scholarly journals Position-Selective Synthesis and Biological Evaluation of Four Isomeric A-Ring Amino Derivatives of the Alkaloid Luotonin A

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 716 ◽  
Author(s):  
Amra Ibric ◽  
Stefan Eckerstorfer ◽  
Martin Eder ◽  
Ivan Louko ◽  
Leopold Tunjic ◽  
...  
Keyword(s):  
Topoisomerase I ◽  
Human Tumor ◽  
Biological Evaluation ◽  
Transfer Hydrogenation ◽  
Amino Compound ◽  
M Cell ◽  
Luotonin A ◽  
Amino Derivatives ◽  
Derivatives Of

Following two orthogonal synthetic routes, a series of all four possible A-ring amino derivatives of the natural product Luotonin A (a known Topoisomerase I inhibitor) was synthesized. In both strategies, intramolecular cycloaddition reactions are the key step. The target compounds were obtained in good yields by mild catalytic transfer hydrogenation of the corresponding nitro precursors. In-vitro evaluation of the antiproliferative activity towards human tumor cell lines revealed the 4-amino compound (5b) to be the most effective agent, showing an interesting profile of cytotoxic activity. Among other effects, a significant G2/M cell cycle arrest was observed for this compound, suggesting that either Topoisomerase I is not the only biological target, or that some atypical mechanism is responsible for inhibition of this enzyme.

scholarly journals Synthesis and cytotoxicity of 3-amino-glycyrrhetinic acid derivatives

2018 ◽  
Vol 7 (1) ◽  
pp. 39-55 ◽  
Author(s):  
Martin Sahn ◽  
Anja Grupe ◽  
Lucie Heller ◽  
Hidayat Hussain ◽  
Ahmed Al-Harrasi ◽  
...  
Keyword(s):  
Parent Compound ◽  
Human Tumor ◽  
In Vitro Cytotoxicity ◽  
Glycyrrhetinic Acid ◽  
Human Tumor Cell Lines ◽  
Amino Esters ◽  
Cytotoxic Compound ◽  
Amino Derivatives ◽  
Derivatives Of

The aim of this study was to prepare 3-hydroximino- and 3-amino derivatives of glycyrrhetinic acid and derivatives to evaluate their in vitro cytotoxicity for a panel of human tumor cell lines. Thus, commercially available glycyrrhetinic acid (1) was acetylated or oxidized at position C-3 and transformed into a variety of different esters and amides followed by their conversion to 3-oximes and amines. While the parent compound was not cytotoxic at all, the 3-amino esters are highly cytotoxic. Interestingly, 3-amino amides were significantly less cytotoxic than 3-amino esters. The (3b, 18b, 20b) Benzyl 3-amino-11-oxoolean-12-en-30-oate was the most cytotoxic compound of this series showing an EC50 = 1.3 mM for 518A2 melanoma cells.

Design and synthesis of herboxidiene derivatives that potently inhibit in vitro splicing

2021 ◽  
Vol 19 (6) ◽  
pp. 1365-1377
Author(s):  
Arun K. Ghosh ◽  
Srinivasa Rao Allu ◽  
Guddeti Chandrashekar Reddy ◽  
Adriana Gamboa Lopez ◽  
Patricia Mendez ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Design And Synthesis ◽  
In Vitro Splicing ◽  
Enantioselective Syntheses ◽  
Derivatives Of

Enantioselective syntheses of C-6 modified derivatives of herboxidiene and their biological evaluation in splicing inhibitory assay.

Synthesis, characterization and in vitro and in vivo anticancer activity of Pt(iv) derivatives of [Pt(1S,2S-DACH)(5,6-dimethyl-1,10-phenanthroline)]

2017 ◽  
Vol 46 (21) ◽  
pp. 7005-7019 ◽  
Author(s):  
Benjamin W. J. Harper ◽  
Emanuele Petruzzella ◽  
Roman Sirota ◽  
Fernanda Fabiola Faccioli ◽  
Janice R. Aldrich-Wright ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Biological Evaluation ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

Synthesis and biological evaluation in vitro and in vivo of functionalized Pt(iv) derivatives of Pt56MeSS.

scholarly journals Synthesis and Biological Evaluation of Novel Triple-Modified Colchicine Derivatives as Potent Tubulin-Targeting Anticancer Agents

Cells ◽  
2018 ◽  
Vol 7 (11) ◽  
pp. 216 ◽  
Author(s):  
Urszula Majcher ◽  
Greta Klejborowska ◽  
Magdalena Kaik ◽  
Ewa Maj ◽  
Joanna Wietrzyk ◽  
...  
Keyword(s):  
Cell Lines ◽  
Anticancer Agents ◽  
Binding Free Energy ◽  
3D Structure ◽  
Human Tumor ◽  
Biological Evaluation ◽  
Energy Estimates ◽  
Colchicine Derivatives ◽  
Mcf 7

Specific modifications of colchicine followed by synthesis of its analogues have been tested in vitro with the objective of lowering colchicine toxicity. Our previous studies have clearly shown the anticancer potential of double-modified colchicine derivatives in C-7 and C-10 positions. Here, a series of novel triple-modified colchicine derivatives is reported. They have been obtained following a four-step strategy. In vitro cytotoxicity of these compounds has been evaluated against four human tumor cell lines (A549, MCF-7, LoVo, and LoVo/DX). Additionally, the mode of binding of the synthesized compounds was evaluated in silico using molecular docking to a 3D structure of β-tubulin based on crystallographic data from the Protein Data Bank and homology methodology. Binding free energy estimates, binding poses, and MlogP values of the compounds were obtained. All triple-modified colchicine derivatives were shown to be active at nanomolar concentrations against three of the investigated cancer cell lines (A549, MCF-7, LoVo). Four of them also showed higher potency against tumor cells over normal cells as confirmed by their high selectivity index values. A vast majority of the synthesized derivatives exhibited several times higher cytotoxicity than colchicine, doxorubicin, and cisplatin.

scholarly journals Novel Ester and Acid Derivatives of the 1,5-Diarylpyrrole Scaffold as Anti-Inflammatory and Analgesic Agents. Synthesis and in Vitro and in Vivo Biological Evaluation

2010 ◽  
Vol 53 (2) ◽  
pp. 723-733 ◽  
Author(s):  
Mariangela Biava ◽  
Giulio C. Porretta ◽  
Giovanna Poce ◽  
Claudio Battilocchio ◽  
Fabrizio Manetti ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Analgesic Agents ◽  
Anti Inflammatory ◽  
Derivatives Of

scholarly journals Synthesis, Antitumor Activity, and Docking Analysis of New Pyrido[3’,2’:4,5]furo(thieno)[3,2-d]pyrimidin-8-amines

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3952 ◽  
Author(s):  
Sirakanyan ◽  
Spinelli ◽  
Geronikaki ◽  
Hakobyan ◽  
Sahakyan ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Heterocyclic Compounds ◽  
Phosphorus Oxychloride ◽  
Docking Analysis ◽  
Structure Activity ◽  
Biological Tests ◽  
Amino Derivatives ◽  
Chloro Derivatives ◽  
Derivatives Of

Continuing our research in the field of new heterocyclic compounds, herein we report on the synthesis and antitumor activity of new amino derivatives of pyrido[3’,2’:4,5](furo)thieno[3,2-d]pyrimidines as well as of two new heterocyclic systems: furo[2–e]imidazo[1,2-c]pyrimidine and furo[2,3-e]pyrimido[1,2-c]pyrimidine. Thus, by refluxing the 8-chloro derivatives of pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidines with various amines, the relevant pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidin-8-amines were obtained. Further, the cyclization of some amines under the action of phosphorus oxychloride led to the formation of new heterorings: imidazo[1,2-c]pyrimidine and pyrimido[1,2-c]pyrimidine. The possible antitumor activity of the newly synthesized compounds was evaluated in vitro. The biological tests evidenced that some of them showed pronounced antitumor activity. A study of the structure–activity relationships revealed that the compound activity depended mostly on the nature of the amine fragments. A docking analysis was also performed for the most active compounds.

Design, synthesis, and biological evaluation of new series of 2-amido-1,3,4-thiadiazole derivatives as cytotoxic agents

2016 ◽  
Vol 71 (3) ◽  
pp. 205-210 ◽  
Author(s):  
Ali Almasirad ◽  
Loghman Firoozpour ◽  
Maliheh Nejati ◽  
Najmeh Edraki ◽  
Omidreza Firuzi ◽  
...  
Keyword(s):  
Human Tumor ◽  
Inhibitory Effect ◽  
Biological Evaluation ◽  
Cytotoxic Agents ◽  
Antitumor Activities ◽  
Design Synthesis ◽  
Ethidium Bromide Staining ◽  
Thiadiazole Derivatives ◽  
Synthesis And Biological Evaluation

AbstractA series of novel 1,3,4-thiadiazole derivatives bearing an amide moiety were designed, synthesized, and evaluated for their in vitro antitumor activities against HL-60, SKOV-3 and MOLT-4 human tumor cell lines by MTT assay. Ethyl 2-((5-(4-methoxybenzamido)-1,3,4-thiadiazol-2-yl)thio)acetate (5f) showed the best inhibitory effect against SKOV-3 cells, with an IC50 value of 19.5 μm. In addition, the acridine orange/ethidium bromide staining assay in SKOV-3 cells suggested that the cytotoxic activity of 5f occurs via apoptosis.

Activity of Topotecan, a New Topoisomerase I Inhibitor, Against Human Tumor Colony-Forming Units In Vitro

1992 ◽  
Vol 84 (23) ◽  
pp. 1816-1820 ◽  
Author(s):  
H. A. Burris ◽  
A.-R. Hanauske ◽  
R. K. Johnson ◽  
M. H. Marshall ◽  
J. G. Kuhn ◽  
...  
Keyword(s):  
Topoisomerase I ◽  
Human Tumor ◽  
Topoisomerase I Inhibitor ◽  
Colony Forming Units

Synthesis and Biological Evaluation of Acetylcholinesterase Inhibitor Macakurzin C and Its Derivatives

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 1131-1134 ◽  
Author(s):  
Hyoungsu Kim ◽  
Seung-Hoon Baek ◽  
Hongjun Jang
Keyword(s):  
Inhibitory Activity ◽  
Acetylcholinesterase Inhibitor ◽  
Biological Evaluation ◽  
Hydroxyl Groups ◽  
Structural Requirements ◽  
Ache Inhibitory Activity ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

The derivatives of macakurzin C containing a modified D ring and protected C(3)/C(5)-hydroxyl groups were synthesized and their in vitro AChE inhibitory activity and neurotoxicity were evaluated to identify the structural requirements for the activities. The results indicated that C(3)-benzyl-protected derivative has a more potent AChE inhibitory activity (IC50, 2.6 μM) and a less neurotoxicity (GI50, >100 μM) than synthetic macakurzin C (IC50, 9.1 μM; GI50, 16.6 μM).

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