75391-17-2

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 5292-53-5 diethyl benzalmalonate 
• 1145-55-7 α-Cyanzimtsaeure-tert-butylester 
• 100-52-7 benzaldehyde 
• 75391-16-1 2-Phenyl-2-N-pyrrolyl-ethan-1,1-dicarbonsaeure 
• 75391-18-3 3-Phenyl-3-N-pyrrolylpropionsaeurenitril 

Downstream Products

• 154284-02-3 C₁₆H₁₇NO₄ 
• 154284-01-2 2-ethoxycarbonyl-4-phenyl-1,2,3,4-tetrahydropyrrolo<1,2-a>pyrazin-1-one 
• 154284-00-1 N-ethyl-N-<(α-pyrrol-1-yl)phenetyl>carbamate 
• 154283-88-2 1-cyclopentylimino-3-phenyl-2,3-dihydro-1H-pyrrolizine 
• 154283-99-5 3-phenyl-3-(pyrrol-1-yl)propionyl azide 
• 154283-91-7 N,N-dimethyl-3-phenyl-3-(pyrrol-1-yl)propionic acid 
• 154283-98-4 4-phenyl-1,2,3,4-tetrahydropyrrolo<1,2-a>pyrazin-1-one 
• 154283-97-3 1-oximino-3-phenyl-2,3-dihydro-1H-pyrrolizine 
• 154283-87-1 1-methylimino-3-phenyl-2,3-dihydro-1H-pyrrolizine 

Relevant academic research and scientific papers

Novel benzylidenephenylpyrrolizinones with pleiotropic activities potentially useful in Alzheimer's disease treatment

This work describes the synthesis and the biological evaluation of novel benzylidenephenylpyrrolizinones as potential antioxidant, metal chelating or amyloid β (βA) aggregation inhibitors. Some derivatives exhibited interesting results in regard to several of the performed evaluations and appear as valuable Multi-Target Directed Ligands with potential therapeutic interest in Alzheimer's disease. Among them, compound 29 particularly appears as a valuable radical and NO scavenger, a Cu(II) and Fe(II) chelating agent and exhibits moderate βA aggregation inhibition properties. These activities, associated to a good predictive bioavailability and a lack of cytotoxicity, design it as a promising hit for further in vivo investigation.

Synthesis and preliminary behavioural evaluation in mice of new 3-aryl-3-pyrrol-1-ylpropanamides, analogues of FGIN-1-27 and FGIN-1-43

The 2-aryl-3-indoleacetamides FGIN-1-27 and FGIN-1-43 have already been characterized in-vitro as potent and specific ligands for the mitochondrial DBI receptor. This affinity was associated with psychotropic properties in several rodent behavioural tasks (in particular anxiolytic action) via enhancement of GABA transmission through neurosteroid production. The synthesis of new 3-aryl-3-pyrrol-1-ylpropanamides 1a-i, analogues of FGIN-1-27 and FGIN-1-43, is described in four steps starting from the corresponding arylaldehydes. Preliminary evaluation of these compounds in behavioural studies (spontaneous locomotor activity and anxiolytic activity) in mice was also undertaken.

Synthesis and CNS activity of new 3-amino-3-arylpropionic acid derivatives

The synthesis of new analogues of methylphenidate and modafinil, derived from 3-amino-3-arylpropionic acids, is described. Central pharmacological properties were studied in mice.

An Efficient Synthesis of New Phenylpyrrolizine and Phenylpyrrolopyrazine Derivatives

Synthesis of new 3-phenyl-2,3-dihydro-1H-pyrrolizine derivatives is achieved starting from 3-amino-3-phenylpropionic acid via an iminium salt.The reactivity of this system is studied and the new 4-phenyl-1,2,3,4-tetrahydropyrrolopyrazin-1-one deriv

Synthesis and Structure-Activity Relationships of 1-Acyl-4-(2-methyl-3-pyridyl)cyanomethyl)piperazines as PAF Antagonists

A second generation of (cyanomethyl)piperazines, 1-acyl-4-((2-methyl-3-pyridyl)cyanomethyl)piperazines, with increased oral activity was prepared and evaluated in vitro in PAF-induced platelet aggregation assay (PAG) and in vivo in a PAF-induced hypotension test in normotensive rats (HYP).Oral activity was ascertained through a PAF-induced mortality test in mice (MOR).Attachment of a methyl group at position 2 of our earlier pyridine derivatives resulted in an improvement of 1 order of magnitude or greater in the ID50 of the oral test.Three different types of acylsubstituents of similar potency emerge from this work: N-(diphenylmethylamino)acetyl, 3-substituted 3-hydroxy-3-phenylpropionyl, and N-substituted 3-amino-3-phenylpropionyl groups.The most interesting compounds, 26 (UR-12460, PAG IC50 = 0.040 μM, HYP, ID50 = 0.021 mg/kg iv, MOR, ID50 = 0.30 mg/kg po) and 58 (UR-12519, PAG IC50 = 0.041 μM, HYP, ID50 = 0.015 mg/kg iv, MOR, ID50 = 0.044 mg/kg po), compare favorably with WEB-2086.Compounds 26 and 58 were also tested in active anaphylactic shock (AAS) and endotoxin-induced mortality (EIM) tests.On the basis of these data, compounds 26 and 58 have been selected for further pharmacological development.

(2-Alkyl-3-pyridyl)methylpiperazine derivatives as PAF antagonists

The present invention relates to new (2-alkyl-3-pyridyl) methylpiperazine derivatives of general formula I: wherein R1, R2 and Z are as defined in Claim 1. The invention also relates to processes for their preparation and to pharmaceutical compositions containing them. These compounds are potent, orally active PAF antagonists and, consequently, they are useful in the treatment of the diseases in which this substance is involved.