18522-89-9Relevant articles and documents
Synthesis and biological evaluation of triazole based uracil derivatives as novel DPP-4 inhibitors
Li, Qing,Han, Li,Zhang, Bin,Zhou, Jinpei,Zhang, Huibin
, p. 9598 - 9611 (2016)
A series of triazole based uracil derivatives were designed and synthesized as novel DPP-4 inhibitors. Compound A01 was identified as a lead compound for SAR studies focused on the structural modification at the S2′ subsite of DPP-4. The novel analogues A02-A25 were obtained by modifying the substituents at the phenyl group, and B01-B09, by introducing the carbonyl group. On screening in DPP-4, compounds B03, B04 and B08 showed a significant improvement in DPP-4 inhibitory activities compared to compound A01 and showed comparable activities to the marketed DPP-4 inhibitor, alogliptin. Docking studies revealed new favorable binding modes of designed compounds in the S2′ subsite and proved that structural modifications in the S2′ subsite were an effective option to increase the inhibition of DPP-4. In vitro DPP-8 and DPP-9 tests indicated that all compounds showed excellent selectivity against DPP-8 and DPP-9. Further in vivo evaluation showed that compound B04 could significantly improve oral glucose tolerance in ICR mice and dose-dependently reduced glucose levels in type 2 diabetic C57BL/6 mice. These data suggest that compound B04 could be a promising DPP-4 inhibitor for future treatment of T2DM.
A tripodal ligand constructed from mesoionic carbene donors
Lee, Wei-Tsung,Dickie, Diane A.,Metta-Magana, Alejandro J.,Smith, Jeremy M.
, p. 12842 - 12846 (2013)
A tripodal ligand constructed solely from mesoionic carbene donors is reported. The donor strength of this ligand is lower than most imidazol-2-ylidene-based tris(carbene)borate ligands, as measured by IR spectroscopy of {NiNO}10 and {Mn(CO)3}+ derivatives. The attenuated donor strength is proposed to be due to the collective electron-withdrawing effect of the ligand's aryl substituents.
An Admix Approach to Determine Counter Anion Effects on Metal-Free Arylation Reactions with Diaryliodonium Salts
Seidl, Thomas L.,Stuart, David R.
, p. 11765 - 11771 (2017)
A method to determine the effect of counter anions in metal-free arylation reactions of diaryliodonium salts is described. This approach avoids the independent synthesis of individual diaryliodonium salts and potentially enables assessment of a large number of different counter anions, including those that are synthetically challenging to install. Diaryliodonium tosylate salts serve as a general precursor for this approach, and an azide arylation reaction was used to develop this strategy. Further optimization and representative scope of azide arylation is demonstrated in yields that range from 74-95% (89% average). The use of this method as a screening tool has also been validated with arylation reactions of three different nucleophiles employing diphenyliodonium tosylate.
Modular synthesis of alkyne-substituted ruthenium polypyridyl complexes suitable for click coupling
Gerken, James B.,Rigsby, Matthew L.,Ruther, Rose E.,Pérez-Rodríguez, Riviam J.,Guzei, Ilia A.,Hamers, Robert J.,Stahl, Shannon S.
, p. 2796 - 2798 (2013)
A modular synthetic method has been developed for the preparation of Ru polypyridyl complexes bearing a terminal alkyne. This method proceeds through a readily accessible intermediate with a silyl-protected alkyne and allows access to a variety of five- and six-coordinate Ru complexes. These complexes can be easily attached to azide-functionalized electrode surfaces with only slight perturbation of the redox properties of the parent complex.
A Metal-Free Synthesis of N-Aryl Oxazolidin-2-Ones by the One-Pot Reaction of Carbon Dioxide with N-Aryl Aziridines
Sonzini, Paolo,Damiano, Caterina,Intrieri, Daniela,Manca, Gabriele,Gallo, Emma
supporting information, p. 2961 - 2969 (2020/07/06)
The cost-effective TPPH2/TBACl-catalyzed (TPPH2=dianion of tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride) carbon dioxide cycloaddition to N-aryl aziridines was successful in synthesizing N-aryl oxazolidin-2-ones. A cataly
Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes
Jana, Sampad,Adhikari, Sweta,Cox, Michael R.,Roy, Sudeshna
supporting information, p. 1871 - 1874 (2020/02/20)
α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid (TFA). This work provides the first regioselective method to access 4-fluoro-1,5-disubstituted-1,2,3-triazoles.
Iron and Ruthenium Glycoporphyrins: Active Catalysts for the Synthesis of Cyclopropanes and Aziridines
Damiano, Caterina,Gadolini, Sebastiano,Intrieri, Daniela,Lay, Luigi,Colombo, Cinzia,Gallo, Emma
supporting information, p. 4412 - 4420 (2019/11/03)
In view of the relevance of cyclopropanes and aziridines as synthetic building blocks as well as active parts in biological and pharmaceutical compounds, the development of sustainable synthetic procedures for obtaining these products continues to be a si
Design, synthesis and anti-platelet aggregation activity study of ginkgolide-1,2,3-triazole derivatives
Cui, Jian,Hu, Lean,Shi, Wei,Cui, Guozhen,Zhang, Xumu,Zhang, Qing-Wen
, (2019/06/19)
Ginkgolides are the major active component of Ginkgo biloba for inhibition of platelet activating factor receptor. An azide-alkyne Huisgen cycloaddition reaction was used to introduce a triazole nucleus into the target ginkgolide molecules. A series of ginkgolide-1,2,3-triazole conjugates with varied functional groups including benzyl, phenyl and heterocycle moieties was thus synthesized. Many of the designed derivatives showed potent antiplatelet aggregation activities with IC50 values of 5~21 nM.
Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction
Yadav, Dolly,Singh, Nem,Kim, Tae Wu,Kim, Jae Young,Park, No-Joong,Baeg, Jin-Ook
supporting information, p. 2677 - 2685 (2019/06/13)
The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.
Synergistic combination of visible-light photo-catalytic electron and energy transfer facilitating multicomponent synthesis of β-functionalized α,α-diarylethylamines
Wu, Yanan,Zhang, Yipin,Jiang, Mingjie,Dong, Xunqing,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian
supporting information, p. 6405 - 6408 (2019/06/07)
A synthetic strategy with the visible-light photo-catalytic synergistic combination of electron and energy transfer processes has been developed. The mild reaction conditions allow the radical-radical cross-coupling phenomenon for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids (diarylphosphine oxides), 1,1-diarylethylenes and arylazides.
