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Experimental and computational studies on the formation of three para-benzyne analogues in the gas phase

Experimental and computational studies on the formation of three gaseous, positively-charged para-benzyne analogues in a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer are reported. The structures of the cations were examined by isolating them and allowing them to react with various neutral reagents whose reactions with aromatic carbon-centered sigma-type mono- and biradicals are well understood. Cleavage of two iodine-carbon bonds in N-deuterated 1,4-diiodoisoquinolinium cation by collision-activated dissociation (CAD) produced a long-lived cation that showed nonradical reactivity, which was unexpected for a para-benzyne. However, the reactivity closely resembles that of an isomeric enediyne, N-deuterated 2-ethynylbenzonitrilium cation. A theoretical study on possible rearrangement reactions occurring during CAD revealed that the cation formed upon the first iodine atom loss undergoes ring-opening before the second iodine atom loss to form an enediyne instead of a para-benzyne. Similar results were obtained for the 5,8-didehydroisoquinolinium cation and the 2,5-didehydropyridinium cation. The findings for the 5,8-didehydroisoquinolinium cation are in contradiction with an earlier report on this cation. The cation described in the literature was regenerated by using the literature method and demonstrated to be the isomeric 5,7-didehydro- isoquinolinium cation and not the expected 5,8-isomer. Pick the right isomer! The generation of three positively charged para-benzyne analogues was attempted in an FT-ICR mass spectrometer. The experimental and quantum chemical findings indicate that the monoradical precursors for the para-benzynes undergo ring-opening faster than formation of the para-benzyne by iodine atom elimination, thus generating enediyne isomers of the para-benzynes (see scheme). Copyright

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Isoquinoline – Wikipedia,
Isoquinoline | C9H284N – PubChem

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Thiazolo[3,4-b]isoquinolines

Isoquinoline derivatives of the formula STR1 wherein the symbol A1 represents an isoquinol-8-yl, 3-methylisoquinol-8-yl, 3-hydroxymethylisoquinol-5-yl, 3-carboxymethylisoquinol-5-yl, quinol-5-yl, thienopyridyl, benzimidazolyl, thienyl or thiazolyl radical, a 4-(or 5-)carboxyalkylthiazol-2-yl radical in which the alkyl moiety is linear or branched and contains 1 to 4 carbon atoms, or a 1,3,4-thiadiazol-2-yl, pyrazolyl, imidazolyl, pyrimidinyl, pyridazinyl or pyrazinyl radical, monocyclic heterocyclic rings within the definition of A1 being optionally substituted by a linear or branched alkyl radical containing 1 to 4 carbon atoms, in the (S) or (R,S) form or mixtures thereof, and salts thereof possess useful pharmocological properties, in particular antiviral activity.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H265N – PubChem

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Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor

Anxiety and depression are common, highly comorbid psychiatric diseases that account for a large proportion of worldwide medical disability. Glyoxalase 1 (GLO1) has been identified as a possible target for the treatment of anxiety and depression. GLO1 is a Zn2+-dependent enzyme that isomerizes a hemithioacetal, formed from glutathione and methylglyoxal, to a lactic acid thioester. To develop active inhibitors of GLO1, fragment-based drug discovery was used to identify fragments that could serve as core scaffolds for lead development. After screening a focused library of metal-binding pharmacophores, 8-(methylsulfonylamino)quinoline (8-MSQ) was identified as a hit. Through computational modeling and synthetic elaboration, a potent GLO1 inhibitor was developed with a novel sulfonamide core pharmacophore. A lead compound was demonstrated to penetrate the blood-brain barrier, elevate levels of methylglyoxal in the brain, and reduce depression-like behavior in mice. These findings provide the basis for GLO1 inhibitors to treat depression and related psychiatric illnesses.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Related Products of 23687-27-6. In my other articles, you can also check out more blogs about 23687-27-6

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Isoquinoline – Wikipedia,
Isoquinoline | C9H290N – PubChem