• Bulletin of the Korean Chemical Society
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• 제11권1호
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• pp.22-25
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• 1990

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with mesityl oxide or 3-penten-2-one in acetic acid-ethanol (1:1) gave 3,4,6,9-tetrahydro-6,9-dioxopyridazino[1,2-a][1,2, 3]triazines (9,11) and 3,4,6,11-tetrahydro-6,11-dioxo[1,2,3]triazino[1,2- b]phthalazines (10,12), respectively. The condensation of 1 and 2 with crotonaldehyde, cinnamaldehyde or acrylaldehyde under the same reaction condition gave only N-alkylidene derivatlives (3-8). When the N-alkylidene derivatives isolated from the reaction of 1 and 2 with crotonaldehyde and cinnamaldehyde (3-6) were refluxed in acetic acid, the corresponding heterocyclic compounds (13-16) were obtained.

• Journal of Industrial and Engineering Chemistry
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• 제68권
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• pp.6-13
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• 2018

Well-modified amino-appended ${\beta}$-cyclodextrin ($AA-{\beta}-CD$) with an amino group at the primary face of the ${\beta}-CD$ was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. $AA-{\beta}-CD$ was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly.

• Bulletin of the Korean Chemical Society
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• 제16권11호
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• pp.1037-1042
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• 1995

The reaction of acetophenone 1-ureidoethylidenehydrazones 6 with a mixture of triphenylphosphine, carbon tetrachloride, and triethylamine in dichloromethane provides a general route to 1-(1-phenylethenyl)-5-(N-substituted amino)-1,2,4-triazoles 11 via the electrocyclization of the expected azino carbodiimide intermediates 9 to give the resonance stabilized azomethine imine 10a followed by a proton abstraction from the methyl group by amide anion. However, the same reaction of benzaldehyde 1-ureidoethylidenehydrazones 5 was unsuccessful. Under the same conditions, the reactions of benzaldehyde 1-N-acylureidoethylidenehydrazones 7 or acetophenone 1-N-acylureidoethylidenehydrazones 8 afforded 4H-1,2,4-triazolo[1,5-c][1,3,5]oxadiazines 16 or 17 via the zwitterionic species 15, or a [4+2] intramolecular cycloaddition from the carbodiimide intermediates 14, respectively.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-1
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• pp.89-89
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• 2003

Numerous lead compounds, based on multipurpose privileged structures, can be generated that address a variety of targets from a gene family of interest, irrespective of therapeutic area. Solid-phase organic synthesis has been emerged as a powerful technique in generating combinatorial libraries of small organic molecules useful for drug discovery. Heterocyclic compounds provide scaffolds on which pharmacophores can be arranged to yield potent and selective drugs and a variety of heterocycles have been synthesized on solid support. (omitted)

• Bulletin of the Korean Chemical Society
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• 제11권3호
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• pp.228-231
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• 1990

Some substituted pyridazin-6-ones(1-4) and two uracils(10,12) have been converted to the corresponding $N_1$-(2-oxopropyl)pyridazine-6-ones(6-9), 1,3-bis(2-oxopropyl)-5-fluorouracil(11) and 2-(2-oxopropylthio)uracil(13) respectively by reaction with 4-bromoacetoacetic acid. Also, 4,5-dichloro-1-(3-carbomethoxy-2-oxopropyl)pyrida zin-6-one(15) and 4,5-dichloro-3-nitro-1-(3-carbomethoxy-2-oxopropyl)pyridazin-6-one(16) was synthesized from the corresponding pyridazin-6-ones(1,2) and methyl 4-bromoacetoacetate.

• Bulletin of the Korean Chemical Society
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• 제9권6호
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• pp.359-362
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• 1988

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with 1,3-diketones or 1,3-dialdehydes in polyphosphoric acid gave 6,9-dihydro-6,9-dioxopyridazino [1,2-a][1,2,3]triazines (3-6) and 6,11-dihydro-6,11-dioxo[1,2,3]triazino[1,2-b]phtha lazines (7-10), respectively. The condensation of 2 with 2,4-pentanedione in acetic acid gave N-alkylidene intermediate (11), which was cyclized to 9 by treatment with polyphosphoric acid.

• Biomolecules & Therapeutics
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• 제27권5호
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• pp.492-501
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• 2019

Nitrogen-containing heterocycles such as quinoline, quinazolinones and indole are scaffolds of natural products and have broad biological effects. During the last years those structures have been intensively synthesized and modified to yield new synthetic molecules that can specifically inhibit the activity of dysregulated protein kinases in cancer cells. Herein, a series of newly synthesized isoquinolinamine (FX-1 to 8) and isoindoloquinazolinone (FX-9, FX-42, FX-43) compounds were evaluated in regards to their anti-leukemic potential on human B- and T- acute lymphoblastic leukemia (ALL) cells. Several biological effects were observed. B-ALL cells (SEM, RS4;11) were more sensitive against isoquinolinamine compounds than T-ALL cells (Jurkat, CEM). In SEM cells, metabolic activity decreased with $10{\mu}M$ up to 26.7% (FX-3), 25.2% (FX-7) and 14.5% (FX-8). The 3-(p-Tolyl) isoquinolin-1-amine FX-9 was the most effective agent against B- and T-ALL cells with IC50 values ranging from 0.54 to $1.94{\mu}M$. None of the tested compounds displayed hemolysis on erythrocytes or cytotoxicity against healthy leukocytes. Anti-proliferative effect of FX-9 was associated with changes in cell morphology and apoptosis induction. Further, influence of FX-9 on PI3K/AKT, MAPK and JAK/STAT signaling was detected but was heterogeneous. Functional inhibition testing of 58 kinases revealed no specific inhibitory activity among cancer-related kinases. In conclusion, FX-9 displays significant antileukemic activity in B- and T-ALL cells and should be further evaluated in regards to the mechanisms of action. Further compounds of the current series might serve as templates for the design of new compounds and as basic structures for modification approaches.

• 대한화학회지
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• 제66권3호
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• pp.185-193
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• 2022

본 연구에서는 tetrazine과 oxadiazole 등의 질소가 많이 함유되어 있는 헤테로 고리화합물을 가진 음이온과 NH₂OH, NH₂NH₂, CH₈N₆, C₂H₅N₅ 등의 양이온들과의 이온 결합을 통하여 생성된 에너지 염(energetic salts)에 대하여 열역학적 안정성, 밀도, 그리고 폭발 성능 등을 밀도 범함수 이론(dentisy functional theory, DFT)을 이용하여 계산하고 기존의 고성능 에너지 물질들과 비교하였다. 분자 구조 최적화 및 안정화 에너지는 B3LYP/cc-pVDZ 이론 수준에서 그리고 엔탈피 계산은 G2MP2 이론 수준에서 계산하였으며 폭발 성능은 Kamlet-Jacobs 방정식을 통하여 계산하였다. 결과적으로 크기가 작은 NH₃OH⁺(1)와 NH₂NH₃⁺(2) 양이온을 활용한 에너지 염은 폭발 성능 향상에 도움이 되며, 상대적으로 아미노기(-NH₂)가 많은 CH₉N₆⁺(3) 양이온은 안정성을 높이는데 효과적일 것으로 예측되었다.

• 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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• 제51권3호
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• pp.244-250
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• 2007

항암작용이 기대되는 일련의 새로운 6-allylthio-3-aminopyridazine 유도체를 allylthiolation, amination을 이용하여 합성하였다. 피리다진 핵은 hydrazine monohydrate와 maleic anhydride의 축합반응으로 제조하였다. 3,6- Dichloropyridazine은 3,6-dihydroxypyridazine을 POCl3에 가하여 합성하였다. 6-Allythio-3-chloropyridazine은 3,6- dichloropyridazine에 allylmercaptan과 sodium hydroxide을 이용하여 얻었다. Morpholine, piperazine, pyrazole, imidazole, pyrrolidine, piperidine, perhydroazepine 및 perhydroazocine와 같은 질소 친핵체를 갖는 hetero환을 피리 다진 환의 3번 위치에 도입시켜 6-allylthio-3-aminopyridazine 합성하였다. 이 과정은 아민 친핵체의 친핵성 치환반응 으로 n-buthanol에서 NH4Cl를 가하고 24~48시간 동안 환류시켜 진행하였다.