Chemo- and regioselectivity in the reactions of polyfunctional pyrroles

Marth, Gabriella; Anderson, Rosaleen J.; Thompson, Barry G.; Ashton, Mark; Groundwater, Paul W.

doi:10.1016/j.tet.2010.06.006

Cited by 7 publications

(6 citation statements)

References 6 publications

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“…1. 9,10 Atrovastatin (Lipitor) is a drug for lowering the cholesterol. 11 There have been considerable studies on the effects of substituents and the design of the pyrrole skeleton, which contain active substituents.…”

Section: Introductionmentioning

confidence: 99%

An efficient one-pot synthesis of tetra-substituted pyrroles

et al. 2011

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Section: Introductionmentioning

confidence: 99%

An efficient one-pot synthesis of tetra-substituted pyrroles

et al. 2011

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“…Therefore, we employed bipyrrole dicarbaldehyde 8 as the starting material . Reductive dehalogenation of 8 led to the formation of the corresponding dechlorinated product 9 as a highly fluorescent bright yellow solid in 52% yield . Subsequent McMurry coupling of 9 with Zn/TiCl 4 /CuCl provided the desired porphycene 1 as a blue-purple crystalline solid in 24% yield.…”

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confidence: 98%

“…11 Reductive dehalogenation of 8 led to the formation of the corresponding dechlorinated product 9 as a highly fluorescent bright yellow solid in 52% yield. 12 Subsequent McMurry coupling of 9 with Zn/TiCl 4 /CuCl provided the desired porphycene 1 as a blue-purple crystalline solid in 24% yield. The latter method not only provided a slightly better two-step yield from 8 (10 vs 13%) but also led to easier isolation of the product.…”

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confidence: 99%

“…It exhibits intense fluorescence and reasonable singlet oxygen sensitization and affords stable metal complexes, including the first Zn(II) complex among tetrasubstituted porphycenes, which upon ligation with pyridine exhibits supramolecular chirality in its crystal lattice. Interestingly, we found 3,6,13,16substituted porphycene is quite unique and is endowed with all of the good attributes of so far known 2,7, 12,9,10,19,2,7,12,positions are ideal for subsequent manipulation, and at present, efforts are underway in this direction along with synthesis of new members of this class of macrocycles. Unhesitatingly, we can state 3,6,13,16-substituted porphycene opens a new vista in the ever-growing porphycene chemistry.…”

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confidence: 99%

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3,6,13,16-Tetrasubstituted Porphycene: The Missing Link in Porphycene Chemistry

2020

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We have introduced the first 3,6,13,16-tetrasubstituted porphycene as its tetramethoxy analogue. This substitution pattern is one of the most general patterns yet missing in this isomeric porphyrin chemistry. This porphycene exhibits intense fluorescence along with the ability to coordinate with divalent metal ions; in particular, it forms the first stable Zn(II) complex among the tetrasubstituted porphycenes. Notably, the molecular structure of Zn1•Py displays supramolecular chirality.

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“…Some examples of pharmaceutical compounds with pyrrole ring skeletons are shown in Fig. 1 42,43 . In addition, pyrrole is an important core moiety in many biological compounds such as chlorophyll, heme, vitamin B 12 , bile pigments, and alkaloids.…”

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confidence: 99%

Design, synthesis, in silico and biological evaluations of novel polysubstituted pyrroles as selective acetylcholinesterase inhibitors against Alzheimer’s disease

Pourtaher

Hasaninejad

Iraji

2022

Sci Rep

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The objective of this study was to design new polysubstituted pyrrole derivatives as selective acetylcholinesterase (AChE) inhibitors to target Alzheimer's disease. In this context, a highly efficient, one-pot, sequential, multi-component synthesis of a diverse range of polysubstituted pyrroles was developed through a sequential domino strategy by the condensation of amines with 1,1-bis(methylthio)-2-nitroethene (BMTNE), Knovenagle reaction of arylglyoxals with malono derivatives and subsequent Michael addition and intramolecular cyclization reaction in EtOH at reflux. Thirty-nine synthesized compounds were evaluated as AChE and butyrylcholinesterase (BChE) inhibitors. Among the synthesized compounds, compound 4ad (IC50 = 2.95 ± 1.31 µM) was the most potent and selective AChE inhibitor with no significant inhibition against butyrylcholinesterase BChE. A kinetic study of 4ad revealed that this compound inhibited AChE in an uncompetitive mode. Based on a molecular modeling study, compound 4ad due to its small size properly fitted into the active site of AChE compared to BChE and stabilized by H-bond and hydrophobic interactions with the critical residues of the AChE binding pocket. Consequently, it was proposed that the 4ad derivative can be an ideal lead candidate against AD with a simple and practical operation of synthetic procedures.

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Chemo- and regioselectivity in the reactions of polyfunctional pyrroles

Cited by 7 publications

References 6 publications

An efficient one-pot synthesis of tetra-substituted pyrroles

An efficient one-pot synthesis of tetra-substituted pyrroles

3,6,13,16-Tetrasubstituted Porphycene: The Missing Link in Porphycene Chemistry

Design, synthesis, in silico and biological evaluations of novel polysubstituted pyrroles as selective acetylcholinesterase inhibitors against Alzheimer’s disease

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