Pyrroles and Fused Pyrroles: Synthesis and Therapeutic Activities

Mohamed, Mosaad S.; Fathallah, Samar S.

doi:10.2174/1570193x113106660018

Cited by 56 publications

(31 citation statements)

References 100 publications

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“…60 We also found that α-chlorocyclohexanone under the reaction conditions EtOH/NaOH (polar basic medium) might undergo what is called Favorskii rearrangement, 61 rearrangement of an α-halo ketone upon treatment with a base; the reaction continues through cyclopropanone intermediate formed by nucleophilic attack [EtO -]. In addition to the possibility of condensation with amine to give the anil (Fig.…”

Section: Chemistrymentioning

confidence: 94%

Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

Fatahala

Khedr

Mohamed

2017

ACSi

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A series of fused pyrroles were synthesized and tested for their in vivo anti-inflammatory activity. Among 14 examined derivatives, 5 derivatives (1b-e, g and 5b), showed a promising anti-inflammatory activity equivalent to reference anti-inflammatory drugs (indomethacin and ibuprofen). A molecular docking study was conducted to interpret the biological activities of the tested compounds. The docking results were complementary with the phase of the biological survey and confirmed the biological effects.

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Section: Chemistrymentioning

confidence: 94%

Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

Fatahala

Khedr

Mohamed

2017

ACSi

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“…Pyrroles are very common in naturally occurring bioactive compounds such as heme, chlorophyll, vitamin B12, etc . Heterocycles containing pyrrole skeleton are important because of their significant biological efficacies that include anti‐bacterial, anti‐viral, anti‐inflammatory, anti‐tumoral, anti‐oxidant activities . In 2013, Li et al .…”

Section: Ultrasound‐assisted Heterocycles Synthesis In Ionic Liquidsmentioning

confidence: 99%

Ultrasound and Ionic Liquid: An Ideal Combination for Organic Transformations

Kaur¹,

Sharma²,

Banerjee³

2018

ChemistrySelect

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Combination of ultrasound and suitable ionic liquid is a powerful tool to carry out diverse organic transformations. In many occasions, this fruitful combination helps to get the desire products without using any further catalysts even at room temperature. Recyclability of ionic liquid makes a protocol cost effective also. The present review deals with the ultrasound‐assisted organic synthesis in various ionic liquids either as catalyst or reaction media.

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“…For example, Atorvastatin (marketed by Pfizer as Lipitor 1 ) is a blockbuster drug widely used as a cholesterol-lowering agent, Zomepirac is an effective nonsteroidal anti-inflammatory drug and Sunitinib is used as a multitargeted receptor tyrosine kinase inhibitor for the treatment of renal cancer (Khajuria et al, 2016;Ye et al, 2017;Nomiyama et al, 2017). While a plethora of methods for the synthesis of this scaffold have been developed, there still remains a great need to find noncatalytic eco-compatible and efficient methodologies for the synthesis of functionalized pyrroles from inexpensive and available starting materials, as well as their use as building blocks for the preparation of new pyrrole-fused heterocycles (Esté vez et al, 2014;Mohamed & Fatahala, 2014). Therefore, we report herein the crystal structures of novel pyrrole derivatives, which are shown in Scheme 1, where the found stereochemistry of the amino group is represented.…”

Section: Introductionmentioning

confidence: 99%

A series of (E)-5-(arylideneamino)-1-tert-butyl-1H-pyrrole-3-carbonitriles and their reduction products to secondary amines: syntheses and X-ray structural studies

2018

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An efficent access to a series of N-(pyrrol-2-yl)amines, namely (E)-1-tert-butyl-5-[(4-chlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, CHClN, (7a), (E)-1-tert-butyl-5-[(2,4-dichlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, CHClN, (7b), (E)-1-tert-butyl-5-[(pyridin-4-ylmethylene)amino]-1H-pyrrole-3-carbonitrile, CHN, (7c), 1-tert-butyl-5-[(4-chlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, CHClN, (8a), and 1-tert-butyl-5-[(2,4-dichlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, CHClN, (8b), by a two-step synthesis sequence (solvent-free condensation and reduction) starting from 5-amino-1-tert-butyl-1H-pyrrole-3-carbonitrile is described. The syntheses proceed via isolated N-(pyrrol-2-yl)imines, which are also key synthetic intermediates of other valuable compounds. The crystal structures of the reduced compounds showed a reduction in the symmetry compared with the corresponding precursors, viz. Pbcm to P-1 from compound (7a) to (8a) and P2/c to P-1 from compound (7b) to (8b), probably due to a severe change in the molecular conformations, resulting in the loss of planarity observed in the nonreduced compounds. In all of the crystals, the supramolecular assembly is controlled mainly by strong (N,C)-H...N hydrogen bonds. However, in the case of (7a)-(7c), C-H...Cl interactions are strong enough to help in the three-dimensional architecture, as observed in Hirshfeld surface maps.

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Pyrroles and Fused Pyrroles: Synthesis and Therapeutic Activities

Cited by 56 publications

References 100 publications

Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

Ultrasound and Ionic Liquid: An Ideal Combination for Organic Transformations

A series of (E)-5-(arylideneamino)-1-tert-butyl-1H-pyrrole-3-carbonitriles and their reduction products to secondary amines: syntheses and X-ray structural studies

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