26280-19-3

Upstream product

• 1192-58-1 N-methylpyrrole aldehyde 
• 98-88-4 benzoyl chloride 
• 21898-43-1 2-(1-methyl-1H-pyrrol-2-yl)-2-oxoacetic acid 
• 21898-59-9 1-methylpyrrole-2-acetic acid 
• 80096-44-2 (5-benzoyl-1-methyl-1H-pyrrol-2-yl)acetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis, antimicrobial, and anti-inflammatory activities of acetamido pyrrolyl azoles

The acetamido pyrrolyl oxazoles/thiazoles/imidazoles were prepared and tested for their antimicrobial and anti-inflammatory activities. The nitro substituted acetamido pyrrolyl thiazole (11f) and pyrrolyl imidazole (12f) exhibited promising antibacterial activity against K. pneumoniae. The compound 12f showed good antifungal activity against P. chrysogenum. The methoxy acetamido pyrrolyl oxazole (10c) displayed potential anti-inflammatory activity.

2-ARYL-ACETIC ACIDS, THEIR DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Selected 2-arylacetic acids, their derivatives and pharmaceutical compositions that contain these compounds are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The compounds are used for the prevention and treatment of pathologies deriving from said activation. In particular, 2(ortho)-substituted arylacetic acids or their derivatives, such as amides and sulfonamides, lack cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrophil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bullous pemphigoid, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

3-(4-Aroyl-1-methyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamides as a New Class of Synthetic Histone Deacetylase Inhibitors. 2. Effect of Pyrrole-C2 and/or -C4 Substitutions on Biological Activity

Previous SAR studies (Part 1: Mai, A.; et al. J. Med. Chem. 2003, 46, 512-524) performed on some portions (pyrrole-C4, pyrrole-N 1, and hydroxamate group) of 3-(4-benzoyl-1-methyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamide (1a) highlighted its 4-phenylacetyl (1b) and 4-cynnamoyl (1c) analogues as more potent compounds in inhibiting maize HD2 activity in vitro. In the present paper, we investigated the effect on anti-HD2 activity of chemical substitutions performed on the pyrrole-C2 ethene chains of 1a-c, which were replaced with methylene, ethylene, substituted ethene, and 1,3-butadiene chains (compounds 2). Biological results clearly indicated the unsubstituted ethene chain as the best structural motif to get the highest HDAC inhibitory activity, the sole exception to this rule being the introduction of the 1,3-butadienyl moiety into the 1a chemical structure (IC50(2f) = 0.77 μM; IC 50(1a) = 3.8 μM). IC50 values of compounds 3, prepared as 1b homologues, revealed that between benzene and carbonyl groups at the pyrrole-C4 position a hydrocarbon spacer length ranging from two to five methylenes is well accepted by the APHA template, being that 3a (two methylenes) and 3d (five methylenes) are more potent (2.3- and 1.4-fold, respectively) than 1b, while the introduction of a higher number of methylene units (see 3e,f) decreased the inhibitory activities of the derivatives. Particularly, 3a (IC50 = 0.043 μM) showed the same potency as SAHA in inhibiting HD2 in vitro, and it was 3000- and 2.6-fold more potent than sodium valproate and HC-toxin and was 4.3- and 6-fold less potent than trapoxin and TSA, respectively. Finally, conformationally constrained forms of 1b,c (compounds 4), prepared with the aim to obtain some information potentially useful for a future 3D-QSAR study, showed the same (4a,b) or higher (4c,d) HD2 inhibiting activities in comparison with those of the reference drugs. Molecular modeling and docking calculations on the designed compounds performed in parallel with the chemistry work fully supported the synthetic effort and gave insights into the binding mode of the more flexible APHA derivatives (i.e., 3a). Despite the difference of potency between 1b and 3a in the enzyme assay, the two APHA derivatives showed similar antiproliferative and cytodifferentiating activities in vivo on Friends MEL cells, being that 3a is more potent than 1b in the differentiation assay only at the highest tested dose (48 μM).

Synthesis and structure-activity relationships of aroylpyrrole alkylamide bradykinin (B2) antagonists

The synthesis and structure-activity relationships of a novel series of aroylpyrrole alkylamides as potent selective bradykinin B2 receptor antagonists are described. Several members of this series display nanomolar affinity at the B2 receptor and show activity in an animal model of antinociception.

1,3,6-trihydro-6-aza-3-oxapentalen-2-one derivatives for the treatment of neoplasia

1,3,6-Trihydro-6-Aza-3-Oxapentalen-2-One Derivatives for inhibiting neoplastic conditions.

Preparation of 5-(arylcyanohydroxymethyl)-1-loweralkylpyrrole-2-acetic acid derivatives

5-(Arylcyanohydroxymethyl)-1-loweralkylpyrrole-2-acetic acid derivatives are prepared by the protic acid catalyzed reaction of aroylcyanides with 1-loweralkylpyrrole-2-acetic acid derivatives, which is then converted by treatment with alkali metal hydroxides or heat to form 5-aroyl-1-loweralkylpyrrole-2-acetic acid or derivatives thereof.

Aroyl-substituted pyrroles

The compounds are of the class of 5-aroyl-pyrrole alkanoic acids and corresponding acid derivatives thereof useful as anti-inflammatory agents and as synthetic intermediates.