• Bulletin of the Korean Chemical Society
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• 제33권8호
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• pp.2603-2608
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• 2012

A novel mononuclear supramolecule of copper(II) has been synthesized with Ippyt ligand (Ippyt=3-(4'-imidazole phenyl)-5-(pyrid-2''-yl)-1,2,4-triazole) (1). Compound 1, namely [$Cu(Ippyt)_2(H_2O)_2$], has been characterized by single-crystal X-ray diffraction, IR spectrum, elemental analysis and thermogravimetric analysis. Structure determination reveals that the elongated-octahedral geometry is formed in the vicinity of the copper (II) atom being coordinated by four nitrogen atoms from two Ippyt ligands occupying the equatorial position and two oxygen atoms from two coordinated water molecules in the axial position, which together form the $N_4O_2$ donor set. Hydrogen bonding interactions between nitrogen and oxygen atoms result in the set up of a supramolecular network architecture. Biological properties including antibacterial activity and superoxide dismutase (SOD) mimetic activity of compound 1 have been investigated by agar diffusion method and the modified Marklund method, respectively. The results indicate that compound 1 exhibits a stronger antibacterial efficiency than the parent ligand and it also has a certain radical-scavenging activity.

• 대한화학회지
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• 제54권4호
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• pp.414-418
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• 2010

Ethyl 1-aminotetrazole-5-carboxylate (1)를 hydrazine hydrate와 반응시켜서 대응하는aminohydrazide 2를 합성한 후에, 화합물 2를carbon disulfide와 반응시켜서 1,3,4-oxadiazole-5-thiol structure 3을 합성하였다. 얻어진 화합물 3을 either chloroacetone 또는 ethyl chloroacetate와 반응시켜서S-acyl 1,3,4-oxadiazole 유도체인 4 와 5를 합성하였으며, 또한 hydrazine hydrate와 반응시켜서 4-amino-1,2,4-triazole-5-thiol 유도체인 6을 합성하였으며, 화합물 6을 glacial acetic acid와 반응시켜서 6-methyl-1,3,4-triazolo[3,4-b]-1,3,4-thiadiazole (7)을 합성하였다. 한편, 알려진 방법에 따라서, 화합물 1로부터 tetrazolo[5,1-f]-1,2,4-triazine 9을 얻은 다음에, 화합물 9를 carbon disulfide와 반응시켜서 8-thione 유도체인 10을 합성한 후에, 대응하는 화합물 11, 12 및 13을 합성하였다. 얻어진 화합물13을 이용하여1,2,4-triazolo[4,3-d]tetrazolo[5,1-f]-1,2,4-triazines 14와 15를 합성하였다. 새롭게 합성한 화합물들의 화학구조를 확인하였으며, 합성한 화합물들에 대한 항균 활성시험을 수행하였다.

• 대한화학회지
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• 제54권6호
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• pp.737-743
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• 2010

5-Amino-1,3-diaryl-pyrazoles 1a-c 와 다양한 aryl amine의diazonium salts를 반응시켜서 1,3-diaryl-5-amino-4-arylazopyrazoles 3a-l을 합성하였으며, 몇 가지 화합물은 5-amino-1,3-diaryl-4-nitroso-1H-pyrazoles 2a-c와 aryl amine의 diazonium salts를 반응시켜서 얻었다. 합성한 azo 유도체 화합물 3a-l을 DMF 용매 속에서 cupric acetate와 산화반응시켜서 2,4,6-triaryl-2,4-dihydropyrazolo [4,3-d]-1,2,3-triazoles 4a-l을 합성하였으며, 합성한 cyclic triazoles에 대한 형광 특성을 측정하였다. 한편, Diazotization of sodium nitrite/ortho-phosphoric acid 조건에서 5-amino-1,3-diaryl-1H-pyrazoles 1a-c를 diazotization화 반응시킨 다음에, aryl amines과 반응시켜서 o-aminoazo compounds 5a-f를 합성하였다. 합성한 화합물 5a-f를 pyridine/cupric acetate 반응 조건에서 반응시켜서 triazole 6a-f들을 합성하였으며, 얻어진 화합물 6a-f을 aryl diazonium salts과 반응시켜서 화합물 7a-j을 합성하였다. 합성한 염료 화합물을 polyesters에 분산염료와 정착성을 측정하였다.

• Bulletin of the Korean Chemical Society
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• 제33권12호
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• pp.4074-4078
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• 2012

The first step in the common pathway for the biosynthesis of branched chain amino acids is catalyzed by acetohydroxyacid synthase (AHAS). The AHAS is found in plants, fungi and bacteria. With an aim to identify new anti-tuberculosis drugs that inhibit branched chain amino acid biosynthesis, we screened a chemical library against Mycobacterium tuberculosis AHAS. The screening identified four compounds, AVS 2087, AVS 2093, AVS 2236, and AVS 2387 with $IC_{50}$ values of 0.28, 0.21, 3.88, and $0.25{\mu}M$, respectively. Moreover, these four compounds also showed strong inhibition against reconstituted AHAS with $IC_{50}$ values of 0.37, 0.26, 1.0, and $1.18{\mu}M$, respectively. The basic scaffold of the AVS group consists of 1-pyrimidin-2-yl-1H-[1,2,4]-triazole-3-sulfonamide. The most active compound, AVS 2387, showed the lowest total interaction energy -8.75 Kcal/mol and illustrates its binding mode by hydrogen bonding with $H_{\varepsilon}$ of Gln517 with the distance of $2.24{\AA}$.

• 생명과학회지
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• 제29권7호
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• pp.755-761
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• 2019

코직산(Kojic acid)은 생리활성물질로서 많이 알려져 있으며 antibacterial, antifungal과 같은 효능을 나타낸다. 또한 티로시나아제(tyrosinase) 억제제로서 작용하여 멜라닌 생성을 저해시키기 때문에 화장품 산업에 있어서도 미백효과를 가지는 중요한 소재로서 각광받고 있다. 본 연구에서는 독립적으로 항산화 효과를 나타내는 유도체와 코직산(Kojic acid)을 연결하여 새로운 기능성을 가지는 신규 화합물을 발굴하고자 하였으며, 클릭 반응(Click reaction)을 통해 트리아졸(triazle)로 연결하여 신규 코직산 컨쥬게이트(conjugated) 화합물을 합성하였다. 먼저 신규 코직산 컨쥬게이트(conjugated) 화합물의 티로시나아제(tyrosinase) 억제 효과에 대해서 연구한 결과 대부분의 화합물이 코직산(Kojic acid)보다 우수한 티로시나아제(tyrosinase) 억제 효과를 나타냈다. 이와 같은 결과로 미루어 보아 신규 코직산 컨쥬게이트(conjugated) 화합물은 항산화용 건강보조식품 조성물 및 항산화 소재, 노화방지 및 미백 기능을 가진 피부외용제 조성물의 유효성분으로 개발될 가능성이 매우 높다고 사료된다.

• Bulletin of the Korean Chemical Society
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• 제33권12호
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• pp.4180-4184
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• 2012

The target compounds 6-11a-e were synthesized by condensing 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-f with various aromatic carboxylic acids in the presence of phosphorous oxychloride. The structures of newly synthesized compounds were characterized by IR, $^1H$ NMR, $^{13}C$ NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were screened for their antibacterial activity. Almost all the tested compounds were potent against four different strains of bacteria when compared with that of reference drug ciprofloxacin. Compounds 6c, 6e, 8d, 9b, 9e, 11a and 11b showed nearly equal or lower MIC values than standard drug, against all four tested bacterial strains but rest of the compounds showed excellent antibacterial activities.

• Bulletin of the Korean Chemical Society
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• 제33권12호
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• pp.3943-3949
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• 2012

A series of aromatic hydrazides 3a-j were prepared by refluxing esters 2a-j with hydrazine hydrate in methanol, which were prepared by the esterification of 1a-j. Acetohydrazides 3a-j upon treatment with carbon disulfide and methanolic potassium hydroxide yielded potassium dithiocarbazate salts 4a-j, which on refluxing with hydrazine hydrate yielded substituted 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-j. The target compounds 6a-j were synthesized by condensing furan-3-carboxylic acid in the presence of polyphosphoric acid under reflux. The structures of newly synthesized compounds were characterized by IR, $^1H$ NMR, $^{13}C$ NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were screened for their urease, acetylcholine esterase inhibition, antioxidant and alkaline phosphatase inhibition activity. Almost all of the compounds 6a-j showed good to excellent activities against urease and acetylcholine esterase more than the reference drugs. Compounds 6f and 6g were more potent scavenger of free radicals than the reference n-propyl gallate. Compound 6b and 6h showed excellent activities of alkaline phosphatase as compare to the reference $KH_2PO_4$.