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1

Synthesis and antifungal activity of new salicylic acid derivatives

Wodnicka A., Huzar E., Krawczyk M., Kwiecień H.

Polish Journal of Chemical Technology

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2017

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Vol. 19, nr 1

143--148

EN

A simple one-step procedure for synthesis of 1-methoxy-1-oxoalkan-2-yl salicylates and 1-methoxy-1-oxoalkan-2-yl 2-[(1-methoxy-1-oxoalkan-2-yl)oxy]benzoates by reaction of salicylic acid with several methyl 2-bromoalkanoates was developed. The reactions were carried out in N,N-dimethylformamide (DMF) in the presence of anhydrous potassium carbonate. Conditions for regioselective synthesis of target compounds were established. The developed procedure could be easily applied in the industrial production process. The new salicylic acid derivatives were obtained with satisfactory yields and were characterized by MS and 1H NMR spectra. The fungicidal activity of the prepared compounds was tested in vitro against seven species of plant pathogenic fungi. The best results were observed for 1-methoxy-1-oxoalkan-2-yl salicylates which showed moderate or good activity against Botrytis cinerea and Rhizoctonia solani.

2

Chemia i aktywność biologiczna czosnku (Allium sativum)

Kwiecień H.

Wiadomości Chemiczne

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2008

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[Z] 62, 9-10

901-942

EN

Garlic (Allium sativum) has historically been one of the most common vegetables to serve as a both spice and medical herb in many countries. One of the outstanding features of the chemical composition of garlic is the large amount of unique organosulfur compounds, which provide its characteristic flavor and odor and most of its potent biological activity. Two classes of primary organosulfur compounds are found in whole garlic cloves: γ-glutamyl-S-alk(en)yl-L-cysteines and S-alk(en)yl-L-cysteine sulfoxides (alliin, metiin, propiin, isallin) (Fig. 1, 2) [5-15]. When garlic is crushed or cut, S-alk(en)yl--L-cysteine sulfoxides are exposed to the enzyme alliinase and thiosulfinates, via intermediate sulfenic acids are formed (Fig. 6) [29-33]. The major thiosulfinate, allicin is a reactive intermediate species that can be transformed, into a variety of compounds including diallyl, methyl allyl and mono- di-, tri-, tetrasulfides, vinyldithiins and ajoenes (Fig. 7-9) [37-49]. Garlic belongs to the Allium species, which accumulate only fructans as their nonstructural carbohydrates [52-59]. Garlic is also known for its production of some unique furostanol saponins, e.g. proto-eruboside-B and sativoside-B1 (Fig. 10-12) [60-63]. The Allium species also contain high levels of flavonides, including apigenin, myricetin and quercetin (Fig. 13) [64, 65], moderate levels of vitamins as well as free amino acids (Arg, Gln, Asn, Glu, and Lys) [66-69]. It was found that the amino acid fraction of Aged Garlic Extract (AGE) contain Maillard reaction products, N-fructosyl glutamine (Fru-Glu), Nα-(1-deoxy-D-fructos-1-yl)-L-arginine (Fru-Arg) (Fig. 14, 15) [74-76], as well as tetrahydro-?-carboline derivatives (Fig. 16, 17) [77-82]. Recently, allixin (Fig. 18), a novel phytoalexin, with the structure 4H-pyran-4-one, as a novel substance with neurotrophic activity has been reported to by synthesized by garlic [83-85]. Garlic has the ability to accumulate the selenium from soil and the major selenium compound in both Se-enriched and unenriched garlic was identified as γ-glutamyl-Se-methyl selenocysteine along with lesser amounts of Se-methyl selenocysteine, selenocysteine, selenomethionine among other compounds (Fig. 19) [86-96]. Pharmacological investigations have shown that garlic has a wide spectrum of actions, not only it is antimicrobial [97], but it also has beneficial effects in regard to cardiovascular and cancer diseases [2, 3, 14, 42]. A number of organosulfur substances derived from garlic such as allicin, allicin-derived organosulfur compounds including sulfides, ajoene, steroidal saponins, flavonides, Fru-Arg, Fru-Glu, organic seleno-compounds and tetrahydro-?-carboline derivatives have been found to have strong antioxidant properties. It has been suggested that garlic can prevent cardiovascular disease, inhibit platelet aggregation, decrease the synthesis of cholesterol and prevent cancer. Thus it may either prevent or delay chronic diseases associated with aging.

3

Study on the Synthesis, Reduction and Reductive Amination of Nitroindan-1-ones. Preparation of N-beta-Hydroxyethyl Derivatives of 6-Aminoindan-1-one and Indan-1,6-diamine

Wodnicka A., Kwiecień H.

Polish Journal of Chemistry

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2008

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Vol. 82, nr 11

2133-2140

EN

Synthesis of 6-aminoindan-1-one and 7-amino-5,6-dimethoxyindan-1-one by nitration of corresponding indanones, followed by selective palladium catalyzed reduction under mild conditions has been described. Reactions of the amines with oxirane leading to N,N-bis-(beta-hydroxyethyl) derivatives were performed. The study of reductive amination of 6-nitroindan-1-one and 5,6-dimethoxy-7-nitroindan-1-one via azines to the corresponding amines as well as synthesis of N,N-bis-(beta-hydroxyethyl) derivatives of the amines was also described.

4

Synthesis of 2-Alkylbenzofurans via Acid-catalyzed Cyclization of 1,1-Dimethoxy-2-phenoxyalkanes

Kwiecień H., Witczak M., Rosiak A.

Polish Journal of Chemistry

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2004

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Vol. 78 / nr 2

249-254

EN

Treatment of 2-phenoxyalkanals 1a-e with methanol at room temperature under homoor heterogeneous acid-catalysis conditions leads to formation of diacetal as well as some quantities of appropriate 2-alkylbenzofurans. 2-Alkylbenzofurans3a-e were obtained in high yields viacyclization of the 1,1-dimethoxy-2-phenoxyalkanes 2a-e under mild conditions over Amberlyst 15.

5

Synthesis of 2-Alkyl-5-nitrobenzofurans via 2-(2-Formyl-4-nitrophenoxy)alkanoic Acids

Kwiecień H.

Polish Journal of Chemistry

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2004

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Vol. 78 / nr 10

1865-1869

EN

Two reaction methods were employed to prepare alumoxanes of general formula [(RO)AlO]n. The first one from Et3Al, H2O and ROH [R = CH3, (CH3)2CH]; the second one from Et3Al, ROH [R = (CH3)2CH, CH3(CH2)9] and H2O. The properties, chemical composition, aggregation and proposed structure of the final products are discussed based on gel permeation chromatography, molecular weight determination and spectroscopic data.

6

Palladium catalyzed reduction of 2-phenoxyalkanoic acids derivatives to 2-phenoxyalkanals

Witczak M., Kwiecień H.

Polish Journal of Applied Chemistry

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2003

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Vol. 47, nr 4

249-261

EN

The Rosenmund reduction of 2-phenoxyalkanoyl chloride 1 leads to the formation of the 2-phenoxyalkanal 2 as the main product and a mixture of phenyl-alkyl ether 4 and Z, E diastereoisomers of phenyl-alkenyl ether 3, as a by-product. The optimisation of the parameters: catalyst and poison to starting chlorides weight ratio of reduction allows to obtain 2-phenoxyalkanals in good yields. Whereas palladium-catalysed reduction of 2,6-dimethoxy-1,3,5-triazine 2-phenoxyalkanoate produced the corresponding 2-phenoxyalkanals in moderate yields only.

PL

Redukcja Rosenmunda chlorku 2-fenoksyalkanowego prowadzi do 2-fenoksyalkanalu jako produktu głównego i mieszaniny eterów: fenylowo-alkanowego oraz Z i E disatereoizomerów eterów fenylowo-alkenowych. Optymalizacja parametrów: stosunku wagowego katalizatora i dezaktywatora do wyjściowego chlorku pozwoliła otrzymać 2-fenoksyalkanal z dobrą wydajnością. Katalizowana palladem redukcja estru 2,6-dimetoksy-1,3,5-triazyny kwasu 2-fenoksyalkanowego prowadziła natomiast do otrzymania 2-fenoksyalkanalu z umiarkowaną wydajnością.

7

Optimization of the parameters of 2-(2-formylphenoxy)hexanoic acid cyclization. Synthesis of 2-alkylbenzofurans

Miszczyszyn M., Kwiecień H.

Polish Journal of Applied Chemistry

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2002

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Vol. 46, nr 1

21-29

EN

The intramolecular cyclization of 2-(2-formylphenoxy)hexanoic acid (FPHA) to 2-butylbenzofuran under the Perkin reaction conditions has been investigated. The influence of important parameters on the 2-butylbenzofuran yield in relation to 2-(2-formylphenoxy)hexanoic acid introduced (response function) has been described by regression equations in the form of a second order polynomial. The optimum values of: acetic anhydride to FPHA molar ratio, reaction time, acetic acid to FPHA molar ratio have been determined. 2-Butylbenzofuran and some of benzene-ring-halogenated 2-alkylbenzofurans have been obtained in moderate yields from corresponding 2-(2-formylphenoxy)alkanoic acids with the use of optimal conditions.

8

Otrzymywanie i właściwości wybranych kwasów 2-(2-acylofenoksy)alkanowych oraz ich zastosowanie w syntezie nowych benzofuranów i 1,4-benzoksazepin

Kwiecień H.

Prace Naukowe Politechniki Szczecińskiej. Instytut Technologii Chemicznej Organicznej

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2001

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Nr 548(3)

5-140

9

Synthesis and properties of new 2-alkyl-1,4-benzoxazepine derivatives. Part 3. Synthesis and cyclization of 2-(2-carboxyphenoxy)alkanamides

Kwiecień H.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 10

2254-2260

EN

A series of novel 2-(2-carboxyphenoxy)alkanamides 4a-f have been obtained as result of condensation of salicylaldehydes with 2-halo esters, amination of prepared esters, 1a-f with methylamine followed by oxidation of amides 3a-f with sodium chlorite. The intramolecular cyclization of amides 4a-f to 1,4-benzoxazepin-3,5-dione system has been investigated.