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Journal articles on the topic 'Triazole isosters'

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Author: Grafiati

Published: 11 March 2023

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1

Franco, Daiana Portella, Lucas Caruso, Nathalia Fonseca Nadur, Thiago Moreira Pereira, Renata Barbosa Lacerda, and Arthur Eugen Kümmerle. "Recent Advances in Microwave-Assisted Synthesis and Functionalization of 1,2,3- and 1,2,4-triazoles." Current Organic Chemistry 25, no. 23 (December 16, 2021): 2815–39. http://dx.doi.org/10.2174/1385272825666211011111408.

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Triazoles are five-membered aromatic heterocyclics, which exhibit two isosteric forms (1,2,3-triazoles and 1,2,4-triazoles), as well as multiple applications in medicinal, agricultural, supramolecular, and materials sciences. Famous examples of triazoles include drugs, such as fluconazole, ribavirin, cefatrizine, and tazobactam, as well as herbicides, such as cafenstrole and metosulam. This review aims to present the recent major examples of the application of microwave-assisted organic synthesis (MAOS) to the syntheses and endfunctionalizations of 1,4- and 1,5-disubstituted 1,2,3-triazoles, 1,2,4-triazoles, 3-amino-1,2,4- triazoles, 1,2,4-triazol-3-one, and 1,2,4-triazol-3-thiol derivatives. Notably, the previous reviews on triazole syntheses have not exclusively elucidated the relevance of MAOS techniques in the obtention and derivatization of these compounds.

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2

Sahu, Adarsh, Preeti Sahu, and Ramkishore Agrawal. "A Recent Review on Drug Modification Using 1,2,3-triazole." Current Chemical Biology 14, no. 2 (November 19, 2020): 71–87. http://dx.doi.org/10.2174/2212796814999200807214519.

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Motivated by evidence garnered from literature probing the use of triazoles in drug discovery and development, we reported the utilization of bioisosteric replacement and molecular hybridization in this review. Bio-isosteric replacement has played a significant role in modulating rapid and versatile strategy in synthesizing molecules with multifaceted medicinal properties. Molecular hybridization seeks to conjugate two molecular fragments with diverse applications under very mild reaction conditions. In this regard, 1,2,3-triazole is a well-known scaffold with widespread occurrence in medicinal compounds. It is characterized to have several bioactivities such as anti-microbial, anti-cancer, anti-viral, analgesic, anti- inflammatory effects. Furthermore, the structural features of 1,2,3-triazoles enable it to mimic different functional groups justifying its use as bio-isostere for the synthesis of new molecules of medicinal interest, which we have reported briefly.

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3

Panja, Atanu, and Kumaresh Ghosh. "Triazole-amide isosteric pyridine-based supramolecular gelators in metal ion and biothiol sensing with excellent performance in adsorption of heavy metal ions and picric acid from water." New Journal of Chemistry 43, no. 2 (2019): 934–45. http://dx.doi.org/10.1039/c8nj04380a.

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Pyridine-based gelators 1–4 of triazole-amide isosteric relationship have been considered in metal ion sensing, heavy metal and picric acid adsorption from water. The change from triazole to isosteric amide has marked effect on gelling properties of the gelators.

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4

Alagodla, Ramesh, Paturu Rama Subba Reddy, Sravanthi Vemireddy, Devdutt Chaturvedi, and Halmuthur M. Sampath Kumar. "Synthesis of Novel 1,2,3-Triazolyl L-Serinol Palmitoyl Muramyl Dipeptide Derivatives." Asian Journal of Chemistry 35, no. 3 (2023): 763–70. http://dx.doi.org/10.14233/ajchem.2023.27553.

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In this research, a structural variant of muramyl dipeptide (MDP) is designed wherein, the entire N-acetyl group was replaced by a bio-isosteric 1,2,3-triazole moiety with serinol lipid substitution at 4th position. The protecting groups such as benzyl and benzylidine were removed sequentially to evolve three novel derivatives with increasing polarity as seen in the MDP-lipid 21-23 derivatives. A synthesis strategy involving triazolyl click chemistry to combine MDP scaffold to the serinol lipid head group is developed. The new derivatives were characterized using NMR, ESI-MS and MALDI. Preliminary data from in vitro screening of the compounds inferred the immuno-potentiating properties.

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5

Wu, Jun, Nikolaos Kaplaneris, Shaofei Ni, Felix Kaltenhäuser, and Lutz Ackermann. "Late-stage C(sp2)–H and C(sp3)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling." Chemical Science 11, no. 25 (2020): 6521–26. http://dx.doi.org/10.1039/d0sc01260b.

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C–H glycosylations of complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed glycosylation provided access to complex C-glycosides and fluorescent-labeled glycoamino acids.

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6

Rečnik, Lisa-Maria, Wolfgang Kandioller, and Thomas L. Mindt. "1,4-Disubstituted 1,2,3-Triazoles as Amide Bond Surrogates for the Stabilisation of Linear Peptides with Biological Activity." Molecules 25, no. 16 (August 6, 2020): 3576. http://dx.doi.org/10.3390/molecules25163576.

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Peptides represent an important class of biologically active molecules with high potential for the development of diagnostic and therapeutic agents due to their structural diversity, favourable pharmacokinetic properties, and synthetic availability. However, the widespread use of peptides and conjugates thereof in clinical applications can be hampered by their low stability in vivo due to rapid degradation by endogenous proteases. A promising approach to circumvent this potential limitation includes the substitution of metabolically labile amide bonds in the peptide backbone by stable isosteric amide bond mimetics. In this review, we focus on the incorporation of 1,4-disubstituted 1,2,3-triazoles as amide bond surrogates in linear peptides with the aim to increase their stability without impacting their biological function(s). We highlight the properties of this heterocycle as a trans-amide bond surrogate and summarise approaches for the synthesis of triazole-containing peptidomimetics via the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). The impacts of the incorporation of triazoles in the backbone of diverse peptides on their biological properties such as, e.g., blood serum stability and affinity as well as selectivity towards their respective molecular target(s) are discussed.

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7

Wales, Steven M., Katherine A. Hammer, Amy M. King, Andrew J. Tague, Dena Lyras, Thomas V. Riley, Paul A. Keller, and Stephen G. Pyne. "Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria." Organic & Biomolecular Chemistry 13, no. 20 (2015): 5743–56. http://dx.doi.org/10.1039/c5ob00576k.

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Designed binaphthyl-based, cationic peptidomimetic antimicrobials targeting C. difficile, incorporating a click-derived 1,2,3-triazole ester isostere at the C-terminus MICs of 4 μg mL⁻¹ against three human isolates of C. difficile.

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8

Tautz, Markus, Juan Torras, Santiago Grijalvo, Ramón Eritja, César Saldías, Carlos Alemán, and David Díaz Díaz. "Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels." RSC Advances 9, no. 36 (2019): 20841–51. http://dx.doi.org/10.1039/c9ra03316e.

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9

Tautz, Markus, César Saldías, Antonio Diego Lozano-Gorrín, and David Díaz Díaz. "Use of a bis-1,2,3-triazole gelator for the preparation of supramolecular metallogels and stabilization of gold nanoparticles." New Journal of Chemistry 43, no. 35 (2019): 13850–56. http://dx.doi.org/10.1039/c9nj03427g.

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10

Junaid, Lim, Zhou, Chui, and Dolzhenko. "Fused Heterocyclic Systems with an s-Triazine Ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines." Molecules 24, no. 8 (April 12, 2019): 1453. http://dx.doi.org/10.3390/molecules24081453.

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Purine isosteres present excellent opportunities in drug design and development. Using isosteres of natural purines as scaffolds for the construction of new therapeutic agents has been a valid strategy of medicinal chemistry. Inspired by the similarity to isoguanine, we attempted to develop a practical method for the preparation of 5-aza-isoguanines. Several synthetic approaches were explored to establish a robust general protocol for the preparation of these compounds. The significant difference in the reactivity of the C-5 and C-7 electrophilic centers of 1,2,4-triazolo[1,5-a][1,3,5]triazines (5-azapurines) towards nucleophiles was demonstrated. The most practical and general method for the preparation of 5-aza-isoguanines involved a regioselective reaction of ethoxycarbonyl isothiocyanate with a 5-aminotriazole. The intramolecular ring closure of the resulted product followed by the S-methylation afforded 7-methylthio-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one, which could be effectively aminated with various amines. The resulted 5-aza-isoguanines resemble a known purine nucleoside phosphorylase inhibitor and could be interesting for further investigations as potential anticancer agents.

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11

Rani, Alisha, Gurjaspreet Singh, Akshpreet Singh, Ubair Maqbool, Gurpreet Kaur, and Jandeep Singh. "CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review." RSC Advances 10, no. 10 (2020): 5610–35. http://dx.doi.org/10.1039/c9ra09510a.

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The review lays emphasis on the significance of 1,2,3-triazoles synthesized via CuAAC reaction having potential to act as anti-microbial, anti-cancer, anti-viral, anti-inflammatory, anti-tuberculosis, anti-diabetic, and anti-Alzheimer drugs.

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12

Rjabovs, Vitālijs, Pāvels Ostrovskis, Daniels Posevins, Gļebs Kiseļovs, Viktors Kumpiņš, Anatoly Mishnev, and Māris Turks. "Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly." European Journal of Organic Chemistry 2015, no. 25 (July 23, 2015): 5572–84. http://dx.doi.org/10.1002/ejoc.201500695.

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13

Bachl, Jürgen, Judith Mayr, Francisco J. Sayago, Carlos Cativiela, and David Díaz Díaz. "Amide–triazole isosteric substitution for tuning self-assembly and incorporating new functions into soft supramolecular materials." Chemical Communications 51, no. 25 (2015): 5294–97. http://dx.doi.org/10.1039/c4cc08593k.

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14

Rep, Valentina, Martina Piškor, Helena Šimek, Petra Mišetić, Petra Grbčić, Jasna Padovan, Vesna Gabelica Marković, et al. "Purine and Purine Isostere Derivatives of Ferrocene: An Evaluation of ADME, Antitumor and Electrochemical Properties." Molecules 25, no. 7 (March 29, 2020): 1570. http://dx.doi.org/10.3390/molecules25071570.

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Novel purine and purine isosteres containing a ferrocene motif and 4,1-disubstituted (11a−11c, 12a−12c, 13a−13c, 14a−14c, 15a−15c, 16a, 23a−23c, 24a−24c, 25a−25c) and 1,4-disubstituted (34a−34c and 35a−35c) 1,2,3-triazole rings were synthesized. The most potent cytotoxic effect on colorectal adenocarcinoma (SW620) was exerted by the 6-chloro-7-deazapurine 11c (IC50 = 9.07 µM), 6-chloropurine 13a (IC50 = 14.38 µM) and 15b (IC50 = 15.50 µM) ferrocenylalkyl derivatives. The N-9 isomer of 6-chloropurine 13a containing ferrocenylmethylene unit showed a favourable in vitro physicochemical and ADME properties including high solubility, moderate permeability and good metabolic stability in human liver microsomes.

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15

Bock, Victoria D., Dave Speijer, Henk Hiemstra, and Jan H. van Maarseveen. "1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics." Organic & Biomolecular Chemistry 5, no. 6 (2007): 971. http://dx.doi.org/10.1039/b616751a.

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16

Häring, Marleen, Julio Rodríguez-López, Santiago Grijalvo, Markus Tautz, Ramón Eritja, Víctor S. Martín, and David Díaz Díaz. "Isosteric Substitution of 4H-1,2,4-Triazole by 1H-1,2,3-Triazole in Isophthalic Derivative Enabled Hydrogel Formation for Controlled Drug Delivery." Molecular Pharmaceutics 15, no. 8 (February 15, 2018): 2963–72. http://dx.doi.org/10.1021/acs.molpharmaceut.7b01049.

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17

Grob, Nathalie M., Roger Schibli, Martin Béhé, Ibai E. Valverde, and Thomas L. Mindt. "1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs." ACS Medicinal Chemistry Letters 12, no. 4 (March 16, 2021): 585–92. http://dx.doi.org/10.1021/acsmedchemlett.0c00636.

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18

Sahu, Adarsh, Debashree Das, Ram Kishore Agrawal, and Asmita Gajbhiye. "Bio-isosteric replacement of amide group with 1,2,3-triazole in phenacetin improves the toxicology and efficacy of phenacetin-triazole conjugates (PhTCs)." Life Sciences 228 (July 2019): 176–88. http://dx.doi.org/10.1016/j.lfs.2019.05.004.

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19

Zálešák, František, Jan Slouka, and Jakub Stýskala. "General Synthesis of 1-Aryl-6-azaisocytosines and Their Utilization for the Preparation of Related Condensed 1,2,4-Triazines." Molecules 24, no. 19 (October 1, 2019): 3558. http://dx.doi.org/10.3390/molecules24193558.

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A simple general synthesis of 1-aryl-6-azaisocytosine-5-carbonitriles 4 is described. This method is based on coupling diazonium salts with cyanoacetylcyanamide 2 and then cyclization of the formed 2-arylhydrazono-2-cyanoacetylcyanamides 3. The 6-azaisocytosines 4 were studied with respect to tautomeric equilibrium and the transformation of functional groups, and used in the synthesis of the condensed heterocyclic compounds: Purine isosteric imidazo[2,1-c]-[1,2,4]triazine 8 and the 1,2,4-triazino[2,3-a]quinazolines 9–12.

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20

Corredor, Miriam, Jordi Bujons, Mar Orzáez, Mónica Sancho, Enrique Pérez-Payá, Ignacio Alfonso, and Angel Messeguer. "Optimizing the control of apoptosis by amide/triazole isosteric substitution in a constrained peptoid." European Journal of Medicinal Chemistry 63 (May 2013): 892–96. http://dx.doi.org/10.1016/j.ejmech.2013.03.004.

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21

Shultz, Michael D., Dyuti Majumdar, Donovan N. Chin, Pascal D. Fortin, Yun Feng, Ty Gould, Christina A. Kirby, Travis Stams, Nigel J. Waters, and Wenlin Shao. "Structure–Efficiency Relationship of [1,2,4]Triazol-3-ylamines as Novel Nicotinamide Isosteres that Inhibit Tankyrases." Journal of Medicinal Chemistry 56, no. 17 (August 14, 2013): 7049–59. http://dx.doi.org/10.1021/jm400826j.

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22

Karas, John, Fazel Shabanpoor, Mohammed Akhter Hossain, James Gardiner, Frances Separovic, John D. Wade, and Denis B. Scanlon. "Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide: Application to an Analogue of Human Insulin-Like Peptide 3." International Journal of Peptides 2013 (October 28, 2013): 1–8. http://dx.doi.org/10.1155/2013/504260.

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Nonreducible cystine isosteres represent important peptide design elements in that they can maintain a near-native tertiary conformation of the peptide while simultaneously extending the in vitro and in vivo half-life of the biomolecule. Examples of these cystine mimics include dicarba, diselenide, thioether, triazole, and lactam bridges. Each has unique physicochemical properties that impact upon the resulting peptide conformation. Each also requires specific conditions for its formation via chemical peptide synthesis protocols. While the preparation of peptides containing two lactam bonds within a peptide is technically possible and reported by others, to date there has been no report of the chemical synthesis of a heterodimeric peptide linked by two lactam bonds. To examine the feasibility of such an assembly, judicious use of a complementary combination of amine and acid protecting groups together with nonfragment-based, total stepwise solid phase peptide synthesis led to the successful preparation of an analogue of the model peptide, insulin-like peptide 3 (INSL3), in which both of the interchain disulfide bonds were replaced with a lactam bond. An analogue containing a single disulfide-substituted interchain lactam bond was also prepared. Both INSL3 analogues retained significant cognate RXFP2 receptor binding affinity.

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23

Zavodskaya, Anna V., Vladimir V. Bakharev, Victor E. Parfenov, Alexander A. Gidaspov, Pavel A. Slepukhin, Maksim L. Isenov, and Oleg S. Eltsov. "Synthesis of new 5-aza-isosteres of guanine containing aryl and hetaryl substituents on the 1,2,4-triazole ring." Tetrahedron Letters 56, no. 9 (February 2015): 1103–6. http://dx.doi.org/10.1016/j.tetlet.2015.01.151.

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24

Monceaux, Christopher J., Chiho Hirata-Fukae, Polo C. H. Lam, Maxim M. Totrov, Yasuji Matsuoka, and Paul R. Carlier. "Triazole-linked reduced amide isosteres: An approach for the fragment-based drug discovery of anti-Alzheimer’s BACE1 inhibitors." Bioorganic & Medicinal Chemistry Letters 21, no. 13 (July 2011): 3992–96. http://dx.doi.org/10.1016/j.bmcl.2011.05.007.

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25

Lim, Felicia Phei Lin, and Anton V. Dolzhenko. "1,3,5-Triazine-based analogues of purine: From isosteres to privileged scaffolds in medicinal chemistry." European Journal of Medicinal Chemistry 85 (October 2014): 371–90. http://dx.doi.org/10.1016/j.ejmech.2014.07.112.

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26

Nishimura, Natsu, Ai Kato, and Isamu Maeba. "Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin." Carbohydrate Research 331, no. 1 (March 2001): 77–82. http://dx.doi.org/10.1016/s0008-6215(01)00017-9.

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27

Zhang, Jian-Wei, Man-Cheng Hu, Shu-Ni Li, Yu-Cheng Jiang, and Quan-Guo Zhai. "Microporous rod metal–organic frameworks with diverse Zn/Cd–triazolate ribbons as secondary building units for CO2 uptake and selective adsorption of hydrocarbons." Dalton Transactions 46, no. 3 (2017): 836–44. http://dx.doi.org/10.1039/c6dt04433f.

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Three rod MOFs exhibiting remarkable CO₂ uptake and high CO₂ and C₂-hydrocarbons over CH₄ selectivity, as well as high isosteric heat of adsorption for C₂H₂.

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28

Bakharev, Vladimir V., Victor E. Parfenov, Irina V. Ul'yankina, Anna V. Zavodskaya, Evgeniya V. Selezneva, Alexander A. Gidaspov, Oleg S. Eltsov, and Pavel A. Slepukhin. "Synthesis of new 5-aza-isosteres of guanine—5-aminosubstituted 1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones." Tetrahedron 70, no. 38 (September 2014): 6825–30. http://dx.doi.org/10.1016/j.tet.2014.07.058.

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29

Lim, Felicia Phei Lin, and Anton V. Dolzhenko. "ChemInform Abstract: 1,3,5-Triazine-Based Analogues of Purine: From Isosteres to Privileged Scaffolds in Medicinal Chemistry." ChemInform 45, no. 45 (October 23, 2014): no. http://dx.doi.org/10.1002/chin.201445288.

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30

Chopra, Pratiksha N., and Jagdish K. Sahu. "Biological Significance of Imidazole-based Analogues in New Drug Development." Current Drug Discovery Technologies 17, no. 5 (December 23, 2020): 574–84. http://dx.doi.org/10.2174/1570163816666190320123340.

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In the field of heterocyclic medicinal chemistry, especially five-membered ring structures containing a nitrogen atom, imidazole core is an imperative aromatic heterocycle which is usually present in naturally occurring products and synthetic bioactive molecules. The occurrence of imidazole moiety in therapeutic compounds may be beneficial in terms of improving water-soluble properties due to its two nitrogen atoms which leads to the creation of hydrogen bonds. The imidazole nucleus has also been recognized as an important isostere of triazole, pyrazole, thiazole, tetrazole, oxazole, amide etc. for the purpose of designing and development of various biologically active molecules. Moreover, imidazole core as an attractive binding site could interact with diverse cations and anions as well as biomolecules through different reactions in the human biological system thus displaying extensive biological activities. This effort thoroughly provides a wide-ranging assessment in current drug discovery and developments of imidazolebased analogues in the entire series of synthetic medicinal chemistry as antibacterial and antifungal, anticancer, anti-tubercular, analgesic and anti-inflammatory, anti-neuropathic, antihypertensive, anti-allergic, anti-parasitic, antiviral, antidepressant, anti-obesity and so on, altogether with their prospective approaches in diagnostic and pathological field. It is expected that the present review will be supportive on behalf of new opinions in the search for rational strategies of more efficacious and less toxic medicinal agents and drugs containing imidazole core.

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31

Bauer, Michaela, Wei Wang, Mélanie M. Lorion, Chuan Dong, and Lutz Ackermann. "Internal Peptide Late-Stage Diversification: Peptide-Isosteric Triazoles for Primary and Secondary C(sp3 )−H Activation." Angewandte Chemie International Edition 57, no. 1 (December 5, 2017): 203–7. http://dx.doi.org/10.1002/anie.201710136.

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32

Bauer, Michaela, Wei Wang, Mélanie M. Lorion, Chuan Dong, and Lutz Ackermann. "Internal Peptide Late-Stage Diversification: Peptide-Isosteric Triazoles for Primary and Secondary C(sp3 )−H Activation." Angewandte Chemie 130, no. 1 (December 5, 2017): 209–13. http://dx.doi.org/10.1002/ange.201710136.

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33

Perissutti, Elisa, Francesco Frecentese, Ferdinando Fiorino, Beatrice Severino, Donatella Cirillo, Vincenzo Santagada, and Giuseppe Caliendo. "Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres." Journal of Heterocyclic Chemistry 44, no. 4 (July 2007): 815–19. http://dx.doi.org/10.1002/jhet.5570440410.

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34

Nishimura, Natsu, Ai Kato, and Isamu Maeba. "ChemInform Abstract: Synthesis of Pyrrolo[2,1-f][1,2,4]triazine C-Nucleosides. Isosteres of Sangivamycin, Tubercidin, and Toyocamycin." ChemInform 32, no. 26 (May 25, 2010): no. http://dx.doi.org/10.1002/chin.200126214.

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35

Fedorczyk, Bartlomiej, Piotr F. J. Lipiński, Anna K. Puszko, Dagmara Tymecka, Beata Wilenska, Wioleta Dudka, Gerard Y. Perret, Rafal Wieczorek, and Aleksandra Misicka. "Triazolopeptides Inhibiting the Interaction between Neuropilin-1 and Vascular Endothelial Growth Factor-165." Molecules 24, no. 9 (May 6, 2019): 1756. http://dx.doi.org/10.3390/molecules24091756.

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Inhibiting the interaction of neuropilin-1 (NRP-1) with vascular endothelial growth factor (VEGF) has become an interesting mechanism for potential anticancer therapies. In our previous works, we have obtained several submicromolar inhibitors of this interaction, including branched pentapeptides of general structure Lys(Har)-Xxx-Xxx-Arg. With the intent to improve the proteolytic stability of our inhibitors, we turned our attention to 1,4-disubstituted 1,2,3-triazoles as peptide bond isosteres. In the present contribution, we report the synthesis of 23 novel triazolopeptides along with their inhibitory activity. The compounds were synthesized using typical peptide chemistry methods, but with a conversion of amine into azide completely on solid support. The inhibitory activity of the synthesized derivatives spans from 9.2% to 58.1% at 10 μM concentration (the best compound Lys(Har)-GlyΨ[Trl]GlyΨ[Trl]Arg, 3, IC50 = 8.39 μM). Synthesized peptidotriazoles were tested for stability in human plasma and showed remarkable resistance toward proteolysis, with half-life times far exceeding 48 h. In vitro cell survival test resulted in no significant impact on bone marrow derived murine cells 32D viability. By means of molecular dynamics, we were able to propose a binding mode for compound 3 and discuss the observed structure–activity relationships.

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36

Caulkett, Peter W. R., Geraint Jones, Mary McPartlin, Nigel D. Renshaw, Sarah K. Stewart, and Brian Wright. "Adenine isosteres with bridgehead nitrogen. Part 1. Two independent syntheses of the [1,2,4]triazolo[1,5-a][1,3,5]triazine ring system leading to a range of substituents in the 2, 5 and 7 positions." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1995): 801. http://dx.doi.org/10.1039/p19950000801.

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37

Ivanenkov, Yan A., Renat S. Yamidanov, Ilya A. Osterman, Petr V. Sergiev, Vladimir A. Aladinskiy, Anastasia V. Aladinskaya, Victor A. Terentiev, et al. "Identification of N-Substituted Triazolo-azetidines as Novel Antibacterials using pDualrep2 HTS Platform." Combinatorial Chemistry & High Throughput Screening 22, no. 5 (August 8, 2019): 346–54. http://dx.doi.org/10.2174/1386207322666190412165316.

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Aim and Objective: Antibiotic resistance is a serious constraint to the development of new effective antibacterials. Therefore, the discovery of the new antibacterials remains one of the main challenges in modern medicinal chemistry. This study was undertaken to identify novel molecules with antibacterial activity. Materials and Methods: Using our unique double-reporter system, in-house large-scale HTS campaign was conducted for the identification of antibacterial potency of small-molecule compounds. The construction allows us to visually assess the underlying mechanism of action. After the initial HTS and rescreen procedure, luciferase assay, C14-test, determination of MIC value and PrestoBlue test were carried out. Results: HTS rounds and rescreen campaign have revealed the antibacterial activity of a series of Nsubstituted triazolo-azetidines and their isosteric derivatives that has not been reported previously. Primary hit-molecule demonstrated a MIC value of 12.5 µg/mL against E. coli Δ tolC with signs of translation blockage and no SOS-response. Translation inhibition (26%, luciferase assay) was achieved at high concentrations up to 160 µg/mL, while no activity was found using C14-test. The compound did not demonstrate cytotoxicity in the PrestoBlue assay against a panel of eukaryotic cells. Within a series of direct structural analogues bearing the same or bioisosteric scaffold, compound 2 was found to have an improved antibacterial potency (MIC=6.25 µg/mL) close to Erythromycin (MIC=2.5-5 µg/mL) against the same strain. In contrast to the parent hit, this compound was more active and selective, and provided a robust IP position. Conclusion: N-substituted triazolo-azetidine scaffold may be used as a versatile starting point for the development of novel active and selective antibacterial compounds.

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Bakharev, Vladimir V., Victor E. Parfenov, Irina V. Ul'yankina, Anna V. Zavodskaya, Evgeniya V. Selezneva, Alexander A. Gidaspov, Oleg S. Eltsov, and Pavel A. Slepukhin. "ChemInform Abstract: Synthesis of New 5-Aza-isosteres of Guanine-5-Aminosubstituted 1,2,4-Triazolo[1,5-a]-1,3,5-triazin-7-ones." ChemInform 46, no. 6 (January 23, 2015): no. http://dx.doi.org/10.1002/chin.201506175.

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Ostrowski, T., and J. Zeidler. "Synthesis of 5-ethynyl-1- -D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (isosteric to EICAR) and its derivatives." Nucleic Acids Symposium Series 52, no. 1 (September 1, 2008): 585–86. http://dx.doi.org/10.1093/nass/nrn296.

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CAULKETT, P. W. R., G. JONES, M. MCPARTLIN, N. D. RENSHAW, S. K. STEWART, and B. WRIGHT. "ChemInform Abstract: Adenine Isosteres with Bridgehead Nitrogen. Part 1. Two Independent Syntheses of the (1,2,4)Triazolo(1,5-a)(1,3,5)triazine Ring System Leading to a Range of Substituents in the 2, 5 and 7 Positions." ChemInform 26, no. 34 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199534183.

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Bradbury, Robert H., John S. Major, Alec A. Oldham, Janet E. Rivett, David A. Roberts, Anthony M. Slater, David Timms, and David Waterson. "1,2,4-Triazolo[4,3-a]pyrazine derivatives with human renin inhibitory activity. 2. Synthesis, biological properties and molecular modeling of hydroxyethylene isostere derivatives." Journal of Medicinal Chemistry 33, no. 9 (September 1990): 2335–42. http://dx.doi.org/10.1021/jm00171a006.

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Sampognaro, Anthony J., Mark D. Wittman, Joan M. Carboni, Chiehying Chang, Ann F. Greer, Warren W. Hurlburt, John S. Sack, and Dolatrai M. Vyas. "Proline isosteres in a series of 2,4-disubstituted pyrrolo[1,2-f][1,2,4]triazine inhibitors of IGF-1R kinase and IR kinase." Bioorganic & Medicinal Chemistry Letters 20, no. 17 (September 2010): 5027–30. http://dx.doi.org/10.1016/j.bmcl.2010.07.045.

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BRADBURY, R. H., J. S. MAJOR, A. A. OLDHAM, J. E. RIVETT, D. A. ROBERTS, A. M. SLATER, D. TIMMS, and D. WATERSON. "ChemInform Abstract: 1,2,4-Triazolo(4,3-a)pyrazine Derivatives with Human Renin Inhibitory Activity. Part 2. Synthesis, Biological Properties, and Molecular Modeling of Hydroxyethylene Isostere Derivatives." ChemInform 22, no. 8 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199108220.

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Focken, Thilo, Sultan Chowdhury, Alla Zenova, Michael E. Grimwood, Christine Chabot, Tao Sheng, Ivan Hemeon, et al. "Design of Conformationally Constrained Acyl Sulfonamide Isosteres: Identification of N-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)methane-sulfonamides as Potent and Selective hNaV1.7 Inhibitors for the Treatment of Pain." Journal of Medicinal Chemistry 61, no. 11 (May 8, 2018): 4810–31. http://dx.doi.org/10.1021/acs.jmedchem.7b01826.

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Roma, Giorgio, Giancarlo Grossi, Mario Di Braccio, Daniela Piras, Vigilio Ballabeni, Massimiliano Tognolini, Simona Bertoni, and Elisabetta Barocelli. "1,8-Naphthyridines VII. New substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides and their isosteric analogues, exhibiting notable anti-inflammatory and/or analgesic activities, but no acute gastrolesivity." European Journal of Medicinal Chemistry 43, no. 8 (August 2008): 1665–80. http://dx.doi.org/10.1016/j.ejmech.2007.10.010.

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Kumar, Sachin, Sukhbir Lal Khokra, and Akash Yadav. "Triazole analogues as potential pharmacological agents: a brief review." Future Journal of Pharmaceutical Sciences 7, no. 1 (May 25, 2021). http://dx.doi.org/10.1186/s43094-021-00241-3.

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Abstract Background A large number of studies have recently reported that, because of their significant biological and pharmacological properties, heterocyclic compounds and their derivatives have attracted a strong interest in medicinal chemistry. The triazole nucleus is one of the most important heterocycles which has a feature of natural products as well as medicinal agents. Heterocyclic nitrogen is abundantly present in most medicinal compounds. The derivatization of triazole ring is based on the phenomenon of bio-isosteres in which substituted the oxygen atom of oxadiazole nucleus with nitrogen triazole analogue. Main text This review focuses on recent synthetic procedure of triazole moiety, which comprises of various pharmacological activities such as antimicrobial, anticonvulsant, anti-inflammatory, analgesic, antitubercular, anthelmintic, antioxidant, antimalarial, antiviral, etc.. Conclusion This review highlights the current status of triazole compounds as different multi-target pharmacological activities. From the literature survey, triazole is the most widely used compound in different potential activities.

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Lal, Kashmiri, Aman Kumar, Yajat Rohila, and Vijay Kumar. "A Mini Review on Pharmacological Significance of Isatin-1,2,3-Triazole Hybrids." Current Topics in Medicinal Chemistry 23 (February 2, 2023). http://dx.doi.org/10.2174/1568026623666230202160925.

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Abstract: Molecular hybridization is one of the recent stratagems in medicinal chemistry to synthesize a novel hybrid molecule having better affinity and efficacy by combining two or more pharmacophoric moieties. Molecular hybridization, i.e., a linker or framework integration technique, can be used to connect the two pharmacophoric components. It has often been found that hybrid compounds perform more effectively and possess lower toxicity than their parent molecules. In order to create a new generation of effective and safe therapeutic candidates, such as anti-cancer, anti-viral, anti-HIV, antioxidant, and antibacterial, for a variety of frontline diseases, several articles have been published that discuss the molecular hybridization of preclinically or clinically proven compounds. Isatin and its derivatives have been studied extensively due to diversified biological activities, including antitumor, antimicrobial, anti-inflammatory, analgesic, antiviral, antioxidant, anticonvulsant activity, etc. Similarly, 1,2,3-triazoles have received significant interest as a bio-isostere in medicinal chemistry for generating a large number of pharmaceutically significant molecules. As it possesses diversified physiochemical properties, such as hydrogen bond formation capacity, ease of synthesis, moderate dipole moment, stability towards acidic/basic hydrolysis, inertness towards oxidizing/reducing agents, and good binding potential with several biological targets, isatin is an important choice of the medicinal chemists for the novel medication development. The aim of the current review is to summarize the research articles showing the pharmacological significance of hybrid molecules containing isatin and 1,2,3-triazole moieties. The present review may assist chemists in designing and synthesizing isatin-1,2,3-triazole hybrids with better efficacy and low cytotoxicity.

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Perissutti, Elisa, Francesco Frecentese, Ferdinando Fiorino, Beatrice Severino, Donatella Cirillo, Vincenzo Santagada, and Giuseppe Caliendo. "Microwave Solvent-Free Regioselective 1,3-Dipolar Cycloaddition in the Synthesis of 1,4-Substituted[1,2,3]-triazoles as Amide Bond Isosteres." ChemInform 38, no. 47 (November 20, 2007). http://dx.doi.org/10.1002/chin.200747133.

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"Synthesis and Cytotoxic Activity of New Pyrimido[1,2-c]quinazolines, [1,2,4]triazolo[4,3-c]quinazolines and (quinazolin-4-yl)-1H-pyrazoles Hybrids." Biointerface Research in Applied Chemistry 12, no. 4 (October 17, 2021): 5217–33. http://dx.doi.org/10.33263/briac124.52175233.

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New hybrid compounds with functionalized quinazoline derivatives and derived tricyclic compounds with varied condensed six and five-membered ring systems were synthesized from simple compounds. The 4-quinazolinimine, 2H-pyrimido[1,2-c] quinazolin-2-one, the pyrido[1,2-c]quinazoline and the [1,2,4]triazolo[4,3-c]quinazoline systems were synthesized starting form the key 4-azido compound and its isosteric analogue; 4-hydrazinyl derivative. Furthermore, a hybrid compound incorporating varied active motifs, the substituted tricyclic structural analog; 3-oxo-2-(quinazolin-4-yl)-2,3-dihydro-1H-pyrazole derivative, in which the pyrazole ring was attached to the quinazoline system via substitution at quinazoline-C4, was also prepared. The synthesized compounds were studied for their cytotoxic activity against the human breast cancer (MCF-7) cell line. The tested compounds possess a high effect against the breast cancer cell line (MCF-7), and compounds 6b, 6e, 8, and 11 showed comparable results to those obtained for the reference drug doxorubicin. The results also showed the effect of substituents in the pyrimidoquinazoline and triazoloquinazoline ring systems on the cytotoxic activity. Additionally, the docking studies revealed that the compounds 6b, 6e, 8, and 11 bound well within the active sites of EGFRWT and EGFRT790M kinases and could be the lead molecules in the discovery of anticancer agents targeting inhibition of EGFRWT and EGFRT790M.

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