CD Tesis

Sintesis Dan Evaluasi Aktivitas Biologis Senyawa Turunan 1,3,5-Triaril Pirazolin Sebagai Inhibitor Enzim Tirosinase

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Pyrazoline is a heterocyclic azo compound consisting of two nitrogen atoms and
three carbon atoms. 2-pyrazoline compounds are the best known class for their various
biological activities such as antiviral, antimicrobial, anticancer, anti-inflammatory and
antioxidant. The aim of this study was to synthesize a substituted 2-pyrazoline compound
at position 1,3,5 of the pyrazoline ring with a phenyl ring as a substituent containing a
sulfonamide or methoxy group. Furthermore, its inhibitory activity against the tyrosinase
enzyme of the fungus Agaricus bisporus was determined in silico and in vitro. The 1,3,5-
triaryl pyrazoline derivative compounds were synthesized through a stepwise reaction,
namely the synthesis of hydrazine compounds followed by the synthesis of pyrazoline
compounds. Hydrazine compounds were synthesized through a diazotasi-reduction
reaction of sulfanilamide, while pyrazoline compounds were obtained from the
cyclocondensation reaction of chalcone compounds (E)-3-(2,3-dimethoxyphenyl)-1-(4-
methoxyphenyl)prop-2-en-1-one with hydrazine under alkaline conditions. The tyrosinase
inhibitory activity was evaluated by molecular docking of the synthesized compound
against the crystal structure of the fungal tyrosinase enzyme Agaricus bisporus bound to
tropolone (PDB ID: 2Y9X) using the Molecular Operating Environment 2020 (MOE)
program and in vitro assay on the tyrosinase enzyme from the same fungus. .
In this study, the compound 1,3,5-triaryl pyrazoline (17) was successfully
synthesized with a satisfactory yield of 93%. The molecular structure was confirmed
through analysis of UV, FTIR, NMR and HRMS spectroscopic data. The molecular
docking results showed that the pyrazoline compound 17 which has three methoxy
substituents and a sulfonamide substituent has a good affinity for the tyrosinse enzyme.
This interaction is similar to the interaction of the positive control asam kojat with a
binding factor value of 11. The 17 compound has a bond free energy value of S = -7.6
kcal/mol, better than asam kojat (S = -5.23 kcal). /mole). However, the pyrazoline
compound 17 showed no better inhibitory activity than the positive control, asam kojat.
Where the IC50 value of the 17 compound is higher than that of asam kojat. The compound
17 is known to have an IC50 value of 262.15 μM, while asam kojat has an IC50 value of
88.52 μM. However, the compound 17 is still a potential candidate for tyrosinase enzymes
inhibitor with further development.
Keywords: Hyperpigmentation, melanin, molecular docking, pyrazoline, and tyrosinase

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Ketersediaan

Informasi Detail

Judul Seri

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No. Panggil

10 05. 221 (0005)

Penerbit

Pekanbaru : Universitas Riau – Pascasarjana – Tesis Kimia., 2021

Deskripsi Fisik

xii, 67 hlm.: ill.: 29 cm

Bahasa

Indonesia

ISBN/ISSN

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Klasifikasi

10 05. 221 (0005)

Tipe Isi

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Tipe Media

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Tipe Pembawa

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Edisi

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Subjek

KIMIA

Info Detail Spesifik

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Pernyataan Tanggungjawab

FATAH

Versi lain/terkait

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