• 공업화학
• /
• 제4권1호
• /
• pp.132-143
• /
• 1993

Aminomethyl레진을 chloromethyl레진(Merrifield레진)으로부터 또는 polystyrene레진을 직접 amidoalkylation하여 각각 합성하였다. 두 종류의 aminomethyl레진을 이용하여 5개의 ${\varepsilon}$-aminocaproic acid(ACA)가 차례로 커플링 된 spacer arm을 가진 레진들을 각각 합성하였다. Chloromethyl레진으로부터 합성된 aminomethyl레진의 경우 ACA를 매번 커플링 할 때마다 25~30%의 유리 아미노기의 양이 감소하였으며, 직접 amidoalkylation에 의해 합성한 amlnomethyl 레진의 경우 매 커플링 단계 마다 3~5%의 유리 아미노기의 양이 감소하였다. 4-Nitroso-5-aminopyrazole 기능기를 가진 레진은 직접 amidoalkylation하여 얻은 레진에 ACA를 spacer arm으로 커플링시켜 얻은 레진과 5-phenyl-7-methylpyrazole[4,3-c][1,2,4]oxadiazin-3-one을 반응시켜 얻었다. 4-Nitroso-5-aminopyrazole 기능기를 가진 레진을 이용하여 ${\alpha}$-아미노기가 보호된 여러 가지 아미노산의 활성에스테르 레진들을 합성하였다. 4-Nitroso-5-aminopyrazole 기능기를 가진 활성 에스테르 레진은 N-acylation 반응에 매우 뛰어난 반응성을 나타내었다. 또한 입체장애 효과 없이 아미노산 유도체의 종류에 거의 무관하게 아실화 반응이 일어났으며 90~96%의 수율로 펩티드들을 합성할 수 있었다. 얻어진 펩티드들은 NMR을 비롯한 여러 가지 물리적 방법으로 그 순도를 확인하였다.

• Archives of Pharmacal Research
• /
• 제20권4호
• /
• pp.330-337
• /
• 1997

Thiocarboxamidocinnamonitrile derivatives 2 under bar a-f reacted with 3-aminopyrazole derivative 3 under bar a-c to give the pyrazole[3, 2-b]pyrimidine derivatives 6 under bar a-p. Compounds 6 under bar a-p were used as starting material for syntheses of several heterocylic coompounds. Dehydrogenation of 6 under bar gave pyrazole[3, 2-b]pyrimidines 10 under bar a-d while its reaction with diethyl oxalate gave 11 under bar. Reactions of 6 under bar with formic acid gave pyrazolopyrimidines 17 under bar a-j, and pyrazolopyrimidopyrimidines 18 under bar a-j.

• Archives of Pharmacal Research
• /
• 제10권1호
• /
• pp.14-17
• /
• 1987

Several new imidazo [1, 2-b] pyrazole, pyrazolo [5, 1-c]-1, 2, 4-triazine and pyrazolo [5, 1-c] triazole derivatives were prepared from the reaction of 3-antipyrinyl-5-aminopyrazole or its diazonium salt with .alpha.-chloroacetyl derivatives.

• 대한화학회지
• /
• 제55권5호
• /
• pp.781-786
• /
• 2011

An easy and efficient route for the synthesis of some imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines 3-6, imidazo[1,2-c]pyrazolo[4,3-e]triazine 8, pyrazolo[4,3-e]triazolo[1,5-c]pyrimidines 12-15 and pyrazolo-[3',4':4,5]pyrimido[1,6-b]triazines 16, 17 was described through the reaction of readily available 5-aminopyrazole-4-carbonitrile 1 with different reagents. The in vitro antimicrobial activity of some synthesized compounds was examined. Most of the tested compounds proved to be active as antibacterial and antifungal agents.

• Archives of Pharmacal Research
• /
• 제13권3호
• /
• 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.

• Bulletin of the Korean Chemical Society
• /
• 제33권9호
• /
• 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.

• Bulletin of the Korean Chemical Society
• /
• 제33권2호
• /
• pp.647-650
• /
• 2012

Promising anticancer compounds of the type 1,6-disubstituted 4,5,6,7-tetrahydropyrazolo[3,4-c]pyridin-7-ones were identified. The target compounds were readily synthesized in a large scale via a sequence of reactions starting from the commercially available primary amines. Their in vitro anti-proliferative activity has been evaluated on prostate (DU-145), colon (HT-29 and HCT-116) and melanoma (A375P) human cancer cell lines. The relationships between the structure and the anticancer activity, covering all tested cancer cell lines, revealed that the compound 5c with 2,4-dimethylphenyl substituent at $R^2$ was the most potent with the $IC_{50}$ values in the range as low as 0.16 to $0.40{\mu}M$.