The synthesis and biological activity of the 3-ferrocenylpropenamides derived from 5(4H)-oxazolones

被引：1

作者：

Wieczorek-Blauz, Anna ^{[1
]}

Bzauz, Andrzej ^{[2
]}

Rychlik, Blazej ^{[2
]}

Plazuk, Damian ^{[1
]}

机构：

[1] Univ Lodz, Fac Chem, Dept Organ Chem, Tamka 12, PL-91403 Lodz, Poland

[2] Univ Lodz, Fac Biol & Environm Protect, Dept Mol Biophys, Cytometry Lab, 141-143 Pomorska St, PL-90236 Lodz, Poland

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2021年 / 953卷

关键词：

FERROCENYL; DERIVATIVES; MODE; INHIBITORS; DESIGN; ESTERS; SERIES; ALPHA; CELLS;

D O I：

10.1016/j.jorganchem.2021.122026

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We described a synthesis of new 3-ferrocenylpropenamides prepared by oxazolone-ring opening reac-tion with various primary and secondary amines. The antiproliferative activities of the obtained com-pounds were screened on human tumor cell lines (HCT116, SW620, Colo 205, MCF-7, HepG2 and A549). We found that the newly prepared compounds showed cytotoxicity in micromolar range, with the most active piperidinyl derivative 6b with IC50 values 8.1 mu M (MCF-7), 9.6 mu M (SW620) and 13.2 mu M (Colo 205). Cell cycle analysis showed that 6b increases number of G2/M arrested cells. (c) 2021 Elsevier B.V. All rights reserved.

引用

页数：7

共 50 条

[21] [Et3NH][HSO4]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones
Parveen, Mehtab
Ahmad, Faheem
Malla, Ali Mohammed
Azaz, Shaista
Silva, Manuela Ramos
Pereira Silva, P. S.
RSC ADVANCES, 2015, 5 (65) : 52330 - 52346
[22] New Heterocyclic Compounds Derived from 4,6-Diamino-3-cyano-2-methylthiopyridine and their Biological Activity
Ghattas, Abd El-Badih A. G.
Khodairy, Ahmed
Moustafa, Hassan M.
Hussein, Bahgat R. M.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) : 879 - 888
[23] Synthesis, structure and biological activity of 3(5)-trifluoromethy1-1H-pyrazoles derived from hemicurcuminoids
Nieto, Carla I.
Pilar Cabildo, M.
Pilar Cornago, M.
Sanz, Dionisia
Claramunt, Rosa M.
Alkorta, Ibon
Elguero, Jose
Garcia, Jose A.
Lopez, Ana
Acuna-Castroviejo, Dario
JOURNAL OF MOLECULAR STRUCTURE, 2015, 1100 : 518 - 529
[24] Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues
Ruffoni, Alessandro
Casoni, Alessandro
Pellegrino, Sara
Gelmi, Maria Luisa
Soave, Raffaella
Clerici, Francesca
TETRAHEDRON, 2012, 68 (07) : 1951 - 1962
[25] Synthesis and Biological Activity Evaluation of Novel 5-Methyl-7-phenyl-3H-thiazolo[4,5-b]pyridin-2-ones
Lozynskyi, Andrii
Konechnyi, Yulian
Senkiv, Julia
Yushyn, Ihor
Khyluk, Dmytro
Karpenko, Olexandr
Shepeta, Yulia
Lesyk, Roman
SCIENTIA PHARMACEUTICA, 2021, 89 (04)
[26] Synthesis of dihydro-2H-pyran-3(4H)-one
Mityuk, Andrey P.
Denisenko, Aleksandr V.
Grygorenko, Oleksandr O.
Tolmachev, Andrey A.
ARKIVOC, 2012, : 226 - 230
[27] Synthesis of 3-(trifluoromethyl)-1-(perfluorophenyl)-1H-pyrazol-5(4H)-one derivatives via Knoevenagel condensation and their biological evaluation
Dengale, Sujata G.
Akolkar, Hemantkumar N.
Karale, Bhausaheb K.
Darekar, Nirmala R.
Mhaske, Sadhana D.
Shaikh, Mubarak H.
Raut, Dipak N.
Deshmukh, Keshav K.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2021, 68 (04) : 657 - 668
[28] Synthesis of 2H-1,4-Benzoxazin-3(4H)-ones via Smiles Rearrangement
Zhou, Jia-Zhou
Li, Zhu-Bo
Yang, Hao
He, Xiao-Yan
Wang, Li-Ying
Tian, Xiao
Lv, Ting Ting
Zuo, Hua
ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (07) : 2947 - 2950
[29] Synthesis of Novel Heterocycles Derived from 4-Arylmethylene-2-phenyl-1,3-oxazole-5(4H)-ones
Youssef, Ahmed S. A.
Kandeel, Kamal A.
Abou-Elmagd, Wael S. I.
Haneen, David S. A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (03) : 809 - 816
[30] Synthesis and biological activity of ethyl 2-(5-methyl-3-arylisoxazole-4-carboxamido)-4-alkylthiazole-5-carboxylate
Wang, Wei
Wang, Lie-Ping
Mao, Min-Zhen
Zhang, Xiao-Guang
Zheng, Xiao-Rui
Huang, Xiao-Ying
Xue, Chao
Ning, Bin-Ke
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2018, 193 (03) : 164 - 167

← 1 2 3 4 5 →