Synthesis of chalcone precursor via Cu(I) catalyzed 1,3‐dipolar reaction of functionalized acetylene and pyrazole embedded dipole

Abstract

A new class of functionalized pyrazole bearing 1,2,3-triazole has been synthesized via Cu(I) mediated 1,3-dipolar cycloaddition of pyrazole bearing azide with various aromatic/heteroaromatic bearing terminal dipolarophile (acetylene). Structures of the newly synthesized compounds were explicated by analytical and spectral analysis. All the newly synthesized compounds were evaluated for their in-vitro antibacterial and antioxidant activity. Among the synthesized compound, triazole bearing 2,5-thiazolidinone 5b (20 ± 0.70) and triazole bearing thiocarboamide 5e (19 ± 0.70) showed good antibacterial activity against Escherichia coli and Pseudomonas aeruginosa, respectively. The newly synthesized compounds further tested for their ability to bleach DPPH radical using DPPH scavenging assay. Among the synthesized compounds 1,2,3-triazole bearing 2,5-thiazolidinone 5b (58.81%) exhibited good DPPH scavenging activity compared to the rest of the compounds. From the X-ray and Hirshfield analysis, it was observed that compound 3, crystallizes in a triclinic crystal system with a P-1 space group. The major intercontacts present in these molecules are H…H (39.7%), C…H (23.9%), N…H (20.3%).

Synthesis of Pyrazoline‐Embedded 1,2,3‐Triazole Derivatives via 1,3‐Dipolar Cycloaddition Reactions with in vitro and in silico Studies

“…Synthetic routes for the synthesis of 1,2,3 triazole hybrids by the click chemistry method have been reported [26–29] . But, few reports of pyrazoline bearing 1,2,3 triazole derivatives showing α‐glycosidase and α‐amylase activity are found in literature [30–36] .…”

“…[25] Synthetic routes for the synthesis of 1,2,3 triazole hybrids by the click chemistry method have been reported. [26][27][28][29] But, few reports of pyrazoline bearing 1,2,3 triazole derivatives showing α-glycosidase and α-amylase activity are found in literature. [30][31][32][33][34][35][36] Inspired by this, we have synthesized pyrazoline bearing 1,2,3-triazole and they were subjected for α-glycosidase and α-amylase inhibitory and antioxidant activity.…”

“…Similarly, 1,2,3-triazoles are also a symbolic five membered heterocyclic scaffolds having a vibrant biological activities, representing a sensational method of synthesis via click chemistry involving 1,3-dipolar cycloaddition reaction [17] between azide and terminal alkynes [18] through high regioselectivity .These 1,2,3 triazoles are associated with variety of biological activities such as cytotoxic, [19] anti-inflammatory, [20] antioxidant, [21] antifungal, [22] anticancer [23] and antidiabetics [24] and antibacterial. [25] Synthetic routes for the synthesis of 1,2,3 triazole hybrids by the click chemistry method have been reported.…”

Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

“…Nagaraja et al (2020) reported the synthesis and antimicrobial activity of a series of eight pyrazole chalcones bearing a 1,2,3-triazole ring 55a – 55h ( Figure 20 ), including two chalcone dimers 55c and 55d [ 95 ]. The Click Chemistry reaction between azide pyrazole-chalcone and propargylated substituents achieved the final compounds with 61–77% yield.…”

Sustainable synthesis of highly diastereoselective & fluorescent active spirooxindoles catalyzed by copper oxide nanoparticle immobilized on microcrystalline cellulose

“…[36] Metallic nanoparticles have distinct qualities, particularly their large surface area, high stability, and easy separation, which makes them applicable to a wide range of catalytic applications. [37] Transition metals such as Sc, [38] Cu, [39][40][41] Zn, [19] Ni, [42] Ag, [43] and Ru [44] were employed as catalysts in organic synthesis for one-pot 1,3-dipolar cycloaddition. However, there exist a few drawbacks in the use of metal oxide nanoparticles like agglomeration, leaching, and poor recovery of catalysts.…”