Bulletin of the Korean Chemical Society

  • 제30권1호
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  • Pages.83-91
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  • 2009
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of Novel Allylthio Heterocyclo(or aryl)alkylaminopyridazines and Their Anticancer Activity against SK-Hep-1 Cells

  • 발행 : 2009.01.20
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초록

To develop new anticancer agents, 3-allylthio-6-aminopyridazine derivatives were synthesized from maleic anhydrides or phthalic anhydrides by formation of a pyridazine nucleus, dichlorination, allylthiolation and amination. The pyridazine nuclei were obtained by condensing a hydrazine monohydrate with maleic anhydride. An allylthio group as a pharmacologically active group was introduced into one side of a pyridazine ring. Arylalkylamines with benzene or pyridine moieties or heterocycloalkylamines with heterocycle moieties such as morpholine, piperidine, or pyrrolidine were also introduced into the para-position of allylthio pyridazine. These new compounds showed antiproliferative activities against SK-Hep-1 human liver cancer cells in MTT assays. These compounds are thus promising candidates for chemotherapy of hepatocellular carcinomas. Two compounds, 20c and 22a, showed higher potencies for inhibiting growth of hepatocellular carcinoma cells than did K6 ($ID_50$=1.08 mM). This suggests the potential anticancer activity of these two compounds.

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참고문헌

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피인용 문헌

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  2. Novel Alkylaminopyridazine Derivatives: Synthesis and Their Anti-proliferative Effects against MCF-7 Cells vol.34, pp.11, 2013, https://doi.org/10.5012/bkcs.2013.34.11.3317
  3. Design, Synthesis, and Biological Evaluation of Selenium-incorporated Aminopyridazines as Anticancer Agents vol.36, pp.6, 2015, https://doi.org/10.1002/bkcs.10319
  4. Synthesis and Antiproliferative Activities of Chloropyridazine Derivatives Retain Alkylsulfonyl Moiety vol.37, pp.11, 2016, https://doi.org/10.1002/bkcs.10967
  5. ChemInform Abstract: Synthesis of Novel Allylthio Heterocyclo(or aryl)alkylaminopyridazines and Their Anticancer Activity Against SK-Hep-1 Cells. vol.40, pp.28, 2009, https://doi.org/10.1002/chin.200928141
  6. Synthesis and anticancer activities of new 3-allylthio-6-(mono or disubstituted)aminopyridazines vol.33, pp.2, 2010, https://doi.org/10.1007/s12272-010-0201-x
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  8. RKO 대장암세포에서 3-헵틸아미노-6-알릴티오피리다진과 3-디펜틸아미노-6-알릴티오피리다진의 항암기전 vol.60, pp.3, 2009, https://doi.org/10.17480/psk.2016.60.3.101
  9. Base Promoted Three-Component Annulation of 4-Diazoisochroman-3-imines with Dimethylsulfonium Ylides: Synthesis of Highly Functionalized Isochromeno[4,3-c]pyridazines vol.86, pp.1, 2021, https://doi.org/10.1021/acs.joc.0c02204