SYNTHESIS AND CYTOTOXICITY OF 4-[(E)-HETARYL-VINYL]-6,6-DIMETHYL-2-OXO-1,2,5,6-TETRAHYDRO-PYRIDINE-3-NITRILES

被引:0
|
作者
Jansone, Daina [1 ]
Popelis, Juris [1 ]
Jaschenko, Elina [1 ]
Gulbe, Anita [1 ]
Shestakova, Irina [1 ]
Fleisher, Mendel [1 ]
Belyakov, Sergey [1 ]
Abele, Edgars [1 ]
机构
[1] Latvian Inst Organ Synth, 21 Aizkraukles St, LV-1006 Riga, Latvia
来源
HETEROCYCLIC LETTERS | 2012年 / 2卷 / 02期
关键词
4,6,6-trimethyl-2-oxo-1,2,3,4-tetrahydropyridine-3-nitrile; 4-[(E)-hetaryl-vinyl]-6,6dimethyl; 2-oxo-1,2,5,6-tetrahydro-pyridine-3-nitriles; heteroaromatic aldehydes; condensation; cytotoxicity;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A detailed investigation of condensation of 4,6,6-trimethyl-2-oxo-1,2,3,4-tetrahydropyridine-3nitrile with heteroaromatic aldehydes in the presence of catalytic amounts of NaOH in EtOH was presented. 4-[(E)-Hetaryl-vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydro-pyridine-3-nitriles were isolated in 50-97 % yields. The cytotoxicity of studied compounds towards HT-1080 (human fibrosarcoma), MG22A (mouse hepatoma) and 3T3 (mouse embryonic fibroblasts) was described. 4-[(E)-2-(6-Bromo-2-pyridyl)-vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydro-pyridine3- nitrile exhibit high activity against MG-22A cancer cell line.
引用
收藏
页码:198 / 205
页数:8
相关论文
共 50 条
  • [41] The synthesis of 4-(5-aryl-2-oxo-2,3-dihydro-3-furanylidene)amino-2,3-dimethyl-5-oxo-1-phenylpyrazolines
    Roubtsov, E
    Zalesov, VV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2001, (08): : 1130 - 1131
  • [42] 2-Amino-4-(4-chlorophenyl)-7,7dimethyl-5-oxo- 5,6,7,8-tetrahydro-4Hchromene-3-carbonitrilepropan-2-one monosolvate
    Mohamed, Shaaban K.
    Akkurt, Mehmet
    Tahir, Muhammad N.
    Abdelhamid, Antar A.
    Albayati, Mustafa R.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1965 - +
  • [43] CONDENSED TETRAHYDROBENZOTHIAZOLES .4. SYNTHESIS OF SOME 2-SUBSTITUTED 4,5,6,7-TETRAHYDRO-BENZOTHIAZOLES AND THEIR 5,5-DIMETHYL-7-OXO DERIVATIVES
    UDAPUDI, VT
    MAHAJANSHETTI, CS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (12): : 1269 - 1272
  • [44] SYNTHESIS AND RECYCLIZATION OF 2-AMINO-4-ARYL-7,7-DIMETHYL-5-OXO-3-THIOCARBAMOYL-5,6,7,8-TETRAHYDRO-4H-BENZO[B]PYRANS
    SHARANIN, YA
    GONCHARENKO, MP
    ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (02): : 460 - 463
  • [45] The synthesis and crystal structure of 2-amino-7,7-dimethyl-4-phenyl-5-oxo-5,6,7,8-tetrahydro,4-H-chromene-3-carbonitrile
    Gao, Y
    Cui, GY
    Guo, ZB
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2001, 20 (06) : 505 - 507
  • [46] 4-(4-Bromophenyl)-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione
    Xie, Min
    Deng, Changquan
    Zheng, Jie
    Zhu, Yulin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1980 - U4023
  • [47] 2-Amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-3-nitro-4,6,7,8-tetrahydro-5H-chromen-5-one hemihydrate
    Nesterov, VN
    Kislyi, VP
    Sabutis, JL
    Nesterov, VV
    Wiedenfeld, DJ
    Semenov, VV
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O741 - O744
  • [48] (R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6-tetrahydropyridin-3-yl]sulfonium
    Gordillo, Paola G.
    Teran, Joel L.
    Juarez, Jorge R.
    Mendoza, Angel
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O239 - U1208
  • [49] Synthesis of 4-(5-Aryl-2-oxo-2,3-dihydro-3-furanyliden)- amino-2,3-dimethyl-5-oxo-1-phenylpyrazolines [1]
    Rubtsov, A.E.
    Zalesov, V.V.
    Chemistry of Heterocyclic Compounds, 2001, 37 (08) : 1038 - 1039
  • [50] 4-(4-Fluorophenyl)-3-methyl-6-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
    Wang, J
    Zhu, SL
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O47 - O48