Synthesis and biological evaluation of novel 4,7-dihydroxycoumarin derivatives as anticancer agents

被引：30
作者：
Govindaiah, Pilli [1 ]
Dumala, Naresh [2 ]
Grover, Paramjit [2 ]
Prakash, M. Jaya [1 ]
机构：
[1] Natl Inst Technol, Dept Chem, Rourkela 769008, Odisha, India
[2] CSIR Indian Inst Chem Technol, Appl Biol Div, Toxicol Unit, Hyderabad 500007, Telangana, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2019年 / 29卷 / 14期
关键词：
4,7-Dihydoxycoumarin; Acryloylcyanohydrazone; Anticancer; Cell cycle; Tubulin; Molecular docking; CYTOTOXIC ACTIVITY; MOLECULAR DOCKING; COUMARIN HYBRIDS; POTENT; HYDRAZONES; INHIBITORS; BEARING; DESIGN;
D O I：
10.1016/j.bmcl.2019.05.008
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of novel 4,7-dihydroxycoumarin based acryloylcyanohydrazone derivatives were synthesized and evaluated for antiproliferative activity against four different cancer cell lines (A549, HeLa, SKNSH, and MCF7). Most of the compounds displayed potent cytotoxicity with IC50 values ranging from 3.42 to 31.28 mu M against all the tested cancer cell lines. The most active compound, 8h was evaluated for pharmacological mechanistic studies on cell cycle progression and tubulin polymerization inhibition assay. The results revealed that the compound 8h induced the cell cycle arrest at G2/M phase and inhibited tubulin polymerization with IC50 = 6.19 mu M. Experimental data of the tubulin polymerization inhibition assay was validated by molecular docking technique and the results exhibited strong hydrogen bonding interactions with amino acids (ASN-101, TYR-224, ASN-228, LYS-254) of tubulin.
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收藏
页码：1819 / 1824
页数：6
相关论文
共 33 条
[1]   Coumarins from Angelica decursiva inhibit α-glucosidase activity and protein tyrosine phosphatase 1B [J].
Ali, Md Yousof ;
Jannat, Susoma ;
Jung, Hyun Ah ;
Jeong, Hyong Oh ;
Chung, Hae Young ;
Choi, Jae Sue .
CHEMICO-BIOLOGICAL INTERACTIONS, 2016, 252 :93-101
[2]   Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents [J].
Basanagouda, Mahantesha ;
Jambagi, Vishwanath B. ;
Barigidad, Nivedita N. ;
Laxmeshwar, Sandeep S. ;
Devaru, Venkatesh ;
Narayanachar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 74 :225-233
[3]   Design, synthesis and molecular modeling of new 4-phenylcoumarin derivatives as tubulin polymerization inhibitors targeting MCF-7 breast cancer cells [J].
Batran, Rasha Z. ;
Kassem, Asmaa F. ;
Abbas, Eman M. H. ;
Elseginy, Samia A. ;
Mounier, Marwa M. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (12) :3474-3490
[4]   New Coumarin Derivatives as Anti-Breast and Anti-Cervical Cancer Agents Targeting VEGFR-2 and p38 MAPK [J].
Batran, Rasha Z. ;
Dawood, Dina H. ;
El-Seginy, Samia A. ;
Ali, Mamdouh M. ;
Maher, Timothy J. ;
Gugnani, Kuljeet S. ;
Rondon-Ortiz, Alejandro N. .
ARCHIV DER PHARMAZIE, 2017, 350 (09)
[5]  
Behrami A, 2012, J CHEM PHARM RES, V4, P2495
[6]  
Burger AM, 2014, CANCER DRUG DISCOV D, P23, DOI 10.1007/978-1-4614-9135-4_2
[7]   Recent advances in microtubule-stabilizing agents [J].
Cao, Ya-Nan ;
Zheng, Ling -Li ;
Wang, Dan ;
Liang, Xiao-Xia ;
Gao, Feng ;
Zhou, Xian-Li .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :806-828
[8]   Novel sulfonamide bearing coumarin scaffolds as selective inhibitors of tumor associated carbonic anhydrase isoforms IX and XII [J].
Chandak, Navneet ;
Ceruso, Mariangela ;
Supuran, Claudiu T. ;
Sharma, Pawan K. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (13) :2882-2886
[9]   Synthesis, characterization, molecular docking and cytotoxic activity of novel plumbagin hydrazones against breast cancer cells [J].
Dandawate, Prasad ;
Khan, Ejazuddin ;
Padhye, Subhash ;
Gaba, Himanshi ;
Sinha, Swati ;
Deshpande, Jyoti ;
Swamy, K. Venkateswara ;
Khetmalas, Madhukar ;
Ahmad, Aamir ;
Sarkar, Fazlul H. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (09) :3104-3108
[10]   Microtubule-binding agents: a dynamic field of cancer therapeutics [J].
Dumontet, Charles ;
Jordan, Mary Ann .
NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (10) :790-803
1234