Polar Solvent–Mediated Synthesis of Terminal Alkyne Derivatives of Thiazoles and Evaluation of Their Antidiabetic Activity

A series of bornyl derivatives of p-(benzyloxy)phenylpropionic acid were prepared, and their hypoglycemic activities were examined by an oral glucose tolerance test in mice. The results of this test revealed two compounds, 1 and 3, that can reduce the blood level of glucose similarly to reference compound vildagliptin. Both compounds were tested in an experiment on mice with metabolic disorders: the C57BL/6Ay strain. Along with hypoglycemic properties, the two compounds showed different abilities to correct lipid metabolism disorders. In silico prediction revealed that the studied substances are most likely bifunctional multitarget hypoglycemic compounds whose mechanism of action is based on a pronounced reduction in insulin resistance and a strong incretin-mimetic effect. The difference in the size of effects of these compounds on biochemical parameters of blood in the experiment on C57BL/6Ay mice was in good agreement with the computational prediction of the priority ranking of biological targets for these compounds. These results indicate that bornyl derivatives of p-(benzyloxy)phenylpropionic acid have a good potential as new agents for diabetes mellitus treatment due to their hypoglycemic and lipid-normalizing properties.

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Synthesis of alkyne derivatives of a novel triazolopyrazine as A2A adenosine receptor antagonists

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2004.11.062 ◽

2005 ◽

Vol 15 (3) ◽

pp. 511-515 ◽

Cited By ~ 43

Author(s):

Gang Yao ◽

Serajul Haque ◽

Li Sha ◽

Gnanasambandam Kumaravel ◽

Joy Wang ◽

...

Keyword(s):

Adenosine Receptor ◽

Receptor Antagonists ◽

A2a Adenosine Receptor ◽

Derivatives Of ◽

Alkyne Derivatives

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Alkyne derivatives of [CoMn(CO)9]

Inorganica Chimica Acta ◽

10.1016/s0020-1693(00)81858-7 ◽

1984 ◽

Vol 88 (1) ◽

pp. L5-L6 ◽

Cited By ~ 11

Author(s):

P.J. Manning ◽

L.K. Peterson

Keyword(s):

Derivatives Of ◽

Alkyne Derivatives

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Insertion of terminal alkyne into Pt–N bond of the square planar [PtI2(Me2phen)] complex

Dalton Transactions ◽

10.1039/c7dt03644b ◽

2017 ◽

Vol 46 (45) ◽

pp. 15819-15826 ◽

Cited By ~ 2

Author(s):

Michele Benedetti ◽

Federica De Castro ◽

Vincenza Lamacchia ◽

Concetta Pacifico ◽

Giovanni Natile ◽

...

Keyword(s):

Terminal Alkynes ◽

Terminal Alkyne ◽

Square Planar ◽

Derivatives Of

The reactivity of [PtX2(Me2phen)] complexes (X = Cl, Br, I; Me2phen = 2,9-dimethyl-1,10-phenanthroline) with terminal alkynes is reported. Bromo and iodo derivatives lead to the formation of Pt(ii) alkenyl derivatives of the type [PtX2{κ2-N,C-(Z)-N̲1–N10–C̲C(H)(R)}] (N1–N10 = Me2phen) containing a Pt–N–C–C–N–C six membered metallacycle.

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Synthesis of 1H-1,2,3-Triazoles from Alkyne Derivatives of 1,3,5-Triazines by Huisgen\'s Reaction

10.3390/ecsoc-16-01097 ◽

2012 ◽

Author(s):

Julio A. Seijas ◽

M. Pilar Vázquez-Tato ◽

María García-Fernández ◽

Alberto Díaz-Seivane ◽

Xesús Feás

Keyword(s):

Derivatives Of ◽

Alkyne Derivatives

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Interfacial hydration determines orientational and functional dimorphism of sterol-derived Raman tags in lipid-coated nanoparticles

Proceedings of the National Academy of Sciences ◽

10.1073/pnas.2105913118 ◽

2021 ◽

Vol 118 (33) ◽

pp. e2105913118

Author(s):

Xingda An ◽

Ayan Majumder ◽

James McNeely ◽

Jialing Yang ◽

Taranee Puri ◽

...

Keyword(s):

Lipid Membrane ◽

Growth Factor Receptor ◽

Noble Metal Nanoparticles ◽

Terminal Alkyne ◽

Lipid Layer ◽

Coated Nanoparticles ◽

Selective Targeting ◽

Epidermal Growth ◽

High Concentrations ◽

Derivatives Of

Lipid-coated noble metal nanoparticles (L-NPs) combine the biomimetic surface properties of a self-assembled lipid membrane with the plasmonic properties of a nanoparticle (NP) core. In this work, we investigate derivatives of cholesterol, which can be found in high concentrations in biological membranes, and other terpenoids, as tunable, synthetic platforms to functionalize L-NPs. Side chains of different length and polarity, with a terminal alkyne group as Raman label, are introduced into cholesterol and betulin frameworks. The synthesized tags are shown to coexist in two conformations in the lipid layer of the L-NPs, identified as “head-out” and “head-in” orientations, whose relative ratio is determined by their interactions with the lipid–water hydrogen-bonding network. The orientational dimorphism of the tags introduces orthogonal functionalities into the NP surface for selective targeting and plasmon-enhanced Raman sensing, which is utilized for the identification and Raman imaging of epidermal growth factor receptor–overexpressing cancer cells.

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ChemInform Abstract: PREPARATION AND ANTIDIABETIC ACTIVITY OF SOME SULFONYLUREA DERIVATIVES OF 3,5-DISUBSTITUTED PYRAZOLES

Chemischer Informationsdienst ◽

10.1002/chin.197928241 ◽

1979 ◽

Vol 10 (28) ◽

Author(s):

R. SOLIMAN

Keyword(s):

Antidiabetic Activity ◽

Derivatives Of

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A Family of Externally-Functionalised Coordination Cages

Chemistry ◽

10.3390/chemistry3040088 ◽

2021 ◽

Vol 3 (4) ◽

pp. 1203-1214

Author(s):

Garrett D. Jackson ◽

Max B. Tipping ◽

Christopher G. P. Taylor ◽

Jerico R. Piper ◽

Callum Pritchard ◽

...

Keyword(s):

Binding Constants ◽

Monomethyl Ether ◽

Terminal Alkyne ◽

Bridging Ligands ◽

Diverse Range ◽

Exterior Surface ◽

Click Reactions ◽

Coordination Cages ◽

Synthetic Routes ◽

Derivatives Of

New synthetic routes are presented to derivatives of a (known) M8L12 cubic coordination cage in which a range of different substituents are attached at the C4 position of the pyridyl rings at either end of the bis(pyrazolyl-pyridine) bridging ligands. The substituents are (i) –CN groups (new ligand LCN), (ii) –CH2OCH2–CCH (containing a terminal alkyne) groups (new ligand LCC); and (iii) –(CH2OCH2)3CH2OMe (tri-ethyleneglycol monomethyl ether) groups (new ligand LPEG). The resulting functionalised ligands combine with M2+ ions (particularly Co2+, Ni2+, Cd2+) to give isostructural [M8L12]16+ cage cores bearing 24 external functional groups; the cages based on LCN (with M2+ = Cd2+) and LCC (with M2+ = Ni2+) have been crystallographically characterised. The value of these is twofold: (i) exterior nitrile or alkene substituents can provide a basis for further synthetic opportunities via ‘Click’ reactions allowing in principle a diverse range of functionalisation of the cage exterior surface; (ii) the exterior –(CH2OCH2)3CH2OMe groups substantially increase cage solubility in both water and in organic solvents, allowing binding constants of cavity-binding guests to be measured under an increased range of conditions.

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