Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells

被引:34
|
作者
Tandon, Vishnu K. [1 ]
Maurya, Hardesh K. [2 ]
Kumar, Sandeep [3 ]
Rashid, Aijaz [4 ]
Panda, Dulal [4 ]
机构
[1] Inst Engn & Technol, Dept Appl Sci, Lucknow 226020, Uttar Pradesh, India
[2] Cent Inst Med & Aromat Plants, Med Chem Dept, Lucknow 226015, Uttar Pradesh, India
[3] Univ Lucknow, Dept Chem, Lucknow 226007, Uttar Pradesh, India
[4] Indian Inst Technol, Dept Biosci & Bioengn, Bombay 400076, Maharashtra, India
来源
RSC ADVANCES | 2014年 / 4卷 / 24期
关键词
BIOLOGICAL EVALUATION; 1,4-NAPHTHOQUINONE DERIVATIVES; ANTIBACTERIAL AGENTS; NUCLEOPHILIC-SUBSTITUTION; KINETIC STABILIZATION; MICROTUBULE DYNAMICS; AQUEOUS SUSPENSION; ANTICANCER AGENTS; ANTIFUNGAL AGENTS; ORGANIC-REACTIONS;
D O I
10.1039/c3ra47720g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This article describes the preparation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones by an environmentally benign short synthetic route with the goal of finding 1,4-naphthoquinone derivatives that induce apoptosis in cancer cells. We have identified three most active naphthoquinones 10, 12 and 15 that potently induce apoptosis in human cervical carcinoma (HeLa) cells. One of these three compounds perturbed both microtubule and actin filaments.
引用
收藏
页码:12441 / 12447
页数:7
相关论文
共 50 条
  • [1] Synthesis of Mixed Aryl 2,3-Diarylsulphanyl-1,4-naphthoquinones
    Singh, W. Marjit
    Baruah, Jubaraj B.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (08) : 1433 - 1442
  • [2] SYNTHESIS OF ACETYLATED GLYCOSIDES OF 2,3-DIHYDROXY-1,4-NAPHTHOQUINONES
    POLONIK, SG
    TOLKACH, AM
    UVAROVA, NI
    KHIMIYA PRIRODNYKH SOEDINENII, 1984, (01): : 121 - 122
  • [3] SYNTHESIS OF N-ALKYLAMINOSUBSTITUTED 2,3-BISAMINO-1,4-NAPHTHOQUINONES
    RUBASHKO, SV
    MIKHALINA, TV
    FOKIN, EP
    IZVESTIYA SIBIRSKOGO OTDELENIYA AKADEMII NAUK SSSR SERIYA KHIMICHESKIKH NAUK, 1990, (06): : 121 - 127
  • [4] Synthesis of 2,3-Disubstituted 1,4-Naphthoquinones as Antiplatelet Agents
    Lien, Jin-Cherng
    Wu, Chi-Rei
    Hour, Mann-Jen
    Huang, Li-Jiau
    Huang, Tur-Fu
    Kuo, Sheng-Chu
    ARCHIV DER PHARMAZIE, 2008, 341 (10) : 639 - 644
  • [5] An unusual heterocyclization of 2,3-diacetylenyl-1,4-naphthoquinones
    Shvartsberg, MS
    Ivanchikova, ID
    Lebedeva, NI
    TETRAHEDRON LETTERS, 2000, 41 (30) : 5757 - 5760
  • [6] SYNTHESIS OF 2,3-DIALKYL-6,7-DICHLORO-1, 4-NAPHTHOQUINONES AND 2,3-DIALKYL-6,7-DIBROMO-1,4-NAPHTHOQUINONES
    ASHNAGAR, A
    BRUCE, JM
    LLOYDWILLIAMS, P
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03): : 559 - 561
  • [7] Palladium-catalysed cross coupling of arylboronic acids with 2-chloro-1,4-naphthoquinones: the synthesis of 2-aryl- and 2,3-bisaryl-1,4-naphthoquinones
    Best, WM
    Sims, CG
    Winslade, M
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (06) : 401 - 404
  • [8] Diene synthesis of 2,3-dialkyl-1,4-naphthoquinones related to vitamin K
    Fieser, LF
    Wieghard, CW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 : 153 - 155
  • [9] SYNTHESIS OF 2-ALKYL-1,4-NAPHTHOQUINONES BY ALKYLBORATION
    ERNST, BP
    LAATSCH, H
    SYNTHESIS-STUTTGART, 1992, (05): : 461 - 462
  • [10] SYNTHESIS OF 2-PIPERAZINODERIVATIVES OF 1,4-NAPHTHOQUINONES
    BEREZHNAYA, VN
    SHISHKINA, RP
    FOKIN, EP
    IZVESTIYA SIBIRSKOGO OTDELENIYA AKADEMII NAUK SSSR SERIYA KHIMICHESKIKH NAUK, 1987, (02): : 101 - 104