• Archives of Pharmacal Research
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• 제13권1호
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• pp.97-100
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• 1990

A convenient route is reported for the synthesis of fused pyrrolo [2, 3-d][1, 3]-oxazine and pyrrolo [2, 3-d]-pyrimidine derivatives from 2-amino-1-benzyl-3-t-butoxy-carbonyl-4, 5-dimethylpyrrole.

• 대한화학회지
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• 제66권6호
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• pp.442-450
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• 2022

생리학적 활성을 보일 것으로 기대되는 다양한 pyrrolopyrimidine 유도체를 O-arylation과 Suzuki 짝지움 반응을 통해 합성하였다. 금속 촉매 Cu를 사용하고 마이크로파 조사 조건에서O-arylation을 성공적으로 진행하여 pyrrolo[3,2-d]pyrimidine의 4번 위치에 phenol기를 도입할 수 있었다. 또한, 금속촉매 Pd를 사용하는 Suzuki짝지움 반응도 마이크로파를 사용하여 pyrrolo[3,2-d]pyrimidine의 4번 위치에 aryl 기를 도입할 수 있었다. 유도체의 다양화를 위한 반응 조건으로 마이크로파를 사용함으로써 긴 반응 시간과 열전달 효율성 문제를 가지고 있는 전통적인 열 반응의 단점을 획기적으로 극복할 수 있었다. 본 연구 결과는 신약개발 연구에 중요한 역할을 할 것으로 기대되는 pyrrolo[3,2-d]pyrimidine 유도체를 다양화하는데 사용할 수 있다.

• Bulletin of the Korean Chemical Society
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• 제29권11호
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• pp.2231-2236
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• 2008

• Bulletin of the Korean Chemical Society
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• 제35권2호
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• pp.617-621
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• 2014

An efficient and selective method for the synthesis of ethyl 2-amino/aryloxy-3-aryl-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylate derivatives has been developed. The main process involved the reaction of diethyl 1-phenyl-3-((triphenylphosphoranylidene)amino)-1H-pyrrole-2,4-dicarboxylate and aromatic isocyanates, followed by addition of amines/phenols in the presence of catalytic amount of sodium ethoxide or solid potassium carbonate.

• Bulletin of the Korean Chemical Society
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• 제26권5호
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• pp.719-728
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• 2005

A novel 2-amino-4-(8-quinolinol-5-yl)-1- (p-tolyl)-pyrrole-3-cabonitrile (2) was obtained by the reaction of 2-[2-bromo-1-(8-hydroxyquinolin-5-yl)-ethylidene]-malononitrile (1) with p-toluidene. The new synthon compound (2) could be annelated to the corresponding pyrrolo[2,3-d]pyrimidines (4, 6, 7, 26-28), triazolo[1,5-c]pyrrolo[3,2-e]pyrimidines (10, 29, 30), pyrrolo[2,3-c]pyrazoles (11-15), pyrrolo[1,2-a]pyrrolo[3,2-e] pyrimidine (17) and imidazo[1,2-c]pyrrolo[3,2-e]pyrimidines (18-25) via the reaction with some reagents such as acetic anhydride, formamide, triethyl orthoformate, hydrazine hydrate, hydroxylamine, ethylenediamine, carbon disulfide and phosphorus oxychloride. Chemical and spectroscopic evidences for the structures of these compounds are presented. The antifungal and antibacterial activity of the newly synthesized comounds were evaluated.

• Bulletin of the Korean Chemical Society
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• 제35권12호
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• pp.3502-3508
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• 2014

The first synthetic route to 5'-norcarbocyclic C-nucleoside [7-oxa-7,9-dideazadenosine (furo[3,2-d]pyrimidine) and 9-deazaadenosine (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,3-dihydroxy cyclopentane was described. The key C-C bond formation from sugar to base precursor was performed using Knoevenagel-type condensation from a ketone derivative. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. Compound 26 showed significant anti-leukemic activity.

• Journal of Microbiology and Biotechnology
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• 제20권2호
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• pp.433-437
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• 2010

In the course of screening for novel modulators of cell cycle progression and apoptosis as anticancer drug candidates, we generated an analog of sangivamycin, MCS-C2, which was elucidated as 4-amino-6-bromo-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide. In the present study, we evaluated the molecular mechanisms of MCSC2-induced cell cycle arrest and apoptosis in A549 human lung cancer cells. To investigate the effects of MCS-C2 on cell cycle progression in A549 cells, we measured the DNA content of A549 cells treated with $5\;{\mu}M$ MCS-C2 using flow cytometry. The analysis revealed an appreciable $G_2$ phase arrest in treated cells. This event was associated with significant upregulation of p53 and $p21^{Cip1}$. In addition, the TUNEL assay was used to examine apoptotic induction in treated cells, and the effects of MCS-C2 on the expression of apoptosis-associated proteins were examined by Western blot. Apoptotic induction in MCS-C2-treated A549 cells was associated with cytochrome c release from mitochondria, which in turn resulted in the activation of caspase-9 and -3 and the cleavage of poly(ADP-ribose) polymerase (PARP). Based on these results, we conclude that MCS-C2 is a candidate therapeutic agent for the treatment of human lung cancer via upregulation and activation of p53.