Senyawa Furan Karboksamida: Sintesis dan Uji Aktivitas Penghambatan α-Glukosidase

Ramadhani, Ersya Yanu (2023) Senyawa Furan Karboksamida: Sintesis dan Uji Aktivitas Penghambatan α-Glukosidase. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Diabetes merupakan penyakit yang ditandai dengan peningkatan kadar gula darah yang dapat menyebabkan kerusakan jangka panjang, disfungsi, dan kegagalan berbagai organ terutama mata, ginjal, saraf, jantung, dan pembuluh darah. Diabetes terbagi menjadi dua tipe utama, tetapi diabetes tipe 2 merupakan penyakit yang lebih umum dijumpai (sekitar 90-95%). Inhibitor enzim α-glukosidase dimanfaatkan untuk mengatasi penyakit diabetes tipe 2, tetapi memiliki efek samping utama berupa perut kembung, diare, kram perut, serta dapat bersifat toksik pada hati. Hal ini mendorong untuk dikembangan senyawa-senyawa baru yang dapat berperan sebagai inhibitor enzim α-glukosidase yang lebih efektif dan memiliki efek samping yang minimal. Furan karboksamida sebagai hibrid dari asam furoat dan isoniasid (14) merupakan kelompok senyawa yang berpotensi sebagai inhibitor enzim α-glukosidase yang baik. Sintesis senyawa-senyawa furan karboksamida pada umumnya menggunakan pereaksi tionil klorida yang masuk dalam daftar Chemical Weapons Conventions dan Undang-Undang Republik Indonesia Nomor 9 Tahun 2008 tentang Penggunaan Bahan Kimia dan Larangan Penggunaan Bahan Kimia sebagai Senjata Kimia; atau menggunakan pereaksi berbahaya atau memiliki efektivitas rendah. Sehubungan dengan hal tersebut, maka perlu dikembangkan metode sintesis senyawa-senyawa furan karboksamida tanpa melibatkan tionil klorida maupun pereaksi berbahaya atau memiliki efektivitas rendah. Penelitian yang dilakukan berhasil mengembangkan metode sintesis senyawa-senyawa furan karboksamida, dan diterapkan untuk mendapatkan empat senyawa furan karboksamida berupa N’-(5-bromofuran-2-karbonil)isonikotinohidrazida (29a), N’-(5-nitrofuran-2-karbonil)isonikotinohidrazida (29b), N’-(3-metilfuran-2-karbonil)isonikotinohidrazida (29c), dan N’-(furan-3-karbonil)isonikotinohidrazida (30). Senyawa-senyawa (29a-c, 30) diperoleh dengan rendemen sebesar 58-83%, dan lebih aktif menghambat enzim α-glukosidase dari pada obat standar akarbosa (1). Senyawa (30) memiliki aktivitas yang paling baik dengan IC50 67,16 ± 0,06 µM.
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Diabetes is a disease characterized by the increasing of blood sugar levels which can cause the long-term damage, dysfunction, and failure in various organs, especially the eyes, kidneys, nerves, heart, and blood vessels. Diabetes is divided into two main types, but type 2 diabetes is the more common one (around 90-95%). α-Glucosidase enzyme inhibitors (AGI) are used to treat type 2 diabetes, but have major side effects such as flatulence, diarrhea, stomach cramps, and can be toxic to the liver. This disadvantagements encourages the development of new compounds that can act as more effective inhibitors of the α-glucosidase enzyme and have minimal side effects. Furan carboxamide as a hybrid of furoic acid and isoniazid (14) is a group of compounds that have the potential as a good inhibitors of α-glucosidase enzyme. Commonly, the synthesis of furan carboxamide compounds utilizes thionyl chloride reagent which is included in the list of Chemical Weapons Conventions and Law of the Republic of Indonesia Number 9 of 2008 concerning the Use of Chemicals and Prohibitions on the Use of Chemicals as Chemical Weapons; or using reagents that are hazardous or have low effectiveness. In this regard, it is necessary to develop a new method for synthesizing furan carboxamide compounds without involving thionyl chloride or reagents that are dangerous or have low effectivity. The research conducted has successfully developed a new method for synthesizing furan carboxamide compounds, and was applied to obtain four furan carboxamide compounds, namely N’-(5-bromofuran-2-carbonyl)isonicotinohydrazide (29a), N’-(5-nitrofuran-2-carbonyl)isonicotinohydrazide(29b), N’-(3-methylfuran-2- carbonyl)isonicotinohydrazide (29c), and N’-(furan-3carbonyl)isonicotinohydrazide (30). The compounds (29a-c, 30) were obtained with a yield of 58-83%, and were more active in inhibiting α-glucosidase enzyme than the standard drug acarbose (1). Compound (30) had the best activity with an IC50 67,16 ± 0,06 µM.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Furan karboksamida, asam furankarboksilat, isoniasid, inhibitor α-glukosidase, Furan carboxamide, furancarboxylic acid, isoniazid, α-glucosidase inhibitor
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Ersya Yanu Ramadhani
Date Deposited:	11 Sep 2023 02:02
Last Modified:	11 Sep 2023 02:02
URI:	http://repository.its.ac.id/id/eprint/103949

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