Design, synthesis and biological evaluation of N-arylphenyl-2,2-dichloroacetamide analogues as anti-cancer agents.
Our earlier research has shown that N-phenyl-2,2-dichloroacetamide analogues had much higher anti-cancer activity than the lead compound sodium dichloroacetate (DCA). In this current study, a variety of N-arylphenyl-2,2-dichloroacetamide analogues were synthesized via Suzuki coupling reaction and their anti-cancer activity was evaluated. The results showed that N-terphenyl-2,2-dichloroacetamide analogues had satisfactory anti-cancer activity. Among them, N-(3,5-bis(benzo[d][1,3]dioxol-5-yl)phenyl)-2,2-dichloroacetamide (6 k) had an IC(50) of 2.40 μM against KB-3-1 cells, 1.04 μM against H460 cells and 1.73 μM against A549 cells.
Key Laboratory of Bioorganic Phosphorus and Chemical Biology, The Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
Tianwen
T
Li
Yongchong
Y
Yang
Changmei
C
Cheng
Amit K
AK
Tiwari
Kamlesh
K
Sodani
Yufen
Y
Zhao
Ioana
I
Abraham
Zhe-Sheng
ZS
Chen
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D052117:Benzodioxoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D013329:Structure-Activity Relationship
D000081:Acetamides; D000970:Antineoplastic Agents; D052117:Benzodioxoles; C580578:N-(3,5-bis(benzo(d)(1,3)dioxol-5-yl)phenyl)-2,2-dichloroacetamide; C032619:2,2-dichloroacetamide