Synthesis and Antiproliferative and Antimicrobial Activity of Methyl-6-Amino-3-Acyl-4-Aryl-5-Cyano-4H-Pyran-2-Carboxylates and their Derivatives

被引:17
作者
Sheverdov, V. P. [1 ]
Andreev, A. Yu. [1 ]
Nasakin, O. E. [1 ]
Gein, V. L. [2 ]
机构
[1] Ulyanov Chuvash State Univ, Cheboksary 428015, Russia
[2] Perm State Pharmaceut Acad, Perm 614990, Russia
关键词
pyrans; decyclization; antitumor activity; methyl 2,4-dioxobutanoates; tumor cells; inhibition;
D O I
10.1007/s11094-014-1114-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Antiproliferative and antimicrobial activity of methyl-6-amino-3-acyl-4-aryl-5-cyano-4H-pyran-2-carboxylates and their analogs that were synthesized from methyl-2,4-dioxobutanoates was studied. Studies of their antiproliferative activity at the USA National Cancer Institute under the program NCI 60 Cell One-Dose Screen found that methyl-6-amino-5-cyano-4-(furan-2-yl)-3-(3-methoxybenzoyl)-4H-pyran-2-carboxylate had the highest activity, greater than those of busulfan and cisplatin. Methyl-6-amino-3-acetyl-4-phenyl-5-cyano-4H-pyran-2-carboxylate had antimicrobial activity that was comparable with that of chloramine.
引用
收藏
页码:379 / 382
页数:4
相关论文
共 18 条
  • [1] Anticancer activities of some newly synthesized pyridine, pyrane, and pyrimidine derivatives
    Amr, Abdel-Galil E.
    Mohamed, Ashraf M.
    Mohamed, Salwa F.
    Abdel-Hafez, Nagla A.
    Hammam, Abu El-Fotooh G.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) : 5481 - 5488
  • [2] Aver'yanova E. V., 2010, PHYSL ACTIVE COMPOUN
  • [3] Eid Fathy A., 2004, Acta Pharmaceutica (Zagreb), V54, P13
  • [4] Synthesis of new 2-thiouracil-5-sulphonamide derivatives with antibacterial and antifungal activity
    Fathalla, OA
    Awad, SM
    Mohamed, MS
    [J]. ARCHIVES OF PHARMACAL RESEARCH, 2005, 28 (11) : 1205 - 1212
  • [5] Goodman M., 1973, ORGANIC MOL ACTION
  • [6] JOSHI KC, 1988, J INDIAN CHEM SOC, V65, P202
  • [7] Total synthesis of (+)-exiguolide
    Kwon, Min Sang
    Woo, Sang Kook
    Na, Seong Wook
    Lee, Eun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) : 1733 - 1735
  • [8] Structural simplification of bioactive natural products with multicomponent synthesis.: 2.: Antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones
    Magedov, Igor V.
    Manpadi, Madhuri
    Ogasawara, Marcia A.
    Dhawan, Adriana S.
    Rogelj, Snezna
    Van Slambrouck, Severine
    Steelant, Wim F. A.
    Evdokimov, Nikolai M.
    Uglinskii, Pavel Y.
    Elias, Eerik M.
    Knee, Erica J.
    Tongwa, Paul
    Antipin, Mikhail Yu.
    Kornienko, Alexander
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (08) : 2561 - 2570
  • [9] Friedlander reaction on 2-amino-3-cyano-4H-pyrans:: Synthesis of derivatives of 4H-pyran[2,3-b] quinoline, new tacrine analogues
    Martínez-Grau, A
    Marco, JL
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (24) : 3165 - 3170
  • [10] Mashkovskii M. D., 2007, DRUGS