Synthesis and cytotoxic activity of N-(2-pyridylsulfenyl)urea derivatives.: A new class of potential antineoplastic agents.

被引:24
作者
Gil, MJ
Mañú, MA
Arteaga, C
Migliaccio, M
Encío, I
González, A
Martínez-Merino, V
机构
[1] Univ Publ Navarra, Dept Quim, Pamplona 31006, Spain
[2] Univ Publ Navarra, Dpto Ciencias Salud, Pamplona 31008, Spain
关键词
D O I
10.1016/S0960-894X(99)00373-X
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Starting from a 3D-model for the antineoplastic activity of diarylsulfonylureas several new features were proposed and tested. Both types of assayed compounds, the N-(2-pyridylsulfonyl)urea and N-(2-pyridylsulfenyl)urea derivatives, inhibited by 50% the growth of the CCRF-CEM cell line at a dosage near to 1 mu M The N-(2-pyrimidinyl) derivative of the sulfenylurea 6c showed a better profile against HT-29, K-562 and HTB-54 tumor cell lines than the corresponding sulfonylurea 6b. Structural modifications on aryl systems affected differently to the cytotoxic activity shown by the compounds against each cell line. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2321 / 2324
页数:4
相关论文
共 17 条
[2]  
Ehlhardt WJ, 1997, DRUG METAB DISPOS, V25, P701
[3]   EFFICACY OF SULOFENUR AND A 2ND-GENERATION DIARYLSULFONYLUREA, N-[5-(2,3-DIHYDROBENZOFURYL)SULFONYL]-N'-(3,4-DICHLOROPHENYL)UREA (LY295501), AGAINST COLON ADENOCARCINOMA XENOGRAFTS [J].
HOUGHTON, PJ ;
CHESHIRE, PJ ;
MYERS, L ;
LUTZ, L ;
TOTH, J ;
GRINDEY, GB ;
HOUGHTON, JA .
ANTI-CANCER DRUGS, 1995, 6 (02) :317-323
[4]   Antitumor diarylsulfonylureas: Novel agents with unfulfilled promise [J].
Houghton, PJ ;
Houghton, JA .
INVESTIGATIONAL NEW DRUGS, 1996, 14 (03) :271-280
[5]   NOVEL AGENTS EFFECTIVE AGAINST SOLID TUMORS - THE DIARYLSULFONYLUREAS - SYNTHESIS, ACTIVITIES, AND ANALYSIS OF QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
HOWBERT, JJ ;
GROSSMAN, CS ;
CROWELL, TA ;
RIEDER, BJ ;
HARPER, RW ;
KRAMER, KE ;
TAO, EV ;
AIKINS, J ;
POORE, GA ;
RINZEL, SM ;
GRINDEY, GB ;
SHAW, WN ;
TODD, GC .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2393-2407
[6]   Impermeant antitumor sulfonylurea conjugates that inhibit plasma membrane NADH oxidase and growth of HeLa cells in culture. Identification of binding proteins from sera of cancer patients [J].
Kim, C ;
MacKellar, WC ;
Cho, NM ;
Byrn, SR ;
Morre, DJ .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 1997, 1324 (02) :171-181
[7]   Molecular modelling of the isothiazolo[5,4-b]pyridin-3(2H)-one derivatives [J].
MartinezMerino, V ;
Garcia, JI ;
Mayoral, JA ;
Gil, MJ ;
Zabalza, JM ;
Fayet, JP ;
Vertut, MC ;
Carpy, A ;
Gonzalez, A .
TETRAHEDRON, 1996, 52 (26) :8947-8956
[8]  
MARTINEZMERINO V, 1995, QSAR MOL MODELLING C, P478
[9]   SYNTHESIS OF 2,2'-DITHIOBIS-3-PYRIDINECARBOXYLIC AND 2,2'-TRITHIOBIS-3-PYRIDINECARBOXYLIC ACID-DERIVATIVES AS NEW POTENTIAL RADIOSENSITIZERS RADIOPROTECTORS [J].
MONGE, A ;
MARTINEZMERINO, V ;
FERNANDEZALVAREZ, E .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (01) :23-28
[10]  
Morre DJ, 1995, BBA-BIOMEMBRANES, V1240, P201