Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

Bayomi, Said M.; El‐Kashef, Hassan A.; El‐Ashmawy, Mahmoud B.; Nasr, Magda N.; El‐Sherbeny, Magda A.; Badria, Farid A.; Abou-Zeid, Laila A.; Ghaly, Mariam A.; Abdel-Aziz, Naglaa I.

doi:10.1007/s00044-012-0116-9

Cited by 49 publications

(32 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cyclovalone demonstrated antioxidant activity, antitumor, anti inflammatory, hepatoprotective and cytotoxic activity [4][5][6][7] . The structure-activity relationships (SAR) including the antioxidant activity of cyclovalone derivatives have been studied.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Free Radical-Scavenging Activities of Di-Mannich Bases of Cyclovalone Derivatives

Jatmika¹,

Purwati²,

Salim

et al. 2017

Orient. J. Chem

View full text Add to dashboard Cite

Novel di-Mannich bases of cyclovalone derivatives (1) have been synthesized and evaluated their antioxidant activity using DPPH free radical-scavenger method. The structures of the compounds were confirmed on the basis of FT-IR, 1 H-NMR, 13 C-NMR and mass spectral data. The result of antioxidant evaluation showed that di-Mannich derivative of cyclovalone with diethylamine ((2E,6E)-2,6-bis({3-[(diethylamino)methyl]-4-hydroxy-5-methoxyphenyl} methylidene) cyclohexan-1-one) (2a) exhibited the highest antioxidant activity with IC 50 = 39.0 µM. Structure-activity relationship study showed that the higher pKa of the Mannich base, the higher activity (the lower IC 50 ) of the compound.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Free Radical-Scavenging Activities of Di-Mannich Bases of Cyclovalone Derivatives

Jatmika¹,

Purwati²,

Salim

et al. 2017

Orient. J. Chem

View full text Add to dashboard Cite

show abstract

“…[10][11][12][23][24][25] For further investigation of the effects of α,β-unsaturated ketone moiety, in this communication, two series of curcumin derivatives (10a-f, 11a-f, 12a-f and 13a-f with α,β-unsaturated ketone moieties, and 16a-f with a α,β-saturated ketone moiety, Fig. 3) were synthesized and tested for their antiproliferative activities in five human carcinoma cell lines.…”

mentioning

confidence: 99%

Synthesis and Antiproliferative Effect of Novel Curcumin Analogues

Liu

Xia

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Novel curcumin analogues with α,β-unsaturated ketone moiety and/or α,β-saturated ketone structure were synthesized from curcumin via alkylation at the central carbon and the phenolic hydroxy groups, and hydrogenation of α,β-unsaturated ketone moiety. The antiproliferative activities were tested in five human solid tumor cell lines in vitro. Most of the compounds exhibited increased antiproliferative activities comparing with that of curcumin. Structure-activity relationship (SAR) analysis revealed that the α,β-unsaturated ketone structure was not required for antiproliferative activity of these curcumin analogues. Among these compounds, 1,7-bis(3-methoxy-4-(3-(4-methylpiperazinyl-1-yl)propoxy)phenyl)-4,4-dibenzylheptane-3,5-dione (16f) was the most effective one with IC 50 value below 1 µm, which was 9-to 81-fold more potent than curcumin.

show abstract

“…Literature survey highlighted the importance of tetrazole-containing compounds (A; Figure 1) as antitumor agents (Bayomi et al, 2016;Arshad et al, 2014;Jedhe et al, 2013;Bhaskar and Mohite, 2010). On the other hand, compounds with Chalcone-based structure (B; Figure 1) were described as cytotoxic agents that act via different mechanisms including induction of apoptosis and inhibition of cell proliferation (Sankappa Rai et al, 2015;Bayomi et al, 2015;Bayomi et al, 2013;de Vasconcelos et al, 2013;Sharma et al, 2013;Murad et al, 2012). Some pyrazoline derivatives (Yuan et al, 2014;Viale et al, 2013;Nitulescu et al, 2013) were also reported (C; Figure 1) to inhibit different enzymes that are involved in the cell division.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, In Vitro Antiproliferative Evaluation and Molecular Docking of New tetrazole-chalcone and tetrazole-pyrazoline Hybrids

2018

J App Pharm Sci

View full text Add to dashboard Cite

New hybrids of tetrazole moiety with different chalcone derivatives were synthesized. The reaction of these chalcones with hydrazine hydrate resulted in the formation of tetrazole-pyrazoline hybrids. Evaluation of the in vitro antiproliferative activity of all newly synthesized hybrids against three cancer cell lines and Vero-B normal cell line, using MTT-based assay, was performed. Most of the chalcone derivatives exerted superior activity against colon HCT-116 and prostate PC-3 cell lines, in comparison with cisplatin (IC 50 = 20 and 5 µg/ml) and 5-FU (IC 50 = 17.3 and 21.4 µg/ml), respectively. Compound 5a was found to be the most active antiproliferative agent against colon HCT-116 and prostate PC-3 cell lines (IC 50 = 0.6 and 1.6 µg/ml) with high selectivity indices (SI = 6.66 and 2.50), respectively. Compound 8f, in particular, displayed a wider spectrum of activity that included, in addition, excellent effect against breast MCF-7 cell lines with SI = 2.75. The available docking results revealed a good binding of 5b with HDAC2 and CYP17A1 that endorses the in vitro biological activity against the tested colon and prostate cell lines.

show abstract

Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

Cited by 49 publications

References 28 publications

Synthesis and Free Radical-Scavenging Activities of Di-Mannich Bases of Cyclovalone Derivatives

Synthesis and Free Radical-Scavenging Activities of Di-Mannich Bases of Cyclovalone Derivatives

Synthesis and Antiproliferative Effect of Novel Curcumin Analogues

Synthesis, In Vitro Antiproliferative Evaluation and Molecular Docking of New tetrazole-chalcone and tetrazole-pyrazoline Hybrids

Contact Info

Product

Resources

About