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Current Pharmaceutical Design 2019Triazenes are a very useful and diverse class of compounds that have been studied for their potential in the treatment of many tumors including brain tumor, leukemia and... (Review)
Review
Triazenes are a very useful and diverse class of compounds that have been studied for their potential in the treatment of many tumors including brain tumor, leukemia and melanoma. Novel compounds of this class continue to be developed as either anticancer compounds or even with other therapeutic applications. This review focused on several types of triazenes from the simplest ones like 1,3-dialkyl-3-acyltriazenes to the more complex ones like combi-triazenes with an emphasis on how triazenes have been developed as effective antitumor agents.
Topics: Antineoplastic Agents; Humans; Neoplasms; Triazenes
PubMed: 31244412
DOI: 10.2174/1381612825666190617155749 -
Angewandte Chemie (International Ed. in... Sep 2002Triazenes (RN=N-NR'R") are a class of compounds that hold much promise in preparative chemistry as they are reactive groups which are both stable and adaptable to... (Review)
Review
Triazenes (RN=N-NR'R") are a class of compounds that hold much promise in preparative chemistry as they are reactive groups which are both stable and adaptable to numerous synthetic transformations. Useful to scientists in pharmacology, total synthesis, polymer technology, and the construction of novel ring systems, to name a few areas, triazenes also have a tendency to surprise chemists with new reactions and increasing applicability. This review highlights some of the recent advances and diversity possible with these types of systems.
Topics: Antineoplastic Agents, Alkylating; Combinatorial Chemistry Techniques; Triazenes
PubMed: 12298030
DOI: 10.1002/1521-3773(20020916)41:18<3338::AID-ANIE3338>3.0.CO;2-7 -
Bioorganic & Medicinal Chemistry Letters Mar 2022Several diaryl triazene derivatives were synthesized and tested for their ability to inhibit cytochrome P450 1A1 and 1B1 as a potential means to prevent and treat...
Several diaryl triazene derivatives were synthesized and tested for their ability to inhibit cytochrome P450 1A1 and 1B1 as a potential means to prevent and treat cancer. These compounds are more planar than their conformational flexible aryl morpholino triazene counterparts that were previously shown to inhibit the above enzymes. As a result, the diaryl triazenes are more likely to exhibit increased binding to the enzyme active sites and inhibit these enzymes more strongly than the aryl morpholino triazenes. The data indicates that the diaryl triazenes inhibit cytochrome P450 1A1 and 1B1 one to two orders of magnitude more strongly than the aryl morpholino triazenes. Furthermore, compounds 8-10 strongly inhibited cytochrome P450 1B1 with IC50 values of 51 nM, 740 nM, and 590 nM respectively. Thus, diaryl triazenes should be further investigated as a potential chemopreventive agent.
Topics: Cytochrome P-450 CYP1A1; Cytochrome P-450 CYP1B1; Cytochrome P-450 Enzyme Inhibitors; Dose-Response Relationship, Drug; Humans; Molecular Structure; Morpholinos; Structure-Activity Relationship; Triazenes
PubMed: 35063631
DOI: 10.1016/j.bmcl.2022.128570 -
Bioorganic & Medicinal Chemistry Letters Jul 2016Many cytochrome P450 1A1 and 1B1 (CYP1A1 and CYP1B1) inhibitors, such as resveratrol, have planar, hydrophobic, aromatic rings in their structure and exhibit anti-cancer...
Many cytochrome P450 1A1 and 1B1 (CYP1A1 and CYP1B1) inhibitors, such as resveratrol, have planar, hydrophobic, aromatic rings in their structure and exhibit anti-cancer activity. Aryl morpholino triazenes have similar structural features and in addition contain a triazene unit consisting of three consecutive, conjugated nitrogen atoms. Several aryl morpholino triazenes, including 4-[(E)-2-(3,4,5-trimethoxyphenyl)diazenyl]-morpholine (2), were prepared from a reaction involving morpholine and a diazonium ion produced from different aniline derivatives, such as 3,4,5-trimethoxyaniline. The aryl morpholino triazenes were then screened at 100μM for their ability to inhibit CYP1A1 and CYP1B1 using ethoxyresorufin as the substrate. Triazenes that inhibited the enzymes to less than 80% of the uninhibited enzyme activity were assayed to determine their IC50 value. Compound 2 was the only triazene to inhibit both CYP1A1 and CYP1B1 to the same degree as resveratrol with IC50 values of 10μM and 18μM, respectively. Compounds 3 and 6 selectively inhibited CYP1B1 over CYP1A1 with IC values of 2μM and 7μM, respectively. Thus, aryl morpholino triazenes are a new class of compounds that can inhibit CYP1A1 and CYP1B1 and potentially prevent cancer.
Topics: Cytochrome P-450 CYP1A1; Cytochrome P-450 CYP1B1; Cytochrome P-450 Enzyme Inhibitors; Dose-Response Relationship, Drug; Humans; Molecular Structure; Morpholinos; Structure-Activity Relationship; Triazenes
PubMed: 27265259
DOI: 10.1016/j.bmcl.2016.05.064 -
Current Topics in Medicinal Chemistry 2020Due to the rapid development of microbial resistance, finding new molecules became urgent to counteract this problem.
BACKGROUND
Due to the rapid development of microbial resistance, finding new molecules became urgent to counteract this problem.
OBJECTIVE
The objective of this work is to access 1,2,3-triazene-1,3-disubstituted, a class of molecule with high therapeutic potential.
METHODS
Here we describe the access to 17 new triazene including six with an imidazole-1,2,3-triazene moiety and eleven with an alkyl-1,2,3-triazene moiety and their evaluation against five strains: two gram (-): Escherichia coli ATCC 25921 and Pseudomonas aeruginosa ATCC 27253; two gram (+) : Staphylococcus aureus ATCC 38213 and Enterococcus faecalis ATCC 29212; and one fungi: Candida albicans ATCC 24433.
RESULTS
All strains were sensitive and the best MIC, 0.28 µM, is observed for 4c against Escherichia coli ATCC 25921. Compound 9, 3-isopropynyltriazene, appears to be the most interesting since it is active on the five evaluated strains with satisfactory MIC 0.32 µM against Escherichia coli and Pseudomonas aeruginosa and 0.64 µM against Enterococcus faecalis and Pseudomonas aeruginosa.
CONCLUSION
Comparing the structure activity relationship, electron withdrawing groups appear to increase antimicrobial activity.
Topics: Anti-Infective Agents; Candida albicans; Drug Evaluation, Preclinical; Enterococcus faecalis; Escherichia coli; Microbial Sensitivity Tests; Molecular Structure; Pseudomonas aeruginosa; Small Molecule Libraries; Staphylococcus aureus; Structure-Activity Relationship; Triazenes
PubMed: 31985378
DOI: 10.2174/1568026620666200127143005 -
International Journal of Dermatology 1976
Topics: Chemical Phenomena; Chemistry; Dacarbazine; Humans; Melanoma; Triazenes
PubMed: 1245371
DOI: 10.1111/j.1365-4362.1976.tb05098.x -
IARC Scientific Publications 1994
Review
Topics: Alkylation; Animals; DNA; DNA Adducts; Humans; Triazenes
PubMed: 7806322
DOI: No ID Found -
Journal of Biochemical and Molecular... Oct 2023Multidrug resistance (MDR) causes difficulties in the treatment of infections and cancer. Research and development studies have become increasingly important for the...
Multidrug resistance (MDR) causes difficulties in the treatment of infections and cancer. Research and development studies have become increasingly important for the strategy of preventing MDR. There is a need for new multitarget drug research and advancement to reduce the development of drug resistance in drug-drug interactions and reduce cost and toxic effects. This study aimed to determine the effects of multi-target triazene compounds on antibacterial, antifungal, antiviral, cytotoxic, and larvicidal activities were investigated in vitro. A series of 12 novel of 1,3-diaryltriazene-substituted sulfadiazine (SDZ) derivatives were synthesized, and the obtained pure products characterized in detail by spectroscopic and analytic methods (FT-IR, H-NMR, C-NMR, and melting points). The antibacterial and antifungal activities of these derivatives (AH1-12) were determined by broth microdilution method. All derivatives have been evaluated in cell-based assays for cytotoxic and antiviral activities against Modified Vaccinia Virus Ankara. The larvicidal efficacy of these chemical compounds was also investigated by using Lucilia sericata (L. sericata) larvae. Twelve 1,3-diaryltriazene-substituted SDZ derivatives (AH1-12) were designed and developed as potent multitargeted compounds. Among them, the AH1 derivative showed the most antibacterial and antifungal activity. Besides, synthesized derivatives AH2, AH3, AH5, and AH7 showed higher antiviral activity than SDZ. All synthesized derivatives showed higher cytotoxic activity than SDZ. Also, they showed larvicidal activity at 72 h of the experiment. As a result, these compounds might be great leads for the development of next-generation multitargeted agents.
Topics: Sulfadiazine; Antifungal Agents; Triazenes; Spectroscopy, Fourier Transform Infrared; Antineoplastic Agents; Anti-Bacterial Agents; Antiviral Agents; Microbial Sensitivity Tests; Structure-Activity Relationship
PubMed: 37466109
DOI: 10.1002/jbt.23467 -
The Journal of Organic Chemistry Apr 2013In-situ-generated neutral 1-(benzylideneamino)- and novel anionic 1-(sulfonimido)-azolylidenes react with organic azides to afford diverse classes of push-pull triazenes...
In-situ-generated neutral 1-(benzylideneamino)- and novel anionic 1-(sulfonimido)-azolylidenes react with organic azides to afford diverse classes of push-pull triazenes and triazene salts. The scope of the heterocyclic core and substituents at the N1 and N3 positions of NHC precursors together with the thermal properties of resulting compounds were examined.
Topics: Azoles; Benzylidene Compounds; Molecular Structure; Stereoisomerism; Sulfonamides; Triazenes
PubMed: 23390958
DOI: 10.1021/jo302697q -
Angewandte Chemie (International Ed. in... Apr 2012
Topics: Benzene Derivatives; Catalysis; Methylation; Molecular Structure; Triazenes; Trifluoroacetic Acid
PubMed: 22318969
DOI: 10.1002/anie.201107414