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Syntezy wybranych zasad Mannicha o aktywności przeciwbakteryjnej i przeciwgrzybiczej in vitro

Nowicka A., Liszkiewicz H., Nawrocka W. P.

Wiadomości Chemiczne

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2014

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[Z] 68, 3-4

161--186

EN

The Mannich reaction is a three-component condensation reaction involving an active hydrogen containing compound, formaldehyde and a primary or a secondary amine. The Mannich reaction is one of the most important basic reaction types in organic chemistry. This kind of aminoalkylation is important for the synthesis and modification of biologically active compounds. Many studies have shown that Mannich bases possesses potent biological activities: antibacterial, antifungal, anti-inflammatory and antimalarial properties. Mannich bases – substituted products containing different heterocyclic moiety in their structures seem to be suitable candidates for further chemical modifications and might be of interest as pharmacologically active compounds. The main goal of this article is to present synthesis and antimicrobial activity of selected Mannich bases. The Mannich reaction is known to be very useful for the synthesis of antibacterial compounds. The Mannich bases, containing various heterocyclic systems were identified as potent antimicrobial agents. Obtained in Mannich reaction derivatives of antibacterial drugs: ciprofloxacine, norfloxacine demonstrate higher antibacterial activity than used drugs, while derivatives of drugs: ibuporofen or phenytoine changed the profile of action of new synthesized compounds.

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Syntezy i aktywność biologiczna wybranych zasad Mannicha

Nawrocka W. P., Nowicka A.

Wiadomości Chemiczne

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2014

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[Z] 68, 11-12

981--1008

EN

The Mannich reaction is important for the synthesis and modification of biologically active compounds. Mannich bases – substituted products containing different heterocyclic system in their structures seem to be suitable candidates for further chemical modifications and might be of interest as pharmacologically active compounds. The main goal of this article is to present synthesis and biological activity of selected Mannich bases. Based on a review of the chemical literature, Mannich bases showed a multipharmacological effects. The Mannich bases, containing various heterocyclic systems were identified as potent anticancer agents. Presented compounds exhibit cytotoxic, antiproliferate in vitro, anticonvulsant, antioxidative, antiinflaminatory and analgesic activity. Some of them can be used in a treatment of diabetes and hypertension.

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Crystal and Molecular Structures of Model Schiff-Mannich Bases

Woźniak K., Grech E., Szady-Chełmieniecka A.

Polish Journal of Chemistry

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2000

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Vol. 74, nr 5

717-728

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Crystal and molecular structure of 2-(N,N-diethylamino)-methyl-4-bromo-6-formylphenol

Woźniak K., Anulewicz R., Grech E., Szady A.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 2

460-469

EN

Structural and spectroscopic properties of solid 2-(N,N-diethylamino)-methyl-4-bromo-6-formylphenol have been investigated. There are two molecules of the title compound in the independent part of the unit cell with only minor structural differences. This is an example of a Mannich base containing a neutral [O-H...N] intramolecular hydrogen bonding. Single crystal X-ray diffraction shows that the title molecule is dominated by neutral Kekule structures. Being involved in a strong intramolecular [O-H...N] hydrogen bonding, 2-(N,N-diethylamino)-methyl-4-bromo-6-formylphenol forms its crystal lattice by means of different types of weak intermolecular [C-H...O], and C-H...Br hydrogen bonds.

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Chiral recognition studies of amino acids by chiral calix[4]resorcinarenes in Langmuir films

Pietraszkiewicz M., Prus P., Fabianowski W.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 6

1068-1075

EN

Two chiral, lipophilic calix[4]resorcinarenes of Mannich-base type, containing (S((-)-phenylethylamine (CAL11-PhEt), and (1R,2S)(-)-norephedrine (CAL11-EPh) form Langmuir monolayers on water surface. Chiral discrimination of amino acids: alanine, valine, leucine and tryptophan was observed by the changes in the surface area, which was different for D- and L-forms.