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Triazole (Htrz) refers to either one of a pair of isomeric chemical compounds with molecular formula C₂H₃N₃, having a five-membered ring of two carbon atoms and three nitrogen atoms.

The two isomers are:

1,2,3-Triazole
1,2,4-Triazole

1H-1,2,3-Triazole
2H-1,2,3-Triazole
1H-1,2,4-Triazole
4H-1,2,4-Triazole

Derivatives

The triazole antifungal drugs include fluconazole, isavuconazole, itraconazole, voriconazole, pramiconazole, ravuconazole, and posaconazole.

The triazole plant protection fungicides include epoxiconazole, triadimenol, propiconazole, metconazole, cyproconazole, tebuconazole, flusilazole and paclobutrazol.

Benzotriazole is used in chemical photography as a restrainer and fog-suppressant.

Importance in agriculture

Due to spreading resistance of plant pathogens towards fungicides of the strobilurin class,^[1] control of fungi such as Septoria tritici or Gibberella zeae^[2] relies heavily on triazoles.

Importance in chemical synthesis

The azide alkyne Huisgen cycloaddition is a mild and selective reaction that gives 1,2,3-triazoles as products. The reaction has been widely used in bioorthogonal chemistry and in organic synthesis. Triazoles are relatively stable functional groups and triazole linkages can be used in a variety of applications (for example, replacing the phosphate backbone of DNA.^[3])

Related heterocycles

Imidazole, an analog with two nonadjacent nitrogen atoms
Pyrazole, an analog with two adjacent nitrogen atoms
Tetrazole, an analog with four nitrogen atoms

External links

Synthesis of 1,2,3-triazoles (overview of recent methods)

References

^ Gisi U, Sierotzki H,Cook A, McCaffery A (2002): Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides. Pest Management Science 58: 859–867. [1]
^ Klix MB, Verreet J-A, Beyer M (2007): Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development. Crop Protection 26:683-690. [2]
^ Hiroyuki Isobe et al. (2008) Triazole-Linked Analogue of Deoxyribonucleic Acid (TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA, Org. Lett. 10 (17), pp 3729–3732.[3]

UpToDate Contents

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3. カンジダ性外陰膣炎 candida vulvovaginitis
4. 爪真菌症：マネージメント onychomycosis management
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English Journal

Synthesis and in vitro antimicrobial activity of new 4-phenyl-5-methyl-4H-1,2,4-triazole-3-thione derivatives.

Popiołek L, Kosikowska U, Dobosz M, Malm A.SourceDepartment of Organic Chemistry, Medical University , Lublin , Poland.
Journal of enzyme inhibition and medicinal chemistry.J Enzyme Inhib Med Chem.2013 Jun;28(3):479-88. doi: 10.3109/14756366.2011.653352. Epub 2012 Feb 5.
This study presents the synthesis, spectral analysis and antimicrobial evaluation of a new series of substituted 1,2,4-triazole (5a-i) and 1,3,4-thiadiazole derivatives (9a, c, g, h). New compounds were obtained by cyclization reaction of acyl thiosemicarbazide derivatives in the presence of alkalin
PMID 22304453

Chemotherapy of leishmaniasis. Part XII: Design, synthesis and bioevaluation of novel triazole integrated phenyl heteroterpenoids as antileishmanial agents.

Suryawanshi SN, Tiwari A, Kumar S, Shivahare R, Mittal M, Kant P, Gupta S.SourceDivision of Medicinal Chemistry, CSIR-Central Drug Research Institute, Lucknow 226 001, India. Electronic address: shivajins@yahoo.co.in.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2013 May 15;23(10):2925-8. doi: 10.1016/j.bmcl.2013.03.055. Epub 2013 Mar 26.
A novel series of triazole integrated phenyl heteroterpenoids have been synthesized and screened for their in vitro activity against intracellular amastigote form of Leishmania donovani. Among all tested compounds, compound 3a was found to be the most active with IC50 6.4μM and better selectivity i
PMID 23582274

Triazole derivatives: A series of Darapladib analogues as orally active Lp-PLA2 inhibitors.

Wang K, Xu W, Zhang W, Mo M, Wang Y, Shen J.SourceState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2013 May 15;23(10):2897-901. doi: 10.1016/j.bmcl.2013.03.062. Epub 2013 Mar 26.
This Letter reports our efforts towards the optimization of our previously identified series of imidazole and triazole derivatives that lead to the discovery of a series of orally active Lp-PLA2 inhibitors in C57 mice. These inhibitors are characterized by the presence of a diamine side chain in the
PMID 23575276

Japanese Journal

爪白癬治療薬クレナフィン<sup>®</sup>爪外用液10%

Ｄｒｕｇ　Ｄｅｌｉｖｅｒｙ　Ｓｙｓｔｅｍ 32(1), 60-64, 2017
NAID 130005611922

Trialkylamine Derivatives Containing a Triazole Moiety as Promising Ergosterol Biosynthesis Inhibitor: Design, Synthesis, and Antifungal Activity

ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 65(1), 82-89, 2017
NAID 130005187750

CATALYTIC CYCLIZATION OF 2,3-DIBROMOPROPIONATES WITH BENZYL AZIDES TO AFFORD 1-BENZYL-1,2,3-TRIAZOLE-4-CARBOXYLATE : THE USE OF A NONTOXIC BISMUTH CATALYST

Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 92(3), 423-430, 2016-03-01
NAID 40020766380