Sintesis N'-((E)-7-bromo-2-oksoindolin-3-ilidena)sinamohidrazida dan N'-((E)-7-kloro-2-oksoindolin-3-ilidena)sinamohidrazida

Qolbi, Syifaul (2026) Sintesis N'-((E)-7-bromo-2-oksoindolin-3-ilidena)sinamohidrazida dan N'-((E)-7-kloro-2-oksoindolin-3-ilidena)sinamohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Inflamasi merupakan respons biologis tubuh terhadap cedera jaringan atau infeksi patogen. Obat antiinflamasi yang tersedia saat ini memiliki efek samping berupa gangguan pencernaan akibat penghambatan enzim siklooksigenase-1 (COX-1), sehingga diperlukan pengembangan kandidat obat antiinflamasi baru yang lebih selektif terhadap enzim siklooksigenase-2 (COX-2). Senyawa hidrazon yang mengandung inti isatin dan sinamohidrazida diketahui memiliki potensi sebagai agen antiinflamasi karena keberadaan gugus azometin (C=N) serta substituen halogen yang dapat meningkatkan interaksi dengan sisi aktif enzim COX-2. Pada penelitian ini, sintesis N’-((E)-7-bromo-2-oksoindolin-3-ilidena)sinamohidrazida (5a) dan N’-((E)-7-kloro-2-oksoindolin-3-ilidena)sinamohidrazida (5b) dilakukan melalui pendekatan analisis retrosintesis. Sintesis dilakukan dalam dua tahap. Tahap pertama merupakan reaksi hidrazinolisis metil trans-sinamat (9) dengan hidrazin hidrat (8), sehingga diperoleh sinamohidrazida (7) berupa padatan putih dengan rendemen 60%. Tahap kedua merupakan reaksi kondensasi sinamohidrazida (7) dengan 7-bromoisatin (6a) dan 7-kloroisatin (6b) pada kondisi refluks menggunakan katalis asam sulfat pekat dalam pelarut etanol, sehingga diperoleh senyawa hidrazon (5a) dan (5b). Senyawa N’-((E)-7-bromo-2-oksoindolin-3-ilidena)sinamohidrazida (5a) berhasil disintesis sebagai padatan berwarna kuning kehijauan dengan rendemen 80%, sedangkan N’-((E)-7-kloro-2-oksoindolin-3-ilidena)sinamohidrazida (5b) diperoleh sebagai padatan berwarna kuning dengan rendemen 50%. Identifikasi struktur kedua senyawa hasil sintesis dikonfirmasi menggunakan spektroskopi NMR (^1H dan ^13C), FTIR, dan HRMS. Hasil penelitian menunjukkan bahwa kedua senyawa hidrazon berhasil disintesis melalui jalur sintesis yang dirancang dan berpotensi untuk dikembangkan lebih lanjut sebagai kandidat agen antiinflamasi yang selektif terhadap COX-2.
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Inflammation is a biological response of the body to tissue injury or pathogenic infection. Currently available anti-inflammatory drugs are associated with gastrointestinal adverse effects resulting from the inhibition of cyclooxygenase-1 (COX-1), highlighting the need for the development of novel anti-inflammatory drug candidates with greater selectivity toward cyclooxygenase-2 (COX-2). Hydrazone derivatives containing isatin and cinnamohydrazide scaffolds have shown considerable potential as anti-inflammatory agents due to the presence of the azomethine (C=N) moiety and halogen substituents, which may enhance interactions with the active site of the COX-2 enzyme. In this study, the hydrazone derivatives N’-((E)-7-bromo-2-oxoindolin-3-ylidene)cinnamohydrazide (5a) and N’-((E)-7-chloro-2-oxoindolin-3-ylidene)cinnamohydrazide (5b) were synthesized using a retrosynthetic analysis approach. The synthesis was carried out in two stages. The first stage involved the hydrazinolysis of methyl trans-cinnamate (9) with hydrazine hydrate (8), affording cinnamohydrazide (7) as a white solid in 60% yield. The second stage consisted of the condensation of cinnamohydrazide (7) with 7-bromoisatin (6a) and 7-chloroisatin (6b) under reflux conditions using concentrated sulfuric acid as the catalyst in ethanol, yielding the hydrazone derivatives (5a) and (5b). N’-((E)-7-bromo-2-oxoindolin-3-ylidene)cinnamohydrazide (5a) was successfully obtained as a yellowish-green solid in 80% yield, whereas N’-((E)-7-chloro-2-oxoindolin-3-ylidene)cinnamohydrazide (5b) was obtained as a yellow solid in 50% yield. The structures of the synthesized compounds were confirmed by ^1H and ^13C nuclear magnetic resonance (NMR), Fourier-transform infrared (FTIR), and high-resolution mass spectrometry (HRMS). The results demonstrated that both hydrazone derivatives were successfully synthesized through the proposed synthetic pathway and show promising potential for further development as selective COX-2 anti-inflammatory agents.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Hidrazon; Isatin; Sinamohidrazida; Sinamat; Antiinflamasi Hydrazone; Isatin; Cinnamohydrazide; Cinnamate; Anti-inflammatory
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 > 47201-(S1) Undergraduate Thesis
Depositing User:	Syifaul Qolbi
Date Deposited:	04 Aug 2026 04:31
Last Modified:	04 Aug 2026 04:31
URI:	http://repository.its.ac.id/id/eprint/143073

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