Synthesis and hydrolytic stability of novel 3-[18F]fluoroethoxybis(1-methylethyl)silyl]propanamine-based prosthetic groups

in Journal of Fluorine Chemistry (2011), 132(4), 250-257

Two new silicon-based prosthetic groups, derived from 3-[ethoxybis(1-methylethyl)silyl]propanamine, have been prepd. in good yields. These silicon groups bearing an acid or an azide group were coupled to ... [more ▼]

Two new silicon-based prosthetic groups, derived from 3-[ethoxybis(1-methylethyl)silyl]propanamine, have been prepd. in good yields. These silicon groups bearing an acid or an azide group were coupled to a model tripeptide (Leu-Gly- Gly) either through a classical amide bond formation or through "click chem." via the Huisgen cycloaddn. The radiolabeling with fluorine-18 by substitution of the ethoxy group at silicon has been carried out with success in 51-54% decay cor. radiochem. yields. Radiolabeled peptides were easily prepd. by direct 18F-fluorination of the silicon-bearing tripeptide or by coupling the peptide with a radiolabeled silicon-based prosthetic group. Their stabilities in physiol. medium were studied and proved poor. [less ▲]

Synthesis and in vitro binding studies of piperazine-alkyl-naphthamides: Impact of homology and sulphonamide/carboxamide bioisosteric replacement on the affinity for 5-HT1A, alpha(2A), D4.2, D3 and D2L receptors

in Bioorganic & Medicinal Chemistry Letters (2010), 20

Synthesis and in vitro binding studies of substituted piperidine naphthamides. Part II: Influence of the substitution on the benzyl moiety on the affinity for D-2L, D-4.2, and 5-HT2A receptors

in Bioorganic & Medicinal Chemistry Letters (2007), 17(6), 1570-1574

In continuation of our work on N-(piperidin-4-yl)-naphthamides, the effect of substituted benzyl groups on D-2L, D-4.2, and 5-HT2A receptor affinity was evaluated. In the 1-naphthamide series most ... [more ▼]

In continuation of our work on N-(piperidin-4-yl)-naphthamides, the effect of substituted benzyl groups on D-2L, D-4.2, and 5-HT2A receptor affinity was evaluated. In the 1-naphthamide series most compounds were highly selective for D-4.2 over D-2L, and 5-HT2A receptors. Halogen and methyl substitution in position 3 or 4 of the benzyl group increased D-4.2 affinity. In the 2-naphthamide series a similar high D-4.2 over D-2L selectivity was retained while 5-HT2A affinity was increased. 3-Methoxy, 3-methyl, and 4-methyl substituents were favorable for D-4.2 affinity while halogens reduced affinity. 2-Naphthamides with a 3-bromo- or a 3-methyl group were mixed D-4.2/5-HT2A ligands similar to their unsubstituted parent compound. All compounds from both series with significant affinity for D-4.2 and 5-HT2A receptors were antagonists. (c) 2007 Elsevier Ltd. All rights reserved. [less ▲]

Synthesis and interfacial properties of bolaform surfactants issued from alkenyl D-xyloside

in GLEN Congress (2010)

Synthesis and organocatalytic applications of imidazol(in)ium-2- thiocarboxylates

in European Journal of Organic Chemistry (2011), (35), 7083-7091

Five imidazol(in)ium-2-thiocarboxylates bearing cyclohexyl, mesityl, or 2,6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding imidazol(in)ium chlorides or ... [more ▼]

Five imidazol(in)ium-2-thiocarboxylates bearing cyclohexyl, mesityl, or 2,6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding imidazol(in)ium chlorides or tetrafluoroborates in a one-pot, two-step procedure involving the in situ generation of free N-heterocyclic carbenes (NHCs) with a strong base followed by trapping with carbonyl sulfide. The resulting NHC•COS zwitterions were isolated in high yields and characterized by IR and NMR spectroscopy. The molecular structure of SIMes•COS was determined by X-ray diffraction analysis. Experimental data and DFT calculations indicated that the negative charge on the thiocarboxylate anion is preferentially delocalized on the sulfur atom. Thermogravimetric analysis showed that the NHC•COS zwitterions undergo thermolysis at temperatures ranging between 110 and 180 °C in the solid state. They are also rather labile in solution. Unlike the related NHC•CS2 betaines, which are highly stable, crystalline materials, they displayed the same type of behavior as the analogous carboxylate adducts, which readily lose their CO2 moiety upon heating or dissolution. Thus, imidazol(in)ium-2-thiocarboxylates acted as convenient NHC precursors in two model organocatalytic transformations. Of the five thiocarboxylates examined, ICy•COS was the most efficient at promoting the acylation of benzyl alcohol with vinyl acetate, whereas SIMes•COS afforded the highest activity in benzoin condensation. [less ▲]

Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells

in European Journal of Medicinal Chemistry (2012), 54

Synthesis and pharmacological evaluation of 4,6-disubstituted 2,2-dimethylchromans structurally related to the KATP channel opener cromakalim

Conference (2001, May)

Synthesis and pharmacological evaluation of a second generation of pyridothiadiazine 1,1-dioxides acting as AMPA potentiators.

in Bioorganic & Medicinal Chemistry (2008), 16(23), 9948-56

Taking into account structure-activity relationships obtained with our previous series, new diversely substituted 1,2,4-pyridothiadiazine 1,1-dioxides were designed to obtain novel AMPA potentiators. The ... [more ▼]

Taking into account structure-activity relationships obtained with our previous series, new diversely substituted 1,2,4-pyridothiadiazine 1,1-dioxides were designed to obtain novel AMPA potentiators. The aim of this work was focused on the improvement of lipophilicity, which is well known as a critical parameter to obtain in vivo active central nervous system agents. For this purpose, two positions on the pyridine ring were privileged to insert selected groups. Among the synthesized compounds emerged 7-chloro-4-ethyl-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxide (12d), which was evaluated in two memory tests in Wistar rats and showed cognition enhancing effects after intraperitoneal injection at doses as low as 0.3mg/kg. [less ▲]

Synthesis and pharmacological evaluation of ATP-sensitive potassium channel openers related to cromakalim: introduction of arylsulfonylurea or benzothiadiazinedioxide moieties

Poster (1998, September)

Synthesis and pharmacological evaluation of cromakalim analogues as potassium channel activators

Poster (2002, November 15)