アゾール
WordNet
- relating to or containing the azo radical
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/11/22 17:09:38」(JST)
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Azoles are a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom (i.e. nitrogen, sulfur, or oxygen) as part of the ring.[1] Their names originate from the Hantzsch–Widman nomenclature. The parent compounds are aromatic and have two double bonds; there are successively reduced analogs (azolines and azolidines) with fewer. One, and only one, lone pair of electrons from each heteroatom in the ring is part of the aromatic bonding in an azole. Names of azoles maintain the prefix upon reduction (e.g., pyrazoline, pyrazolidine). The numbering of ring atoms in azoles starts with the heteroatom that is not part of a double bond, and then proceeds towards the other heteroatom.
Imidazole and other five-membered aromatic heterocyclic systems with two nitrogens are extremely common in nature and form the core of many biomolecules, such as histidine.
Contents
- 1 Compound classes
- 2 Use as anti-fungal agents
- 3 References
- 4 External links
Compound classes
- Nitrogen only
- N,O compounds
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-
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1,2,3-oxadiazole
(unstable)
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Oxadiazole
(1,2,4-Oxadiazole)
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Furazan
(1,2,5-oxadiazole)
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- N,S compounds
-
-
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Thiadiazole
(1,2,3-Thiadiazole)
-
-
-
Use as anti-fungal agents
Skeletal formula of fluconazole - an antifungal medication
The search for antifungal agents with acceptable toxicity profiles led first to the discovery of ketoconazole, the first azole-based oral treatment of systemic fungal infections, in the early 1980s. Later, triazoles fluconazole and itraconazole, with a broader spectrum of antifungal activity and improved safety profile were developed. In order to overcome limitations such as sub-optimal spectra of activity, drug-drug interactions, toxicity, development of resistance and unfavorable pharmacokinetics, analogues were developed. Second-generation triazoles, including voriconazole, posaconazole and ravuconazole, are more potent and more active against resistant pathogens.[2]
References
This article incorporates material from the Citizendium article "Azole", which is licensed under the Creative Commons Attribution-ShareAlike 3.0 Unported License but not under the GFDL.
- ^ Eicher, T.; Hauptmann, S. (June 2003). The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications (2nd ed.). John Wiley & Sons. ISBN 3527307206.
- ^ Maertens, J. A. (2004-03-01). "History of the development of azole derivatives". Clinical Microbiology and Infection. 10 Suppl 1: 1–10. doi:10.1111/j.1470-9465.2004.00841.x. ISSN 1198-743X. PMID 14748798.
External links
- Azoles at the US National Library of Medicine Medical Subject Headings (MeSH)
- Nomenclature, IUPAC
UpToDate Contents
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English Journal
- The novel NF-κB inhibitor DHMEQ synergizes with celecoxib to exert antitumor effects on human liver cancer cells by a ROS-dependent mechanism.
- Lampiasi N, Azzolina A, Umezawa K, Montalto G, McCubrey JA, Cervello M.SourceInstitute of Biomedicine and Molecular Immunology "Alberto Monroy", National Research Council, Palermo, Italy. lampiasi@ibim.cnr.it
- Cancer letters.Cancer Lett.2012 Sep 1;322(1):35-44. Epub 2012 Feb 16.
- In a previous work of ours dehydroxymethyl-epoxyquinomicin (DHMEQ), an inhibitor of NF-κB, was shown to induce apoptosis through Reactive Oxygen Species (ROS) production in hepatoma cells. The present study demonstrated that DHMEQ cooperates with Celecoxib (CLX) to decrease NF-κB DNA binding and t
- PMID 22343223
- K-Ras mutation-mediated IGF-1-induced feedback ERK activation contributes to the rapalog resistance in pancreatic ductal adenocarcinomas.
- Wei F, Liu Y, Bellail AC, Olson JJ, Sun SY, Lu G, Ding L, Yuan C, Wang G, Hao C.SourceDepartment of Hepatobiliary & Pancreas Surgery and Hematology & Oncology, The First Hospital, Jilin University, China.
- Cancer letters.Cancer Lett.2012 Sep 1;322(1):58-69. Epub 2012 Feb 14.
- Mammalian target of rapamycin complex 1 (mTORC1) is frequently activated in human cancers; however, clinical trials of rapalog (the mTORC1 inhibitors) have shown that pancreatic ductal adenocarcinomas (PDACs) resist to the treatment. Rapalog treatment activated the extracellular signal-regulated kin
- PMID 22342683
Japanese Journal
- ERG11 mutations are associated with high-level azole resistance in clinical Candida tropicalis isolates, a Singapore study
- Mycoscience : official journal of the Mycological Society of Japan 58(2), 111-115, 2017-03
- NAID 40021141378
- Azole-resistant Aspergillus fumigatus Containing a 34-bp Tandem Repeat in cyp51A Promoter is Isolated from the Environment in Japan
- A New Amino Acid Substitution at G150S in Lanosterol 14-α Demethylase (Erg11 protein) in Multi-azole-resistant <I>Trichosporon asahii</I>
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- neticonazole hydrochloride