• 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.

• Journal of Integrative Natural Science
• /
• v.8 no.1
• /
• pp.30-39
• /
• 2015

The crystal structure of the potential active 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7, 9-dimethyl-5-oxo-4, 5, 6, 7-tetrahydropyrano [2, 3-d] pyrazolo [3, 4-b] pyridine-3-carbonitrile ($C_{21}H_{22}N_5O_6S$) has been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group P-1 with unit cell dimension a=8.1201(9)${\AA}$, b=12.2684(4)${\AA}$ and c=12.387(2)${\AA}$ [${\alpha}=69.573^{\circ}$, ${\beta}=12.168^{\circ}$ and ${\gamma}=76.060^{\circ}$]. In the structure the pyrazole, pyridine and pyran are almost coplanar each other. The crystal packing is stabilized by intermolecular C-H...O and N-H... O hydrogen bond interaction.

• Applied Biological Chemistry
• /
• v.32 no.4
• /
• pp.401-407
• /
• 1989

A series of novel 1,3-substituted-5-chloropyrazole-4-carboxylic acid oxime esters was synthesized. Their chemical strictures were elucidated on $^1H,\;^{13}C-NMR$ and IR spectra, Fifteen such compounds were screened for their antifungal activity against R. solani, P. oryzae, B. cinerea, P. graminearum, P. capsici and G. cingulata. The results showed that pyrazole-oxime esters with electron withdrawing groups(III, XIII, XIV) had better biological activities than these with electron releasing groups.

• Bulletin of the Korean Chemical Society
• /
• v.35 no.8
• /
• pp.2375-2380
• /
• 2014

In the present investigation, a series of some novel 1,3-diaryl/heteroarylprop-2-en-1-one derivatives (3a-j) have been synthesized and evaluated for their in vitro cytotoxicity against three cancer cell lines, two hepatocarcinoma cell lines HUH-7, Hep-3b and one leukemia cancer cell line MOLT-4. Based on these results, structure-activity relationship (SAR) was studied on modification of $R^1$ and $R^2$ to identify the compound with maximum potency. Amongst the compounds, 3b and 3d strongly inhibited the growth of Hep-3b and MOLT-4 cells with $IC_{50}$ value of 3.39 and $3.63{\mu}M$ respectively. The results obtained from the inhibitory study had further been supported by the reactive oxygen species (ROS) measurement using flow cytometry in MOLT-4 cells. These observations collectively reveal that compounds comprising 1,3-diarylprop-2-en-1-one framework with pyrazole ring at position-3 and heteroaryl/aryl substituents at position-1 can be used as promising anticancer agents.

• Journal of the Korean Applied Science and Technology
• /
• v.14 no.1
• /
• pp.95-102
• /
• 1997

The synthetic method of pyrazole was performed by 1,3-dipolar cycloaddition with dipolarophile instead of the reaction between diazomethane and acetylene. The cycloaddition mechanism and reactivity of 3-phenyloxadiazole derivatives with dipolarophiles was investigated. In order to investigate the mechanism and reactivity of this cycloaddition, the effect of substituents having various kinds of electron withdrawing or releasing groups were examinated. Considering the effect of substituents, an electron withdrawing group attached at the 4-carbon position in 3-phenyloxadiazole derivatives decrease the reaction rate because of the lack of electron density in oxadiazole ring. The reaction rate of 3-phenyloxadiazole derivatives with dipolarophiles were more conveniently measured using UV than using a volumetric analysis which was used before. From the result of this study, it was that the cycloaddition was found to be a first-order reaction depending upon the concentration of 3-phenyloxadiazole only.

• Journal of the Korean Chemical Society
• /
• v.45 no.5
• /
• pp.448-453
• /
• 2001

Pyrazoloazines are extremely useful in agriculture and medicine. The main objective of this article is to synthesize some new pyrazoloazines. Ethyl 3-amino-1H-pyrazole-4-carboxylate undergoes diazotization, couples with activated methylene compounds and cyclizes to form pyrazolo[5,1-c][1,2,4]tri-azine derivatives. The title compound also reacts with $\alpha$-substituted cinnamonitriles to produce pyrazolo[1,5-a]pyrimidine derivatives. Structures of newly synthesized compounds are established via chemical and spectral methods.

• Journal of the Korean Chemical Society
• /
• v.55 no.2
• /
• pp.256-261
• /
• 2011

A new series of bis acetylated hybrid pyrazoles were synthesized and characterized by their melting point, elemental analysis, MS, FT-IR, one-dimensional $^1H$, and $^{13}C$ NMR spectroscopic data. All the synthesized compounds were tested for their in vitro antifungal activities against Candida sp. namely Candida albicans, Candida glabrata, Candida parapsilosis, Candida dubliniensis and Candida tropicalis. A close inspection of the in vitro anticandidal activity profile in differently electron donating ($CH_3$ and $OCH_3$) and electron withdrawing (-F, -Cl, and Br) functional group substituted phenyl rings of novel hybrid pyrazoles exerted strong anticandidal activity against all the tested Candida species.

• Archives of Pharmacal Research
• /
• v.13 no.4
• /
• pp.351-354
• /
• 1990

2, 3-diphenyl-4-cyano-pyrrole-5-thione (4) was either by the reaction of benzoin (1) and cyanothioacetamide (3) followed by cyclization using AcOH/sodium acetate or by refluxing a mixture of benzoin (1) and cyanothioacethamide in pyridine to afford directly 4. Several new pyrrole and pyrazole derivatives were synthesised using 4 as synthon. The structure of the newly synthesised derivatives were based on celemental and spectral data studies. Methylation of the SH group in 4 afforded 5. Reaction of 4 with ethyl bromo acetate afforded (6). Treatment of (5) and (6) with hydrazine hydrate afforded the same pyrazole derivative (10) through the intermediate (9). Treatment of 6 with aniline and phenylhydrazine afforded the pyrrole derivatives 8a, b respectively. Treatment of 6 while dill HCI gave 2, 3-diphenyl-4-cyano-pyrrole-5-one (7). Treatment of 6 with $NH_3$/EtOH afforded the amidic derivatives (11) with treatment of 6 $NH_3$/ heat then acidification it gave the carboxylic derivatives (12).

• Journal of Life Science
• /
• v.24 no.10
• /
• pp.1070-1077
• /
• 2014

In this study, the estrogen receptor agonist propyl pyrazole triol (PPT), which has high-affinity with the estrogen receptor alpha, was subcutaneously injected into adult male mice every 2 days for 8, 16 and 24 days, after which histological changes in accessory genital glands, including the prostate and seminal vesicle, and the liver were observed. The body and genital gland weights decreased in the PPT group relative to those of the control group. However, the liver weight was two times greater in the PPT group. The luminal area of the prostate and seminal vesicle organs was lower in the PPT group, and the epithelial cell height of the prostate was increased relative to that of the control. There were many secretory vacuoles in the supranuclear cytoplasm of epithelial cells in the seminal vesicles of the control group, but these were not observed in the PPT group. The short sinusoidal diameter of the liver was 147.0%, 198.7%, and 223.3% greater in the PPT group than in the control group after 8, 16, and 24 days of treatment, respectively. These results suggest that PPT administration affected the reproductive organs and the liver and that the histological changes increased in accordance with a rise in the concentration of PPT. Overall, the PPT treatment caused changes in the epithelial cell height and resulted in atrophy of the luminal area of the prostate, leading to altered fertility. The sinusoidal diameter of the liver dramatically increased in response to the administration of PPT, increasing the liver weight.

• The Korean Journal of Pesticide Science
• /
• v.9 no.1
• /
• pp.97-101
• /
• 2005

Flupyrazofos (O,O-diethyl O-1-phenyl-3-trifluoromethylpyrazo-5-yl phosphorothioate) is an organophosphorus insecticide with a pyrazole moiety which is newly developed and commercialized by SUNGBO chemical company and Korean Research Institute of Chemical Technology for effectively control against diamond back moth. This study was conducted to determine the composition and quantity of impurities in technical 1 (94.5%), technical 2 (97.6%) and purified (99.2%) flupyrazofos using GLC/MSD. Bimolecular inhibition rate constant($k_i$) with acethylcholinesterase (in vitro) and $I_{50}$ with mouse brain acetylcholinesterase (in vivo) were measured for comparing inhibitory patterns of two technicals and purified flupyrazofos. Impurities of flupyrazofos were identified as O,O,O-triethylthio-phosphoric acid (TEA), 1-phenyl-3-trifluoromethyl-5-ethoxy pyrazole(PTMEP), O,O-diethyl O-1-phenyl-3-trifluoromethylpyrazo-5-yl phosphoric acid ester(flupyrazofos oxen), O,S-diethyl O-1-phenyl-3-trifluoromethylpyrazo-5-yl phosphorothionate (S-ethyl flupyrazofos). In in vitro, technical 1 showed the fastest inhibition on AChE activity among them. And technical 1 and 2 showed 40% higher in vivo inhibition against mouse brian AChE than purified flupyrazofos did. These results could be caused by the impurities such as flupyrazofos oxen and S-methyl flupyrazofos contained in technical grades of flupyrazofos.