irradiated under the same condition, in which 2-ethylamino-1,4-naphthoquinone 12 was obtained in ca. 100% yield.

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Naphthoquinone-1,2-Diazaide-Sulfonyl기 치환 Polysiloxane의 합성과 그 감광특성 (Synthesis and Photocharacteristics of Polysiloxane substituted Naphthoquinone-1,2-diazide sulfonyl group)

  • 강두환;정낙진
    • 공업화학
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    • 제2권4호
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    • pp.348-355
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    • 1991
  • Hexamethylcyclotrisiloxane($D_3$), tetramethylcyclotetrasiloxane(TMCTS)을 공중합 시켜 Si-H 결합을 함유한 polysiloxane 공중합체를 합성하고 allylamine과 반응시켜 amino 기를 도입시킨후 naphthoquinone-1,2-diazide-5-sulfonyl chloride 와 반응시켜 naphthoquinone-1,2-diazide-5-sulfonyl 기가 도입된 polysiloxane을 합성하였다. 생성 공중합체의 열적특성을 측정한 결과, 열분해온도는 $360{\sim}450^{\circ}C$ 정도였으며 또한 감광특성은 backbone 수지의 분자량이나 증감제의 종류에 따라 영향을 받았다. Sensitivity는 $50{\sim}120mJ/cm^2$였고 contrast(${\gamma}$)는 1.4~2.1였으며 backbone 수지의 분자량이 증가함에 따라 약간 감소하였다.

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페놀 화합물로부터 HMG-CoA reductase 저해 활성 물질 탐색 (Screening of Phenolic Compounds with Inhibitory Activities against HMG-CoA Reductase)

  • 손건호;이주연;이정순;강삼식;손호용;권정숙
    • 생명과학회지
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    • 제27권3호
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    • pp.325-333
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    • 2017
  • 심혈관계 질환은 질환별 사망률 순위에 있어서 세계에서는 1위이며, 우리나라에서는 2위인 질병이다. 심혈관계 질환 발생의 주 위험 요인인 콜레스테롤은 HMG-CoA reductase에 의해 간에서 신생합성이 조절된다. 현재 고콜레스테롤혈증 치료에 statin이 널리 사용되고 있지만 광범위한 부작용이 보고되고 있어서 이를 대체하거나 보조할 수 있는 천연물 유래의 기능성 물질 개발이 필요한 실정이다. 따라서 본 연구에서는 혈장 콜레스테롤 감소 활성을 가지는 물질을 발굴하고자 71종의 페놀 및 그와 관련된 화합물들을 대상으로 10ug/ml 농도에서 HMG-CoA reductase 저해 활성을 탐색하였다. 그 결과, 1,4-naphthoquinone의 HMG-CoA reductase 저해율이 99.4%로 가장 높았고, 다음으로 plumbagin 91.4%, pentagalloyl ${\beta}-D-glucose$ 46.6%, 2,4-dihydroxybenzoic acid 40.9%, shikonin 37.7%, 1,2-naphthoquinone 36.6%, trans-cinnamic acid 32.0%, acetonylgeraniin 30.2%, benzoic acid 28.5%, geraniin 28.3%, gentisic acid 22.3%의 순이었다. $IC_{50}$값을 계산한 결과, 1,4-naphthoquinone가 $2.1{\mu}g/ml$로 가장 낮았으며, plumbagin과 pentagalloyl ${\beta}-D-glucose$은 각각 $5.8{\mu}g/ml$$13.1{\mu}g/ml$으로 나타났다. 1,4-naphthoquinone과 plumbagin의 경우, $5{\mu}g/ml$에서도 각각 90.3%와 43.3%의 저해율을 나타내었다.

PS 판용 1,2-Naphthoquinone-(2)diazide-5-sulfonic Acid Ester Derivatives의 합성 및 응용 (Studies on 1,2-Naphthoquinone-(2)diazide-5-sulfonic Acid Ester Derivatives for Pre-sensitized Offset Plates)

  • 구양서;명영찬;안종일;김선호
    • 공업화학
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    • 제10권8호
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    • pp.1169-1174
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    • 1999
  • 본 연구에서는 sodium 2-diazo-1-naphthoquinone-5-sulfonate를 chlorination하여 2-diazo-naphthoquinone-5-sulfonyl chloride(NQD-Cl)를 합성하였다. NQD-Cl을 여러 종류의 hydroxybenzophenone 유도체와 esterification하여 hydroxy group이 2-diazo-naphthoquinone-5-sulfonyl(NQD) group으로 치환된 여러 종류의 1,2-naphthoquinone-(1,2)-diazide-5-sulfonic acid esters(NQD0ester) 유도체를 합성하였다. NQD-ester 유도체의 용해도를 증가시키기 위해 methoxy group이 도입된 유도체와 이와 비교를 위해 hydroxy group만을 가지는 benzophenone 유도체를 사용하여 비교하였다. 각각의 NQD-ester 유도체의 용해특성을 조사하였으며, novolac수지와 혼용(formulation)하여 감광액을 제조하여 알루미늄판에 도포, 건조하여 PS판을 제조하였다. PS판의 감광특성과 광퇴색도와 화상형성에 적합한 노광시간을 조사하였으며, 상대감도를 gray scale(GS)법으로 조사하였다. 치환된 NQD group 의 수에 따라 GS법에 의한 상대감도가 다르게 나타나는 것을 알 수 있었다. Methoxy group이 도입된 NQD-ester유도체는 좋은 용해특성을 보여주었으며 시판되는 PS판과 동일한 노광조건에서 비교해 본 결과 보다 우수한 감도를 보였다.

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봉선화의 항균활성성분(抗菌活性成分)과 항균력(抗菌力)에 관(關)한 연구(硏究) (Isolation and Antimicrobial Activity of a Naphthoquinone from Impatiens balsamina)

  • 강수철;문영희
    • 생약학회지
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    • 제23권4호
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    • pp.240-247
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    • 1992
  • Impatiens balsamina Linne(Balsaminaceae) known as 'BONG SUN HWA' in Korea and has been used for the treatment of scrofulosis, carbunculus and dysenteria etc. Bioassay-guided fractionation of MeOH extract from the whole plants of Impatiens balsamina has afforded a simple naphthoquinone derivative, 2-methoxy-1,4-naphthoquinone. The structure of this compound was established by spectroscopic methods. This compound possessed strong antifungal activity against Candida albicans, AspergiIlus niger, Crytococcus neoformans and Epidermophyton floccusum. The activity of 2-methoxy-1,4-naphthoquinone on E. floccusum $(MIC{\;}:{\;}5.0{\;}{\mu}g/ml)$ was the same potency as that of nystatin. It showed also strong antibacterial activity against gram-positive bacteria Bacillus subtilis as well as gram-negative bacteria Salmonella typhimurium. Although the activity of this compound on gram-negative bacteria was lower than that of gram-positive bacteria.

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항응고성의 3-(N-Arylamino)-1,4-Naphthoquinone 유도체 합성(III) (Synthesis of Anticoagulant 3-(N-Aryalmino)-1,4-Naphthoquinones(III))

  • 유충규
    • 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.

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