Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

被引：32
|
作者：
Chen, Chien-Ting [1 ]
Hsu, Mei-Hua [1 ]
Cheng, Yung-Yi [1 ]
Liu, Chin-Yu [1 ]
Chou, Li-Chen [1 ]
Huang, Li-Jiau [1 ]
Wu, Tian-Shung [2 ,3 ]
Yang, Xiaoming [4 ]
Lee, Kuo-Hsiung [2 ,4 ]
Kuo, Sheng-Chu [1 ,2 ]
机构：
[1] China Med Univ, Grad Inst Pharmaceut Chem, North Sect, Taichung, Taiwan
[2] China Med Univ Hosp, Chinese Med Res & Dev Ctr, Taichung, Taiwan
[3] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan
[4] Univ N Carolina, UNC Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2011年 / 46卷 / 12期
关键词：
Selenophene; Melanoma; Structure-activity relationships (SAR); Anticancer activity; Quinolin-4-one analogs; POTENT ANTITUMOR AGENTS; TUBULIN POLYMERIZATION; BIOLOGICAL EVALUATION; CATALYZED AMIDATION; ANTIMITOTIC AGENTS; CYTOTOXICITY; INHIBITION; 2-PHENYL-4-QUINOLONES; 2-ARYL-4-QUINOLONES; DERIVATIVES;
D O I：
10.1016/j.ejmech.2011.10.017
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：6046 / 6056
页数：11
相关论文
共 50 条
  • [31] Synthesis, DFT computations, molecular docking studies and anticancer activity of 2-(4-fluorophenyl)-3-(5-methylisoxazol-3-yl)thiazolidin-4-one
    Ramesh, Gaddam
    Rathnakar, Bethi
    Narsaiah, Chelimela
    Rameshwar, Nimma
    Srinivas, Marri
    Namratha, Vaddiraju
    Durgaiah, Gandamalla
    Reddy, Yellu Narsimha
    Reddy, Byru Venkatram
    Satyanarayana, Mavurapu
    CHEMICAL DATA COLLECTIONS, 2022, 39
  • [32] Synthesis of 5-and 6-substituted 2-(4-dimethylaminophenyl)-1, 3-benzoxazoles and their in vitro and in vivo evaluation as imaging agents for amyloid plaque
    Hausner, Sven H.
    Alagille, David
    Koren, Andrei O.
    Amici, Louis
    Staley, Julie K.
    Cosgrove, Kelly P.
    Baldwin, Ronald M.
    Tamagnan, Gilles D.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (02) : 543 - 545
  • [33] Synthesis and Phytotoxic Activity of New Pyridones Derived from 4-Hydroxy-6-Methylpyridin-2(1H)-one
    Demuner, Antonio Jacinto
    Moreira Valente, Vania Maria
    Almeida Barbosa, Luiz Claudio
    Rathi, Akshat H.
    Donohoe, Timothy J.
    Thompson, Amber L.
    MOLECULES, 2009, 14 (12): : 4973 - 4986
  • [34] SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL 6-(SUBSTITUTED BENZYLIDENE)-2-METHYLTHIAZOLO [2,3-b] OXAZOL-5(6H)-ONE AS POTENTIAL ANTICANCER AGENTS
    Kini, Deepthi D.
    Mathews, Jessy Elizabeth
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2020, 11 (05): : 2199 - 2205
  • [35] Synthesis and Antimicrobial Activity of 4-Hydroxy-2-[5-Nitrofuran(Thien)-2-Yl]-6h-1,3-Oxazin-6-Ones
    Chernov, N. M.
    Koshevenko, A. S.
    Yakovlev, I. P.
    Anan'eva, E. P.
    Ksenofontova, G. V.
    Shchegolev, A. E.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2017, 51 (08) : 644 - 647
  • [36] Design and Efficient Synthesis of New 4-Amino-Substituted 2-(4-Bromobenzyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines of Anticancer Interest and Their In Silico Study
    Arora, Sahil
    Thakur, Shikha
    Kaki, Venkata Rao
    Kumar, Raj
    SYNTHESIS-STUTTGART, 2025, 57 (01): : 240 - 250
  • [37] X-ray Structure Analyses of 4-Hydroxy-1-Methylquinolin-2(1H)-One, 6-Ethyl-4-Hydroxy-2 H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione, (E)-4-(2-Benzylidene-Hydrazineyl)Quinolin-2(1H)-One and Diethyl (E)-2-(2-(1-Methyl-2-Oxo-1,2-Dihydro-Quinolin-4-yl)Hydrazineylidene) Succinate
    Aly, Ashraf A.
    Nieger, Martin
    Braese, Stefan
    Bakheet, Momtaz E. M.
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2023, 53 (01) : 38 - 49
  • [38] Synthesis of Some Novel Fused Pyrimido[4",5":5′,6′]- [1,2,4]triazino[3′,4′:3,4] [1,2,4]triazino[5,6-b]indoles with Expected Anticancer Activity
    Ali, Rania S.
    Saad, Hosam A.
    MOLECULES, 2018, 23 (03):
  • [39] Synthesis and In-Vitro Antitumor Activity of Selected 7-Fluoro-6-(4-methyl-1-piperazinyl)-2-(thiosubstituted)-4(3H)-quinazolinones
    Abdel-Jalil, Raid J.
    Al-Momani, Ehab
    Tahtamooni, Lubna
    Machulla, H. -Juergen
    Voelter, Wolfgang
    LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (05) : 360 - 366
  • [40] Synthesis, analgesic and antimicrobial activity of substituted 2-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxo-4-phenylbut-2-enoates
    Sharavyeva, Yu. O.
    Siutkina, A. I.
    Chashchina, S. V.
    Novikova, V. V.
    Makhmudov, R. R.
    Shipilovskikh, S. A.
    RUSSIAN CHEMICAL BULLETIN, 2022, 71 (03) : 538 - 542
12345