Synthesis, cytotoxicity and antitumor activity of 2,3-diarylcyclopent-2-ene-1-ones

被引：12
|
作者：
Nam, NH
Kim, Y
You, YJ
Hong, DH
Kim, HM
Ahn, BZ [1 ]
机构：
[1] Chungnam Natl Univ, Coll Pharm, Taejon 305764, South Korea
[2] Res Inst Biosci & Biotechnol, Taejon 305600, South Korea
来源：
ARCHIVES OF PHARMACAL RESEARCH | 2002年 / 25卷 / 05期
关键词：
2,3-diarylcyclopent-2-ene-1-ones; cytotoxicity; and antitumor activity;
D O I：
10.1007/BF02976928
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Two series of 2,3-diarylcyclopent-2-ene-1-ones including 2-aryl-3-(2,5-dihydroxyphenyl)cyclopent-2-ene-1-ones (2asimilar to2f) and 3-aryl-2-(3',4',5'-trimethoxyphenyl)cyclopent-2-ene-1-one (3a-3j) were synthesized and evaluated for the cytotoxicity against three tumor cell lines; B16F10, HCT116 and A431. It was found that the 3,4,5-trimethoxy substituent was optimal for the bioactivity of compounds in series 2. Meanwhile, compounds in series 3 exhibited the most potent cytotoxicity with 3-aryl ring being 4-methoxyphenyl (compound 3f), (3-hydroxy-4-methoxy)phenyl (compound 3e), or (3-amino-4-methoxy)phenyl (compound 3j).
引用
收藏
页码：600 / 607
页数：8
相关论文
共 50 条
  • [1] Synthesis, cytotoxicity and antitumor activity of 2,3-Diarylcy-clopent-2-ene-1-ones
    Nguyen-Hai Nam
    Yong Kim
    Young-Jae You
    Dong-Ho Hong
    Hwan-Mook Kim
    Byung-Zun Ann
    Archives of Pharmacal Research, 2002, 25 : 600 - 607
  • [2] Synthesis and photochromic properties of oxime derivatives of 2,3-diarylcyclopent-2-en-1-ones
    Valerii Z. Shirinian
    Dmitry V. Lonshakov
    Andrey G. Lvov
    Alexey A. Shimkin
    Mikhail M. Krayushkin
    Photochemical & Photobiological Sciences, 2013, 12 : 1717 - 1725
  • [3] Synthesis and Comparative Photoswitching Studies of Unsymmetrical 2,3-Diarylcyclopent-2-en-1-ones
    Shirinian, Valerii Z.
    Lvov, Andrey G.
    Krayushkin, Mikhail M.
    Lubuzh, Elena D.
    Nabatov, Boris V.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08): : 3440 - 3451
  • [4] Synthesis and photochromic properties of oxime derivatives of 2,3-diarylcyclopent-2-en-1-ones
    Shirinian, Valerii Z.
    Lonshakov, Dmitry V.
    Lvov, Andrey G.
    Shimkin, Alexey A.
    Krayushkin, Mikhail M.
    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2013, 12 (09) : 1717 - 1725
  • [5] Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones
    Shirinian, Valerii Z.
    Lonshakov, Dmitry V.
    Kachala, Vadim V.
    Zavarzin, Igor V.
    Shimkin, Alexey A.
    Lvov, Andrew G.
    Krayushkin, Mikhail M.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18): : 8112 - 8123
  • [6] Synthesis and spectral properties of a novel family of photochromic diarylethenes-2,3-diarylcyclopent-2-en-1-ones
    Shirinian, Valerii Z.
    Shimkin, Alexey A.
    Lonshakov, Dmitry V.
    Lvov, Andrey G.
    Krayushkin, Mikhail M.
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2012, 233 : 1 - 14
  • [7] Photo- and PH-switchable fluorescent diarylethenes based on 2,3-diarylcyclopent-2-en-1-ones with dialkylamino groups
    Shirinian, Valerii Z.
    Lonshakov, Dmitry V.
    Lvov, Andrey G.
    Kavun, Alexey M.
    Yadykov, Anton V.
    Krayushkin, Mikhail M.
    DYES AND PIGMENTS, 2016, 124 : 258 - 267
  • [8] Antitumor activity of novel pyrrolo[2,3-d]pyrimidin-4-ones
    Atapour-Mashhad, Hoda
    Tayarani-Najaran, Zahra
    Davoodnia, Abolghasem
    Moloudi, Raheleh
    Mousavi, Seyed Hadi
    DRUG AND CHEMICAL TOXICOLOGY, 2011, 34 (03) : 271 - 276
  • [9] Design, synthesis, and cytotoxicity of novel angular pyranoquinolin-2-ones as antitumor agents.
    Yang, ZY
    Xia, Y
    Xia, P
    Tachibana, Y
    Bastow, K
    Lee, KH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U926 - U926
  • [10] Synthesis and in vitro and in vivo antitumor activity of 2-phenylpyrroloquinolin-4-ones
    Ferlin, MG
    Chiarelotto, G
    Gasparotto, V
    Dalla Via, L
    Pezzi, V
    Barzon, L
    Palù, G
    Castagliuolo, L
    JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) : 3417 - 3427
12345