Determination of 6-Nitro-7-(4'-Nitrophenyl)-5-Ethyl-4,7-Dihydropyrazolo[1,5-a]Pyrimidine-3-Carboxylate as a Potential Antitumor Agent by Voltammetry

被引:0
|
作者
Mozharovskaia, P. N. [1 ]
Ivoilova, A. V. [1 ]
Terekhova, A. A. [1 ]
Tsmokalyuk, A. N. [1 ]
Ivanova, A. V. [1 ]
Kozitsina, A. N. [1 ]
Rusinov, V. L. [1 ,2 ]
机构
[1] Ural Fed Univ, Ekaterinburg 620002, Russia
[2] Russian Acad Sci, Postovskii Inst Organ Synth, Ural Branch, Ekaterinburg 620137, Russia
关键词
quantitative substance analysis; square-wave voltammetry; pyrazolopyrimidines; nitro group; glassy-carbon electrode; antitumor agent; DRUG; NANOPARTICLES;
D O I
10.1134/S1061934823020089
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
6-Nitro-7-(4'-nitrophenyl)-5-ethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1) is one of promising antitumor compounds exhibiting biological activity against type 2 casein kinase, which is currently considered as a promising target in chemotherapy. Using the method of cyclic voltammetry, it was shown that the electrochemical activity of compound 1 in a mixed solution of Tris-HCl and ethanol (1 : 1) at pH 7.5 on a glassy-carbon electrode is due to the electrochemical reduction of the nitro group conjugated with the phenyl ring. A method was developed for the determination of compound 1 by direct cathodic square-wave voltammetry. The linearity region of the corresponding calibration curve obtained in a solution of a mixture of Tris-HCl and ethanol (1 : 1) at pH 7.5 is 5-500 mg/L (R-2 = 0.988), the limit of detection is 0.8 mg/L, the limit of quantification is 2.4 mg/L. The accuracy of the developed procedure is close to 100%, the relative standard deviation is 1.4%.
引用
收藏
页码:378 / 384
页数:7
相关论文
共 50 条
  • [41] Synthesis and X-ray structural studies of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine L-arginine and piperidine salts
    Slepukhin, Pavel A.
    Voinkov, Egor K.
    Ulomskiy, Eugeny N.
    Savateev, Konstantin V.
    Kopchuk, Dmitry S.
    Zyryanov, Grigory V.
    Fedotov, Victor V.
    Charushin, Valery N.
    Chupakhin, Oleg N.
    Rusinov, Vladimir L.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (10) : 989 - 992
  • [42] SYNTHESIS OF 2-TRIFLUOROMETHYL-4,7-DIHYDRO-7-OXO-(1,2,4)TRIAZOLO[1,5-a]PYRIMIDINE-6-CARBOXYLIC ACID DERIVATIVES AS POTENTIAL ANTIMYCO-BACTERIAL AND ANTIMICROBIAL AGENTS
    El-Koussi, Nawal A.
    BULLETIN OF PHARMACEUTICAL SCIENCES, 2008, 31 : 109 - 121
  • [43] Discovery of ((S)-5-(Methoxymethyl)-7-(1-methyl-1H-indol-2-yl)-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone As a Potent and Selective IKur Inhibitor (vol 55, pg 3036, 2012)
    Finlay, Heather J.
    Lloyd, John
    Vaccaro, Wayne
    Kover, Alexander
    Yan, Lin
    Bhave, Gauri
    Prol, Joseph
    Tram Huynh
    Bhandaru, Rao
    Caringal, Yolanda
    DiMarco, John
    Gan, Jinping
    Harper, Tim
    Huang, Christine
    Conder, Mary Lee
    Sun, Huabin
    Levesque, Paul
    Blanar, Michael
    Atwal, Karnail
    Wexler, Ruth
    JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (17) : 7133 - 7133
  • [44] Three-component green synthesis of 6-ethoxycarbonyl-5-methyl-7-(thien-2-yl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine, a promising antituberculosis drug
    Titova, Yu. A.
    Fedorova, O. V.
    Rusinov, G. L.
    Charushin, V. N.
    RUSSIAN CHEMICAL BULLETIN, 2019, 68 (12) : 2271 - 2274
  • [45] Three-component green synthesis of 6-ethoxycarbonyl-5-methyl-7-(thien-2-yl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine, a promising antituberculosis drug
    Yu. A. Titova
    O. V. Fedorova
    G. L. Rusinov
    V. N. Charushin
    Russian Chemical Bulletin, 2019, 68 : 2271 - 2274
  • [46] IMINO-ENAMINE TAUTOMERISM OF DIHYDROAZOLOPYRIMIDINES .3. 5-ARYL-SUBSTITUTED 4,7(6,7)-DIHYDRO-1,2,4-TRIAZOLO[1,5-A]PYRIMIDINES
    DESENKO, SM
    ORLOV, VD
    LIPSON, VV
    SHISHKIN, OV
    LINDEMAN, SV
    STRUCHKOV, YT
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1991, (11): : 1539 - 1544
  • [47] REACTION OF 3-AMINOPYRAZOLE-4-CARBOXAMIDES WITH ETHYL 3-ETHOXY-METHYLENE-2,4-DIOXOVALERATE - SYNTHESIS OF 6-ACETYL-7-CARBETHOXY-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXAMIDE
    KURIHARA, T
    SAKAMOTO, Y
    HETEROCYCLES, 1979, 12 (03) : 397 - 400
  • [48] NITROGEN BRIDGEHEAD COMPOUNDS .12. REACTION OF THE ETHYL 6-METHYL-L-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATE WITH IMINIUM CHLORIDES
    HERMECZ, I
    BITTER, I
    HORVATH, A
    TOTH, G
    MESZAROS, Z
    TETRAHEDRON LETTERS, 1979, (27) : 2557 - 2558
  • [49] IPSO-SUBSTITUTION OF AN ACYL GROUP IN REACTIONS OF 3-ACYL-SUBSTITUTED ETHYL 7,8-DIFLUORO-5-OXO-5,9A-DIHYDROPYRAZOLO[1,5-A]QUINOLINE-4-CARBOXYLATES WITH ELECTROPHILIC REAGENTS
    AZEV, YA
    SHORSHNEV, SV
    ALEXEEV, SG
    CHARUSHIN, VN
    CHUPAKHIN, ON
    MENDELEEV COMMUNICATIONS, 1993, (03) : 99 - 100
  • [50] One-pot four-component synthesis of methyl 4-(4-chlorophenyl)-5,7-dioxo-1-phenyl-1,4,5,6,7,8-hexahydropyrazolo [4′,3′:5,6] pyrano [2,3-d] pyrimidine-3-carboxylate; a green approach
    Yadav, Maruti B.
    Lim, Kwon Taek
    Kim, Jong Su
    Jeong, Yeon Tae
    TETRAHEDRON LETTERS, 2021, 65