2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol

Untung, Joko; Iskandarsyah, Iskandarsyah; Hayun, Hayun

doi:10.3390/m949

Cited by 5 publications

(5 citation statements)

References 13 publications

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“…The syntheses were performed according to the method used for the synthesis of di-Mannich bases of curcumin and the synthesis of 2-[(2,6-dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3[(E)-2-{3- [(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5yl}etheyl]-6-methoxyphenol reported previously [ 21 , 22 ]. Compound 1a–1e (2 mmol) separately were dissolved in ethanol, cooled in an ice bath, and diethylamine (5–7 mmol) and formaldehyde solution 37% (5–7 mmol) were added slowly.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Cytotoxicity Evaluation of Novel Asymmetrical Mono-Carbonyl Analogs of Curcumin (AMACs) against Vero, HeLa, and MCF7 Cell Lines

Bahtiar

Hayun

2018

Sci. Pharm.

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A series of novel asymmetrical mono-carbonyl analogs of curcumin (AMACs) were synthesized and evaluated for cytotoxic activity using BSLT and MTT assay against Vero, HeLa, and MCF7 cell lines. The structures of the synthesized compounds were confirmed by FTIR, 1H-NMR, 13C-NMR, and mass spectral data. The results of the cytotoxicity evaluation showed that the synthesized compounds exhibited moderate to very high toxic activity in BSLT (LC50 value 29.80–1704.23 µM); most of the compound exhibited cytotoxic activity against HeLa cell lines, which is comparable to the activity of cisplatin (IC50 value 40.65–95.55 µM), and most of the compound tested against MCF7 cell lines exhibited moderate to very high cytotoxic activity (IC50 value 7.86–35.88 µM). However, the selectivity index (SI) of the compounds was low (<1–1.96). Among the synthesized compounds, compound 1b was the most cytotoxic and selective against MCF7 cell lines. It could be considered for further development to obtain the more active and selective chemotherapeutic agents against breast cancer.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Cytotoxicity Evaluation of Novel Asymmetrical Mono-Carbonyl Analogs of Curcumin (AMACs) against Vero, HeLa, and MCF7 Cell Lines

Bahtiar

Hayun

2018

Sci. Pharm.

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“…These results were in line with several Mannich bases of phenolic compounds reported earlier. [11][12] Fig. The electron-donating groups directly attached to the aromatic ring is one factor that can enhance free radical scavenger.…”

Section: Antioxidant Activitymentioning

confidence: 99%

“…[7][8][9] Many aminoalkyl derivatives have been prepared using the Mannich reaction to develop more potent bioactive compounds. [10][11] Some Mannich bases derived from phenol compounds, such as several chalcones, thymol, and flavanone, exhibited better antioxidant activity than the corresponding parent compounds. [12][13] However, there was no report about the effect of Mannich bases substitutions on the biological activity of vanillic acid.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidant Activity Study of New Mannich Bases Derived From Vanillic Acid

Hayun¹,

Gavrila²,

Silviana³

et al. 2020

RJC

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We synthesized five new Mannich bases compounds from vanillic acid and evaluated for their antioxidant activities using a free-radical DPPH and FRAP methods. The compounds' structures were confirmed based on infrared, proton NMR, carbon NMR, and mass spectra. In this study, the compound 5-(pyrrolidin-1-ylmethyl)vanillic acid (2e) showed the best free-radical scavenger activity, while compound 2-[(diethylamino)methyl]vanillic acid (2c) showed the best as a ferric reductant. Mannich bases enhanced the free-radical scavenger activity but decreasing the ferric reduction potential of the parent compounds. The compounds were found to be moderate antioxidant agents.

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“…The design and development of dopamine with vanillin derivatives via the Mannich condensation reaction based on Mannich base derivatives has been conducted previously using many different bioactive molecules, such as aminoalkyl derivatives, 11 chiral types, β-amino-carbonyl compounds, peptides, alkaloids, antibiotics, and vitamins. 12 Additionally, Mannich base bioactivity includes antioxidative, 13 antifungal, 14 anti-inflammatory, 15 analgesic, 16 anticancer, 17 vasorelaxing, 18 antimalarial, 19 and antitubercular 20 activities.…”

Section: Introductionmentioning

confidence: 99%

Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities

Mani

Ahamed

Ali

et al. 2021

DDDT

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Purpose This study aimed to determine the extent of contribution of dopamine to antioxidant and anti-tyrosinase activities, by dopamine addition to vanillin. This study achieved the synthesis of dopamine-associated vanillin Mannich base derivatives prepared via a one-step reaction involving a green chemistry approach, and investigation of antioxidant and anti-tyrosinase activities. Methods Novel one-pot synthesis of Mannich base dopamine-connected vanillin ( 1a-l ) derivatives can be achieved via green chemistry without using a catalyst. Newly-prepared compounds were characterised with FTIR and NMR ( 1 H and 13 C) spectra, mass spectra, and elemental analyses. In total, 12 compounds ( 1a-l ) were synthesised and their antioxidant and anti-tyrosinase activities evaluated. Antioxidant activities of 2,2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO), hydrogen peroxide (H 2 O 2 ), and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and diammonium assays, ABTS •+ radical scavenging, and linoleic acid peroxidation were used to screen all synthesised compounds ( 1a-l ) for anti-tyrosinase activities and cytotoxicity against MCF-7 and Vero cell lines;. Results The compound 1k inhibited (IC 50 :11.02µg/mL) the DPPH-scavenging activity to a greater extent than the standard BHT (IC 50 :25.17µg/mL), and showed high activity in H 2 O 2 and NO scavenging assays. Compound 1e was more potent (96.21%) against ABTS and compound 1k was more potent (95.28%) against 2,2ʹ-azobis(2-amidinopropane)dihydrochloride antioxidant than the standard trolox. All synthesised compounds were screened for anti-tyrosinase inhibitory activity. Compound 1e had higher activity against tyrosinase (IC 50 =10.63 µg/mL), than kojic acid (IC 50 =21.52µg/mL), and was more cytotoxic (GI 50 0.01µM) against MCF-7 cell line than the doxorubicin standard and other tested compounds. Conclusion In this study, all compounds were found to possess significant antioxidant and anti-tyrosinase activities. Compounds 1e and 1k performed well, compared with other compounds, in all assays. In addition, this study successfully identified several promising molecules that exhibited antioxidant and anti-tyrosinase activities.

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2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol

Cited by 5 publications

References 13 publications

Synthesis and Cytotoxicity Evaluation of Novel Asymmetrical Mono-Carbonyl Analogs of Curcumin (AMACs) against Vero, HeLa, and MCF7 Cell Lines

Synthesis and Cytotoxicity Evaluation of Novel Asymmetrical Mono-Carbonyl Analogs of Curcumin (AMACs) against Vero, HeLa, and MCF7 Cell Lines

Synthesis and Antioxidant Activity Study of New Mannich Bases Derived From Vanillic Acid

Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities

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