Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs.

@article{Chen2011SynthesisAI,
  title={Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs.},
  author={Chien-ting Chen and Mei-Hua Hsu and Yung-Yi Cheng and Chin Yu Liu and Li-Chen Chou and Li‐Jiau Huang and Tian-Shung Wu and Xiao-ming Yang and Kuo Hsiung Lee and Sheng-Chu Kuo},
  journal={European journal of medicinal chemistry},
  year={2011},
  volume={46 12},
  pages={
          6046-56
        }
}
6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure-activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent… Expand
Design and synthesis of 6,7-methylenedioxy-4-substituted phenylquinolin-2(1H)-one derivatives as novel anticancer agents that induce apoptosis with cell cycle arrest at G2/M phase.
TLDR
6,7-methylenedioxy-4-(2,4-dimethoxyphenyl)quinolin-2(1H)-one (12e) displayed potent cytotoxicity against several different tumor cell lines at a sub-micromolar level and was identified as a new lead compound that merits further optimization and development as an anticancer candidate. Expand
Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives
In continuance of our search for newer antiproliferative agents we report herein the synthesis and antiproliferative studies of two series (5a–j and 10a–c) of heterocyclic compounds. All the newExpand
Synthesis and Biological Activity of 6-Selenocaffeine: Potential Modulator of Chemotherapeutic Drugs in Breast Cancer Cells
TLDR
Overall, this work highlights an emerging methodology to synthesize organoselenium compounds and points out the differential roles of 6-selenocaffeine in the modulation of the cytotoxicity of anticancer agents. Expand
Oxidative ring expansion of 3-hydroxy-3-phenacyloxindoles using phenyliodine diacetate and molecular iodine: Synthesis of 2-hydroxy-2-aryl/alkyl-2,3-dihydroquinolin-4(1H)-ones
Abstract Oxidation of tertiary alcohol of the type 3-hydroxy-3-phenacyloxindoles using the combination of phenyliodine diacetate and molecular iodine in methanol results in oxidative cleavage ofExpand
Studies on free radical scavenging, cancer cell antiproliferation, and calf thymus DNA interaction of Schiff bases.
Thirty-nine Schiff bases were synthesized by performing microwave-assisted condensation of the corresponding aldehydes and aromatic amines. Their reactive nitrogen species (RNS) scavenging activityExpand
A review on anticancer potential of bioactive heterocycle quinoline.
TLDR
This review has compiled and discussed specifically the anticancer potential of quinoline derivatives, which could provide a low-height flying bird's eye view of theQuinoline derived compounds to a medicinal chemist for a comprehensive and target oriented information for development of clinically viable anticancer drugs. Expand
Direct synthesis of 2-aryl-4-quinolones via transition-metal-free intramolecular oxidative C(sp(3))-H/C(sp(3))-H coupling.
A novel, metal-free oxidative intramolecular Mannich reaction was developed between secondary amines and unmodified ketones, affording a simple and direct access to a broad range ofExpand
CCT 327 enhances TRAIL-induced apoptosis through the induction of death receptors and downregulation of cell survival proteins in TRAIL-resistant human leukemia cells
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) has potential application in cancer therapy and it has the ability to selectively kill cancer cells without affecting normal cells.Expand
An efficient one-pot synthesis of thiophene-fused pyrido[3,2-a]azulenes via Gewald reaction
A simple and efficient procedure was developed for the synthesis of 11H(2H)-4-oxothiophene[3′,4′:6,5]pyrido[3,2-a]azulene-10-carboxylates (3) in moderate to good yields via the Gewald reaction ofExpand
Pyridine Based Antitumour Compounds Acting at the Colchicine Site.
TLDR
The designed principles behind the structural modifications and the achieved effect on the biological activity upon inclusion of these heterocycles are discussed and lessons from the achievements and failures have been extracted and future perspectives delineated. Expand
...
1
2
3
...

References

SHOWING 1-10 OF 30 REFERENCES
Design and synthesis of 2-(3-benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one analogues as potent antitumor agents that inhibit tubulin assembly.
TLDR
Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents. Expand
Design, synthesis, and preclinical evaluation of new 5,6- (or 6,7-) disubstituted-2-(fluorophenyl)quinolin-4-one derivatives as potent antitumor agents.
TLDR
Sodium 2-(3-fluorophenyl)-5-hydroxy-6-methoxy-4-oxo-1,4-dihydroquinolin-5-yl phosphate (15), the monophosphate of 3b, exceeded the activity of doxorubicin and was comparable to CHM-1-P-Na in a Hep3B xenograft nude mice model. Expand
Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds: identification as antimitotic agents interacting with tubulin.
TLDR
Compounds 24, 26, and 27 were potent inhibitors of tubulin polymerization, with activity nearly comparable to that of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4. Expand
Antimitotic activity of 5-hydroxy-7-methoxy-2-phenyl-4-quinolones.
TLDR
The synthesis of 5-hydroxyl group, a 7-methoxy group, and an unsubstituted N1 were essential for the antimitotic activity and a fluoro group at the 3'- or 2'-position and a methoxy or a chloro group atThe 3'-position were found to be highly advantageous for both the cell cycle arrest and the antiproliferative activities. Expand
Synthesis and preclinical evaluations of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one monosodium phosphate (CHM-1-P-Na) as a potent antitumor agent.
TLDR
Compound 4 was rapidly converted into 1 following iv and po administration and also possessed excellent antitumor activity in a SKOV-3 xenograft nude mice model and is highly promising for development as an anticancer clinical trials candidate. Expand
Synthesis and biological relationships of 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents.
TLDR
3'-Fluoro-6-methoxy-2-phenyl-4-quinolone-3-carboxylic acid (68) had the highest in vitro cytotoxic activity among all tested carboxYlic acid derivatives and their salts. Expand
6-Alkylamino- and 2,3-dihydro-3'-methoxy-2-phenyl-4-quinazolinones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization.
TLDR
Six of the 6-substituted heterocyclic 2-phenyl-4-quinozolinones showed significant cytotoxicity against a panel of human tumor cell lines with EC(50) values in the low micromolar to nanomolar concentration ranges. Expand
Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents.
TLDR
Cytotoxicity and antitubulin activity were closely correlated, with the most active compounds having effects comparable to those of colchicine, podophyllotoxin, and combretastatin A-4. Expand
Antitumor agents. 150. 2',3',4',5',5,6,7-substituted 2-phenyl-4-quinolones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization.
TLDR
A good correlation was found between cytotoxicity and inhibition of tubulin polymerization and a series of 6,7-methylenedioxy-subst ituted and unsubstituted 2-phenyl-4-quinolones, as well as related compounds. Expand
Antitumor agents. 178. Synthesis and biological evaluation of substituted 2-aryl-1,8-naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization.
TLDR
3'-halogenated compounds (29-36) and compounds 38 and 42-44 were potent inhibitors of tubulin polymerization with activities nearly comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4. Expand
...
1
2
3
...