Synthesis of some sulfonamide incorporating enaminone, quinolone moieties and thiazoloquinazoline derivative induce the cytoprotective enzyme NAD(P) H: Quinone Oxidoreductase 1
نویسندگان
چکیده
Sulfonamide resonant biologically active enaminone derivatives 3, 5, and quinolone derivative 8 have been created. Correspondingly, the thiazoloquinazoline derivative 13 was acquired in decent yield via reaction of 2-isothiocyanate derivative 9 with the L-nor ephedrine 10. The assemblies of the prepared amalgams stood established by microanalysis, IR, 1H-NMR, 13C-NMR and mass spectral information. Furthermore amalgams 3 was proved by X-ray crystallographic analysis. The NQO1 inducer activity of the synthesized compounds was assessed by means of a measurable bioassay in Hepa1c1c7 murine hepatoma cells. The thiazoloquinazoline (13) exhibited remarkable activity. Besides, incorporating the thiazol moiety within a heterocyclic ring system (quinazoline) increases the inducer potency. On the other hand, the enaminone derivatives (3 and 5) and quinoline (8) showed weak activity.
منابع مشابه
NAD(P)H: Quinone Oxidoreductase 1 inducer activity of some enaminone derivatives
The present work reports the synthesis of some enaminone derivatives bearing the biologically active 3,4-dimethoxyphenyl (3) or 3,4,5-trimethoxyphenyl moieties (5 and 7), respectively. The trimethoxybenzene moiety has been previously reported to confer cytotoxic activity. However, we found that, at high micromolar concentrations, the new compounds have the ability to weakly induce the cytoprote...
متن کاملDetection of NAD(P)H: Quinone Oxidoreductase 609C T Polymorphism in Blood and Archival Human Tissues Using a Simple PCR Method
متن کامل
Evaluation of the risk of lung cancer associated with NAD(P)H: quinone oxidoreductase 1 (NQO1) C609T polymorphism in male current cigarette smokers from the Eastern India
NAD(P)H: quinone oxidoreductase 1 (NQO1) is an endogenous cellular defence mechanism against several carcinogenic quinones derived from cigarette smoke. NQO1 C609T polymorphism is a strong determinant of NQO1 structure and function. The people with mutant allele for this polymorphism has significantly reduced NQO1 activity. In this study, we tried to evaluate the risk of lung cancer as...
متن کاملEffects of 5-azacytidine and methyl-group deficiency on NAD(P)H: quinone oxidoreductase and glutathione S-transferase in liver.
Treatment with 5-azacytidine or dietary methyl-group deficiency effected DNA hypomethylation in mouse liver. With these treatments, NAD(P)H: quinone oxidoreductase (EC 1.6.99.2) and some glutathione S-transferase (EC 2.5.1.18) activities were over-expressed, lactate dehydrogenase (EC 1.1.1.27) activity was unaffected and the level of cytochrome P-450 was decreased. The 5-azacytidine induction o...
متن کاملNAD(P)H:quinone oxidoreductase 1 inducer activity of some novel anilinoquinazoline derivatives
UNLABELLED The Kelch-like ECH-associated protein 1 (Keap1)/nuclear factor erythroid 2-related factor 2 (Nrf2)/antioxidant response elements pathway enables cells to survive oxidative stress conditions through regulating the expression of cytoprotective enzymes such as NAD(P)H quinone oxidoreductase 1 (NQO1). This work presents the design and synthesis of novel anilinoquinazoline derivatives (...
متن کامل