Synthesis of trifold-labeled versatile reagent [3,5-
13C and 15N label
Cookson/Zinner-Deucker synthesis
derivatization agent
triazolinedione
Journal
Journal of labelled compounds & radiopharmaceuticals
ISSN: 1099-1344
Titre abrégé: J Labelled Comp Radiopharm
Pays: England
ID NLM: 7610510
Informations de publication
Date de publication:
Dec 2023
Dec 2023
Historique:
revised:
05
10
2023
received:
13
08
2023
accepted:
06
10
2023
medline:
11
12
2023
pubmed:
21
11
2023
entrez:
20
11
2023
Statut:
ppublish
Résumé
Triazolinediones are an important class of derivatization agents that have found application in various research disciplines. Their unique reactivity often allows precise and selective tagging of relevant molecular scaffolds to facilitate structural elucidation, tracking in biological systems, and stabilization of labile compounds. Recent research efforts mainly focused on the development of novel fluorescent and ionizable or isotopically labeled tags improving the quantification and identification of the parent molecule by suitable analytical methods. However, these concepts often lack the ability to improve properties facilitating the analysis by nuclear magnetic resonance (NMR) spectroscopy. We herein describe the first synthesis of
Substances chimiques
4-phenyl-1,2,4-triazoline-3,5-dione
4233-33-4
Indicators and Reagents
0
Triazoles
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
461-466Informations de copyright
© 2023 John Wiley & Sons, Ltd.
Références
de Bruycker K, Billiet S, Houck HA, Chattopadhyay S, Winne JM, Du Prez FE. Triazolinediones as highly enabling synthetic tools. Chem Rev. 2016;116:3919-3974, and cit. lit. doi:10.1021/acs.chemrev.5b00599
Wurziger H. 4-Phenyl-1,2,4-triazolin-3,5-dion (PTAD) ein vielseitiges Reagenz. Kontakte (Darmstadt). 1985;2:17-21.
Rádl S. 1,2,4-Triazoline-3,5-Diones. Adv Heterocycl Chem. 1997;67:119-205. doi:10.1016/S0065-2725(08)60071-9
Takacs JM, Korol N, Slivka M. 4-Phenyl-1,2,4-triazoline-3,5-dione. In: Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons; 2021. doi:10.1002/047084289X.rp139.pub2
Okumura M, Sarlah D. 4-methyl-1,2,4-triazoline-3,5-dione. In: Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons; 2021. doi:10.1002/047084289X.rn02375
Korobitsyna IK, Khalikova AV, Rodina LL, Shusherina NP. 4-Phenyl-1,2,4-triazoline-3,5-dione in organic synthesis. Chem Heterocycl Compd. 1983;19:117-136. doi:10.1007/BF00506417 translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147-169, February, 1983.
Cookson RC, Gilani SSH, Stevens IDR. 4-Phenyl-1,2,4-triazolin-3,5-dione: a powerful dienophile. Tetrahedron Lett. 1962;3:615-618. doi:10.1016/S0040-4039(00)70917-8
Cookson RC, Gilani SSH, Stevens IDR. Diels-Alder reactions of 4-phenyl-1,2,4-triazoline-3,5-dione. J Chem Soc C. 1967;1967:1905-1909. doi:10.1039/J39670001905
Roy N, Lehn J-M. Dynamic covalent chemistry: a facile room-temperature, reversible, Diels-Alder reaction between anthracene derivatives and N-phenyltriazolinedione. Chem Asian J. 2011;6:2419-2425. doi:10.1002/asia.201100244
Breton GW, Newton KA. Further studies of the thermal and photochemical Diels−Alder reactions of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with naphthalene and some substituted naphthalenes. J Org Chem. 2000;65:2863-2869. doi:10.1021/jo9906429
Breton GW. Acid-catalyzed reactions of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with some polyaromatic hydrocarbons. Adv Chem Lett. 2013;1:68-73. doi:10.1166/acl.2013.1011
Chen JS, Houk KN, Foote CS. Theoretical study of the concerted and stepwise mechanisms of triazolinedione Diels−Alder reactions. J Am Chem Soc. 1998;120:12303-12309. doi:10.1021/ja982050y
Watson LJ, Harrington RW, Clegg W, Hall MJ. Diastereoselective intermolecular ene reactions: synthesis of 4,5,6,7-tetrahydro-1H-benzo[d]imidazoles. Org Biomol Chem. 2012;10:6649-6655. doi:10.1039/C2OB26009C
Gau A-H, Lin G-L, Uang B-J, Liao F-L, Wang S-L. Regio- and diastereoselective ene reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with chiral allylic alcohols and their derivatives. J Org Chem. 1999;64:2194-2201. doi:10.1021/jo980835g
Pastor A, Adam W, Wirth T, Tóth G. Diastereoselective reactions of the tiglic acid functionality mediated by oxazolidine chiral auxiliaries: a mechanistic comparison of DMD and m-CPBA epoxidations versus singlet oxygen and PTAD ene reactions. Eur J Org Chem. 2005;2005:3075-3084. doi:10.1002/ejoc.200500077
Baran PS, Guerrero CA, Corey EJ. The first method for protection−deprotection of the indole 2,3-π bond. Org Lett. 2003;5:1999-2001. doi:10.1021/ol034634x
Adam W, Bottke N, Krebs O. Steric and conformational control of the regioselectivities in the ene reaction with trisubstituted cycloalkenes: comparison of the enophiles singlet oxygen, triazolinedione, and nitrosoarene. Org Lett. 2000;2:3293-3296. doi:10.1021/ol006475c
Ban H, Nagano M, Gavrilyuk J, Hakamata W, Inokuma T, Barbas CF III. Facile and stabile linkages through tyrosine: bioconjugation strategies with the tyrosine-click reaction. Bioconjug Chem. 2013;24:520-532. doi:10.1021/bc300665t
Angermund K, Bunte R, Goddard R, Leitich J, Polansky OE, Zander M. Thermal and photochemical reactions of naphtho[1,2,3,4-def]chrysene with 4-phenyl-1,2,4-triazoline-3,5-dione. Chem Ber. 1988;121:1647-1650. doi:10.1002/cber.19881210917
Wilson RM, Chantarasiri N. The condensation of dicarbonyl compounds with N-phenyltriazolinedione-dienone ylides derived from phenols: the facile preparation of novel quinone methides. J Am Chem Soc. 1991;113:2301-2302. doi:10.1021/ja00006a059
Hall JH. Interaction of electron-deficient 1,2,4-triazoline-3,5-diones with electron-rich polyalkoxybenzenes. J Org Chem. 1983;48:1708-1712. doi:10.1021/jo00158a025
Hall JH, Kaler L, Herring R. Reaction of electron-deficient 1,2,4-triazoline-3,5-diones with electron-rich nitrogen heterocycles. J Org Chem. 1984;49:2579-2582. doi:10.1021/jo00188a013
Breton GW. Acid-catalyzed reaction of 4-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with substituted benzenes. Tetrahedron Lett. 2011;52:733-735. doi:10.1016/j.tetlet.2010.12.024
Hall JH, Krishnan G. 2 + 2 cycloaddition of 4-substituted-1,2,4-triazoline-3,5-diones to diphenylketene. J Org Chem. 1984;49:2498-2500. doi:10.1021/jo00187a040
Breton GW, Shugart JH, Hughey CA, Perala SM, Hicks AD. Synthesis of Δ1-1,2-diazetines via a Diels−Alder cycloaddition approach. Org Lett. 2001;3:3185-3187. doi:10.1021/ol0164942
Breton GW, Hughes JS, Pitchko TJ, Martin KL, Hardcastle K. Unexpected σ bond rupture during the reaction of N-methyl-1,2,4-triazoline-3,5-dione with acenaphthylene and indene. J Org Chem. 2014;79:8212-8220. doi:10.1021/jo5014096
Pilipenko VS, Shusherina NP. Zhurnal Organicheskoi Khimii. 1980;16:2444.
Christoforou A, Nicolaou G, Elemes Y. N-Phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides. Tetrahedron Lett. 2006;47:9211-9213. doi:10.1016/j.tetlet.2006.10.134
Zolfigol MA, Choghamarani AG, Shahamirian M, et al. 4-Phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the aromatization of 1,4-dihydropyridines under mild conditions. Tetrahedron Lett. 2005;46:5581-5584. doi:10.1016/j.tetlet.2005.06.031
Klindert T, Seitz G. 4-Phenyl-1,2,4-triazoline-3,5-dione: a novel dehydrogenating agent for dihydropyridazines. Synth Commun. 1996;26:2587-2596. doi:10.1080/00397919608004571
Nicolaou G, Elemes Y. N-Phenyltriazolinedione as an initiator in the radical addition of thiophenol to alkenes. Tetrahedron Lett. 2008;49:6324-6326. doi:10.1016/j.tetlet.2008.08.067
Rio G, Rio M-J (née Scholl). Stereoisomeric 1,2,4,6,7,9-hexaoxecan derivatives from dimerisation of a 1,2,4-trioxolan; stereospecific interconversion. J Chem Soc Chem Commun. 1982;72-74. doi:10.1039/C39820000072
de Meijere A, Erden I, Weber W, Kaufmann D. Bicyclopropylidene: cycloadditions onto a unique olefin. J Org Chem. 1988;53:152-161. doi:10.1021/jo00236a031
Southgate EH, Pospech J, Fu J, Holycross DR, Sarlah D. Dearomative dihydroxylation with arenophiles. Nat Chem. 2016;8:922-928, and 2016;8:1083 (Corrigendum). doi:10.1038/nchem.2594
Okumura M, Nakamata Nuynh SM, Pospech J, Sarlah D. Arenophile-mediated dearomative reduction. Angew Chem Int Ed. 2016;55:15910-15914. doi:10.1002/anie.201609686
Okumura M, Sarlah D. Arenophile-mediated dearomative functionalization strategies. Synlett. 2018;29:845-855. doi:10.1055/s-0036-1591940
Ban H, Gavrilyuk J, Barbas CF III. Tyrosine bioconjugation through aqueous ene-type reactions: a click-like reaction for tyrosine. J Am Chem Soc. 2010;132:1523-1525. doi:10.1021/ja909062q
Decoene KW, Unal K, Staes A, et al. Triazolinedione protein modification: from an overlooked off-target effect to a tryptophan-based bioconjugation strategy. Chem Sci. 2022;13:5390-5397. doi:10.1039/D1SC06942J
Frey M-L, Simon J, Brückner M, Mailänder V, Morsbach S, Landfester K. Bio-orthogonal triazolinedione (TAD) crosslinked protein nanocapsules affect protein adsorption and cell interaction. Polym Chem. 2020;11:3821-3830. doi:10.1039/D0PY00087F
Hromatka O, Sengstschmid G. Diels-Alder-Reaktionen am Thebain mit cyclischen Azodienophilen. Monatsh Chem - Chem Monthly. 1971;102:1022-1027. doi:10.1007/BF00909928
Shimizu M, Takahashi T, Uratsuka S, Yamada S. Synthesis of highly fluorescent dienophiles for detecting conjugated dienes in biological fluid. J Chem Soc Chem Commun. 1990;1416-1417. doi:10.1039/C39900001416
Murao N, Ishigai M, Sekiguchi N, Takahashi T, Aso Y. Ferrocene-based Diels-Alder derivatization for the determination of 1α-hydroxyvitamin D3 in rat plasma by high-performance liquid chromatography-electrospray tandem mass spectrometry. Anal Biochem. 2005;346:158-166. doi:10.1016/j.ab.2005.08.002
Aberhart DJ, Hsu AC-T. Studies on the adduct of 4-phenyl-1,2,4-triazoline-3,5-dione with vitamin D3. J Org Chem. 1976;41:2098-2102. doi:10.1021/jo00874a006
Higashi T, Suzuki M, Hanai J, et al. A specific LC/ESI-MS/MS method for determination of 25-hydroxyvitamin D3 in neonatal dried blood spots containing a potential interfering metabolite, 3-epi-25-hydroxyvitamin D3. J Sep Sci. 2011;34:725-732. doi:10.1002/jssc.201000911
Teegarden MD, Riedl KM, Schwartz SJ. Chromatographic separation of PTAD-derivatized 25-hydroxyvitamin D3 and its C-3 epimer from human serum and murine skin. J Chromatogr B Analyt Technol Biomed Life Sci. 2015;991:118-121. doi:10.1016/j.jchromb.2015.04.011
Shimizu M, Kamachi S, Nishii Y, Yamada S. Synthesis of a reagent for fluorescence-labeling of vitamin D and its use in assaying vitamin D metabolites. Anal Biochem. 1991;194:77-81. doi:10.1016/0003-2697(91)90153-K
Flagothier J, Warnier C, Dammicco S, Lemaire C, Luxen A. Synthesis of [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione: an agent for specific radiolabelling of tyrosine. RSC Adv. 2013;3:24936-24940. doi:10.1039/c3ra44666b
Al-Momani E, Israel I, Buck AK, Samnick S. Improved synthesis of [18F]FS-PTAD as a new tyrosine-specific prosthetic group for radiofluorination of biomolecules. Appl Radiat Isot. 2015;104:136-142. doi:10.1016/j.apradiso.2015.06.021
Holmquist B, Clarke NJ. Mass spectrometry of steroidal compounds in multiplex samples. WO 2011/072152 (Quest Diagnostics Investments Inc.) 2011.
Ogawa S, Kittaka H, Nakata A, et al. Enhancing analysis throughput, sensitivity and specificity in LC/ESI-MS/MS assay of plasma 25-hydroxyvitamin D3 by derivatization with triplex 4-(4-dimethylaminophenyl)-1,2,4-triazoline-3,5-dione (DAPTAD) isotopologues. J Pharm Biomed Anal. 2017;136:126-133. doi:10.1016/j.jpba.2016.11.030
Cookson RC, Gupte SS, Stevens IDR, Watts CT. 4-Phenyl-1,2,4-triazoline-3,5-dione. Org Synth. 1971;51:121.
Cookson RC, Gupte SS, Stevens IDR, Watts CT. 4-Phenyl-1,2,4-triazoline-3,5-dione. Org Synth, Coll. 1988;6:936. doi:10.15227/orgsyn.051.0121
Zinner G, Deucker W. Zur Synthese von Urazolen. Arch Pharm. 1961;294:370-372. doi:10.1002/ardp.19612940609
Liu X, Pan L, Weng J, et al. Synthesis, structure, and biological activity of novel (oxdi/tri)azoles derivatives containing 1,2,3-thiadiazole or methyl moiety. Mol Divers. 2012;16:251-260. doi:10.1007/s11030-011-9352-z
Becker G, Vlaminck L, Velencoso MM, Du Prez FE, Wurm FR. Triazolinedione-“clicked” poly (phosphoester)s: systematic adjustment of thermal properties. Polym Chem. 2017;8:4074-4078. doi:10.1039/C7PY00813A
Marty M, Schütz J. Improved synthesis of 4-aryl-1,2,4-triazolidine-3,5-diones and 4-aryl-1,2,4-triazoline-3,5-diones. WO 2019/121133 (DSM IP Assets B.V.) 2019.
Zolfigol MA, Chehardoli G, Ghaemi E, et al. N-Bromo reagent mediated oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions. Monatsh Chem - Chem Monthly. 2008;139:261-265. doi:10.1007/s00706-007-0785-0
Heravi MM, Derikvand F, Ghassemzadeh M, Neumüller B. Synthesis, characterization and structure of a tetrameric DABCO-bromine complex: a novel oxidizing agent for oxidation of alcohols to carbonyl compounds. Tetrahedron Lett. 2005;46:6243-6245. doi:10.1016/j.tetlet.2005.07.057
Zolfigol MA, Madrakian E, Ghaemi E, Mallakpour S. Trichloroisocyanuric acid as a novel oxidizing agent for the oxidation of urazoles under both heterogeneous and solvent free conditions. Synlett. 2002;2002:1633-1636. doi:10.1055/s-2002-34213