• Bulletin of the Korean Chemical Society
• /
• v.34 no.2
• /
• pp.437-442
• /
• 2013

A new series of 4-(2-(substituted)pyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazoles (4a-f) and their 1,2-isoxazole analogues (5a-f) has been rationally designed, synthesized and screened against both ROS and MAPK14 kinases. Compounds 4b, 4c and 4e showed moderate inhibitions against both ROS and MAPK14 kinases. Compound 4e has showed the strongest inhibitions with IC50 values of 1.25 ${\mu}M$ and 3.00 ${\mu}M$ against ROS and MAPK14 kinases, respectively. A brief structure-activity relationship study and a molecular modeling study were made revealing a group of essential structural features for good kinase inhibitory activity within this new class of kinase inhibitors.

• Archives of Pharmacal Research
• /
• v.13 no.3
• /
• pp.261-264
• /
• 1990

4-Arylazo-3-phenyl-5-aminopyrazoles (5a, b) and substituted hydroxythiazoles 8a, b were synthesized from the reaction of 4a, b with hydrazine hydrate and mercaptoacetic acid respectively. Compounds 5a, b and 8a, b were also obtained from coupling of 2a, b with 6 and 7, respectively. 4H-1, 4-Benzothiazine 11 was prepared from 1 and 10. The resaction of the diazonium salts 2a-c with diethyl 3-amino-2-cyanopenet-2-en-1, 5-dicarboxylate 12 was also reported.

• Applied Microscopy
• /
• v.39 no.4
• /
• pp.301-309
• /
• 2009

Estrogens induce pronounced structural and functional changes in male and female reproductive system, but the exact mechanisms of estrogen are not fully understood. In relation to estrogen's function, the present study was designed to identify effects of estrogen receptor agonist, 4,4',4"- (4-propyl-[1H]-pyrazole-1,3,5-triyl)tris phenol (PPT) in the reproductive organ of the female mouse. The PPT was subcutaneously given to adult female mice at a weekly dosage of 3 mg in a volume 0.06 mL of vehicle for 3, 5 or 8 weeks whereas controls received weekly injections of the castor oil vehicle. Effects of PPT on reproductive organs were analyzed using a light microscope. PPT induced decreases of body, ovary and adipose tissue weights with experimental time. Ovary diameter of PPT treatment group was reduced as compared with control group. The number of Graffian follicle and corpus luteum was reduced in PPT treatment group. The luminal diameter of uterus was increased in relation with decrease of myometrium and endometrium height by PPT administration. The number of uterine glands was decreased by PPT treatment. These data indicate that PPT treatment induced morphological change of female reproductive organs resulting in alteration of fertility.

• Journal of the Korean Applied Science and Technology
• /
• v.29 no.3
• /
• pp.402-411
• /
• 2012

Natural Bokbunja is used as a material of oriental medicine which it obtains from Rubus or Raspberry. Natural Bokbunja Rubus has natural odor and taste, natural color, and pharmaceutical & chemical characteristics. This experiment tested antimicrobial experiment against microbe and dye experiment against fiber using natural Bokbunja extract. Some conclusions from this characteristics experiment were obtained as follow. The result of antimicrobial experiment could know that ATCC-001(staphylococcus aureus) does not show nearly from 72hrs after cultivation test and ATCC-002(aspergillus niger) shows to propagate continuously according to passage of time. Also, the result of dye experiment could know that cotton and silk using alum mordant($Al_2(SO_4)_3{\cdot}13-14H_2O$) against fiber shows in direction of light beige color. The result of instrument analysis ascertained inorganic components of K(221.100ppm), Mg(17.920ppm), Ca(5.129ppm), Na(2.940ppm), Si(0.638ppm) etc from Bokbunja with ICP/OES, and ascertained organic components of boric acic(1.711), silane(2.142), pyrazole(3.481), propyl isothiocyanate(2.565), furfurole(11.521) etc from Bokbunja with GC/MSD.

• Korean Journal of Weed Science
• /
• v.5 no.2
• /
• pp.155-163
• /
• 1985

Three pyrazole-herbicides, pyrazolate, pyrazoxyfene and benzophenap, were evaluated for their interaction in controlling barnyardgrass (Echinochloa crusgalli) with two chloroacetamide-herbicides, butachlor and pretilachlor. Percent inhibition of barnyardgrass growth by pyrazolate, pyrazoxyfene, and benzophenap was 44%, 64%, and 0%, respectively, when each was applied at the 1.5 leaf-stage of barnyardgrass at a rate of 3㎏ ai per ㏊ as single treatment, and the benzophenap showed 60% inhibition when it was applied at the coleoptile stage. While the lowest rate controlling the 1.5 leaf-stage barnyardgrasses by 98 to 100% of the butachlor and pretilachlor was 1.5㎏ and 200g per ㏊, respectively. All of the combinations of pyrazolate with butachlor, pyrazoxyfene with pretilachlor, and benzophenap with butachlor have shown synergistic interaction in controlling barnyardgrass on the Chisaka's isobole of 90% growth inhibition as well as on the Colby`s interaction efficacy data; synergism indices were 2.44, 1.62 and 1.52 in order. The dose combinations shown the maximal synergism were 1870g of pyrazolate with 140g of butachlor (1:0.075), 33008 of pyrazoxyfene with 338 of pretilachlor (1:0.01), and 3350g of benzophenap with 520g of butachlor (1:0.15) on the ai/㏊ basis.

• Journal of the Korean Chemical Society
• /
• v.54 no.6
• /
• pp.737-743
• /
• 2010

Coupling of 5-amino-1,3-diaryl-pyrazoles 1a-c with diazonium salts of different aryl amines gave a series of novel 1,3-diaryl-5-amino-4-arylazopyrazoles 3a-l. Such compounds could be also obtained by reaction of 5-amino-1,3-diaryl-4-nitroso- 1H-pyrazoles 2a-c with different aryl amines in alkaline medium. Oxidation of azo derivatives 3a-l with cupric acetate, in dimethyl formamide and stream of air, gave 2,4,6-triaryl-2,4-dihydropyrazolo [4,3-d]-1,2,3-triazoles 4a-l. and the fluorescence properties of the cyclic triazoles were studied. Diazotization of 5-amino-1,3-diaryl-1H-pyrazoles 1a-c by sodium nitrite in ortho-phosphoric acid followed by coupling with some aryl amines gave o-aminoazo compounds 5a-f. Cyclisation of compounds 5a-f in pyridine and cupric acetate gave the corresponding triazoles 6a-f. The coupling of compounds 6a-f with different aryl diazonium salts gave compounds 7a-j. The synthesized dyes were applied to polyesters as disperse dyes and the fastness properties were evaluated.

• Applied Microscopy
• /
• v.41 no.4
• /
• pp.265-276
• /
• 2011

The aim of the present study is to validate the effects of treatment with different concentration of estrogen receptor alpha agonist, propyl pyrazole triol (PPT) on the weight and histological structure in the accessory reproductive organs (ventral prostate, seminal vesicle and preputial gland) of male mouse. Treated groups received different doses of PPT 0.01 mg, 0.1 mg and 1.0 mg per week respectively, for 3, 5, and 8 weeks. In general, the weight of reproductive organs was increased in PPT 0.01 mg and 0.1 mg treatment, however decreased in PPT 1.0 mg treatment. Epithelial tissues in the ventral prostate were changed from simple columnar epithelium to squamous or cuboidal epithelium in the treated groups. On week 3, PPT groups caused decrease of epithelial cell height in the ventral prostate. Lumen of the seminal vesicle was narrowed in the treated group. Epithelial cell height of seminal vesicle was reduced in the PPT treatment. Acinus tissue of preputial gland in PPT 1.0 mg treatment was dramatically atrophied than that of control group. These results are useful as a reference to determine the administration concentration of PPT in experiments for understanding the physiological functions of estrogen in the male.

• Applied Microscopy
• /
• v.41 no.1
• /
• pp.37-45
• /
• 2011

Known as a female hormone, estrogen, has an effect on the male reproductive organs. The estrogen has to combine with the estrogen receptor to communicate a signal. Propyl pyrazole triol (PPT) is an estrogen receptor alpha selective agonist with a 410-, or 1,000-fold relative binding affinity for estrogen receptor alpha versus estrogen receptor beta. In this study, adult male mice were treated weekly with subcutaneously injections of PPT (0.01 mg, 0.1 mg, 1mg and 4 mg) suspended in castor oil (as control) for 8 weeks and observed histologically changes in testis, efferent ductule and epididymis. In the high concentrations of PPT 4 mg treatment group, a remarkable reduction was observed in the weight of the body, testis and epididymis. Microscopic examination revealed a reduction in seminiferous tubular diameter of the testis, and epithelial cell height of the epididymis in treated group during the experiment. In addition, as the diameter of the efferent ductule increased gradually, the height of epithelial cells was decreased. PPT 4 mg treatment group caused inhibition of spermatogenesis due to atrophied germinal epithelium in the testis, and decrease of adipocyte size attached to the epididymis. Sperm was not observed in the caudal epididymis of PPT 4 mg treated group. In conclusion, the injection of high concentrations of PPT into adult male mice induced physiological changes, such as an inhibition of spermatogenesis, and also histological changes within the reproductive organs.

• Applied Microscopy
• /
• v.43 no.3
• /
• pp.103-109
• /
• 2013

ICI 182,780 (ICI) is known as an estrogen receptor antagonist, whereas propyl pyrazole triol (PPT) is an estrogen receptor agonist. In this study, ICI or ICI added with PPT was injected into adult male mice. Body and reproductive organ weights were reduced in the ICI added with PPT group compared to the control group. Further, the ICI and ICI added with PPT groups both showed increases in luminal areas of the seminiferous tubules of the testis, whereas cell heights of efferent ductules and the initial segment of the epididymis were reduced. Sperm count in the caudal epididymis was reduced in the ICI and ICI added with PPT groups. These results show that reproductive tissues were more deeply affected in the ICI added with PPT group. We also demonstrated that treatment with ICI resulted in histological changes in the testis, efferent ductule, and epididymis. Further, alternate treatment with ICI and PPT induced abnormalities in reproductive organs. These results indicate that a high concentration of PPT together with ICI may cause histological abnormalities instead of histological restoration in reproductive organs.

• Development and Reproduction
• /
• v.24 no.1
• /
• pp.53-62
• /
• 2020

Natural killer (NK) cells are innate lymphocytes that play an essential role in preventing cancer development by performing immune surveillance to eradicate abnormal cells. Since ex vivo expanded NK cells have cytotoxic activity against various cancers, including breast cancers, their clinical potential as immune-oncogenic therapeutics has been widely investigated. Here, we report that the pyrazole chemical XRP44X, an inhibitor of Ras/ERK activation of ELK3, stimulates NK-92MI cells to enhance cytotoxic activity against breast cancer cells. Under XRP44X stimulation, NK cells did not show notable apoptosis or impaired cell cycle progression. We demonstrated that XRP44X enhanced interferon gamma expression in NK-92MI cells. We also elucidated that potentiation of the cytotoxic activity of NK-92MI cells by XRP44X is induced by activation of the c-JUN N-terminal kinase (JNK) signaling pathway. Our data provide insight into the evaluation of XRP44X as an immune stimulant and that XRP44X is a potential candidate compound for the therapeutic development of NK cells.