Dual Reactivity of 1,2,3,4‐Tetrazole: Manganese‐Catalyzed Click Reaction and Denitrogenative Annulation

2020 ◽  
Vol 60 (1) ◽  
pp. 304-312
Author(s):  
Hillol Khatua ◽  
Sandip Kumar Das ◽  
Satyajit Roy ◽  
Buddhadeb Chattopadhyay
2020 ◽  
Vol 133 (1) ◽  
pp. 308-316
Author(s):  
Hillol Khatua ◽  
Sandip Kumar Das ◽  
Satyajit Roy ◽  
Buddhadeb Chattopadhyay

1998 ◽  
Vol 80 (09) ◽  
pp. 393-398 ◽  
Author(s):  
V. Regnault ◽  
E. Hachulla ◽  
L. Darnige ◽  
B. Roussel ◽  
J. C. Bensa ◽  
...  

SummaryMost anticardiolipin antibodies (ACA) associated with antiphospholipid syndrome (APS) are directed against epitopes expressed on β2-glycoprotein I (β2GPI). Despite a good correlation between standard ACA assays and those using purified human β2GPI as the sole antigen, some sera from APS patients only react in the latter. This is indicative of heterogeneity in anti-β2GPI antibodies. To characterize their reactivity profiles, human and bovine β2GPI were immobilized on γ-irradiated plates (β2GPI-ELISA), plain polystyrene precoated with increasing cardiolipin concentrations (CL/β2GPI-ELISA), and affinity columns. Fluid-phase inhibition experiments were also carried out with both proteins. Of 56 selected sera, restricted recognition of bovine or human β2GPI occurred respectively in 10/29 IgA-positive and 9/22 IgM-positive samples, and most of the latter (8/9) were missed by the standard ACA assay, as expected from a previous study. Based on species specificity and ACA results, IgG-positive samples (53/56) were categorized into three groups: antibodies reactive to bovine β2GPI only (group I) or to bovine and human β2GPI, group II being ACA-negative, and group III being ACA-positive. The most important group, group III (n = 33) was characterized by (i) binding when β2GPI was immobilized on γ-irradiated polystyrene or cardiolipin at sufficient concentration (regardless of β2GPI density, as assessed using 125I-β2GPI); (ii) and low avidity binding to fluid-phase β2GPI (Kd in the range 10–5 M). In contrast, all six group II samples showed (i) ability to bind human and bovine β2GPI immobilized on non-irradiated plates; (ii) concentration-dependent blockade of binding by cardiolipin, suggesting epitope location in the vicinity of the phospholipid binding site on native β2GPI; (iii) and relative avidities approximately 100-fold higher than in group III. Group I patients were heterogeneous with respect to CL/β2GPI-ELISA and ACA results (6/14 scored negative), possibly reflecting antibody differences in terms of avidity and epitope specificity. Affinity fractionation of 23 sera showed the existence, in individual patients, of various combinations of antibody subsets solely reactive to human or bovine β2GPI, together with cross-species reactive subsets present in all samples with dual reactivity namely groups III and II, although the latter antibodies were poorly purified on either column. Therefore, the mode of presentation of β2GPI greatly influences its recognition by anti-β2GPI antibodies with marked inter-individual heterogeneity, in relation to ACA quantitation and, possibly, disease presentation and pathogenesis.


2019 ◽  
Vol 23 (8) ◽  
pp. 860-900 ◽  
Author(s):  
Chander P. Kaushik ◽  
Jyoti Sangwan ◽  
Raj Luxmi ◽  
Krishan Kumar ◽  
Ashima Pahwa

N-Heterocyclic compounds like 1,2,3-triazoles serve as a key scaffolds among organic compounds having diverse applications in the field of drug discovery, bioconjugation, material science, liquid crystals, pharmaceutical chemistry and solid phase organic synthesis. Various drugs containing 1,2,3-triazole ring which are commonly available in market includes Rufinamide, Cefatrizine, Tazobactam etc., Stability to acidic/basic hydrolysis along with significant dipole moment support triazole moiety for appreciable participation in hydrogen bonding and dipole-dipole interactions with biological targets. Huisgen 1,3-dipolar azide-alkyne cycloaddition culminate into a mixture of 1,4 and 1,5- disubstituted 1,2,3-triazoles. In 2001, Sharpless and Meldal came across with a copper(I) catalyzed regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles by cycloaddition between azides and terminal alkynes. This azide-alkyne cycloaddition has been labelled as a one of the important key click reaction. Click synthesis describes chemical reactions that are simple to perform, gives high selectivity, wide in scope, fast reaction rate and high yields. Click reactions are not single specific reaction, but serve as a pathway for construction of simple to complex molecules from a variety of starting materials. In the last few decades, 1,2,3-triazoles attracted attention of researchers all over the world because of their broad spectrum of biological activities. Keeping in view the biological importance of 1,2,3-triazole, in this review we focus on the various synthetic routes for the syntheisis of 1,4-disubstituted 1,2,3-triazoles. This review involves various synthetic protocols which involves copper and non-copper catalysts, different solvents as well as substrates. It will boost synthetic chemists to explore new pathway for the development of newer biologically active 1,2,3-triazoles.


2013 ◽  
Vol 10 (10) ◽  
pp. 738-743 ◽  
Author(s):  
Azadeh Fazeli ◽  
Hossein Oskooie ◽  
Yahya Beheshtiha ◽  
Majid Heravi ◽  
Hassan Valizadeh

Author(s):  
Constantin Stuckhardt ◽  
Maren Wissing ◽  
Armido Studer
Keyword(s):  

Materials ◽  
2021 ◽  
Vol 14 (11) ◽  
pp. 2817
Author(s):  
Biao Yu ◽  
Jingwei He ◽  
Sufyan Garoushi ◽  
Pekka K. Vallittu ◽  
Lippo Lassila

In order to improve the toughness and reduce polymerization shrinkage of traditional bisphenol A-glycidyl methacrylate (Bis-GMA)/triethylene glycol dimethacrylate (TEGDMA) based dental resin system, a hyperbranched thiol oligomer (HMDI-6SH) was synthesized via thiol-isocyanate click reaction using pentaerythritol tetra(3-mercaptopropionate (PETA) and dicyclohexylmethane 4,4′-diisocyanate (HMDI) as raw materials. Then HMDI-6SH was mixed with 1,3,5-Triallyl-1,3,5-Triazine-2,4,6(1H,3H,5H)-Trione (TTT) to prepare thiol-ene monomer systems, which were added into Bis-GMA/TEGDMA resins with different mass ratio from 10 wt% to 40 wt% to serve as anti-shrinking and toughening agent. The physicochemical properties of these thiol-ene-methacrylate ternary resins including functional groups conversion, volumetric shrinkage, flexural properties, water sorption, and water solubility were evaluated. The results showed that the incorporation of HMDI/TTT monomer systems into Bis-GMA/TEGDMA based resin could improve C=C double bond conversion from 62.1% to 82.8% and reduced volumetric shrinkage from 8.53% to 4.92%. When the mass fraction of HMDI/TTT monomer systems in the resins was no more than 20 wt%, the flexural strength of the resin was higher or comparable to Bis-GMA/TEGDMA based resins (p > 0.05). The toughness (it was measured from the stress–strain curves of three-point bending test) of the resins was improved. Water sorption and water solubility tests showed that the hydrophobicity of resin was enhanced with increasing the content of thioester moiety in resin.


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