Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: Promising anticancer agents

被引：190
|
作者：
Aboraia, AS [1 ]
Abdel-Rahman, HM [1 ]
Mahfouz, NM [1 ]
El-Gendy, MA [1 ]
机构：
[1] Assiut Univ, Fac Pharm, Pharmaceut Med Chem Dept, Assiut 71526, Egypt
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 04期
关键词：
anticancer activity; 1,3,4-oxadiazoles; Mannich basest; salicylate analogs;
D O I：
10.1016/j.bmc.2005.09.053
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of 5-(2-hydroxyphenyl)-3-susstituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives was synthesized and 13 of them were selected by the National Cancer Institute (NCl) and evaluated for their in vitro anticancer activity. Seven of the investigated compounds, 3i, 3j, 3k, 3o, 3p, 3q, and 3r, displayed high anticancer activity in the primary assay. These compounds have been selected for a full anticancer screening against a 60-cell panel assay where they showed non-selective broad spectrum and promising activity against all cancer cell lines. Compounds 3j and 3k proved to be the active members in this Study compared to 5-fluorouracil and cyclophosphamide as reference drugs, respectively. Compounds 3j and 3k were identified as promising lead compounds. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1236 / 1246
页数：11
相关论文
共 50 条
  • [41] Crystal structure of 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione, C17H17FN4OS2
    Al-Omary, Fatmah A. M.
    AlRabiah, Haitham
    Ghabbour, Hazem A.
    Quah, Ching Kheng
    Fun, Hoong-Kun
    El-Emam, Ali A.
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2015, 230 (03): : 267 - 268
  • [42] Structural and spectroscopic analysis of 3-[(4-phenylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione with experimental (FT-IR, Laser-Raman) techniques and ab initio calculations
    Al-Omary, Fatmah A. M.
    Karakaya, Mustafa
    Sert, Yusuf
    Haress, Nadia G.
    El-Emam, Ali A.
    Cirak, Cagri
    JOURNAL OF MOLECULAR STRUCTURE, 2014, 1076 : 664 - 672
  • [43] Spectral and luminescent properties of 2-(2-hydroxyphenyl)-5-(2,6-difluorophenyl)-1,3,4-oxadiazole and its methoxy and benzyloxy derivatives
    Yu. M. Artyushkina
    I. E. Mikhailov
    O. N. Burov
    G. A. Dushenko
    O. I. Mikhailova
    Yu. V. Revinskii
    V. I. Minkin
    Russian Journal of General Chemistry, 2016, 86 : 2702 - 2705
  • [44] Vibrational spectroscopic studies (FT-IR, FT-Raman) and quantum chemical calculations on 5-(Adarnantan-1-yl)-3-[(4-fluoroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, a potential chemotherapeutic agent
    Al-Abdullah, Ebtehal S.
    Sebastian, Sr. S. H. Roseline
    Al-Wabli, Reem I.
    El-Emam, Ali A.
    Panicker, C. Yohannan
    Van Alsenoy, Christian
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 133 : 605 - 618
  • [45] 5-(2-Hydroxyphenyl)-4-(p-tolyl)-2,4-dihydro-1,2,4-triazole-3-thione
    Genç, S
    Dege, N
    Çetin, A
    Cansiz, A
    Sekerci, M
    Dinçer, M
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1340 - O1342
  • [46] SYNTHESIS OF NEW MANNICH BASES DERIVED FROM 5-PHENYL-1,3,4-OXADIAZOLE-2-THIONE AND INVESTIGATION OF THE CONFORMATIONAL ISOMERS OF DIMETHYL 5-(5-PHENYL-2-THIOXO-1,3,4-OXADIAZOLE-3-METHYLAMINO)ISOPHTHALATE
    Roman, Gheorghe
    Agache, Costel
    Manciulea, Ileana
    Comanita, Eugenia
    Dumitrescu, Lucia
    REVUE ROUMAINE DE CHIMIE, 2007, 52 (12) : 1103 - 1110
  • [47] Reactivity studies on a novel 4-(2-hydroxyphenyl)-1,3-dihydro-1,5-benzodiazepine-2-thione
    Gharbi, R
    Ben-Youssef, M
    Martin, MT
    Mighri, Z
    JOURNAL OF CHEMICAL RESEARCH, 2005, (04) : 257 - 261
  • [48] Theoretical study on the structure, spectra and thermodynamic property of 5-(2-aryloxy-methylbenzimidazole-1-carbadehyde)-1,3,4-oxadiazole-2-thione
    Li Xue-Mei
    Zhang Jian-Ping
    ACTA PHYSICA SINICA, 2010, 59 (11) : 7736 - 7742
  • [49] 5-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]-1,3,4-oxadiazole-2-thione
    Zhang, Xiao-Ru
    Xu, Min-Hua
    Bi, Sai
    Zhang, Shu-Sheng
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O4368 - O4369
  • [50] Efficient synthesis of novel 2,3-dihydro-1,3,5,4-thiadiazaphosphole derivatives
    Balti, Monaem
    Efrit, Mohamed Lotfi
    JOURNAL OF SULFUR CHEMISTRY, 2016, 37 (04) : 466 - 475
12345