• Bulletin of the Korean Chemical Society
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• v.33 no.9
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• pp.2991-2998
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• 2012

A series of new diarylureas and diarylamides possessing 1,3,4-triarylpyrazole scaffold was synthesized and their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-60 cell line panel were tested. Compounds 9, 11, 12, 14, and 17-21 showed superior potency against A375P to Sorafenib. Over the NCI-60 cancer cell line panel, compound 14 possessing a methoxy group, amide linker, and 4-chloro-3-(trifluoromethyl)phenyl terminal ring showed the highest potency and broad-spectrum anticancer activity. Compound 13 showed high selectivity towards leukemia subpanel over other cancer types.

• YAKHAK HOEJI
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• v.49 no.1
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• pp.60-67
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• 2005

Nonclassical aminobenz[cd]indole antifolates 4, 5 and 6, in which the glutamic acid moiety of the classical antifolates is substituted by 2-phenylglycinamide or 3-aminobenzamide, were synthesized and their in vitro antitumor activity was evaluated. The purpose of this substitution is that the lipophilicity is enhanced due to the aromatic ring of the target compounds for the passive transport through lipid membrane of cells while the hydrogen bonding of the amide is retained in the active site of the enzyme, thymidylate synthase, where the glutamate is originally present. The target compounds were highly cytotoxic against tumor cell lines of murine and human origin with micromolar to nanomolar $IC_{50}$ values. Most effective was compound 4 ($N^6-methyl-N^6$-[4-[(${\alpha}$(S)-aminocarbonylbenzyl) aminocarbonyl]benzyl]-2,6-diaminobenz[cd]indole)with $IC_{50}$ of 2 nM against SW480, human colon adenocarcinoma cell line, which is 650-fold more potent than the reference compound 3.

• Archives of Pharmacal Research
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• v.19 no.3
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• pp.240-242
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• 1996

We have reported the convenient biomimetic methodology for the synthesis of all kinds of substituent pattern benzo[c]phenanthridine alkaloids (Hanaoka et al., 1990; Hanaoka et al., 1991). Regioselective demethylation of C-8 position on oxyfagaridine (5), an intermediate for the synthesis of Fagaridine (4), would afford the precursor for the synthesis of Isofagaridine because the strong hydrogen bonding between amide and hydroxyl group of C-7 position probably resists to be reacted with week base and electrophiles. Thus, a selective alkylation of dihydroxy compound supposed to be possible and be lead to the target compound, Isofagaridine.

• The Korean Journal of Pesticide Science
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• v.10 no.2
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• pp.153-156
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• 2006

As an ongoing research program for the development of environmentally friendly new herbicide, several hydantoin derivatives 5a - 5i possessing amide subgroup were synthesized and shown to have interesting herbicidal activities exhibiting symptoms as Protoporphyrinogen IX oxidase inhibitor under postemergence upland greenhouse screening. Among derivatives tested, compound 5h showed superior herbicidal activity against upland problem weed, digitaria sanguinalis and aeschynomene indica to reference compound fluthiacet-methyl.

• Applied Chemistry for Engineering
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• v.8 no.3
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• pp.510-516
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• 1997

O/W emulsions were prepared by adding water to the solution containing amphiphilic resin and the mixed emulsifier of cetyl alcohol polyoxyethylene(20) sorbitan monooleate. Phase behavoir of these emulsions was studied at various HLB(Hydrophilic Lipophilic Balance) values and temperatures. The polar oil emulsion containing the amphiphilic resin showed improved phase stability at various temperatures. Model compounds which contain one of the functional groups in the amphiphilic resin were used in the polar oil phase in order to study the effect of interaction between the functional group and the emulsifier on the phase stability of emulsion. These model compound emulsions showed the phase stability order of poly(acrylic acid)

• The Journal of Natural Sciences
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• v.7
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• pp.47-51
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• 1995

In order to develope new asymmetric catalyst, we synthesized the following new sulfonamide derivatives start from S-Indoline-2-Carboxylic Acid via the following 5 steps. Hydroxy methyl derivative(1) was thus treated with methane sulfonyl chloride in the presence of triethylamine as base to give mesylated derivative(2) in 85% of isolated yield. The mesylate compound (2) was treated with excess sodium azide to give Azido derivative (4) in 95% isolated yield. Azido compound (3) was then reduced to the corresponding amino derivative in near quntitative yield by the hydrogenation under hydrogen atmospere in the presence of catalytic amount of Pd-C. The amino derivative (4) was converted to its sulfonamide derivatives by the treatment of compound(4) with triisopropyl benzene sulfonyl chloride in the presence of triethyl amine as base. Finally t-BOC group of the compound(5) was removed by the treatement of excess Trifluoro-acetic acid in near quantitative yield to give the target sulfonamide derivative (7) .in this paper we prepared compound(6) in 49% overall yield via the 5 steps of synthesis starting from t-Boc- 2-hydroxy methyl indoline(1) which cab be easily prepared from commercial available S-indoline-2-carboxylic acid by known methods. we plan to apply this new catalyst for the asymmetric reduction , diels-alder reaction, aldolcondensation reaction in due courses.

• Parasites, Hosts and Diseases
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• v.62 no.1
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• pp.42-52
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• 2024

Antimalarial drugs are an urgently need and crucial tool in the campaign against malaria, which can threaten public health. In this study, we examined the cytotoxicity of the 9 antimalarial compounds chemically synthesized using SKM13-2HCl. Except for SKM13-2HCl, the 5 newly synthesized compounds had a 50% cytotoxic concentration (CC₅₀) >100 μM, indicating that they would be less cytotoxic than SKM13-2HCl. Among the 5 compounds, only SAM13-2HCl outperformed SKM13-2HCl for antimalarial activity, showing a 3- and 1.3-fold greater selective index (SI) (CC₅₀/IC₅₀) than SKM13-2HCl in vitro against both chloroquine-sensitive (3D7) and chloroquine -resistant (K1) Plasmodium falciparum strains, respectively. Thus, the presence of morpholine amide may help to effectively suppress human-infectious P. falciparum parasites. However, the antimalarial activity of SAM13-2HCl was inferior to that of the SKM13-2HCl template compound in the P. berghei NK65-infected mouse model, possibly because SAM13-2HCl had a lower polarity and less efficient pharmacokinetics than SKM13-2HCl. SAM13-2HCl was more toxic in the rodent model. Consequently, SAM13-2HCl containing morpholine was selected from screening a combination of pharmacologically significant structures as being the most effective in vitro against human-infectious P. falciparum but was less efficient in vivo in a P. berghei-infected animal model when compared with SKM13-2HCl. Therefore, SAM13-2HCl containing morpholine could be considered a promising compound to treat chloroquine-resistant P. falciparum infections, although further optimization is crucial to maintain antimalarial activity while reducing toxicity in animals.

• Natural Product Sciences
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• v.21 no.3
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• pp.196-204
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• 2015

Nineteen compounds, including one organic acid (1), one anthraquinone (2), one amide (3), and sixteen triterpenoid saponins (4 - 19) were isolated from the leaves of Acanthopanax henryi (Oliv.) Harms (Araliaceae). Their structures were determined on the basis of physicochemical properties and spectral analyses (HR-MS and NMR). Among them, compounds 2, 3, 7, 12 and 19 were new within Araliaceae. Compounds 4, 5, 9 - 11, 13, 14, 16 and 18 were reported for the first time from the Acanthopanax genus. Except for compounds 4 and 9, other compounds were isolated from A. henryi (Oliv.) Harms for the first time. The rare anthraquinone, compound 2, significantly decreased the production of NO and the levels of other inflammatory factors, such as TNF-α and IL-6, in lipopolysaccharide (LPS)-stimulated macrophages in a dose-dependent manner. This is the first time to report anti-inflammatory effect of this compound.

• Archives of Pharmacal Research
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• v.28 no.11
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• pp.1205-1212
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• 2005

2-Thiouracil-5-sulphonic acid N-(4-acetylphenyl) Amide (1) was reacted with a series of aromatic aldehydes giving chalcones 2 (Claisen-Schemidt reaction), some of these chalcones were reacted with urea and thiourea giving pyrimidine-2-one and pyrimidine-2 thione derivatives respectively of the type 3a,b and 4a,b. In addition many chalcones were reacted with hydroxylamine hydrochloride giving isoxazoline derivatives 5a,b. They could also reacted with phenylhydrazine to give pyrazoline derivatives 5a,b, chalcones also were reacted withethylcyano acetate and/or malononitryl in pyridine giving pyran derivatives 7a,c and 8a,c. In another pathway chalcones were epoxidised by $H_{2}O_{2}$ giving epoxides 9a,c which in turn were reacted with phenylhydrazine giving 4-hydroxypyrazoline derivatives 10a,c. In another reaction chalcones were reacted with ethylcyanoacetate in presence of amm.acetate giving pyridone derivatives 11a,d which could be prepared also in exellent yield from compound 1 by its reaction with certain aromatic aldehydes and ethylcyanoacetate in presence of ammonium acetate. Finally, compound 1 was reacted with semicarbazide giving semicarbazone intermediate 12 which in turn was reacted with thionyl chloride giving thiadiazole derivative 13. The biological effects of some of the new synthesized compounds were also investigated.

• Nuclear Engineering and Technology
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• v.34 no.4
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• pp.323-330
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• 2002

Various types of compounds were tested with the aspects of decomposition and formation of residue in a $CO_2$ or 7H$_2$+93$N_2$ atmosphere. The evaporation temperature range of each compound was determined from thermogravimetric curve. Decomposition of dicarbon amide, stearic acid, acrowax and zinc stearate was studied by thermogravimetry in $CO_2$ or in 7H$_2$+93$N_2$ atmosphere. All compounds were decomposed in $CO_2$ atmosphere at lower than 40$0^{\circ}C$, but the residue, ZnO remained for zinc stearate. ZnO did not decompose in $CO_2$ atmosphere up to 130$0^{\circ}C$, but reduced into Zn metal and disappeared in the temperature range of $600^{\circ}C$ to 120$0^{\circ}C$ in 7H$_2$+93$N_2$ atmosphere. The effect of residue, which trapped in closed pores of sintered pellet, on the thermal stability was studied using the resintering test at 1$700^{\circ}C$ in 7H$_2$+93$N_2$ atmosphere. In the case of oxidative sintered pellet with admixing zinc stearate, the cavity formation accompanied with a density drop after resintering is due to the pressure of the Zn gases trapped in the isolated pores.