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

页码：12441 / 12447

页数：7

共 50 条

[21] Synthesis and in vitro antiproliferative evaluation of 3-acyl-2-arylamino-1,4-naphthoquinones
Rios, David
Benites, Julio
Torrejon, Felipe
Theoduloz, Cristina
Valderrama, Jaime A.
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (09) : 4149 - 4155
[22] PHOTOCHEMICAL REDUCTION OF 2,3-DIHYDRO-2,3-METHANO-1,4-NAPHTHOQUINONES WITH XANTHENE
MARUYAMA, K
TANIOKA, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (09) : 2647 - 2648
[23] Synthesis and in vitro antiproliferative evaluation of 3-acyl-2-arylamino-1,4-naphthoquinones
David Ríos
Julio Benites
Felipe Torrejón
Cristina Theoduloz
Jaime A. Valderrama
Medicinal Chemistry Research, 2014, 23 : 4149 - 4155
[24] Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones
Leyva, Elisa
Lopez, Lluvia I.
Garcia de la Cruz, Ramon F.
Espinosa-Gonzalez, Claudia G.
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (03) : 1813 - 1827
[25] Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones
Elisa Leyva
Lluvia I. López
Ramón F. García de la Cruz
Claudia G. Espinosa-González
Research on Chemical Intermediates, 2017, 43 : 1813 - 1827
[26] Synthesis and Transformations of 2-Hydroxy-3-arylazo-1,4-naphthoquinones
A. L. Romanyuk
O. P. Polishchuk
B. L. Litvin
N. I. Ganushchak
Russian Journal of General Chemistry, 2002, 72 : 251 - 254
[27] Synthesis of 2-chloroalkyl-1,4-naphthoquinones and their reactivity in the formation of autocomplexes
Prezhdo, V
Prezhdo, O
Ovsiankina, E
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1995, 51 (14): : 2465 - 2472
[28] PHOTOCHEMISTRY OF EPOXYQUINONES - PHOTOINDUCED CYCLOADDITION OF 2,3-EPOXY-1,4-NAPHTHOQUINONES WITH OLEFINS
MARUYAMA, K
ARAKAWA, S
OYSUKI, T
TETRAHEDRON LETTERS, 1975, (29) : 2433 - 2436
[29] Synthesis and transformations of 2-Hydroxy-3-arylazo-1,4-naphthoquinones
Romanyuk, AL
Polishchuk, OP
Litvin, BL
Ganushchak, NI
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2002, 72 (02) : 251 - 254
[30] ANTICOAGULANTS .I. SYNTHESIS OF 2,3-DISUBSTITUTED 1,4-NAPHTHOQUINONES AND 4-HYDROXYCOUMARINS
KRALT, T
BOTS, JPL
MOED, HD
ARIENS, EJ
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, 1967, 86 (10): : 961 - &

← 1 2 3 4 5 →