Sintesis dan Uji Antioksidan Senyawa Turunan Dihidropirimidinon

Agistya, Hamida Azza (2025) Sintesis dan Uji Antioksidan Senyawa Turunan Dihidropirimidinon. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Dihidropirimidinon merupakan senyawa heterosiklik anggota enam dengan dua atom nitrogen dan empat atom karbon. Struktur dihidropirimidinon dapat dijumpai dalam berbagai obat komersil dan senyawa bahan alam. Senyawa dihidropirimidinon umumnya diperoleh melalui reaksi Biginelli yang melibatkan β-keto ester, a ldehida aromatik, dan urea/tiourea dalam pelarut etanol dengan adanya katalis asam klorida pekat disertai pemanasan refluks. Senyawa
dihidropirimidinon dilaporkan mampu menangkap radikal bebas dan potensial untuk dikembangkan sebagai antioksidan. Turunan ester dari senyawa dihidropirimidinon dengan
gugus nitro pada posisi meta- menunjukkan aktivitas terbaik melalui pengujian tiol-peroksidase demikian pula dengan pengukuran reactive oxygen species dengan metode 2',7'-diklorofluoresin diasetat. Turunan ester senyawa dihidropirimidinon dari aldehida aromatik yang tersubtitusi
gugus metil, fenil, naftil, hidroksi fenil dan hidroksi bromo fenil juga memiliki aktivitas antioksidan yang tinggi melalui uji radikal kumil peroksil. Lebih lanjut, pengujian aktivitas antioksidan senyawa kurkumin-3,4-dihidropirimidinon/tion dengan metode DPPH menunjukkan
bahwa senyawa ini dengan gugus 2-hidroksi-, 4-hidroksi-, dan 3,4-dihidroksibenzaldehida memiliki aktivitas antioksidan yang sangat baik. Dari penelitian ini, dihasilkan senyawa
dihidropirimidinon 1a-h dengan %yield yang beragam yakni
36,15 – 89,78%. Uji aktivitas antioksidan menunjukkan bahwa senyawa 1f memberikan hasil terbaik pada metode DPPH dengan nilai IC50 sebesar 167,04 μg/L (kategori lemah), sedangkan
pada metode ABTS senyawa 1b memeberikan hasil terbaik dengan nilai IC50 sebesar 9,90 μg/L (kategori sangat aktif). Sementara itu, senyawa lainnya menunjukkan reaktivitas yang beragam. ============================================================
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Dihydropyrimidinone is a six-membered heterocyclic compound consisting of two nitrogen atoms and four carbon atoms. The dihydropyrimidinone structure can be found in various
commercial drugs and natural compounds. Dihydropyrimidinones are generally synthesized via the Biginelli reaction, which involves a β-keto ester, an aromatic aldehyde, and urea or thiourea in ethanol solvent, catalyzed by concentrated hydrochloric acid under reflux conditions.
Dihydropyrimidinone compounds have been reported to possess free radical scavenging activity and hold potential for development as antioxidants. Ester derivatives of dihydropyrimidinone with a nitro group at the meta-position have shown the best activity in thiol-peroxidase assays as
well as in reactive oxygen species measurements using the 2',7'-dichlorofluorescin diacetate method. Ester derivatives obtained from aromatic aldehydes substituted with methyl, phenyl, naphthyl, hydroxyphenyl, and hydroxybromophenyl groups also exhibit strong antioxidant activity based on the cumyl peroxyl radical assay. Furthermore, antioxidant activity evaluation of curcumin–3,4-dihydropyrimidinone/thione derivatives using the DPPH method indicated that compounds with 2-hydroxy-, 4-hydroxy-, and 3,4-dihydroxybenzaldehyde groups possess excellent antioxidant activity. In this study, dihydropyrimidinone compounds 1a–h were successfully synthesized with yields ranging from 36,15 – 89,78%. Antioxidant activity testing
showed that compound 1f exhibited the best result in the DPPH method, with an IC50 value of 167.04 μg/L (categorized as weak), while in the ABTS method, compound 1b showed the best result with an IC50 value of 9.90 μg/L (categorized as very active). Meanwhile, the other compounds exhibited varied reactivities.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Dihidropirimidinon, Reaksi Biginelli, Antioksidan, Dihydropyrimidinone, Biginelli Reaction, Antioxidants
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Hamida Azza Agistya
Date Deposited:	07 Aug 2025 03:37
Last Modified:	07 Aug 2025 03:37
URI:	http://repository.its.ac.id/id/eprint/127901

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