Design of potent tyrosinase inhibiting N-arylated-4-yl-benzamides bearing 2-aminothiazole-triazole bi-heterocycles: mechanistic insight through enzyme inhibition, kinetics and computational studies

QR Code

Design of potent tyrosinase inhibiting N-arylated-4-yl-benzamides bearing 2-aminothiazole-triazole bi-heterocycles: mechanistic insight through enzyme inhibition, kinetics and computational studies

By using a convergent methodology, a unique series of N-arylated 4-yl-benzamides containing a bi-heterocyclic thiazole-triazole core was synthesized and the structures of these hybrid molecules, 9a-k, were corroborated through spectral analyses. The in vitro studies of these multi-functional molecul...

Full description

Bibliographic Details
Published in:	RSC Advances
Main Author:	Khan F.M.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Sadiq Butt A.R.; Raza H.; Hassan M.; Ali Shah S.A.; Shahid M.; Kim S.J.
Format:	Article
Language:	English
Published:	Royal Society of Chemistry 2024
Online Access:	https://www.scopus.com/inward/record.uri?eid=2-s2.0-85194053288&doi=10.1039%2fd4ra01063a&partnerID=40&md5=b663ecb384fd7754b1d7b73422febbd8

Similar Items

Design of potent tyrosinase inhibiting N-arylated-4-yl-benzamides bearing 2-aminothiazole-triazole bi-heterocycles: mechanistic insight through enzyme inhibition, kinetics and computational studies
by: Khan, et al.
Published: (2024)

2-Aminothiazole-Oxadiazole Bearing N-Arylated Butanamides: Convergent Synthesis, Tyrosinase Inhibition, Kinetics, Structure-Activity Relationship, and Binding Conformations
by: Raza H.; Rehman Sadiq Butt A.; Athar Abbasi M.; Aziz-ur-Rehman; Zahra Siddiqui S.; Hassan M.; Adnan Ali Shah S.; Ja Kim S.
Published: (2023)

Convergent synthesis of carbonic anhydrase inhibiting bi-heterocyclic benzamides: Structure–activity relationship and mechanistic explorations through enzyme inhibition, kinetics, and computational studies
by: Khan F.M.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Sadiq Butt A.R.; Raza H.; Zafar A.; Ali Shah S.A.; Shahid M.; Seo S.-Y.
Published: (2021)

Synthesis and structure-activity relationship of tyrosinase inhibiting novel bi-heterocyclic acetamides: Mechanistic insights through enzyme inhibition, kinetics and computational studies
by: Butt A.R.S.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Raza H.; Hassan M.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Published: (2019)

Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
by: Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
Published: (2024)

Synthesis and structure-activity relationship of elastase inhibiting novel ethylated thiazole-triazole acetamide hybrids: Mechanistic insights through kinetics and computational contemplations
by: Butt A.R.S.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Raza H.; Shah S.A.A.; Seo S.-Y.
Published: (2019)

Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
by: Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Published: (2022)

Bi-heterocyclic benzamides as alkaline phosphatase inhibitors: Mechanistic comprehensions through kinetics and computational approaches
by: Abbasi M.A.; Nazir M.; ur-Rehman A.; Siddiqui S.Z.; Hassan M.; Raza H.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Published: (2019)

Synthesis of novel N-(1,3-thiazol-2-yl)benzamide clubbed oxadiazole scaffolds: Urease inhibition, Lipinski rule and molecular docking analyses
by: Athar Abbasi M.; Raza H.; Aziz-ur-Rehman; Zahra Siddiqui S.; Adnan Ali Shah S.; Hassan M.; Seo S.-Y.
Published: (2019)

Multi-step synthesis, kinetics and in silico explorations of indole-Phenyl-1,2,4-triazole Bi-heterocyclic hybrids unified with 3-substituted benzamides as elastase inhibitors
by: Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Muhammad S.; Raza H.; Shah S.A.A.; Shahid M.; Chaudhry A.R.; Kim S.J.
Published: (2025)

Multi-step synthesis, kinetics and in silico explorations of indole-Phenyl-1,2,4-triazole Bi-heterocyclic hybrids unified with 3-substituted benzamides as elastase inhibitors
by: Shakila; Abbasi, et al.
Published: (2025)

Synthesis, characterization, enzyme inhibition and molecular docking studies of benzothiazole derivatives bearing alkyl phenyl ether fragments
by: Usman M.; Alam A.; Zainab; Khan M.; Elhenawy A.A.; Ayaz M.; Alanazi M.M.; Latif A.; Shah S.A.A.; Ali M.; Ahmad M.
Published: (2025)

Synthesis, characterization, enzyme inhibition and molecular docking studies of benzothiazole derivatives bearing alkyl phenyl ether fragments
by: Usman, et al.
Published: (2025)

Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
by: Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
Published: (2016)

Synthesis of Bi-heterocyclic sulfonamides as tyrosinase inhibitors: Lineweaver-burk plot evaluation and computational ascriptions
by: Abbasi M.M.; Zia-Ur-Rehman; Aziz-Ur-Rehman; Siddiqui S.Z.; Nazir M.; Hassan M.; Raza H.; Shah S.A.A.; Seo S.-Y.
Published: (2020)

Synthesis and Computational Exploration of Morpholine Bearing Halogenated Sulfonamides as Potential Tyrosinase Inhibitors
by: Abbasi M.A.; Raza H.; Aziz-ur-Rehman; Siddiqui S.Z.; Muhammad S.; Khan F.M.; Shah S.A.A.; Al-Sehemi A.G.; Kim S.J.
Published: (2023)

BSA Binding, molecular docking and in vitro biological screening of some new 1, 2, 4-triazole heterocycles bearing azinane nucleus
by: Iqbal J.; Aziz-Ur-Rehman; Abbasi M.A.; Siddiqui S.Z.; Khalid H.; Laulloo S.J.; Chohan T.A.; Rasool S.; Ali Shah S.A.
Published: (2020)

Synthesis, β-Glucuronidase Inhibition, and Molecular Docking Studies of 1,2,4-Triazole Hydrazones
by: Jamil W.; Kumari D.; Taha M.; Khan M.N.; Baharudin M.S.; Ali M.; Kanwal M.; Lashari M.S.; Khan K.M.
Published: (2018)

Comparative conventional and microwave assisted synthesis of heterocyclic oxadiazole analogues having enzymatic inhibition potential
by: Javid J.; Aziz-ur-Rehman; Abbasi M.A.; Siddiqui S.Z.; Iqbal J.; Virk N.A.; Rasool S.; Ali H.A.; Ashraf M.; Shahid W.; Hussain S.; Ali Shah S.A.
Published: (2021)

Efficient Synthesis of 4-Bromo-N-(1-phenylethyl)benzamide, Arylation by Pd(0) Catalyst, Characterization and DFT Study
by: Raza Shah A.; Rasool N.; Bılal M.; Mubarık A.; Alı Hashmı M.; Nadeem Akhtar M.; Imran M.; Ahmad G.; Siddiqa A.; Adnan Alı Shah S.
Published: (2022)

Synthesis and corrosion inhibition studies of N-((4 and 3-chlorophenyl) carbamothioyl) benzamide in 1M H2SO4
by: Zulkifli N.Z.; Kassim K.; Nordin N.A.
Published: (2017)

Synthesis of 2-{[5-(aralkyl/aryl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(4-methyl-1,3-thiazol-2-yl)acetamides: Novel bi-heterocycles as potential therapeutic agents
by: Ramzan M.S.; Abbasi M.A.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Ashraf M.; Lodhi M.A.; Khan F.A.; Mirza B.
Published: (2018)

Designing of promising medicinal scaffolds for Alzheimer's disease through enzyme inhibition, lead optimization, molecular docking and dynamic simulation approaches
by: Hassan M.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Shahzadi S.; Raza H.; Hussain G.; Shah S.A.A.; Ashraf M.; Shahid M.; Seo S.-Y.; Malik A.
Published: (2019)

In vitro antioxidant and in silico enzyme inhibition studies of Carissa carandas Linn.: potential ingredient for nutraceutical development
by: Zubair M.; Tousif M.I.; Riaz N.; Saleem M.; Nazir M.; Tauseef S.; Hassan A.; Shah S.A.A.; Zengin G.; Hashem A.; Kumar A.; Abd_Allah E.F.
Published: (2024)

Synthesis and biological evaluation of heterocyclic 1,2,4-triazole scaffolds as promising pharmacological agents
by: Kumari M.; Tahlan S.; Narasimhan B.; Ramasamy K.; Lim S.M.; Shah S.A.A.; Mani V.; Kakkar S.
Published: (2021)

Synthesis and Structure-Activity Relationship of 1-(2-Furoyl)Piperazine Bearing Benzamides as Butyrylcholinesterase Inhibitors
by: Abbasi M.A.; Irshad M.; Aziz-ur-Rehman; Siddiqui S.Z.; Junaid H.M.; Shah S.A.A.; Ashraf M.
Published: (2020)

Synthesis, in vitro and in silico studies of novel potent urease inhibitors: N-[4-({5-[(3-Un/substituted-anilino-3-oxopropyl)sulfanyl]-1,3,4-oxadiazol-2-yl}methyl)-1,3-thiazol-2-yl]benzamides
by: Abbasi M.A.; Hassan M.; Aziz-ur-Rehman; Siddiqui S.Z.; Raza H.; Shah S.A.A.; Seo S.-Y.
Published: (2018)

Oxidised low density lipoprotein causes human macrophage cell death through oxidant generation and inhibition of key catabolic enzymes
by: Katouah H.; Chen A.; Othman I.; Gieseg S.P.
Published: (2015)

Convergent synthesis, kinetics and computational attributions of indole-N-phenyltriazole hybrids bearing N-(aryl)butanamides as alkaline phosphatase inhibitors
by: Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Shah S.A.A.; Ayine-Tora D.M.; Shahid M.; Kim S.J.
Published: (2025)

Synthesis, Bacterial biofilm inhibition and cytotoxicity of new N-Alkyl/aralkyl-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-nitrobenzenesulfonamides
by: Abbasi M.A.; Zeb A.; Aziz-Ur-Rehman; Siddiqui S.Z.; Ali Shah S.A.; Shahid M.; Fatima H.
Published: (2020)

Experimental and computational profiling of novel bis-Schiff base derivatives bearing α-naphthalene moiety as potential tyrosinase inhibitors
by: Shah T.A.; Alam A.; Zainab; Khan M.; Elhenawy A.A.; Ayaz M.; Ali M.; Latif A.; Shah S.A.A.; Ahmad M.
Published: (2025)

Exploration of synthetic multifunctional amides as new therapeutic agents for Alzheimer's disease through enzyme inhibition, chemoinformatic properties, molecular docking and dynamic simulation insights
by: Hassan M.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hussain G.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Published: (2018)

Structure–activity relationship and in silico study of unique bi-heterocycles: 5-[(2-amino-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol derivatives
by: Abbasi M.A.; Ramzan M.S.; Aziz-Ur-Rehman; Siddiqui S.Z.; Hassan M.; Raza H.; Shah S.A.A.; Mirza B.; Seo S.-Y.
Published: (2019)

New Cholinesterase inhibitors based on 1,2,4-triazole bearing benzenesulfonohydrazide skeleton: Synthesis, in vitro and in silico studies
by: Othman M.S.; Naz H.; Rahim F.; Ullah H.; Hussain R.; Taha M.; Khan S.; Fareid M.A.; Aboelnaga S.M.; Altaleb A.T.; Iqbal R.; Adnan Ali Shah S.
Published: (2024)

Convergent synthesis, kinetics insight and allosteric computational ascriptions of thiazole-(5-aryl)oxadiazole hybrids embraced with propanamides as alkaline phosphatase inhibitors
by: Butt A.R.S.; Abbasi M.A.; Aziz-Ur-Rehman N.; Siddiqui S.Z.; Muhammad S.; Raza H.; Shah S.A.A.; Shahid M.; Alsehemi A.G.; Kim S.J.
Published: (2023)

A Comprehensive Analysis of Human CYP3A4 Crystal Structures as a Potential Tool for Molecular Docking-Based Site of Metabolism and Enzyme Inhibition Studies
by: Ridhwan M.J.M.; Bakar S.I.A.; Latip N.A.; Ghani N.A.; Ismail N.H.
Published: (2022)

Bacterial Biofilm Inhibition, Hemolytic Activity, and Structure–Activity Relationship of N-(2,3-Dihydro-1,4-Benzodioxin-6-yl)-4-Nitro-N-(Substituted-Benzyl)benzenesulfonamides
by: Muhammad A. Abbasi; Irshad M.; Aziz-ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
Published: (2020)

α-Glucosidase inhibition of lactone intermediates of the iminosugar deoxynojirimycin
by: Haan Y.W.; Al-Bajalan H.M.; Sage E.E.; Elangovan D.; Yajit N.L.M.; Sarizan N.M.; Zitzmann N.; Kiappes J.L.; Hasbullah S.A.; Ismail N.H.; Mackeen M.M.
Published: (2019)

Synthesis and structural analysis of persuasive antibacterial agents and enzyme inhibitors derived from 5-(1-(4-Tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol
by: Aziz-Ur-Rehman; Sattar A.; Abbasi M.A.; Siddiqui S.Z.; Raza M.A.; Ashraf M.; Nazir M.; Shah S.A.A.
Published: (2018)

5-Bromo-2-aryl benzimidazole derivatives as non-cytotoxic potential dual inhibitors of α-glucosidase and urease enzymes
by: Arshad T.; Khan K.M.; Rasool N.; Salar U.; Hussain S.; Asghar H.; Ashraf M.; Wadood A.; Riaz M.; Perveen S.; Taha M.; Ismail N.H.
Published: (2017)