Synthesis of Novel Stigmasterol Derivatives with 1,2,3-Triazole Substituent at the C-3 Position and Their Cytotoxicity Toward HeLa, HGC-27, and HEK-293T Cells

被引:0
作者
Wang, Yong [1 ,2 ]
Wang, Wei [1 ,2 ]
Liu, Cong-Jun [1 ]
Gao, Song [1 ]
Xiong, Yong-Ge [1 ]
Gao, Tian-Zeng [3 ]
Li, Wei-Shi [4 ]
Li, Jing-Jing [1 ]
机构
[1] Zhengzhou Inst Technol, Coll Chem Engn & Food Technol, Zhengzhou 450044, Henan, Peoples R China
[2] Zhengzhou Inst Technol, Postdoctoral Innovat Practice Base, Zhengzhou 450044, Henan, Peoples R China
[3] Henan Ground Biol Sci & Technol Co Ltd, Zhengzhou 450001, Henan, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
stigmasterol; 1,2,3-triazol; antitumor activity; RECENT ADVANCE; STEROIDS; HYDRAZONE;
D O I
10.1007/s10600-024-04261-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Eight new stigmasterol derivatives possessing 1,2,3-triazoles moiety were synthesized by a 1,3-dipolar cycloaddition reaction. All the compounds were characterized by IR, NMR, and HR-MS. In addition, human cervical cancer cells (HeLa), human gastric cancer cells (HGC-27), and human renal epithelial cells (HEK-293T) were selected to study the antitumor activity of the synthesized compounds. The results demonstrated that compounds 3c and 3d exhibited better inhibitory activity against the tested tumor cell lines. The IC50 value of the inhibitory activity on HeLa was 52.3 mu mol center dot L-1 and 31.4 mu mol center dot L-1, and 40.6 mu mol center dot L-1 and 44.6 mu mol center dot L-1 for HGC-27, respectively.
引用
收藏
页码:92 / 97
页数:6
相关论文
共 16 条
[1]   Man-Made Cytotoxic Steroids: Exemplary Agents for Cancer Therapy [J].
Bansal, Ranju ;
Acharya, Pratap Chandra .
CHEMICAL REVIEWS, 2014, 114 (14) :6986-7005
[2]  
Chen SJ, 2011, CHINESE J ORG CHEM, V31, P187
[3]   Synthesis and Biological Activity of Steroids Bearing Aromatic Rings and Heterocycles [J].
Cui Jianguo ;
Liu Liang ;
Gan Chunfang ;
Xiao Qi ;
Huang Yanmin .
PROGRESS IN CHEMISTRY, 2014, 26 (2-3) :320-333
[4]  
Frank E., 2013, MOL BIOL+, V127, P301
[5]   New Synthesis of Castasterone [J].
Khripach, V. A. ;
Zhabinskii, V. N. ;
Gurskii, A. L. ;
Kolosova, A. V. ;
Gulyakevich, O. V. ;
Konstantinova, O. V. ;
Antonchik, A. V. ;
Pap, A. A. .
CHEMISTRY OF NATURAL COMPOUNDS, 2018, 54 (01) :117-123
[6]   New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities [J].
Krstic, Natalija M. ;
Bjelakovic, Mira S. ;
Pavlovic, Vladimir D. ;
Robeyns, Koen ;
Juranic, Zorica D. ;
Matic, Ivana ;
Novakovic, Irena ;
Sladic, Dusan M. .
STEROIDS, 2012, 77 (05) :558-565
[7]   Synthesis of 3-O-propargylated betulinic acid and its 1,2,3-triazoles as potential apoptotic agents [J].
Majeed, Rabiya ;
Sangwan, Payare L. ;
Chinthakindi, Praveen K. ;
Khan, Imran ;
Dangroo, Nisar A. ;
Thota, Niranjan ;
Hamid, Abid ;
Sharma, Parduman R. ;
Saxena, Ajit K. ;
Koul, Surrinder .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 :782-792
[8]   Steroids and Fatty Acid Esters from Cyperus sexangularis Leaf and Their Antioxidant, Anti-Inflammatory and Anti-Elastase Properties [J].
Miya, Gugulethu Mathews ;
Oriola, Ayodeji Oluwabunmi ;
Payne, Bianca ;
Cuyler, Marize ;
Lall, Namrita ;
Oyedeji, Adebola Omowunmi .
MOLECULES, 2023, 28 (08)
[9]   Reaction of pregnenolone with cyanoacetylhydrazine: Novel synthesis of hydrazide-hydrazone, pyrazole, pyridine, thiazole, thiophene derivatives and their cytotoxicity evaluations [J].
Mohareb, Rafat M. ;
Al-Omran, Fatima .
STEROIDS, 2012, 77 (14) :1551-1559
[10]   Synthesis of modified steroids as a novel class of non-ulcerogenic, anti-inflammatory and anti-nociceptive agents [J].
Mohareb, Rafat M. ;
Elmegeed, Gamal A. ;
Abdel-Salam, Omar M. E. ;
Doss, Senot H. ;
William, Marian G. .
STEROIDS, 2011, 76 (10-11) :1190-1203