Synthesis and Cytotoxicity Evaluation of Some 8‐Hydroxyquinoline Derivatives

@article{Shen1999SynthesisAC,
  title={Synthesis and Cytotoxicity Evaluation of Some 8‐Hydroxyquinoline Derivatives},
  author={Ai Yu Shen and SHENG‐NAN Wu and Chih-Tsao Chiu},
  journal={Journal of Pharmacy and Pharmacology},
  year={1999},
  volume={51}
}
Interest in Mannich bases of 8‐hydroxyquinoline stems from reports of their high potency against human cancer cells. In the search for potential anticancer drug candidates, Mannich bases of 8‐hydroxyquinoline (7‐pyrrolidinomethyl‐8‐hydroxyquinoline, 7‐morpholinomethyl‐8‐hydroxyquinoline, 7‐piperidinomethyl‐8‐hydroxyquinoline and 7‐diethylamino‐methyl‐8‐hydroxyquinoline) were synthesised by reaction with various secondary amines and formaldehyde. They were prepared as hydrochlorides. 

Derivatives of the aminated hydroxyquinoline class for treating cancers

The present invention relates to a compound of type hydroxyquinoline migration or metastasis of tumor cells can be prevented aminated. Such compounds are useful for the treatment of cancer.

New heterocycles from 8-hydroxyquinoline via dipolar 1,3-cycloadditions: Synthesis & biological evaluation

Diarylnitrilimine and arylnitriloxide dipoles react with two 8-hydroxyquinoline substrates to give respectively pyrazolinic and isoxazolinic derivatives. The structure of these new heterocycles was

Impact of copper and iron binding properties on the anticancer activity of 8-hydroxyquinoline derived Mannich bases.

Q-4 is identified as a potent and selective anticancer candidate with significant toxicity in drug resistant cells and a linear relationship between the pKa (OH) and IC50 values of the studied 8-hydroxyquinolines was found.

Studies on the structures, cytotoxicity and apoptosis mechanism of 8-hydroxylquinoline rhodium(III) complexes in T-24 cells

The apoptotic mechanism in T- 24 cells treated with 1 was studied by ROS detection, intracellular Ca2+ concentration measurements and caspase-9/3 activity assay, which suggested that complex 1 induced T-24 cell apoptosis by the disruption of mitochondrial-related mechanisms.

Synthesis, Structure Characterization and Antitumor Activity Study of a New Iron(III) Complex of 5-Nitro-8-hydroxylquinoline (HNOQ).

A new iron(III) complex (1) of 5-nitro-8-hydroxylquinoline (HNOQ) was synthesized and structurally characterized in its solid state and solution state by IR, UV-Vis, electrospray ionization (ESI)-MS,

Mannich bases in medicinal chemistry and drug design

  • G. Roman
  • Biology, Chemistry
    European Journal of Medicinal Chemistry
  • 2015

5-Chloroquinolin-8-yl furan-2-carboxylate

In the title compound, C14H8ClNO3, the central ester CO2 group is twisted away from the quinoline and furoyl rings by 57.46 (5) and 2.0‽(1)°, respectively, which results in chains in [001].

Quinoline-derivative coordination compounds as potential applications to antibacterial and antineoplasic drugs.

...

References

SHOWING 1-10 OF 23 REFERENCES

Evaluation of the cytotoxicity of some Mannich bases of acetophenone against the EMT6 tumour.

1-Phenyl-3-(4-morpholinyl)propan-1-one hydrochloride 1 and the related piperidino derivative 2 were shown to have activity against the EMT6 tumour in vitro. Modification of the structures of these

Cytotoxicity and Antimicrobial Activity of Some Naphthol Derivatives

Results indicate that esterification by Bruson reaction of 1‐naphthol Mannich base to TAC enhances the cytotoxicity and antimicrobial activity.

Tumor-targeted delivery of 8-hydroxyquinoline.

Direct radioiodination of metabolic 8-hydroxy-quinolyl-glucuronide, as a potential anti-cancer drug.

  • T. UnakP. Unak
  • Biology, Chemistry
    Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine
  • 1996

Tumor-targeted cell killing with 8-hydroxyquinolyl-glucuronide.

It is suggested that targeted 8-OHQ toxicity combined with local hyperthermia and/or irradiation may be useful for significantly increasing therapeutic gains in vivo.

Specific activation of glucuronide prodrugs by antibody-targeted enzyme conjugates for cancer therapy.

The results show that the targeted-beta-glucuronidase activation of BHAMG can increase the specificity of chemotherapy for rat hepatoma in vitro and suggest that theTargeted activation of glucuronide prodrugs may be useful for cancer therapy.

Metabolism of aniline mustard (N,N-di-(2-chloroethyl)aniline).

Effects of 1‐pyrrolidinylmethyl‐2‐naphthol on contractile force and ionic current in cardiac and vascular smooth myocytes

The results indicate that the suppressive effects of TPY‐β involve a direct depressant action on heart cells and vascular smooth muscle cells, and direct inhibition of voltage‐dependent L‐type Ca2+ channel is involved in the TPy‐β‐mediated vasodilatory action.