Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents. 2013

Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.

A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1-C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC(50) = 0.18 μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC(50) value of 0.09 and 0.12 μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.

UI MeSH Term Description Entries
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole
D017434 Protein Structure, Tertiary The level of protein structure in which combinations of secondary protein structures (ALPHA HELICES; BETA SHEETS; loop regions, and AMINO ACID MOTIFS) pack together to form folded shapes. Disulfide bridges between cysteines in two different parts of the polypeptide chain along with other interactions between the chains play a role in the formation and stabilization of tertiary structure. Tertiary Protein Structure,Protein Structures, Tertiary,Tertiary Protein Structures
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines
D047428 Protein Kinase Inhibitors Agents that inhibit PROTEIN KINASES. Protein Kinase Inhibitor,Inhibitor, Protein Kinase,Inhibitors, Protein Kinase,Kinase Inhibitor, Protein,Kinase Inhibitors, Protein
D049109 Cell Proliferation All of the processes involved in increasing CELL NUMBER including CELL DIVISION. Cell Growth in Number,Cellular Proliferation,Cell Multiplication,Cell Number Growth,Growth, Cell Number,Multiplication, Cell,Number Growth, Cell,Proliferation, Cell,Proliferation, Cellular

Related Publications

Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
September 2011, Bioorganic & medicinal chemistry letters,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
January 2023, Bioorganic & medicinal chemistry letters,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
October 2015, Molecules (Basel, Switzerland),
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
July 2015, Bioorganic & medicinal chemistry letters,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
January 2017, Mini reviews in medicinal chemistry,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
December 2019, BMC chemistry,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
April 2021, International journal of molecular sciences,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
May 2023, Molecules (Basel, Switzerland),
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
September 2020, Bioorganic chemistry,
Hai-Hong Wang, and Ke-Ming Qiu, and Hong-En Cui, and Yu-Shun Yang, and Yin-Luo, and Man Xing, and Xiao-Yang Qiu, and Li-Fei Bai, and Hai-Liang Zhu
January 2021, Medicinal chemistry (Shariqah (United Arab Emirates)),
Copied contents to your clipboard!