pyrrole

3

Preparation of something really pure. This compound (a highly substituted dihydroxy pyrrole) was made by me at least tenth time, but since a slight contamination (1-5%) was always present in the final product, it always had a green fluorescence.

Now, finally I found an easy was to purify the product and I was able to make it in a +99,5% purity.

2

Crystals of sublimed 2-(trifluoroacetyl)pyrrole.

The raw reaction product what was an off-white crystalline compound with a melting point 50 °C was loaded in a test tube and left there for a few months. For now, these crystals formed at the wall what are perfectly pure 2-(trifluoroacetyl)pyrrole.

If this compound is left on a Petri dish for a day, most of it will sublime away.

5

Yesterday I have made something really new and really pure, a highly substituted pyrrole what crystallized on standing during the night to give these nice round crystals at the bottom of the flask.  

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2

These crystals are the first results of a several month long work, they are a quite special substituted pyrrole what could be polymerized quite easily and it will give a conductive polymer.

Even through the crystals have a slight brownish coloration, they are perfectly pure, according to the NMR analysis.

2

I am doing pyrrole chemistry for a while now and there is a quite interesting reaction with this. When I synthesize freshly a pyrrole (with free N-H) and add sodium-hydride, during the formation of the N-Na salt of the pyrrole an intense blue color appears as seen on the picture, but it fades to give a yellowish solution as the gas evolution stops. And it only works if the pyrrole is freshly prepared and it is in a pure form.

The color reminds me to the classic experiment, the solvated electron, what could be done by dissolving a piece of alkali metal in liquid ammonia.

Identification of apoptosis signal-regulating kinase 1 (ASK1) inhibitors among the derivatives of benzothiazol-2-yl-3-hydroxy-5-phenyl-1,5-dihydro-pyrrol-2-one.

PubMed: Identification of apoptosis signal-regulating kinase 1 (ASK1) inhibitors among the derivatives of benzothiazol-2-yl-3-hydroxy-5-phenyl-1,5-dihydro-pyrrol-2-one.

Bioorg Med Chem. 2015 Mar 28;

Authors: Starosyla SA, Volynets GP, Lukashov SS, Gorbatiuk OB, Golub AG, Bdzhola VG, Yarmoluk SM

Abstract
Apoptosis signal-regulating kinase 1 (ASK1) plays important roles in the pathogenesis of type 1 and type 2 diabetes, autoimmune disorders, cancer and neurodegenerative diseases suggesting that small compounds inhibiting ASK1 could be used for the treatment of these pathologies. We have identified novel chemical class of ASK1 inhibitors, namely benzothiazol-2-yl-3-hydroxy-5-phenyl-1,5-dihydro-pyrrol-2-one, using molecular modeling techniques. It was found that the most active compound 1-(6-fluoro-benzothiazol-2-yl)-3-hydroxy-5-[3-(3-methyl-butoxy)-phenyl]-4-(2-methyl-2,3-dihydro-benzofuran-5-carbonyl)-1,5-dihydro-pyrrol-2-one (BPyO-34) inhibits ASK1 with IC50 of 0.52μM in vitro in kinase assay. The structure-activity relationships of 34 derivatives of benzothiazol-2-yl-3-hydroxy-5-phenyl-1,5-dihydro-pyrrol-2-one have been studied and binding mode of this chemical class has been proposed.

PMID: 25882527 [PubMed - as supplied by publisher] http://dlvr.it/9S11sT