Synthesis and Inhibitory Activity Evaluation of 2,6-Disubstituted Purine Derivatives

被引:2
作者
Liu, Hongxia [1 ,2 ]
Li, Libo [3 ]
Qurat-ul-ain, Shaikh [1 ]
Jiang, Tao [1 ]
机构
[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Chinese Minist Educ, Qingdao 266003, Shandong, Peoples R China
[2] Qiqihar Univ, Coll Chem & Chem Engn, Qiqihar 161006, Heilongjiang, Peoples R China
[3] Qiqihar Med Univ, Dept Pharmacol, Qiqihar 161006, Heilongjiang, Peoples R China
关键词
ADENINE-DERIVATIVES; POTENT;
D O I
10.1002/jhet.1959
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel 2,6-disubstituted purine derivatives were designed and synthesized from 2,6-dichloropurine. The structures of target compounds were determined by H-1-NMR, C-13-NMR, and HRMS. The synthesized compounds were evaluated for their inhibitory activities against lung cancer cell lines of A549 and liver cancer cell lines of Bel-7402. 2-(4-Benzyloxy-phenylamino)-6-(cyclohexylamino)purine(3), 2-(4-chloro-phenylamino)-6-(n-butylamino)purine (5), 2-(4-morpholinoamino)-6-(4-hydroxy-phenylamino)purine (9), and 2-(4-O-galactosyl-phenylamino)-6-(cyclohexylamino)purine (12) exhibited moderate inhibitory activity.
引用
收藏
页码:473 / 477
页数:5
相关论文
共 17 条
[1]   A practical synthesis of 2-arylamino-6-alkylaminopurines from 2,6-dichloropurine [J].
Ciszewski, Lech ;
Waykole, Liladhar ;
Prashad, Mahavir ;
Repic, Oljan .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (04) :799-802
[2]   Reversine, a novel Aurora kinases inhibitor, inhibits colony formation of human acute myeloid leukemia cells [J].
D'Alise, Anna Morena ;
Amabile, Giovanni ;
Iovino, Mariangela ;
Di Giorgio, Francesco Paolo ;
Bartiromo, Marta ;
Sessa, Fabio ;
Villa, Fabrizio ;
Musacchio, Andrea ;
Cortese, Riccardo .
MOLECULAR CANCER THERAPEUTICS, 2008, 7 (05) :1140-1149
[3]   Structure-based design of a potent purine-based cyclin-dependent kinase inhibitor [J].
Davies, TG ;
Bentley, J ;
Arris, CE ;
Boyle, FT ;
Curtin, NJ ;
Endicott, JA ;
Gibson, AE ;
Golding, BT ;
Griffin, RJ ;
Hardcastle, IR ;
Jewsbury, P ;
Johnson, LN ;
Mesguiche, V ;
Newell, DR ;
Noble, MEM ;
Tucker, JA ;
Wang, L ;
Whitfield, HJ .
NATURE STRUCTURAL BIOLOGY, 2002, 9 (10) :745-749
[4]   Solution-phase synthesis of 2,6,9-trisubstituted purines [J].
Fiorini, MT ;
Abell, C .
TETRAHEDRON LETTERS, 1998, 39 (13) :1827-1830
[5]   Design, synthesis and in vitro evaluation of mono (2, 2, 2-trifluoroethyl) esters, mono L-amino acid ester prodrugs of acyclic nucleoside phosphonates as anti-HBV agents [J].
Fu, Xiao Zhong ;
Ou, Yu ;
Xin, Jan ;
Yang, Yu She .
CHINESE CHEMICAL LETTERS, 2011, 22 (12) :1387-1390
[6]   N2-substituted O6-cyclohexylmethylguanine derivatives:: Potent inhibitors of cyclin-dependent kinases 1 and 2 [J].
Hardcastle, IR ;
Arris, CE ;
Bentley, J ;
Boyle, FT ;
Chen, YH ;
Curtin, NJ ;
Endicott, JA ;
Gibson, AE ;
Golding, BT ;
Griffin, RJ ;
Jewsbury, P ;
Menyerol, J ;
Mesguiche, V ;
Newell, DR ;
Noble, MEM ;
Pratt, DJ ;
Wang, LZ ;
Whitfield, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (15) :3710-3722
[7]  
Hingoranis S. P. L., 1998, INDIAN J CHEM B, V27B, P498
[8]   Design and Antimicrobial Action of Purine Analogues That Bind Guanine Riboswitches [J].
Kim, Jane N. ;
Blount, Kenneth F. ;
Puskarz, Izabela ;
Lim, Jinsoo ;
Link, Kristian H. ;
Breaker, Ronald R. .
ACS CHEMICAL BIOLOGY, 2009, 4 (11) :915-927
[9]  
Lerchen HG, 2000, J PRAKT CHEM, V342, P753
[10]  
[廖春风 LIAO Chunfeng], 2006, [精细化工, Fine Chemicals], V23, P466