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      KCI등재 SCIE SCOPUS

      Synthesis of Novel 4-(1H-benzimidazol-2-yl)benzene-1,3-diols and their Cytotoxic Activity against Human Cancer Cell Lines

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      https://www.riss.kr/link?id=A104665180

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      다국어 초록 (Multilingual Abstract)

      One-pot synthesis of new biologically active 4-(1H-benzimidazol-2-yl)benzene-l,3-diols has been developed. The compounds were prepared by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s with benzene-l,2-diamines. Their s...

      One-pot synthesis of new biologically active 4-(1H-benzimidazol-2-yl)benzene-l,3-diols has been developed. The compounds were prepared by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s with benzene-l,2-diamines. Their structures were identified using elemental, IR, lH-NMR, and mass spectra analyses. The developed method offers short reaction times, relatively large-scale synthesis, easy and quick isolation of the products, and good yields. The cytotoxicity in vitro against the 4 human cancer cell lines: SW707 (rectal), HCV29T (bladder), A549 (lung), and T47D (breast) was determined. The antiproliferative properties of some compounds studies were stronger than those of cisplatin, which was used as a comparator drug.

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      참고문헌 (Reference)

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      2 Bahrami, K., "Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles" 12 : 1237-1241, 2010

      3 Tong, Y., "Synthesis and evaluation of a new generation of orally efficacious benzimidazole- based poly (ADP-ribose) polymerase-1 (PARP- 1) inhibitors as anticancer agents" 52 : 6803-6813, 2009

      4 Gellis, A., "Synthesis and cytotoxicity evaluation of some benzimidazole- 4,7-diones as bioreductive anticancer agents" 43 : 1858-1864, 2008

      5 Matysiak, J., "Synthesis and antiproliferative activity of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)- 1,3,4-thiadiazoles" 14 : 4483-4489, 2006

      6 Refaat, H. M., "Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives" 45 : 2949-2956, 2010

      7 S. R. Ranganatha, "Synthesis and Cytotoxic Evaluation of Novel 2-(4-(2,2,2-Trifluoroethoxy)-3-methylpyridin-2-ylthio)-1H-benzo[d]imidazole Derivatives" 대한약학회 32 (32): 1335-1343, 2009

      8 Peng, G., "Syntheses, structures and photoluminescence of Ln(III)-Cu(I) coordination polymers based on benzimidazole-5-carboxylate and oxalate ligands" 13 : 599-602, 2010

      9 Bhattacharya, S., "Symmetrical bisbenzimidazoles with benzenediyl spacer: the role of the shape of the ligand on the stabilization and structural alterations in telomeric G-quadruplex DNA and telomerase inhibition" 21 : 1148-1159, 2010

      10 Lahue, B. R., "Substituted benzimidazoles: a novel chemotype for small molecule hKSP inhibitors" 19 : 3405-3409, 2009

      1 Matysiak, J., "Synthesis, antiproliferative and antifungal activities of some 2-(2,4-dihydroxyphenyl)-4H-3,1-benzothiazines" 14 : 2613-2619, 2006

      2 Bahrami, K., "Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles" 12 : 1237-1241, 2010

      3 Tong, Y., "Synthesis and evaluation of a new generation of orally efficacious benzimidazole- based poly (ADP-ribose) polymerase-1 (PARP- 1) inhibitors as anticancer agents" 52 : 6803-6813, 2009

      4 Gellis, A., "Synthesis and cytotoxicity evaluation of some benzimidazole- 4,7-diones as bioreductive anticancer agents" 43 : 1858-1864, 2008

      5 Matysiak, J., "Synthesis and antiproliferative activity of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)- 1,3,4-thiadiazoles" 14 : 4483-4489, 2006

      6 Refaat, H. M., "Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives" 45 : 2949-2956, 2010

      7 S. R. Ranganatha, "Synthesis and Cytotoxic Evaluation of Novel 2-(4-(2,2,2-Trifluoroethoxy)-3-methylpyridin-2-ylthio)-1H-benzo[d]imidazole Derivatives" 대한약학회 32 (32): 1335-1343, 2009

      8 Peng, G., "Syntheses, structures and photoluminescence of Ln(III)-Cu(I) coordination polymers based on benzimidazole-5-carboxylate and oxalate ligands" 13 : 599-602, 2010

      9 Bhattacharya, S., "Symmetrical bisbenzimidazoles with benzenediyl spacer: the role of the shape of the ligand on the stabilization and structural alterations in telomeric G-quadruplex DNA and telomerase inhibition" 21 : 1148-1159, 2010

      10 Lahue, B. R., "Substituted benzimidazoles: a novel chemotype for small molecule hKSP inhibitors" 19 : 3405-3409, 2009

      11 Tavman, A., "Spectral characterization and antimicrobial activity of 4-(5-H/Me/Cl/NO2-1H-benzimidazol- 2-yl)-benzene-1,3-diols and some metal complexes" 29 : 255-272, 2009

      12 White, A. W., "Resistance-modifying agents. 9. Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADPribose) polymerase" 43 : 4084-4097, 2000

      13 Kazimierczuk, Z., "Preparation and properties of the 5,6-dinitro and 4,6(5,7)-dinitro derivatives of benzimidazole and their 1-β-D-ribofuranosides" 8 : 1379-1385, 1989

      14 Thomas, H. D., "Preclinical selection of a novel poly(ADP-ribose) polymerase inhibitor for clinical trial" 6 : 945-956, 2007

      15 Kraut, E. H., "Phase II study of pibenzimol in pancreatic cancer. A southwest oncology group study" 9 : 95-96, 1991

      16 Penning, T. D., "Optimization of phenylsubstituted benzimidazole carboxamide poly(ADP-ribose) polymerase inhibitors: identification of (S)-2-(2-fluoro-4- (pyrrolidin-2-yl)pheny)-1H-benzimidazole-4-carboxamide (A-966492), a highly potent and efficacious inhibitor" 53 : 3142-3153, 2010

      17 Skehan, P., "New colorimetric cytotoxicity assay for anticancer- drug screening" 82 : 1107-1112, 1990

      18 Pescovitz, M. D., "Maribavir: a new oral anti-cytomegalovirus drug" 3 : 435-443, 2008

      19 Penning, T. D., "Discovery of the poly(ADP-ribose) polymerase (PARP) inhibitor 2-[(R)-2-methylpyrrolidin-2-yl]-1H-benzimidazole- 4-carboxamide (ABT-888) for the treatment of cancer" 52 : 514-523, 2009

      20 Singh, S., "Design, synthesis, and in vitro antiproliferative activity of benzimidazole analogues for radiopharmaceutical efficacy" 25 : 245-250, 2010

      21 Zhang, D., "Design, synthesis and antibacterial activity of novel actinonin derivatives containing benzimidazole heterocycles" 44 : 2202-2210, 2009

      22 Kreusch, A., "Crystal structures of human HSP90alpha-complexed with dihydroxyphenylpyrazoles" 15 : 1475-1478, 2005

      23 Matysiak, J., "Application of sulfinyl bis (2,4-dihydroxythiobenzoyl) in the synthesis of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles" 36 : 1621-1630, 2006

      24 Biron, K. K., "Antiviral drugs for cytomegalovirus diseases" 71 : 154-163, 2006

      25 Brain, C. T., "An intramolecular palladiumcatalysed aryl amination reaction to produce benzimidazoles" 43 : 1893-1895, 2002

      26 Yang, D., "A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization" 47-56, 2005

      27 Perry, R. J., "A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles" 58 : 7016-7021, 1993

      28 Won, M. S., "A novel benzimidazole analogue inhibits the hypoxia-inducible factor (HIF)-1 pathway" ScienceDirect 385 : 16-21, 2009

      29 Brough, P. A., "3-(5-Chloro-2,4-dihydroxyphenyl)-pyrazole- 4-carboxamides as inhibitors of the Hsp90 molecular chaperone" 15 : 5197-5201, 2005

      30 Vitale, G., "2-Arylbenzimidazoles as antiviral and antiproliferative agents. Part 2" 5 : 507-516, 2009

      31 Vitale, G., "2-Arylbenzimidazoles as antiviral and antiproliferative agents. Part 1" 4 : 605-615, 2008

      32 Bruno, R. D., "17α-Hydroxylase/17,20 lyase inhibitor VN/124-1 inhibits growth of androgen-independent prostate cancer cells via induction of the endoplasmic reticulum stress response" 7 : 2828-2836, 2008

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      2023 평가예정 해외DB학술지평가 신청대상 (해외등재 학술지 평가)
      2020-01-01 평가 등재학술지 유지 (해외등재 학술지 평가) KCI등재
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      학술지 인용정보

      학술지 인용정보
      기준연도 WOS-KCI 통합IF(2년) KCIF(2년) KCIF(3년)
      2016 1.96 0.2 1.44
      KCIF(4년) KCIF(5년) 중심성지수(3년) 즉시성지수
      1.07 0.87 0.439 0.05
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