Search results for "Tertiary amine"

Design and pharmacology of quinuclidine derivatives as M2-selective muscarinic receptor ligands

2001

In our search for M2-selective muscarinic receptor antagonists, we synthesized 1,3-disubstituted indenes. The effects of different basic moieties with regard to binding and selectivity towards the five distinct muscarinic receptor subtypes were investigated. The results show that the quinuclidine series afforded the most promising compounds in terms of both receptor affinity and M2-subtype selectivity.

Heteroaromatic Inhibitors of the Astacin Proteinases Meprin α, Meprin β and Ovastacin Discovered by a Scaffold-Hopping Approach.

2020

Abstract Astacin metalloproteinases, in particular meprins α and β, as well as ovastacin, are emerging drug targets. Drug‐discovery efforts have led to the development of the first potent and selective inhibitors in the last few years. However, the most recent compounds are based on a highly flexible tertiary amine scaffold that could cause metabolic liabilities or decreased potency due to the entropic penalty upon binding to the target. Thus, the aim of this study was to discover novel conformationally constrained scaffolds as starting points for further inhibitor optimization. Shifting from flexible tertiary amines to rigid heteroaromatic cores resulted in a boost in inhibitory activity. …

Chlorodicyclohexylborane-mediated aldol additions of alpha,alpha'-dioxygenated ketones.

2001

Boron aldol additions of variously O-protected alpha,alpha'-dioxygenated ketones using dicyclohexylboron chloride and a tertiary amine have been investigated. The stereoselectivity of the process was dependent on the protecting group on the alpha-oxygen atoms. Notably, ketones with bulky silyloxy groups gave syn aldols, most likely via Z enolates. This rules out the participation of chelates during the enolization process, at least in the presence of such sterically crowded protecting groups. An alternative explanation is offered.

Antineoplastika, 19. Mitt.: Darstellung vonN-[2-Chlor-4-diethylamino-(1,3,5-triazin-6-yl)]-aminosäuren

1990

4-Chloro-N-methyl-N-nitroaniline

1998

The molecular structure of (p-ClC 6 H 4 )(CH 3 )NNO 2 (or C 7 H 7 ClN 2 O 2 ) contains a planar NNO 2 nitroamino group which is twisted about the N-C phenyl bond by ca 68° from the plane of the aromatic ring. The structural data are in agreement with the spectral results and indicate that there is no conjugation between the aromatic sextet and the nitroamino group. There are no specific intermolecular interactions.

Ferrocene containing chelating ligands 3. Synthesis, spectroscopic characterization, electrochemical behaviour and interaction with metal ions of new…

1995

Abstract Ferrocenecarboxaldehyde reacts with 2-amino-benzoic acid, 2-amino-5-methyl-benzoic acid or 3-amino-2-naphthoic acid to give the corresponding Schiff-base derivatives 2-ferrocenylmethylidenimino-benzoic acid (1), 2-ferrocenylmethylidenimino-5-methyl-benzoic acid (2) and 3-ferrocenylmethylidenimino-2-naphthoic acid (3). 1, 2 and 3 are stable in the solid state but easily hydrolyze in solution. This hydrolysis has been studied kinetically in a methanol-water medium. In order to increase the stability in solution to use these compounds as ligands, the imino group from 1, 2 and 3 was reduced by NaBH4 to give the amino derivatives 2-ferrocenylmethylamino-benzoic acid (4), 2-ferrocenylmet…

ChemInform Abstract: Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn-α,β-Dihydroxy Esters.

2010

Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2-syn/1,3-syn stereoisomer. Through oxidative cleavage of the aldol adducts with periodic acid hydrate, enantiopure syn-α,β-dihydroxy esters with either hydroxyl group differently protected have been prepared. These erythrulose derivatives therefore behave as a chiral hydroxy acetate (glycolate) enolate equivalent.

Multidrug resistance reverting activity and antitumor profile of new phenothiazine derivatives

2008

Abstract A series of easily affordable phenothiazine derivatives bearing a rigid but-2-ynyl amino side chain were synthesized and tested to evaluate the MDR reverting activity and full antitumor profile. Some compounds endowed with remarkable MDR reverting effect were identified, and the most active one ( 6c ) was shown to increase doxorubicin retention in multidrug resistant cells, suggesting a direct interaction with P-glycoprotein. Furthermore, a broad range of cellular activities were observed for different compounds. In particular, the ability of some derivatives to induce antiproliferative effects on resistant cell lines and to interfere with the G 1 phase of the cell cycle, a phase u…

Kemp elimination: a probe reaction to study ionic liquids properties.

2008

The amino induced elimination of benzisoxazole into the relevant o-cyanophenolate ion (Kemp elimination) has been studied in [bmim][BF 4] solution at 298 K. To have information about the interactions between reactants and ionic liquid, the reaction has been carried out at different temperatures (293-313 K). Several primary, secondary, and tertiary amines have been used to study the effect of amine structure on the reaction rate. The collected data show that the amine structure seems to have a crucial role in determining the reaction rate. Furthermore, as different cation or anion structures of an ionic liquid can significantly affect its properties, the title reaction has been performed in …

New propylamine oligopyrrole carboxamides linked to a heterocyclic or anthraquinone system: synthesis, DNA binding, topoisomerase I inhibition and cy…

2003

Continuing our studies on combilexines, compounds consisting of a DNA intercalator linked to a minor groove ligand, new results are presented. The synthesis of a series of new propylamine oligopyrrole carboxamides closely related to netropsin and distamycin A, linked to a heterocyclic or anthraquinone system is reported. The cytotoxic activity in vitro, the DNA binding characteristics and the inhibition of the topoisomerase I of the compounds were studied in order to explain the biological mechanism of action of these new potential combilexines. Some of the synthesised compounds showed cytotoxic activity against human tumour cell lines, as well as DNA binding and topoisomerase I inhibiting …