Synthesis and Free Radical-scavenging Activities of Di-mannich Bases of Cyclovalone Derivatives

Hayun Hayun; Catur Jatmika; Euis Maras Purwati; Sandi Salim; Rosita Kurniawan; Elizabeth Greffiana Chandra; Adam Arditya Fajriawan; Aulika Desthahrina Nareswara

doi:10.13005/ojc/330607

Synthesis and Free Radical-scavenging Activities of Di-mannich Bases of Cyclovalone Derivatives

Hayun Hayun, Catur Jatmika, Euis Maras Purwati, Sandi Salim, Rosita Kurniawan, Elizabeth Greffiana Chandra, Adam Arditya Fajriawan, Aulika Desthahrina Nareswara

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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, ¹H-NMR, ¹³C-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 IC₅₀ = 39.0 µM. Structure-activity relationship study showed that the higher pKa of the Mannich base, the higher activity (the lower IC₅₀) of the compound.

Original language	English
Pages (from-to)	2742-2757
Number of pages	16
Journal	Oriental Journal of Chemistry
Volume	33
Issue number	6
DOIs	https://doi.org/10.13005/ojc/330607
Publication status	Published - 2017

Keywords

Antioxidant
Cyclovalone
Mannich base
Radical scavenger
Synthesis

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title = "Synthesis and Free Radical-scavenging Activities of Di-mannich Bases of Cyclovalone Derivatives",

abstract = "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, 1H-NMR, 13C-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 IC50 = 39.0 µM. Structure-activity relationship study showed that the higher pKa of the Mannich base, the higher activity (the lower IC50) of the compound.",

keywords = "Antioxidant, Cyclovalone, Mannich base, Radical scavenger, Synthesis",

author = "Hayun Hayun and Catur Jatmika and Purwati, {Euis Maras} and Sandi Salim and Rosita Kurniawan and Chandra, {Elizabeth Greffiana} and Fajriawan, {Adam Arditya} and Nareswara, {Aulika Desthahrina}",

year = "2017",

doi = "10.13005/ojc/330607",

language = "English",

volume = "33",

pages = "2742--2757",

journal = "Oriental Journal of Chemistry",

issn = "0970-020X",

publisher = "Bhopal, S.A. Iqbal",

number = "6",

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TY - JOUR

T1 - Synthesis and Free Radical-scavenging Activities of Di-mannich Bases of Cyclovalone Derivatives

AU - Hayun, Hayun

AU - Jatmika, Catur

AU - Purwati, Euis Maras

AU - Salim, Sandi

AU - Kurniawan, Rosita

AU - Chandra, Elizabeth Greffiana

AU - Fajriawan, Adam Arditya

AU - Nareswara, Aulika Desthahrina

PY - 2017

Y1 - 2017

N2 - 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, 1H-NMR, 13C-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 IC50 = 39.0 µM. Structure-activity relationship study showed that the higher pKa of the Mannich base, the higher activity (the lower IC50) of the compound.

AB - 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, 1H-NMR, 13C-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 IC50 = 39.0 µM. Structure-activity relationship study showed that the higher pKa of the Mannich base, the higher activity (the lower IC50) of the compound.

KW - Antioxidant

KW - Cyclovalone

KW - Mannich base

KW - Radical scavenger

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=85042078096&partnerID=8YFLogxK

U2 - 10.13005/ojc/330607

DO - 10.13005/ojc/330607

M3 - Article

AN - SCOPUS:85042078096

SN - 0970-020X

VL - 33

SP - 2742

EP - 2757

JO - Oriental Journal of Chemistry

JF - Oriental Journal of Chemistry

IS - 6

ER -

Synthesis and Free Radical-scavenging Activities of Di-mannich Bases of Cyclovalone Derivatives

Abstract

Keywords

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