A facile route for the synthesis of novel S-linked 1,3,5-triazine tethered peptidomimetics

Krishnamurthy, M. S.; Basavaprabhu,; Sharanabai, Kupendra M; Sureshbabu, Vommina V.

doi:10.1016/j.tetlet.2014.08.075

Cited by 4 publications

(1 citation statement)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sureshbabu and co‐workers [38] reported an efficient one‐pot protocol for the synthesis of N α ‐protected S ‐linked 1,3,5‐triazine tethered peptidomimetics as shown in Scheme 15. A model reaction was optimized treating the iodo derivative of N α ‐protected amino acid 45 with thiourea in acetone under an argon atmosphere at reflux temperature to furnish the intermediate N α ‐protected aminoalkyl isothiouronium salt 46 which was further reacted with formaldehyde (37 % solution in water) and benzylamine using base and solvent.…”

Section: Synthetic Routes For 135‐triazine and Its Analoguesmentioning

confidence: 99%

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Rathod,

Pawar,

Puri

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Nitrogen‐bearing heterocycles are ubiquitous in landscapes and have a great impact on living nature. Structural motifs are present in diverse natural products like vitamins, antibiotics, and alkaloids, as well as pharmaceuticals. The 1,3,5‐Triazines are the primitive class of heterocyclic motifs and are used in various synthetic and medicinal applications. This review covers an exhaustive exploration of literature reports and describes various synthetic strategies and pharmacological activities of 1,3,5‐triazine moiety. Synthetic strategies include multicomponent reaction, metal catalyst reaction, microwave‐assisted strategy, etc. to construct 1,3,5‐triazine moiety. Pharmacological activities include anticancer, antimalarial, antibacterial, antifungal, antiviral, anti‐tubercular, anti‐leishmanial, anti‐inflammatory, histamine antagonist, serotonin antagonist, etc. For anticancer activity, 1,3,5‐triazine moiety‐containing compounds were tested on different cell lines, and inhibitory activity was also mentioned. The involvement of this scaffold in the treatment of various diseases and disorders makes this scaffold important from a research perspective. Therefore, there is a need to present the combined data of research and reviews to the researchers to develop new molecules. For that reason, the review included information from articles published from 1978 onwards.

show abstract

Section: Synthetic Routes For 135‐triazine and Its Analoguesmentioning

confidence: 99%

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Rathod,

Pawar,

Puri

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

A Facile Synthesis of 1,5‐Disubstituted Tetrazole Peptidomimetics by Desulfurization/Electrocyclization of Thiopeptides

et al. 2015

Self Cite

View full text Add to dashboard Cite

The cis-amide bond isostere, 1,5-disubstituted tetrazole,has been introduced in the peptideb ackbone by as imple route startingf rom the thiopeptide. The desired 1,5-disubstituted tetrazole peptidomimetics were synthesized by the desulfurization of thiopeptides by using HgCl 2 in the presence of NaN 3 /TEA in DMF in good yields. Various other thiophilic reagents including hypervalent iodine reagents failed to deliver the tetrazole product with the exception of CBr 4 /PPh 3 ,w hich resulted in moderate yields. The advantage of the presentp rotocol over previousm ethods has been demonstrated by the selective insertion of tetrazole into peptide-thiopeptide hybrids. Also, the protocol is compatible with commonly employed urethane protecting groups (Fmoc, Boc, and Cbz) in peptidec hemistry.T hiopeptide Boc-Pro-y[CSNH]-Val-OMe (2i)a nd two tetrazole pepti-domimeticsC bz-Ala-y[CN 4 ]-Phe-OMe( 3d)a nd Boc-Proy[CN 4 ]-Val-OMe( 3i)w ere obtained as single crystalsa nd their molecular structures have been confirmed by X-ray crystallography.

show abstract

Functionalized Triazines and Tetrazines: Synthesis and Applications

Mondal

Sivaramakrishna

2022

Top Curr Chem (Z)

View full text Add to dashboard Cite

A facile route for the synthesis of novel S-linked 1,3,5-triazine tethered peptidomimetics

Abstract: Peptidomimetics have aroused great interest due to their wide utility in developing new therapeutic agents and in drug design.

Cited by 4 publications

References 38 publications

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

A Facile Synthesis of 1,5‐Disubstituted Tetrazole Peptidomimetics by Desulfurization/Electrocyclization of Thiopeptides

Functionalized Triazines and Tetrazines: Synthesis and Applications

Contact Info

Product

Resources

About