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Zasady Schiffa : wybrane syntezy, reakcje i aktywność biologiczna

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

Wiadomości Chemiczne

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2014

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[Z] 68, 3-4

187--209

EN

Schiff bases are compounds with a functional group that contains a carbon- -nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group. Schiff bases are condensation products of primary amines with carbonyl compound. Several studies showed that the presence of a lone pair of electrons on the nitrogen atom of the azomethine determine biological and chemical properties of imines. Schiff bases are generally excellent chelating agents, because of the special properties of C=N bond. Their metal complexes have been widely studied because they possess anticancer in vitro and herbicidal applications. Imines also have biological importance. Schiff bases are common enzymatic intermediates where an amine reacts with an aldehyde or ketone of a cofactor or a substrate. Imines have been reported for their biological properties such as antibacterial (E. coli, S. aureus), antifungal (C. albicans) activities. A large number of different Schiff bases are active against a wide range of protozoan (T. gypseum, P. viticola).

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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, struktury i aktywność biologiczna pochodnych imidazo[4,5-b] pirydyny. Część II

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

Wiadomości Chemiczne

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2013

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[Z] 67, 3-4

227--250

EN

The main goal of this article is to present selected syntheses, structures and a various biological activity of imidazo[4,5-b]pyridine derivatives. During the past 20 years the biological activity of imidazo[4,5-b]pyridine have been intensively studied. Based on the review of the chemical literature, it was shown that derivatives of imidazole[4,5-b]pyridine showed a multipharmacological effects such as antibacterial effect [20–22] and antituberculotic activity [25–33], nonsteroidal antiinflammatory activity [35–43] and analgesic [44, 45] effect. Among compounds of this class antagonists of angiotensin II receptors that exhibit hypotensive activity are also known [9–11]. Compounds containing imidazo[4,5-b]pyridine moiety can be synthesized from different substrates. The most useful starting compounds for the synthesis of imidazo[4,5-b]pyridine are derivatives of 2,3-diaminopyridine [1–3].

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Syntezy, struktury i aktywność biologiczna pochodnych imidazo[4,5-b] pirydyny. Część 1

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

Wiadomości Chemiczne

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2012

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[Z] 66, 11-12

1071-1095

EN

This review presents most of the literature data about imidazo[4,5-b]pyridine derivatives and their biological activity. The main goal of this paper is to present various methods for the preparation of imidazo[4,5-b]pyridine analogues. There are some drugs, imidazo[4,5-b]pyridine derivatives, registered in the world, which exhibit diverse pharmacological activities. Noberastine [4] represent antihistaminic II generation drug with selective activity to H1 receptors. Tenatoprazole [5] is a novel proton pump inhibitor with a prolonged plasma half-life which possesses antiulcer activity. Sulmazole [3] is a new cardiotonic agent, an A1 adenosine receptor antagonist. Based on the review of the chemical literature, derivatives of imidazole[4,5-b] pyridine showed a multipharmacological effects. Presented compounds exhibit anticancer [14, 17, 19], antidepressant [44, 45], cardiotonic, anticoagulant [37] activities. Some of them can be used in the treatment of heart diseases [3]. There were also described derivatives of imidazo[4,5-b]pyridine with the potential use in the treatment of diabetes [48], hypertension and hyperlipidemia. Some chemical compounds which contain in their structure the imidazo[4,5-b]pyridine system inhibit neurodegeneration [34, 38] and can be used in the treatment of neurodegenerative disorders eg. Parkinson’s disease, Alzheimer’s disease or multiple sclerosis. In addition, some of the imidazo[4,5-b]pyridine possess antivirial [40–42], antimicrobial and cytotoxic activities.

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Aktywność biologiczna pochodnych 2-amino -1H-benzimidazolu. Część I

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

Wiadomości Chemiczne

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2012

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[Z] 66, 9-10

811-838

EN

The main goal of this article is to present a various biological activity of 2-aminobenzimidazole derivatives. During the past 20 years the biological activity of 2-aminobenzimidazole have been studied. 2-Aminobenzimidazole occurs in a broad spectrum of drugs and pharmacological agents with anticancer [21], antibacterial [14], antiviral [10], analgesic or antiaggregatory properties. There are 30 drugs, 2-aminobenzimidazole derivatives, registered in the world. Mebendazole represents a big group of antiparasitic drugs [25]. Antihistaminic II-nd generation drug with selective activity towards H1 receptors represents Astemizol [2]. Antiviral drugs are: Enviroksym and its isomer Zinviroksym and Enviraden [3–5]. Synthesized 2-aminobenzimidazole derivatives are active against HCV [7], HIV [8, 9] or HCHV [11]. Selected compounds exhibit antiviral [3–5], antifungal [22–24] and antiparasitic [26–28] activity. Some of them can be used in the treatment of bacterial infections [12–14]. Many of 2-aminobenzimidazole analogues are histamine H1, H2, H3 and also H4 receptor antagonists [30, 33, 35, 39].

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Aktywność biologiczna pochodnych 2-amino -1H-benzimidazolu. Część II

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

Wiadomości Chemiczne

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2012

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[Z] 66, 9-10

840-865

EN

2-Aminobenzimidazole occur in a broad spectrum of drugs and pharmacological agents with hypotensive [26], antihistaminic, immunotropic [16], antiarrhythmic [25], analgesic [21, 22] or antiaggregatory properties [27]. There are 30 drugs, 2-aminobenzimidazole derivatives, registered in the world which exhibit diverse pharmacological activities. Carbendazim is an antifungal drug, but in 2003 it has been registered as anticancer [1]. They are also voltage sensitive calcium channel blockers [33], inhibitors of vascular endothelial growth factor [12]. The main goal of this article is to present a various biological activity of 2-aminobenzimidazole derivatives. During the past 20 years the biological activity of 2-aminobenzimidazole have been studied. Based on a review of the chemical literature, derivatives of 2-aminobenzimidazole showed a multipharmacological effects such as hypotensive effect [28], antiinflammatory effect [20] or antibacterial activity. Some chemical compounds, which contain in their structure 2-aminobenzimidazole system inhibit neurodegeneration and in the future they may be used in a treatment of Alzheimer’s disease or Parkinson’s disease [32]. Some of described derivatives of 2-aminobenimidazole can be used in a treatment of metabolic syndrome and diabetes [38]. Synthesis of new 2-aminobenzimidazole derivatives with anticancer activity is now one of the most important direction of research conducted on this group of compounds. Present compounds exhibit anticancer, antiproliferate, neuroprotetic and antiinflaminatory activity. Some of them can be used in a treatment of diabetes and hypertension.

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Synthesis and Antiproliferative Activity in vitro of New 2-Aminobenzimidazole Derivatives. Part 2 [1]

Nawrocka W., Sztuba B., Liszkiewicz H., Kowalska M., Wietrzyk J., Nevozhai D., Opolski A.

Polish Journal of Chemistry

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2005

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Vol. 79 / nr 4

709-716

EN

A series of 2-methylpyrimido[1,2-a]benzimidazole derivatives has been synthesized in the reactions of 2-aminobenzimidazole (1) with selected halogeno _-diketones: 1,1,1- trifluoro- 2, 1-chloro-1,1-difluoro- 3, 3-chloro-2,4-pentadione- 4 and with 4-fluorobenzoylacetone 5. 2-Aminobenzimidazole (1) in the reactions with _-chloro- and _- bromocinnamaldehyde gave Schiff bases 10 and 11 which have been subjected to reduction using NaBH4 and 3-benzylideno-1,2-dihydro- (12) and 3-benzylideno-1,2,9,10- tetrahydroimidazo[1,2-a]benzimidazole (13) were obtained. The structures 2-13 were identified by the results of elemental analysis and their IR, 1H NMR and MS spectra. Compounds 2-13 were examined for their antiproliferative activity in vitro against the cells of 3 human cancer cell lines, using SRB (sulphorhodamine B) or MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) technique. Four out of all tested compounds revealed cytotoxic activity in vitro.

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Synthesis and Antiproliferative Activity in vitro of 1-Phenyl-2-(4-aryl-1,3,4,5-tetrahydropyrido[2,3-b] [1,4]diazepin-2-ylidene)ethanone. Part I.

Liszkiewicz H., Kowalska M. W., Głowiak T., Wietrzyk J., Opolski A.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 11

1607-1617

EN

Reaction of 2,3-diaminopyridine with equimolar amount of benzoylacetone in ethanol solution in the presence of catalytic amounts of acetic acid allowed to obtain 3-(2- amino-pyridin-3-ylamino)-1-phenyl-2-buten-1-one (4) instead of 2-methyl-4-phenyl- 3H-pyrido[2,3-b][1,5]diazepine (3) reported in the literature. Treatment of compound 4 with appropriate aromatic aldehydes: benzaldehyde and substituted benzaldehyde (4- methoxy-, 3,4-dimethoxy-, 3,4,5-trimethoxy-, 3-metyl-4-methoxy-, 3-hydroxy-, 4- diethyloamino-) in methanol solution in the presence of equimolar amount of potassium hydroxide gave 1-phenyl-2-(aryl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]-diazepin-2- ylidene)-ethanones (7-13). Structures of compounds 4 and 7 were determined on a single crystal. Compounds 4 and 7-13 were examined for their antiproliferative activity in vitro against the cells of 7 human cancer cell lines, using SRB orMTTtechnique. Two out of all tested compounds revealed cytotoxic activity in vitro.

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Synthesis and pharmacological properties of new derivatives of 2-amino-5-(2-amino-3-pyridyl)-1,3,4-oxadiazole

Liszkiewicz H., Głowiak T., Kowalska M., Rutkowska M., Szeląg A., Barczyńska J., Kędzierska-Goździk L., Błaszczyk F., Dziewiszek W.

Polish Journal of Chemistry

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1999

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vol. 73 nr 2

321-332

EN

Reaction of 2-aminonicotinic acid hydrazide with cyanogens bromide allowed to obtain 2-amino-5-(2-amino-3-pyridyl)-1,3,4-oxadiazole (2), which with 2- or 3-chloropropionyl chloride and 4-chlorobutyryl chloride gave 5-(2-amino-3-pyridyl)-2-(2-chloroproprionylamino)-1,3,4-oxadiazole (5), 5-(2-amino-3-pyridyl)-2-(3-chloroproprionyl- amino)-1,3,4-oxadiazole (6) and 5-(2-amino-3-pyridyl)-2-(4-chlorobutyrylamino)-1,3,4-oxadiazole (7), respectively. Cyclization of chloroacyl derivative 7 led to 5-(2-amino-3-pyridyl)-2-(2-oxo-1-pyrrolidinyl)-1,3,4-oxadiazole (9). Treatment of oxadiazole 2 with appropriate alkylating agents (1,3-dibromopropane or 1,4-dibromobutane) gave 2-azetidynyl-1,3,4-oxadiazole (10) or 2-pyrrolidynyl-1,3,4-oxadiazole (11). Compounds 3,4,7,10 and 11 were tested towards a psychotropic activity. Compound 10 showed anxiolytic properties and an antiserotonin action, which was confirmed in the test of the black-white box and the m-CPP test, respectively. Crystal structure was determined on a single crystal.