Synthesis of pyrazolo[4,3-e][1,2,4]triazine sulfonamides, novel Sildenafil analogs with tyrosinase inhibitory activity. 2014

Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3-go Maja 54, 08-110 Siedlce, Poland. Electronic address: mmojzych@yahoo.com.

Tyrosinase is a multifunctional, glycosylated and copper-containing oxidase which catalyzes the first two steps in mammalian melanogenesis and is responsible for enzymatic browning reactions in damaged fruits during post-harvest handling and processing. Neither hyperpigmentation in human skin nor enzymatic browning in fruits are desirable. These phenomena have encouraged researchers to seek new potent tyrosinase inhibitors for use in foods and cosmetics. This article surveys tyrosinase inhibitors, newly discovered from natural and synthetic sources. The inhibitory strength is comparable to that of the standard inhibitor kojic acid. Also their inhibitory mechanisms are discussed. The new obtained compounds were also tested as PDE5 inhibitors and did not show significant inhibitory effect.

UI MeSH Term Description Entries
D010879 Piperazines Compounds that are derived from PIPERAZINE.
D011687 Purines A series of heterocyclic compounds that are variously substituted in nature and are known also as purine bases. They include ADENINE and GUANINE, constituents of nucleic acids, as well as many alkaloids such as CAFFEINE and THEOPHYLLINE. Uric acid is the metabolic end product of purine metabolism.
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D000068677 Sildenafil Citrate A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION. 1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrate,Acetildenafil,Desmethyl Sildenafil,Desmethylsildenafil,Homosildenafil,Hydroxyhomosildenafil,NCX-911,Revatio,Sildenafil,Sildenafil Lactate,Sildenafil Nitrate,UK 92480-10,UK-92,480-10,Viagra,Citrate, Sildenafil,Lactate, Sildenafil,NCX 911,NCX911,Nitrate, Sildenafil,Sildenafil, Desmethyl,UK 92,480 10,UK 92480 10,UK 9248010
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D014227 Triazines Heterocyclic rings containing three nitrogen atoms, commonly in 1,2,4 or 1,3,5 or 2,4,6 formats. Some are used as HERBICIDES. Triazine,Benzotriazines
D014442 Monophenol Monooxygenase An enzyme of the oxidoreductase class that catalyzes the reaction between L-tyrosine, L-dopa, and oxygen to yield L-dopa, dopaquinone, and water. It is a copper protein that acts also on catechols, catalyzing some of the same reactions as CATECHOL OXIDASE. EC 1.14.18.1. Dopa Oxidase,Phenoloxidase,Tyrosinase,Cresolase,Phenol Oxidase,Phenoloxidase A,Phenoloxidase B,Monooxygenase, Monophenol,Oxidase, Dopa,Oxidase, Phenol

Related Publications

Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
December 2017, Journal of enzyme inhibition and medicinal chemistry,
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
May 2014, Bioorganic & medicinal chemistry,
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
July 2015, Bioorganic & medicinal chemistry,
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
January 2020, Molecules (Basel, Switzerland),
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
December 2024, Journal of enzyme inhibition and medicinal chemistry,
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
May 2022, International journal of molecular sciences,
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
February 2023, International journal of molecular sciences,
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
January 2018, Medicinal chemistry (Shariqah (United Arab Emirates)),
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
August 2020, Molecules (Basel, Switzerland),
Mariusz Mojzych, and Aleksandar Dolashki, and Wolfgang Voelter
May 2014, European journal of medicinal chemistry,
Copied contents to your clipboard!