Sintesis, Studi Molekular Doking, dan Analisis ADME Etil-2-(4-formil-2-metoksifenoksi)asetat dan 2-(4-Formil-2-metoksifenoksi)asetohidrazida

Guntur, Timoteus (2023) Sintesis, Studi Molekular Doking, dan Analisis ADME Etil-2-(4-formil-2-metoksifenoksi)asetat dan 2-(4-Formil-2-metoksifenoksi)asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa 4-hidroksi-3-metoksibenzaldehida 1 merupakan senyawa alami dengan tiga gugus fungsi reaktif berupa gugus aldehida, hidroksil fenol, dan inti aromatis. Berbagai reaksi dapat terjadi melalui ketiga gugus fungsi tersebut dan menghasilkan senyawa-senyawa dengan bioaktivitas beragam seperti antibakteri, antikanker, dan antivirus. Penelitian ini melaporkan sintesis, studi molekular doking, dan analisis profil penyerapan, distribusi, metabolisme, ekskresi (ADME) senyawa etil-2-(4-formil-2-metoksifenoksi)asetat 14 dan 2-(4-formil-2-metoksifenoksi)asetohidrazida 12. Senyawa etil-2-(4-formil-2-metoksifenoksi)asetat 14 dengan persen yield sebesar 67,26% berhasil diperoleh dari reaksi antara 4-hidroksi-3-metoksibenzaldehida 1 dengan etil kloroasetat 15. Reaksi lebih lanjut antara senyawa 14 dengan hidrazin hidrat 13 memberikan senyawa 2-(4-formil-2-metoksifenoksi)asetohidrazida 12 dengan persen yield 90,88%. Studi molekular doking terhadap enzim timidilat kinase (TMPK, identitas 4QGG) menunjukkan bahwa ketiga senyawa (1, 12, 14) menghasilkan skor doking yang tidak berbeda dengan siprofloksasin 28. Kajian molekular doking senyawa 1, 12, 14 terhadap glikoprotein neuraminidase (NA, identitas 3TI6) mengungkap bahwa senyawa 12 memiliki skor doking yang lebih rendah (-6,5 kkal/mol) dari oseltamivir 29 (-6,1 kkal/mol). Analisis profil ADME menyatakan senyawa 1, 12, 14 memenuhi kriteria Lipinski dan Veber.
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4-hydroxy-3-methoxy-benzaldehyde 1 is a naturally occuring compound with three reactive functional groups i.e. aldehyde, phenolic hydroxyl, and aromatic nucleus. The three functional groups mentioned before can undergo many types of reaction and produce derivatives with diverse bioactivities e.g. antibacterial, anticancer, and antiviral. This research reports the synthesis; molecular docking study; and absorption, distribution, metabolism, excretion (ADME) profile analysis of ethyl 2-(4-formyl-2-methoxyphenoxy)acetate 14 and 2-(4-formyl-2-methoxyphenoxy)acetohydrazide 12. Ethyl 2-(4-formyl-2-methoxyphenoxy)acetate 14 with yield of 67,26% was synthesized from the reaction between 4-hydroxy-3-methoxybenzaldehyde 1 with ethyl chloroacetate 15. Further reaction between compound 14 and hydrazine hydrate 13 gave 2-(4-formyl-2-methoxyphenoxy)acetohydrazide 12 with yield of 90,88%. Molecular docking study against thymydilate kinase enzyme (TMPK, ID 4QGG) showed the three compounds (1, 12, 14) provided docking scores similar to cyprofloxacin 28. Molecular docking assessment of compounds 1, 12, 14 against neuraminidase (NA, ID 3TU6) glycoprotein showed compound 12 producing a lower docking score (-6,5 kcal/mol) than oseltamivir 29 (-6,1 kcal/mol). ADME profile analysis states that compounds 1, 12, 14 met the criteria set by Lipinski and Veber.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Vanilin, molekular doking, timidilat kinase, neuraminidase, vanillin, molecular docking, thymidylate kinase
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:	Timoteus Guntur
Date Deposited:	28 Aug 2023 02:51
Last Modified:	28 Aug 2023 02:51
URI:	http://repository.its.ac.id/id/eprint/103514

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