Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies

Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies

Melanogenesis is a process of melanin synthesize, which is a primary response for the pigmentation of human skin. Tyrosinase is a key enzyme, which catalyzes a rate-limiting step of the melanin formation, natural products have shown potent inhibitors, but some of these possess toxicity. Numerous syn...

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Main Authors: Aida Iraji, Ali Nemati, Hona Hosseinpoor, Najmeh Edraki, mahsima Khoshneviszadeh, Mahshid Attarroshan, Hossein Sadeghpour, Mehdi Khoshneviszadeh
Format: Article
Language:English
Published: Shiraz University of Medical Sciences 2020-12-01
Series:Trends in Pharmaceutical Sciences
Subjects:
1
3-indandione
tyrosinase inhibitor
in silico studies
organic synthesis
Online Access:https://tips.sums.ac.ir/article_47117_413de650c0a9c47dd1647abf45d85727.pdf
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spelling doaj-83ab6015bf13431b8f47cd82ec4e097d2021-07-14T06:32:49ZengShiraz University of Medical SciencesTrends in Pharmaceutical Sciences2423-56522020-12-016423324210.30476/tips.2020.88203.106847117Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studiesAida Iraji0Ali Nemati1Hona Hosseinpoor2Najmeh Edraki3mahsima Khoshneviszadeh4Mahshid Attarroshan5Hossein Sadeghpour6Mehdi Khoshneviszadeh7Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, 71348 Shiraz, Iran Central Research Laboratory, Shiraz University of Medical Sciences, 71468 Shiraz, Iranb Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, 71345 Shiraz, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, 71345 Shiraz, IranMedicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, 71348 Shiraz, IranMedicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, 71348 Shiraz, Irana Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, 71348 Shiraz, IranDepartment of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, 71345 Shiraz, IranMedicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, 71348 Shiraz, Iran Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, 71345 Shiraz, IranMelanogenesis is a process of melanin synthesize, which is a primary response for the pigmentation of human skin. Tyrosinase is a key enzyme, which catalyzes a rate-limiting step of the melanin formation, natural products have shown potent inhibitors, but some of these possess toxicity. Numerous synthetic inhibitors have been developed in recent years may lead to the potent anti-tyrosinase agents. Therefore its inhibition may be an efficient way for the development of depigmenting agents. A novel series of 2-arylidine-1H-indene-1,3(2H)-dione analogs were designed, synthesized and screened for their in vitro tyrosinase inhibitory activity. 3d derivative bearing nitrothiophene revealed excellent anti-tyrosinase activity with an IC50 value of 3.55 μM comparable to kojic acid as a positive control. 3d as the most potent inhibitor and 3f as the least active derivative were subjected to in silico evaluations considering the 3D conformations, ΔGb of bindings and interactions within the active site of tyrosinase.https://tips.sums.ac.ir/article_47117_413de650c0a9c47dd1647abf45d85727.pdf13-indandionetyrosinase inhibitorin silico studiesorganic synthesis
collection DOAJ
language English
format Article
sources DOAJ
author Aida Iraji
Ali Nemati
Hona Hosseinpoor
Najmeh Edraki
mahsima Khoshneviszadeh
Mahshid Attarroshan
Hossein Sadeghpour
Mehdi Khoshneviszadeh
spellingShingle Aida Iraji
Ali Nemati
Hona Hosseinpoor
Najmeh Edraki
mahsima Khoshneviszadeh
Mahshid Attarroshan
Hossein Sadeghpour
Mehdi Khoshneviszadeh
Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies
Trends in Pharmaceutical Sciences
1
3-indandione
tyrosinase inhibitor
in silico studies
organic synthesis
author_facet Aida Iraji
Ali Nemati
Hona Hosseinpoor
Najmeh Edraki
mahsima Khoshneviszadeh
Mahshid Attarroshan
Hossein Sadeghpour
Mehdi Khoshneviszadeh
author_sort Aida Iraji
title Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies
title_short Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies
title_full Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies
title_fullStr Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies
title_full_unstemmed Novel heterocyclic hybrid of 2-(aryl)-1H-indene-1,3(2H)-dione targeting tyrosinase: design, biological evaluation and in silico studies
title_sort novel heterocyclic hybrid of 2-(aryl)-1h-indene-1,3(2h)-dione targeting tyrosinase: design, biological evaluation and in silico studies
publisher Shiraz University of Medical Sciences
series Trends in Pharmaceutical Sciences
issn 2423-5652
publishDate 2020-12-01
description Melanogenesis is a process of melanin synthesize, which is a primary response for the pigmentation of human skin. Tyrosinase is a key enzyme, which catalyzes a rate-limiting step of the melanin formation, natural products have shown potent inhibitors, but some of these possess toxicity. Numerous synthetic inhibitors have been developed in recent years may lead to the potent anti-tyrosinase agents. Therefore its inhibition may be an efficient way for the development of depigmenting agents. A novel series of 2-arylidine-1H-indene-1,3(2H)-dione analogs were designed, synthesized and screened for their in vitro tyrosinase inhibitory activity. 3d derivative bearing nitrothiophene revealed excellent anti-tyrosinase activity with an IC50 value of 3.55 μM comparable to kojic acid as a positive control. 3d as the most potent inhibitor and 3f as the least active derivative were subjected to in silico evaluations considering the 3D conformations, ΔGb of bindings and interactions within the active site of tyrosinase.
topic 1
3-indandione
tyrosinase inhibitor
in silico studies
organic synthesis
url https://tips.sums.ac.ir/article_47117_413de650c0a9c47dd1647abf45d85727.pdf
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