Enantiomeric resolution of anti-HIV agents on a cellulose derivative chiral stationary phase

Summary Anti-HIV enantiomeric 1H, 3H-thiazolo[3, 4-a] benzimidazoles have been stereospecifically analyzed by elution on a column of cellulose tris-(4-methyl-phenylbenzoate)ester adsorbed on macroporous silica (Chiralcel^R OJ).The enantiomeric resolution of the compounds examined is linked to a complex and competitive contribution of different factors.     

Pharmacophore modeling as an efficient tool in the discovery of novel noncompetitive AMPA receptor antagonists

A three-dimensional pharmacophore model for the binding of noncompetitive AMPA receptor antagonists was developed in order to map common structural features of highly active compounds. This hypothesis, which consists of two hydrophobic regions, one hydrogen bond acceptor and one aromatic region, was successfully used as framework for the design of a new class of allosteric modulators containing a tetrahydroisoquinoline skeleton and for in silico screening. The promising biological results suggested that the identified molecules might be useful "lead compounds" for future drug development.     

Nuclear magnetic resonance and stereochemistry of vincamone

The stereochemistry in solution of vincamone was deduced by proton magnetic resonance using the paramagnetic shifts reagent Eu(fod)₃. The lanthanide induced shift computer simulation suggests that, at room temperature, the indole group is nearly planar, the rings C and E assume the envelope conformation with N-4 and C-16 as flaps, the ring D is in the chair one and the ethyl side chain prefers a trans position with respect to C-15.     

Reaction of 1-formyladamantane with heterocyclic compounds. Mass spectra,antibacterial and antifungal activity

1-Formyladamantane reacts with some amino derivatives to give I, II, III and IV. 3-Substiluted 2-adamantyl-4-thiazolidinones (V), (VI) and (VII) were obtained by reacting the above compounds with mercaptoacetic acid. Their structure was established by ir, pmr and mass spectroscopy. All compounds synthesized inhibit the growth of gram-negative and gram-positive bacteria and fungi.     

Solution-phase parallel synthesis of novel 1,2,3,4-tetrahydroisoquinoline-1-ones as anticonvulsant agents

Following our previous studies in the field of anticonvulsant agents, we planned a one-pot solution-phase parallel synthesis (SPPS) of a small library of new 1,2,3,4-tetrahydroisoquinoline derivatives. The activity against audiogenic seizures in DBA/2 mice of the newly synthesized compounds has also been evaluated.     

Microwave assisted organic synthesis (MAOS) of small molecules as potential HIV-1 integrase inhibitors

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). In recent years our research group has been engaged in the stucture-function study of this enzyme and in the development of some three-dimensional pharmacophore models which have led to the identification of a large series of potent HIV-1 integrase strand-transfer inhibitors (INSTIs) bearing an indole core. To gain a better understanding of the structure-activity relationships (SARs), herein we report the design and microwave-assisted synthesis of a novel series of 1-H-benzylindole derivatives.     

Electronic and conformational properties of 2,3-benzodiazepine derivatives

Summary The molecular geometries and electronic structures of 2,3-benzodiazepine derivatives have been studied by means of the MNDO-PM3 method. A number of electronic properties have been computed and examined in order to find indication of the role of the electronic characteristics of the different molecules and their pharmacological properties. Theoretical data indicate that both electronic and structural properties appear responsible for the varying degree of anticonvulsant activity exhibited by compounds 1–4.     

Synthesis and stereochemistry of novel [1,2,4]oxadiazolo[4,5-a][1,5]benzodiazepine derivatives

An one-pot synthetic approach to the novel 3a,4,5,6-tetrahydro[1,2,4]oxadiazolo[4,5-a][1,5]benzodiazepine system, by 1,3-dipolar cycloaddition of benzonitriloxides to 1,5-benzodiazepine derivatives, is described. The structure and stereochemistry of the obtained adducts have been assigned by means of spectroscopic measurements.     

Ir and pmr spectra of 2-aryl-4-thiazolidinones. III. Stereochemical analysis of 2-aryl-3-(2-pyridyl)-4-thiazolidinones

The long-range coupling through the sulphur atom observed in a number of 2-aryl-3-(2-pyridyl)-4-thiazolidinones suggests that the C₂ proton and one of methylene protons are in a cis 1,3 diequatorial relationship. Some additional information concerning the preferred orientations of the substituents in this system are given from Eu(fod)₃, [tris(1,1,1,2,2,3,3-heptafluoro-7,7-dimethyloctane-4,6-dionato)]europium, induced shift data.