• Bulletin of the Korean Chemical Society
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• 제33권9호
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• pp.2985-2990
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• 2012

New thiazoline derivatives 7a-c, and thiophenes 9a-c linked to indole moiety were easily prepared via the reaction of the acrylamide derivative 3 with phenacyl bromides 4a-c, depending on the reaction conditions. In addition, the reaction of compound 3 with hydrazonoyl chlorides 11a-f afforded a series of 1,3,4-thiadiazole derivatives 13a-f. Moreover, coupling of 3-(3-methyl-1H-indol-2-yl)-3-oxopropanenitrile (2) with the diazonium salts of 3-phenyl-5-aminopyrazole 16 or 3-amino-1,2,4-triazole 17 gave the corresponding hydrazones 18 and 19, respectively. Cyclization of the latter hydrazones yielded the corresponding pyrazolo[5,1-c]-1,2,4-triazine and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives 20 and 21, respectively. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, $^1H$ NMR and mass spectral data. All the synthesized compounds were tested for in vitro activities against certain strains of fungi such as Aspergillus niger, Aspergillus nodulans, Alternaria alternate. Compounds showed marked inhibition of fungal growth nearly equal to the standards.

• 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.

• Bulletin of the Korean Chemical Society
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• 제24권8호
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• pp.1181-1187
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• 2003

Condensation of 4-cyano-5,6-dimethyl-3-pyridazinone 1 with aromatic aldehydes gave the novel styryl derivatives 2a-c. Refluxing of compound 2a with phosphorus oxychloride furnished 3-chloropyridazine derivative 3. Compound 3 was reacted with thiourea and produced pyridazine-3(2H)thione 4. Thieno[2,3-c]- pyridazines 5a-e were achieved by cycloalkylation of compound 4 with halocompounds in methanol under reflux and in the presence of sodium methoxide. Also, refluxing of compound 4 with N-substituted chloroacetamide in the presence of potassium carbonate afforded thienopyridazines 6a-e. Cyclization of compound 6 with some electrophilic reagents as carbon disulfide and triethyl orthoformate furnished the novel pyrimido[4',5':4,5]thieno[2,3-c]pyridazines 12 and 13a-c, respectively. Diazotisation of compound 6 with sodium nitrite in acetic acid produced the pyridazino[4',3':4,5]thieno[3,2-d][1,2,3]triazines 14a-c. Ternary condensation of compound 1, aromatic aldehydes and malononitrile in ethanol containing piperidine under reflux afforded the novel phthalazines 16a-c. Compound 3 was subjected to some nucleophilic substitution reactions with amines and sodium azide and formed the aminopyridazines 17a, b and tetrazolo[1,5-b]-pyridazine 19, respectively. The structures of the synthesized compounds were established by elemental and spectral analyses.

• The Korean Journal of Physiology and Pharmacology
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• 제28권3호
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• pp.219-227
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• 2024

Bladder cancer remains the 10th most common cancer worldwide. In recent years, metformin has been found to have potential anti-bladder cancer activity while high concentration of IC₅₀ at millimolar level is needed, which could not be reached by regular oral administration route. Thus, higher efficient agent is urgently demanded for clinically treating bladder cancer. Here, by conjugating artesunate to metformin, a novel artesunate-metformin dimer triazine derivative AM2 was designed and synthesized. The inhibitory effect of AM2 on bladder cancer cell line T24 and the mechanism underlying was determined. Anti-tumor activity of AM2 was assessed by MTT, cloning formation and wound healing assays. Decreasing effect of AM2 on lipogenesis was determined by oil red O staining. The protein expressions of Clusterin, SREBP1 and FASN in T24 cells were evaluated by Western blotting. The results show that AM2 significantly inhibited cell proliferation and migration at micromolar level, much higher than parental metformin. AM2 reduced lipogenesis and down-regulated the expressions of Clusterin, SREBP1 and FASN. These results suggest that AM2 inhibits the growth of bladder cancer cells T24 by inhibiting cellular lipogenesis associated with the Clusterin/SREBP1/FASN signaling pathway.