• Bulletin of the Korean Chemical Society
• /
• v.11 no.1
• /
• pp.22-25
• /
• 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
• /
• v.68
• /
• pp.6-13
• /
• 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
• /
• v.16 no.11
• /
• pp.1037-1042
• /
• 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.

• Proceedings of the PSK Conference
• /
• 2003.10a
• /
• pp.89-89
• /
• 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
• /
• v.11 no.3
• /
• pp.228-231
• /
• 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
• /
• v.9 no.6
• /
• pp.359-362
• /
• 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
• /
• v.27 no.5
• /
• pp.492-501
• /
• 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.

• Journal of the Korean Chemical Society
• /
• v.66 no.3
• /
• pp.185-193
• /
• 2022

The theoretical investigation has been performed to predict thermodynamic stability, density, detonation velocity, and detonation pressure of energetic salts produced by pairing of nitrogen-rich anions (tetrazine, oxadiazole etc.) and cations (NH₃OH⁺, NH₂NH₃⁺, CH₉N₆⁺, C₂H₆N₅⁺). All possible geometries and the binding energy for the trigger bond of energetic salts have been optimized at the B3LYP/cc-pVDZ level of theory. The detonation velocity and detonation pressure have been calculated using Kamlet-Jacobs equation, while enthalpy has been predicted at the G2MP2 level of theory. The predicted results reveal that the energetic salts including small sized NH₃OH⁺(1) and NH₂NH₃⁺(2) cations increase detonation property. And also the energetic salts including more amino group (-NH₂) such as CH₉N₆⁺(3) cation increase thermodynamic stability. These results provide basic information for the development the high energy density materials (HEDMs).

• Bulletin of the Korean Chemical Society
• /
• v.33 no.9
• /
• pp.2985-2990
• /
• 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.

• Journal of the Korean Chemical Society
• /
• v.51 no.3
• /
• pp.244-250
• /
• 2007

A series of new 6-allylthio-3-aminopyridazine derivatives was synthesized through allylthiolation, amination and expected for anti-tumor activity. The pyridazine nucleus was obtained by condensing hydrazine monohydrate with maleic anhydride. 3,6-Dichloropyridazine was synthesized from 3,6-dihydroxypyridazine by treating with POCl3. 6-Allylthio-3-chloropyridazine was prepared from the reaction of 3,6-dichloropyridazine with allylmercaptan and sodium hydroxide. The heterocycles with nitrogen nucleophile such as morpholine, piperazine, pyrazole, imidazole, pyrrolidine, piperidine, perhydroazepine, and perhydroazocine were introduced into 3-position of pyridazine ring. The substitution reaction of 6-allylthio-3-chloropyridazine with heteroamines was performed by refluxing for 24~48 h in n-buthanol with NH4Cl.