Bulletin of the Korean Chemical Society

  • 제32권6호
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  • Pages.1891-1896
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  • 2011
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis and Importance of Bulky Aromatic Cap of Novel SAHA Analogs for HDAC Inhibition and Anticancer Activity

  • Chun, Pu-Soon (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kim, Won-Hee (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kim, Jung-Su (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kang, Jin-Ah (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Lee, Hye-Jin (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Park, Ji-Young (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Ahn, Mee-Young (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Kim, Hyung-Sik (College of Pharmacy and Research Institute for Drug Development, Pusan National University) ;
  • Moon, Hyung-Ryong (College of Pharmacy and Research Institute for Drug Development, Pusan National University)
  • 투고 : 2011.03.15
  • 심사 : 2011.04.12
  • 발행 : 2011.06.20
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초록

On the basis of potent HDAC-inhibitory activity and anticancer activity of SAHA, novel SAHA derivatives 3a-d and 7 with a bulky cap such as p-dimethylaminophenyl, 4-phenylaminophenyl, 4-phenyloxyphenyl, 9H-fluorenyl or naphthalenyl ring were synthesized starting from the corresponding aryl amines or naphthalenyl acetic acid using an EDC-mediated amide coupling reaction in the presence of HOBt followed by a nucleophilic addition-elimination reaction with hydroxylamine. Compounds 3b, 3c and 3d showed more potent inhibitory activity on total HDACs (14~27-fold), HDAC1 (8~15-fold), HDAC2 (1.3~25-fold) and HDAC7 (1~3-fold) and more potent anticancer activity (2~22-fold) against MCF-7, MDA-MB-231, MCF-7/Dox, MCF-7/Tam, SK-OV-3, LNCaP and PC3 human cancer cell lines than SAHA.

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피인용 문헌

  1. ChemInform Abstract: Synthesis and Importance of Bulky Aromatic Cap of Novel SAHA Analogues for HDAC Inhibition and Anticancer Activity. vol.42, pp.42, 2011, https://doi.org/10.1002/chin.201142210