Sintesis N`-(4-Hidroksi-3-metoksibenzilidena)- 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida

Rohmah, Binti Ainiatur (2023) Sintesis N`-(4-Hidroksi-3-metoksibenzilidena)- 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Kumarin merupakan senyawa heterosiklik dengan atom oksigen pada posisi 1 dan gugus karbonil pada posisi 2. Kumarin dan turunannya diketahui menunjukkan aktivitas biologis yang beragam seperti antimikroba, antioksidan, antiinflamasi, anti-alzheimer, antikoagulan, kardiotonik, dan antikanker. Senyawa 4-metilumbeliferona yang berkerangka kumarin telah diuji antitumor terhadap sel HCT-116 dan sel KB. Modifikasi struktur dapat dilakukan melalui alkilasi, amidasi, dan penggabungan dengan aldehida pada posisi C7. Penelitian yang dilakukan bertujuan untuk mendapatkan N’-(4-hidroksi-3-metoksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 1. Penelitian dilakukan melalui sintesis 4-metilumbeliferona 6, etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dan 2-((4-metil-2-okso-2H-kromen-7il)oksi)asetohidrazida 2. Senyawa 6 telah diperoleh dengan rendemen 63,82% dari reaksi kondensasi resorcinol 8 dengan etil asetoasetat 9. Etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dengan rendemen 57,40% selanjutnya diperoleh melalui alkilasi 4-metilumbeliferona 6 dengan etil kloroasetat 7. Lebih lanjut, 2-((4-metil-2-okso-2H-kromen-7il)oksi)asetohidrazida 2 dengan rendemen 94,86% diperoleh melalui reaksi antara etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dengan hidrazin hidrat 5. Senyawa N’-(4-hidroksi-3-metoksi-benzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 1 dengan rendemen 83,84% berhasil diperoleh melalui penggabungan 2-((4-metil-2-okso-2H-kromen-7il)oksi)asetohidrazida 2 dengan 4-hidroksi-3-metoksibenzaldehida 3. Semua hasil sintesis dikarakterisasi dengan spektroskopi NMR, FTIR, dan MS. Hasil karakterisasi menunjukkan spektrum yang sesuai dengan struktur senyawa.
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Coumarin are heterocyclic compounds with an oxygen atom at position 1 and a carbonyl group at position 2. Coumarins and their derivatives are known to exhibit diverse biological activities such as antimicrobial, antioxidant, anti-inflammatory, anti-alzheimer's, anticoagulant, cardiotonic and anticancer. The 4-methylumbeliferone is a compound of coumarin framework which has been tested for antitumor against HCT-116 cells and KB cells. Structural modification can be carried out through alkylation, amidation, and combining with aldehydes at the C7 position. The aim of the research was to obtain N'-(4-hydroxy-3-methoxybenzylidene)-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 1. The research was carried out by synthesizing 4-methylumbeliferonE 6, ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 and 2-((4-methyl-2-oxo-2H-chromen-7yl)oxy)acetohydrazide 2. Compound 6 was obtained with a yield of 63.82% from the condensation reaction of resorcinol 8 with ethyl acetoacetate 9. Ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 with a yield of 57, 40% was then obtained by alkylation of 4-methylumbeliferone 6 with ethyl chloroacetate 7. Furthermore, 2-((4-methyl-2-oxo-2H-chromen-7yl)oxy)acetohydrazide 2 with a yield of 94.86% was obtained by the reaction between ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 with hydrazine hydrate 5. The N'-(4-Hydroxy-3-methoxy-benzylidene)-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 1 compound with a yield of 83.84% was successfully obtained by combining 2-((4-methyl-2-oxo-2H-chromen-7yl)oxy)acetohydrazide 2 with 4-hydroxy-3-methoxybenzaldehyde 3. All synthesis results were characterized by NMR, FTIR, and MS spectroscopy. The characterization results show spectrum that matches the structure of compound.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	kumarin, 4-metilumbeliferon, 4-hidroksi-3-metoksibenzaldehida coumarin, 4-methylumbelliferone, 4-hydroxy-3-methoxybenzaldehyde
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Binti Ainiatur Rohmah
Date Deposited:	17 Feb 2023 06:44
Last Modified:	17 Feb 2023 06:44
URI:	http://repository.its.ac.id/id/eprint/97489

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