Synthesis and Cytotoxic Activity of New Vindoline Derivatives Coupled to Natural and Synthetic Pharmacophores

被引：12

作者：

Keglevich, Andras ^{[1
]}

Danyi, Leonetta ^{[1
]}

Rieder, Alexandra ^{[1
]}

Horvath, Dorottya ^{[1
]}

Szigetvari, Aron ^{[2
]}

Dekany, Miklos ^{[2
]}

Szantay, Csaba ^{[2
]}

Latif, Ahmed Dhahir ^{[3
,4
]}

Hunyadi, Attila ^{[3
,5
]}

Zupko, Istvan ^{[4
,5
]}

Keglevich, Peter ^{[1
]}

Hazai, Laszlo ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, Gellert Ter 4, H-1111 Budapest, Hungary

[2] Gedeon Richter Plc, Spectroscop Res Dept, POB 27, H-1475 Budapest 10, Hungary

[3] Univ Szeged, Interdisciplinary Excellence Ctr, Inst Pharmacognosy, Eotvos U 6, H-6720 Szeged, Hungary

[4] Univ Szeged, Interdisciplinary Excellence Ctr, Dept Pharmacodynam & Biopharm, Eotvos U 6, H-6720 Szeged, Hungary

[5] Univ Szeged, Interdisciplinary Ctr Nat Prod, Eotvos U 6, H-6720 Szeged, Hungary

来源：

MOLECULES | 2020年 / 25卷 / 04期

关键词：

organic synthesis; anticancer drugs; Vinca alkaloids; vindoline; pharmacophores; IC50; values; VINBLASTINE; VINCRISTINE; FEASIBILITY; ANTICANCER; INHIBITORS; ALKALOIDS; CHEMISTRY; INDOLE;

D O I：

10.3390/molecules25041010

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

New Vinca alkaloid derivatives were synthesized to improve the biological activity of the natural alkaloid vindoline. To this end, experiments were performed to link vindoline with various structural units, such as amino acids, a 1,2,3-triazole derivative, morpholine, piperazine and N-methylpiperazine. The structure of the new compounds was characterized by NMR spectroscopy and mass spectrometry (MS). Several compounds exhibited in vitro antiproliferative activity against human gynecological cancer cell lines with IC50 values in the low micromolar concentration range.

引用

页数：19

共 50 条

[21] Synthesis and cytotoxic activity of genistein derivatives
Zheng, Xing
Yao, Xu
Liu, Yunmei
Zheng, Zitong
Cao, Jianguo
Liao, Duanfang
MEDICINAL CHEMISTRY RESEARCH, 2010, 19 (09) : 1296 - 1306
[22] SYNTHESIS AND CYTOTOXIC ACTIVITY OF GERANYLMETHOXYHYDROQUINONE DERIVATIVES
Maturana, Evelyn Baeza
Marin, Karen Catalan
Garcia, Joan Villena
Altamirano, Hector Carrasco
Fritis, Mauricio Cuellar
Catalan, Luis Espinoza
JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, 2012, 57 (03): : 1219 - 1223
[23] Synthesis of oleandrin derivatives and their cytotoxic activity
Zhang, Yanzhi
Chen, Xubing
Zhou, Yang
Hou, Jinjun
Long, Huali
Zhang, Zijia
Lei, Min
Wu, Wanying
STEROIDS, 2020, 159
[24] Synthesis and cytotoxic activity of genistein derivatives
Xing Zheng
Xu Yao
Yunmei Liu
Zitong Zheng
Jianguo Cao
Duanfang Liao
Medicinal Chemistry Research, 2010, 19 : 1296 - 1306
[25] Synthesis and Cytotoxic Activity of Imatinib Derivatives
Chen, Shijie
He, Long
Wang, Xuewei
Gong, Xianfeng
Zhang, Hua
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (11) : 2377 - 2382
[26] Synthesis and cytotoxic activity of thiazolofluorenone derivatives
Chabane, H
Pierre, A
Leonce, S
Pfeiffer, B
Renard, P
Thiery, V
Guillaumet, G
Besson, T
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2004, 19 (06) : 567 - 575
[27] Cytotoxic activity of natural labdanes and their semi-synthetic modified derivatives from Croton oblongifolius
Sommit, D
Petsom, A
Ishikawa, T
Roengsumran, S
PLANTA MEDICA, 2003, 69 (02) : 167 - 170
[28] Cytotoxic Activity of Synthetic Chiral Amino Acid Derivatives
de Castro, Pedro P.
Siqueira, Raoni P.
Conforte, Luiza
Franco, Chris H. J.
Bressan, Gustavo C.
Amarante, Giovanni W.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2020, 31 (01) : 193 - 200
[29] SYNTHESIS AND EVALUATION OF CYTOTOXIC ACTIVITY OF NEW ACENAPHTHO TRIAZIN BENZAMIDE DERIVATIVES
Sedeh, Somayeh Adibi
Mohammadi, Mohammad Kazem
Fereidoonnezhad, Masood
Javid, Ali
REVUE ROUMAINE DE CHIMIE, 2020, 65 (05) : 467 - 472
[30] SYNTHESIS AND INVITRO CYTOTOXIC ACTIVITY OF NEW N-DIAZOACETYLGLYCINE DERIVATIVES
DELLALOGGIA, R
FURLANI, A
SAVASTANO, F
SCARCIA, V
EXPERIENTIA, 1976, 32 (05): : 636 - 638

← 1 2 3 4 5 →