Sintesis (E)-N’-(3-(2metoksifenil) Akriloil) Isonikotinohidrazida Dan (E)-N’-(3-(4-metoksifenil)akriloil)Isonikotinohidrazida.

Santoso, Liangga (2022) Sintesis (E)-N’-(3-(2metoksifenil) Akriloil) Isonikotinohidrazida Dan (E)-N’-(3-(4-metoksifenil)akriloil)Isonikotinohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

World Health Organization (WHO) melaporkan bahwa lebih dari 95% penderita diabetes merupakan penderita diabetes tipe II. Penghambatan kinerja enzim α-glukosidase dapat menghambat pencernaan dan absorpsi karbohidrat sehingga menurunkan kadar gula darah dan mencegah hiperglikemik pada penderita diabetes tipe II. Asam sinamat (4a) memiliki bioaktivitas penghambatan terhadap α-glukosidase, dan adanya gugus metoksi pada gugus fenil dapat meningkatkan bioaktivitas asam sinamat. Isoniazid (10) mengandung gugus piridina dan hidrazida yang juga mempunyai bioaktivitas penghambatan terhadap α-glukosidase. Turunan asam sinamat berupa sinamamida (11-13) aktif menghambat enzim α-glukosidase dengan IC50 berturut-turut sebesar 0,31; 7,9 dan 3,9 μM. Sintesis sinamamida dapat dilakukan menggunakan pereaksi kopling HATU (14) dan EDCl.HCl (23)/HOBt (24), tetapi, peraksi kopling tersebut bersifat eksplosif serta menghasilkan hasil samping yang toksik. Senyawa hibrid (E)-N’-(3-(2-metoksifenil)akriloil)isonikotinohidrazida (27a) dan (E)-N’-(3-(4-metoksifenil)-akriloil)-isonikotinohidrazida (27b) masing-masing berhasil disintesis pada penelitian ini dengan rendemen masing-masing sebesar 48% dan 59% tanpa melibatkan pereaksi HATU (14) dan EDCl.HCl (23) / HOBt (24). Sintesis senyawa (27a-b) melibatkan reaksi dengan asam sinamat (28a-b), MNBA (25), DMAP (26) dan isoniazid (10) pada temperatur ruang. Sinamamida (27a-b) hasil sintesis dimurnikan dengan kromatografi kolom gravitasi, diuji kemurnian dengan KLT dan uji titik leleh. Identifikasi struktur senyawa (27a-b) ditetapkan dengan spektrometer NMR, spektrofotometer FTIR, dan spektrometer massa resolusi tinggi (HRESIMS).
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The World Health Organization (WHO) reports that more than 95% of diabetics are type II diabetics. Inhibition of the action of the -glucosidase enzyme will inhibit the digestion and absorption of carbohydrates thereby lowering blood sugar levels and preventing hyperglycaemia in type II diabetics. Cinnamic acid (4a) has inhibitory activity against α-glucosidase. The presence of a methoxy group on the phenyl group can increase the bioactivity of cinnamic acid. Isoniazid (10) contains pyridine and hydrazide groups which also have inhibitory activity against α-glucosidase. Cinnamic acid derivatives in the form of cinnamamide (11-13) were active in inhibiting the α-glucosidase enzyme with IC50 of 0,31; 7,9 and 3,9 μM respectively. The synthesis of cinnamamide has been carried out using coupling reagents such as HATU (14) and EDCl.HCl (23) /HOBt (24). However, this reagent is explosive and produces toxic by-products. Hybrid compounds (E)-N'-(3-(2-methoxyphenyl)acryloyl) isonicotinohydrazide (27a) and (E)-N'-(3-(4-methoxyphenyl)acryloyl)isonicotinohydrazide (27b) were successfully synthesized, respectively. with yields of 48% and 59%. The synthesis of the compound (27a-b) involved the reaction of cinnamic acid (28a-28b) with MNBA (25), DMAP (26), and isoniazid (10) at room temperature. Cinamamide (27a-b) was purified by gravity column chromatography, tested for purity by TLC and melting point test. Compoun (27a-b) identified by NMR spectrometer, FTIR spectrophotometer, and high resolution mass spectrometer (HRESIMS).

Item Type:	Thesis (Other)
Additional Information:	RSKi 541.39 San s-1 2022
Uncontrolled Keywords:	Diabetes, Asam sinamat, Isoniazid, Sinamamida. Diabetes, Asam sinamat, Isoniazid, Sinamamida.
Subjects:	T Technology > TP Chemical technology > TP159.A5 Antioxidants
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Mr. Marsudiyana -
Date Deposited:	07 May 2026 09:00
Last Modified:	08 May 2026 01:38
URI:	http://repository.its.ac.id/id/eprint/133034

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