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1, 2, 3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

evaluation

Speijer D.
GSID: rBUDBjPhV3oJ
VD Bock, D Speijer, H Hiemstra… - Organic & biomolecular …, 2007 - pubs.rsc.org

Since the discovery of CuI-catalysed click chemistry, the field of peptidomimetics has expanded to include 1,4-connected 1,2,3-triazoles as useful peptide bond isosteres. Here, we report the synthesis of triazole-containing analogues of the naturally occurring tyrosinase inhibitor …

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Bock, V. D., Speijer, D., Hiemstra, H., & van Maarseveen, J. H. (2007). 1, 2, 3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics. Organic & biomolecular chemistry, 5(6), 971-975.
Bock, Victoria D., et al. "1, 2, 3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics." Organic & biomolecular chemistry 5.6 (2007): 971-975.
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Synthesis of some new 1, 2, 4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities

evaluation

Bayrak H, Demirbas A, Karaoglu SA.
GSID: 1cXOO7CNNWIJ
H Bayrak, A Demirbas, SA Karaoglu… - European journal of …, 2009 - Elsevier

4-Phenyl-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiol (3) was obtained in basic media via the formation of 2-isonicotinoyl-N-phenylhydrazinecarbothioamide (2), and converted to some alkylated derivatives (4a,b) and Mannich base derivatives (5a–c). 2-[(4-Phenyl-5-pyridin-4-yl-4H-1,…

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Bayrak, H., Demirbas, A., Karaoglu, S. A., & Demirbas, N. (2009). Synthesis of some new 1, 2, 4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. European journal of medicinal chemistry, 44(3), 1057-1066.
Bayrak, Hacer, et al. "Synthesis of some new 1, 2, 4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities." European journal of medicinal chemistry 44.3 (2009): 1057-1066.
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Synthesis of some new 1, 2, 4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities

evaluation

Bayrak H, Demirbas A, Demirbas N.
GSID: JDTlwllibDMJ
H Bayrak, A Demirbas, N Demirbas… - European journal of …, 2009 - Elsevier

5-Pyridin-4-yl-1,3,4-oxadiazole-2-thiol (2) was obtained from the reaction of isonicotinic acid hydrazide with carbon disulfide in basic media and converted into 4-amino-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiol (5) by the treatment with hydrazine hydrate. The synthesis of 3 and 6 …

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Bayrak, H., Demirbas, A., Demirbas, N., & Karaoglu, S. A. (2009). Synthesis of some new 1, 2, 4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. European journal of medicinal chemistry, 44(11), 4362-4366.
Bayrak, Hacer, et al. "Synthesis of some new 1, 2, 4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities." European journal of medicinal chemistry 44.11 (2009): 4362-4366.
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Quantifying chloride binding and salt extraction with poly(methyl methacrylate) copolymers bearing aryl-triazoles as anion receptor side chains.

Chemical communications (Cambridge, England)

McDonald KP, Qiao B, Twum EB, Lee S, Gamache PJ, Chen CH, Yi Y, Flood AH.
PMID: 25233076
Chem Commun (Camb). 2014 Nov 11;50(87):13285-8. doi: 10.1039/c4cc03362k. Epub 2014 Sep 18.

Copolymers of methyl methacrylate and aryl-triazole based anion receptors were quantitatively analyzed. Transfer of structural features (1 : 1 and 2 : 1 complexes) and Cl(-) affinities from the parent receptors was demonstrated. Cl(-)-induced cross-linking changed the polymer's hydrodynamic...

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McDonald KP, Qiao B, Twum EB, et al. Quantifying chloride binding and salt extraction with poly(methyl methacrylate) copolymers bearing aryl-triazoles as anion receptor side chains. Chem Commun (Camb). 2014;50(87):13285-8doi: 10.1039/c4cc03362k.
McDonald, K. P., Qiao, B., Twum, E. B., Lee, S., Gamache, P. J., Chen, C. H., Yi, Y., & Flood, A. H. (2014). Quantifying chloride binding and salt extraction with poly(methyl methacrylate) copolymers bearing aryl-triazoles as anion receptor side chains. Chemical communications (Cambridge, England), 50(87), 13285-8. https://doi.org/10.1039/c4cc03362k
McDonald, Kevin P, et al. "Quantifying chloride binding and salt extraction with poly(methyl methacrylate) copolymers bearing aryl-triazoles as anion receptor side chains." Chemical communications (Cambridge, England) vol. 50,87 (2014): 13285-8. doi: https://doi.org/10.1039/c4cc03362k
McDonald KP, Qiao B, Twum EB, Lee S, Gamache PJ, Chen CH, Yi Y, Flood AH. Quantifying chloride binding and salt extraction with poly(methyl methacrylate) copolymers bearing aryl-triazoles as anion receptor side chains. Chem Commun (Camb). 2014 Nov 11;50(87):13285-8. doi: 10.1039/c4cc03362k. Epub 2014 Sep 18. PMID: 25233076.
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Profile of isavuconazole and its potential in the treatment of severe invasive fungal infections.

Infection and drug resistance

Falci DR, Pasqualotto AC.
PMID: 24187505
Infect Drug Resist. 2013 Oct 22;6:163-74. doi: 10.2147/IDR.S51340.

The triazole class of antifungal drugs comprises first-line agents for the treatment of several invasive fungal diseases. Isavuconazole is a novel broad-spectrum triazole agent. Here we summarize its characteristics and compare it with the currently available antifungal agents. Isavuconazole...

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Falci DR, Pasqualotto AC. Profile of isavuconazole and its potential in the treatment of severe invasive fungal infections. Infect Drug Resist. 2013;6:163-74doi: 10.2147/IDR.S51340.
Falci, D. R., & Pasqualotto, A. C. (2013). Profile of isavuconazole and its potential in the treatment of severe invasive fungal infections. Infection and drug resistance, 6163-74. https://doi.org/10.2147/IDR.S51340
Falci, Diego R, and Pasqualotto, Alessandro C. "Profile of isavuconazole and its potential in the treatment of severe invasive fungal infections." Infection and drug resistance vol. 6 (2013): 163-74. doi: https://doi.org/10.2147/IDR.S51340
Falci DR, Pasqualotto AC. Profile of isavuconazole and its potential in the treatment of severe invasive fungal infections. Infect Drug Resist. 2013 Oct 22;6:163-74. doi: 10.2147/IDR.S51340. PMID: 24187505; PMCID: PMC3810441.
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Exogenously Applied Plant Growth Regulators Enhance the Morpho-Physiological Growth and Yield of Rice under High Temperature.

Frontiers in plant science

Fahad S, Hussain S, Saud S, Hassan S, Ihsan Z, Shah AN, Wu C, Yousaf M, Nasim W, Alharby H, Alghabari F, Huang J.
PMID: 27625658
Front Plant Sci. 2016 Aug 30;7:1250. doi: 10.3389/fpls.2016.01250. eCollection 2016.

A 2-year experiment was conducted to ascertain the effects of exogenously applied plant growth regulators (PGR) on rice growth and yield attributes under high day (HDT) and high night temperature (HNT). Two rice cultivars (IR-64 and Huanghuazhan) were subjected...

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Fahad S, Hussain S, Saud S, et al. Exogenously Applied Plant Growth Regulators Enhance the Morpho-Physiological Growth and Yield of Rice under High Temperature. Front Plant Sci. 2016;7:1250doi: 10.3389/fpls.2016.01250.
Fahad, S., Hussain, S., Saud, S., Hassan, S., Ihsan, Z., Shah, A. N., Wu, C., Yousaf, M., Nasim, W., Alharby, H., Alghabari, F., & Huang, J. (2016). Exogenously Applied Plant Growth Regulators Enhance the Morpho-Physiological Growth and Yield of Rice under High Temperature. Frontiers in plant science, 71250. https://doi.org/10.3389/fpls.2016.01250
Fahad, Shah, et al. "Exogenously Applied Plant Growth Regulators Enhance the Morpho-Physiological Growth and Yield of Rice under High Temperature." Frontiers in plant science vol. 7 (2016): 1250. doi: https://doi.org/10.3389/fpls.2016.01250
Fahad S, Hussain S, Saud S, Hassan S, Ihsan Z, Shah AN, Wu C, Yousaf M, Nasim W, Alharby H, Alghabari F, Huang J. Exogenously Applied Plant Growth Regulators Enhance the Morpho-Physiological Growth and Yield of Rice under High Temperature. Front Plant Sci. 2016 Aug 30;7:1250. doi: 10.3389/fpls.2016.01250. eCollection 2016. PMID: 27625658; PMCID: PMC5003834.
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From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles.

The Journal of organic chemistry

Huang K, Sheng G, Lu P, Wang Y.
PMID: 28474887
J Org Chem. 2017 May 19;82(10):5294-5300. doi: 10.1021/acs.joc.7b00627. Epub 2017 May 10.

An efficient and highly regioselective synthesis of 1-allenyl-5-aryl-1,2,3-triazoles from 1-sulfonyl-4-aryl-1,2,3-triazoles is disclosed. 1-Sulfonyl-4-aryl-1,2,3-triazoles reacted with propargylic alcohols in the presence of trifluoroboron etherate to furnish 1-allenyl-5-aryl-1,2,3-triazoles. When secondary alcohols were used as substrate, the outcome of the reaction was...

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Huang K, Sheng G, Lu P, et al. From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles. J Org Chem. 2017;82(10):5294-5300doi: 10.1021/acs.joc.7b00627.
Huang, K., Sheng, G., Lu, P., & Wang, Y. (2017). From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles. The Journal of organic chemistry, 82(10), 5294-5300. https://doi.org/10.1021/acs.joc.7b00627
Huang, Kai, et al. "From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles." The Journal of organic chemistry vol. 82,10 (2017): 5294-5300. doi: https://doi.org/10.1021/acs.joc.7b00627
Huang K, Sheng G, Lu P, Wang Y. From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles. J Org Chem. 2017 May 19;82(10):5294-5300. doi: 10.1021/acs.joc.7b00627. Epub 2017 May 10. PMID: 28474887.
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Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles.

Organic letters

Wei F, Zhou T, Ma Y, Tung CH, Xu Z.
PMID: 28387509
Org Lett. 2017 Apr 21;19(8):2098-2101. doi: 10.1021/acs.orglett.7b00701. Epub 2017 Apr 07.

Metalated triazoles are the key reactive intermediate of the current click reaction (CuAAC). Bench-stable 5-stannyl triazoles are obtained by a copper-catalyzed interrupted click reaction of easily available terminal alkynes. Subsequent palladium-catalyzed cross-coupling reactions, electrophilic trifluoromethylthiolation and trifluoromethylation, generate diverse...

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Wei F, Zhou T, Ma Y, et al. Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles. Org Lett. 2017;19(8):2098-2101doi: 10.1021/acs.orglett.7b00701.
Wei, F., Zhou, T., Ma, Y., Tung, C. H., & Xu, Z. (2017). Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles. Organic letters, 19(8), 2098-2101. https://doi.org/10.1021/acs.orglett.7b00701
Wei, Fang, et al. "Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles." Organic letters vol. 19,8 (2017): 2098-2101. doi: https://doi.org/10.1021/acs.orglett.7b00701
Wei F, Zhou T, Ma Y, Tung CH, Xu Z. Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles. Org Lett. 2017 Apr 21;19(8):2098-2101. doi: 10.1021/acs.orglett.7b00701. Epub 2017 Apr 07. PMID: 28387509.
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Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles.

Organic letters

Lei X, Gao M, Tang Y.
PMID: 27672715
Org Lett. 2016 Oct 07;18(19):4990-4993. doi: 10.1021/acs.orglett.6b02454. Epub 2016 Sep 27.

A Rh(II)-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with 2,1-benzisoxazoles has been developed, which affords an efficient method for the synthesis of quinazoline derivatives. The transformation represents an unprecedented example which utilizes N-sulfonyl-1,2,3-triazole as an aza-[2C]-component in cycloadditions. Meanwhile, a Rh(II)-catalyzed formal...

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Lei X, Gao M, Tang Y. Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles. Org Lett. 2016;18(19):4990-4993doi: 10.1021/acs.orglett.6b02454.
Lei, X., Gao, M., & Tang, Y. (2016). Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles. Organic letters, 18(19), 4990-4993. https://doi.org/10.1021/acs.orglett.6b02454
Lei, Xiaoqiang, et al. "Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles." Organic letters vol. 18,19 (2016): 4990-4993. doi: https://doi.org/10.1021/acs.orglett.6b02454
Lei X, Gao M, Tang Y. Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles. Org Lett. 2016 Oct 07;18(19):4990-4993. doi: 10.1021/acs.orglett.6b02454. Epub 2016 Sep 27. PMID: 27672715.
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N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles.

The Journal of organic chemistry

Zhu LL, Xu XQ, Shi JW, Chen BL, Chen Z.
PMID: 27031001
J Org Chem. 2016 May 06;81(9):3568-75. doi: 10.1021/acs.joc.6b00185. Epub 2016 Apr 08.

A new method was developed to synthesize N(2)-alkyl-substituted 1,2,3-triazole through N-iodosuccinimide (NIS) mediated iodofuctionalization reaction of the alkene group with bi-, mono-, and unsubstituted NH-1,2,3-triazoles. The favored N-1 type hydrogen bond between the iodonium ion intermediate and 1,2,3-triazole was...

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Zhu LL, Xu XQ, Shi JW, et al. N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles. J Org Chem. 2016;81(9):3568-75doi: 10.1021/acs.joc.6b00185.
Zhu, L. L., Xu, X. Q., Shi, J. W., Chen, B. L., & Chen, Z. (2016). N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles. The Journal of organic chemistry, 81(9), 3568-75. https://doi.org/10.1021/acs.joc.6b00185
Zhu, Li-Li, et al. "N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles." The Journal of organic chemistry vol. 81,9 (2016): 3568-75. doi: https://doi.org/10.1021/acs.joc.6b00185
Zhu LL, Xu XQ, Shi JW, Chen BL, Chen Z. N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles. J Org Chem. 2016 May 06;81(9):3568-75. doi: 10.1021/acs.joc.6b00185. Epub 2016 Apr 08. PMID: 27031001.
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Role of isavuconazole in the treatment of invasive fungal infections.

Therapeutics and clinical risk management

Wilson DT, Dimondi VP, Johnson SW, Jones TM, Drew RH.
PMID: 27536124
Ther Clin Risk Manag. 2016 Aug 03;12:1197-206. doi: 10.2147/TCRM.S90335. eCollection 2016.

Despite recent advances in both diagnosis and prevention, the incidence of invasive fungal infections continues to rise. Available antifungal agents to treat invasive fungal infections include polyenes, triazoles, and echinocandins. Unfortunately, individual agents within each class may be limited...

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Wilson DT, Dimondi VP, Johnson SW, et al. Role of isavuconazole in the treatment of invasive fungal infections. Ther Clin Risk Manag. 2016;12:1197-206doi: 10.2147/TCRM.S90335.
Wilson, D. T., Dimondi, V. P., Johnson, S. W., Jones, T. M., & Drew, R. H. (2016). Role of isavuconazole in the treatment of invasive fungal infections. Therapeutics and clinical risk management, 121197-206. https://doi.org/10.2147/TCRM.S90335
Wilson, Dustin T, et al. "Role of isavuconazole in the treatment of invasive fungal infections." Therapeutics and clinical risk management vol. 12 (2016): 1197-206. doi: https://doi.org/10.2147/TCRM.S90335
Wilson DT, Dimondi VP, Johnson SW, Jones TM, Drew RH. Role of isavuconazole in the treatment of invasive fungal infections. Ther Clin Risk Manag. 2016 Aug 03;12:1197-206. doi: 10.2147/TCRM.S90335. eCollection 2016. PMID: 27536124; PMCID: PMC4977098.
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Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution.

Chemical science

Maugeri L, Asencio-Hernández J, Lébl T, Cordes DB, Slawin AMZ, Delsuc MA, Philp D.
PMID: 28451098
Chem Sci. 2016 Oct 01;7(10):6422-6428. doi: 10.1039/c6sc01974a. Epub 2016 Jun 23.

The halogen bond (XB) donor properties of neutral 1,4-diaryl-5-iodo-1,2,3-triazoles are explored using a combination of computational and experimental results and are shown to be competitive in halogen bonding efficiency with the classic pentafluoroiodobenzene XB donor. The S

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Maugeri L, Asencio-Hernández J, Lébl T, et al. Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution. Chem Sci. 2016;7(10):6422-6428doi: 10.1039/c6sc01974a.
Maugeri, L., Asencio-Hernández, J., Lébl, T., Cordes, D. B., Slawin, A. M. Z., Delsuc, M. A., & Philp, D. (2016). Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution. Chemical science, 7(10), 6422-6428. https://doi.org/10.1039/c6sc01974a
Maugeri, Leonardo, et al. "Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution." Chemical science vol. 7,10 (2016): 6422-6428. doi: https://doi.org/10.1039/c6sc01974a
Maugeri L, Asencio-Hernández J, Lébl T, Cordes DB, Slawin AMZ, Delsuc MA, Philp D. Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution. Chem Sci. 2016 Oct 01;7(10):6422-6428. doi: 10.1039/c6sc01974a. Epub 2016 Jun 23. PMID: 28451098; PMCID: PMC5355977.
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Showing 1 to 12 of 913 entries