- An efficient synthesis of indoloquinoline alkaloid - Neocryptolepine (cryptotackieine)
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A short and convenient method for the synthesis of neocryptolepine (cryptotackieine) is described using Wittig reaction and one-pot reduction-cyclization-dehydration approach as the key steps.
- Parvatkar, Prakash T.,Tilve, Santosh G.
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- NMR determination of pKa values of indoloquinoline alkaloids
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Malaria is one of the most serious global health problems. Isolating new therapeutic agents with potential antimalarial activity from natural sources or preparing such agents either semisynthetically or synthetically is one strategy for solving the proble
- Grycova, Lenka,Dommisse, Roger,Pieters, Luc,Marek, Radek
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- Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
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A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.
- Méndez, María V.,Heredia, Daniel A.,Larghi, Enrique L.,Bracca, Andrea B. J.,Kaufman, Teodoro S.
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- Synthesis and evaluation of the tetracyclic ring-system of isocryptolepine and regioiso-mers for antimalarial, antiproliferative and antimicrobial activities
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A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 μM; 9b: MBIC = 100 μM).
- Albrigtsen, Marte,Andersen, Jeanette H.,Avery, Vicky M.,H?heim, Katja S.,Helgeland, Ida T. Urdal,Kennedy, Emily K.,Lauga, Clémence,Lindb?ck, Emil,Matringe, Théodora,Sydnes, Magne O.,Tan, Kah Ni
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- Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of norneocryptolepine and neocryptolepine
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An innovative acid-assisted cascade transformation of indoles with 2-nitrostyrenes was developed, allowing for the one-pot assembly of heterocyclic scaffolds with four fused rings. This strategy was subsequently employed for the concise total synthesis of two natural products, the alkaloids norneocryptolepine and neocryptolepine.
- Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Arutyunov, Nikolai A.,Gasanova, Amina Z.,Lower, Carolyn,Rubin, Michael
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- Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi
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Neocryptolepine is an alkaloid isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and mass spectrometry. The synthesized compounds were screened for their antifungal profile against six agriculturally important fungi Rhizoctonia solani, Botrytis cinerea (B. cinerea), Fusarium graminearum, Mycosphaerella melonis, Sclerotinia sclerotiorum, and Magnaporthe oryzae. The results of in vitro assay revealed that compounds 5, 21, 24, 35, 40, 45, and 47 presented remarkable antifungal activity against the fungi tested with EC50 values lower than 1 μg/mL. Significantly, compound 24 displayed the most effective inhibitory potency against B. cinerea (EC50 = 0.07 μg/mL), and the data from in vivo experiments revealed that compound 24 demonstrated comparable protective activity with the positive control boscalid. Preliminary mechanism studies indicated that compound 24 showed impressive spore germination inhibitory effectiveness and lower cytotoxicity than azoxystrobin, imparted on normal function of the cell membrane and cell wall, and arrested the normal function of the nucleus. Besides the excellent inhibitory activity against agriculturally important phytopathogenic fungi tested, the designed assemblage possesses several benefits with a high profile of variation in synthesized molecules, the ease of synthesis, and good cost-effectiveness of commercially available synthetic reagents, all of these have highlighted the potential worth of compound 24 as a new and highly efficient agricultural fungicide.
- Gao, Jian-Mei,Lawoe, Raymond Kobla,Liu, Ying-Qian,Shang, Xiao-Fei,Sun, Yu,Yang, Cheng-Jie,Yin, Xiao-Dan,Zhao, Zhong-Min,Zhou, Rui,Zhu, Jia-Kai
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p. 2306 - 2315
(2020/03/10)
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- Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles
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Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C-C and C-N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C-C and C-N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.
- Roy, Subhra Kanti,Purkait, Anisha,Aziz, Sk Md Tarik,Jana, Chandan K.
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supporting information
p. 3167 - 3170
(2020/03/23)
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- Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine
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A novel procedure for the Pd-catalyzed dual annulation reaction to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of the norneocryptolepine to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the intramolecular addition of nitrile according to the mechanism study.
- Yeh, Li-Hsuan,Wang, Hung-Kai,Pallikonda, Gangaram,Ciou, Yu-Lun,Hsieh, Jen-Chieh
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supporting information
(2019/03/19)
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- Application of A ring-modified new cryptolepine derivatives in prevention and control of agricultural plant diseases
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The invention relates to the field of natural medicinal chemistry and the technical field of biological pesticides, and discloses an application of any compound of A ring-modified new cryptolepine derivative ZX-1 to ZX-12 in the prevention and control or resisting of agricultural plant diseases. Bioactivity test shows that the compounds of the present invention have significant inhibitory activityagainst the following six plant diseases: Rape Sclerotinia Rot, Rhizoctonia solani, tomato gray mold, wheat scab, rice blast and watermelon blight, and parts of the compounds have better pathogen inhibition activity than azoxystrobin, and can be developed as leading molecules for natural source alkaloid bactericides. The compound of the present invention are derived from natural structural derivatives of the plant C. sanguinolenta, so the compounds have the characteristics of non-pollution, safety and high efficiency, has the advantages of natural source pesticides, can be developed into botanical pesticides suitable for producing green and pollution-free agricultural products, and belong novel biogenic pesticides.
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Paragraph 0015-0020
(2019/05/16)
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- Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization
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An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.
- Das, Sandip Kumar,Roy, Satyajit,Khatua, Hillol,Chattopadhyay, Buddhadeb
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p. 8429 - 8433
(2018/07/09)
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- Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis
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The invention relates to a method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis, belonging to the technical field of visible light catalytic synthesis. A synthetic route is described in the description, wherein the structural formula of DPZ is described in the description, R is -H, -OMe, -F or -Cl, and R is -Me, -Bn or -Ph; the synthetic process comprises the steps of dissolving a compound 1, the DPZ, K3PO4 and TEMPO into a mixed solvent of CH3CN and water, carrying out a reaction at the constant temperature of 25 DEG C under a blue lamp light source in an oxygen atmosphere, tracking and monitoring by using thin layer chromatography (TLC), and after the reaction is finished, carrying out column chromatographic separation to obtain a compound 2. The method can be used for efficiently preparing the N-(2-formyl phenyl) N-substituted formamide derivatives, and has the advantages of being environmental-friendly, high in reaction efficiency, simple in aftertreatment and low in cost.
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Paragraph 0050; 0051
(2018/02/04)
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- Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch
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An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.
- Zhang, Chenhao,Li, Sanliang,Bure?, Filip,Lee, Richmond,Ye, Xinyi,Jiang, Zhiyong
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p. 6853 - 6860
(2016/10/18)
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- An elegant synthesis of indoloquinoline alkaloid cryptotackieine via Vilsmeier-Haack approach
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An exclusive approach towards the synthesis of indoloquinoline alkaloid cryptotackiene has been illustrated. Primary starting materials with an established procedure like Vilsmeier-Haack cyclization are used followed by nucleophilic azidation, intra-molecular cyclization and a selective methylation to achieve the target.
- Pitchai,Sathiyaseelan,Nepolraj,Gengan
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p. 1290 - 1292
(2015/11/25)
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- Baylis-Hillman acetates in organic synthesis: Convenient one-pot synthesis of α-carboline framework - A concise synthesis of neocryptolepine
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A convenient, facile, and one-pot methodology for the synthesis of α-carbolines from Baylis-Hillman (BH) acetates, involving three steps (reactions), (1) mono alkylation of 2-nitroarylacetonitriles with BH-acetates, (2) reduction of nitro group into amino group using Fe/AcOH and (3) formation of two (five and six membered) rings, is presented. This methodology is successfully applied to the synthesis of bioactive alkaloid neocryptolepine.
- Basavaiah, Deevi,Mallikarjuna Reddy, Daggula
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supporting information
p. 8774 - 8777
(2013/01/15)
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- RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides
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Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright
- Pumphrey, Ashley L.,Dong, Huijun,Driver, Tom G.
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p. 5920 - 5923
(2012/08/07)
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- One-pot access to indolo[2,3- b]quinolines by electrophile-triggered cross-amination/friedel-crafts alkylation of indoles with 1-(2-tosylaminophenyl) ketones
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Activation of C2 and C3 of indoles by molecular iodine (I2) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde can afford highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. The synthetic potential of the protocol has been illustrated by the synthesis of neocryptolepine and its 11-methyl analogue.
- Ali, Shaukat,Li, Ying-Xiu,Anwar, Saeed,Yang, Fang,Chen, Zi-Sheng,Liang, Yong-Min
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p. 424 - 431
(2012/02/13)
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- Highly efficient one-pot synthesis of D-ring chloro-substituted neocryptolepines via a condensation - Pd-catalyzed intramolecular direct arylation strategy
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D-ring chloro-substituted neocryptolepines have been synthesized in excellent yield starting from 3-bromo-2-chloro-1-methylquinolinium triflate via a one-pot condensation - Pd-catalyzed intramolecular direct arylation strategy involving chloroanilines. Th
- Hostyn, Steven,Tehrani, Kourosch Abbaspour,Lemire, Filip,Smout, Veerle,Maes, Bert U.W.
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p. 655 - 659
(2011/03/19)
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- Efficient syntheses of the unknown quinolino[2,3- c ]cinnolines; Synthesis of neocryptolepines
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A facile, efficient, three-step protocol for the synthesis of the unknown quinolino[2,3-c]cinnoline 5 is introduced. In addition, a new approach for the preparation of the biologically active neocryptolepines 8 in good overall yields is described.
- Haddadin, Makhluf J.,Bou Zerdan, Raghida M.,Kurth, Mark J.,Fettinger, James C.
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p. 5502 - 5505
(2011/03/18)
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- Formation of N-heterocycles by the reaction of thiols with glyoxamides: Exploring a connective Pummerer-type cyclisation
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The reaction of thiols with glyoxamides provides a convenient method for the generation of thionium ions and the initiation of Pummerer-type reactions. When the glyoxamides contain tethered aromatic nucleophiles, N-heterocycles are formed by a thionium ion cyclisation. The scope and mechanism of the connective Pummerer-type process has been investigated using a range of thiols, Lewis acids and both mono- and bis-glyoxamides. The utility of the process has been illustrated in a synthesis of the indoloquinoline natural product, neocryptolepine. The Royal Society of Chemistry 2009.
- Miller, Marc,Vogel, Johannes C.,Tsang, William,Merrit, Andrew,Procter, David J.
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experimental part
p. 589 - 597
(2009/07/18)
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- Double reductive cyclization: a facile synthesis of the indoloquinoline alkaloid cryptotackieine
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A new synthesis of the indoloquinoline alkaloid cryptotackieine, isolated from Cryptolepis sanguinolenta, is described which involves a Perkin reaction, a tandem double reduction-double cyclization reaction followed by regioselective methylation at the quinoline nitrogen.
- Parvatkar,Parameswaran,Tilve
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p. 7870 - 7872
(2008/03/11)
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- Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives
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A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents.
- Dhanabal,Sangeetha,Mohan
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p. 6258 - 6263
(2007/10/03)
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- Synthesis of cryptolepine and cryptoteckieine from a common intermediate
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Both cryptolepine 1 and cryptotackieine 3 have been synthesized from 1,3-bis(2-nitrophenyl)propan-2-one. The approach to 1 involved reduction of the NO2 groups, oxidative cyclization with PhI(OAc)2, and N-methylation, whereas 3 was obtained via bromination, Favorskii rearrangement, reduction (in situ cyclization), and N-methylation.
- Ho, Tse-Lok,Jou, Der-Guey
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p. 3823 - 3827
(2007/10/03)
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- Synthesis, cytotoxicity, and antiplasmodial and antitrypanosomal activity of new neocryptolepine derivatives
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On the basis of the original lead neocryptolepine or 5-methyl-5H-indolo[2,3-b]quinoline, an alkaloid from Cryptolepis sanguinolenta, derivatives were prepared using a biradical cyclization methodology. Starting from easily accessible educts, this approach allowed the synthesis of hitherto unknown compounds with a varied substitution pattern. As a result of steric hindrance, preferential formation of the 3-substituted isomers over the 1-substituted isomers was observed when cyclizing N-(3-substituted-phenyl)-N′-[2-(2-trimethylsilylethynyl)phenyl] carbodiimides. All compounds were evaluated for their activity against chloroquine-sensitive as well as chloroquine-resistant Plasmodium falciparum strains, for their activity against Trypanosoma brucei and T. cruzi, and for their cytotoxicity on human MRC-5 cells. Mechanisms of action were investigated by testing heme complexation using ESI-MS, inhibition of β-hematin formation, DNA interactions (DNA-methyl green assay and linear dichroism), and inhibition of human topoisomerase II. Neocryptolepine derivatives with a higher antiplasmodial activity and a lower cytotoxicity than the original lead have been obtained. This selective antiplasmodial activity was associated with inhibition of β-hematin formation. 2-Bromoneocryptolepine was the most selective compound with an IC50 value against chloroquine-resistant P. falciparum of 4.0 μM in the absence of cytotoxicity (IC50 > 32 μM). Although cryptolepine, a known lead for antimalarials also originally isolated from Cryptolepis sanguinolenta, was more active (IC50 = 2.0 μM), 2-bromoneocryptolepine showed a low affinity for DNA and no inhibition of human topoisomerase II, in contrast to cryptolepine. Although some neocryptolepine derivatives showed a higher antiplasmodial activity than 2-bromocryptolepine, these compounds also showed a higher affinity for DNA and/or a more pronounced cytotoxicity. Therefore, 2-bromoneocryptolepine is considered as the most promising lead from the present work for new antimalarial agents. In addition, 2-bromo-, 2-nitro-, and 2-methoxy-9-cyanoneocryptolepine exhibited antitrypanosomal activity in the micromolar range in the absence of obvious cytotoxicity.
- Jonckers, Tim H. M.,Van Miert, Sabine,Cimanga, Kanyanga,Bailly, Christian,Colson, Pierre,De Pauw-Gillet, Marie-Claire,Van den Heuvel, Hilde,Claeys, Magda,Lemière, Filip,Esmans, Eddy L.,Rozenski, Jef,Quirijnen, Ludo,Maes, Louis,Dommisse, Roger,Lemière, Guy L. F.,Vlietinck, Arnold,Pieters, Luc
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p. 3497 - 3508
(2007/10/03)
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- A novel approach to the indoloquinoline alkaloids cryptotackieine and cryptosanguinolentine by application of cyclization of o-vinylsubstituted arylheterocumulenes
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1-Methyl-3-(o-azidophenyl)quinoline-2-one prepared by cyclization of the corresponding o-vinylsubstituted isocyanate under microwave irradiation is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2.
- Fresneda, Pilar M,Molina, Pedro,Delgado, Santiago
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p. 6197 - 6202
(2007/10/03)
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- A divergent approach to cryptotackieine and cryptosanguinolentine alkaloids
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A seven-step synthesis of the 1-methyl-3-(o-azidophenyl)quinolin-2-one, a common intermediate for the synthesis of the cryptotackieine and cryptosanguinolentine alkaloids, is described. This intermediate is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2.
- Fresneda, Pilar M.,Molina, Pedro,Delgado
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p. 7275 - 7278
(2007/10/03)
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- Iminophoshorane-mediated synthesis of the alkaloid cryptotackieine
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A new synthesis of the alkaloid cryptotackieine based on the stepwise formation of the pyridine and indole ring is described. The key step, formation of the appropriate 3-arylquinoline, involves a Staudinger/aza- Wittig/electrocyclic ring-closure process.
- Molina,Fresneda,Delgado
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p. 326 - 329
(2007/10/03)
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- A Convenient Synthesis of Two New Indoloquinoline Alkaloids
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A concise synthesis of two new indoloquinoline-based alkaloids (1 and 2), isolated from Cryptolepis sanguinolenta, is reported. The palladium-catalyzed cross-coupling reaction of 3-bromoquinoline derivatives with N-pivaloylamino phenylboronic acid gave th
- Timári, Géza,Soós, Tibor,Hajós, Gy?rgy
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p. 1067 - 1068
(2007/10/03)
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- Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: Novel cytotoxic, DNA topoisomerase II inhibitors
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In furtherance of our SAR study on the chemistry and antitumor activity of fused nitrogen heteroaromatic compounds, a series of linear, methyl- substituted derivatives of 5H- and 6H-indolo[2,3-b]quinolines were synthesized according to the modified Graebe-Ullmann reaction. To establish the relationship between the physicochemical and biological activities of indolo[2,3-b]quinolines, their lipophilic properties, cytotoxic and antimicrobial activity, and ability to induce topoisomerase II dependent pSP65 DNA cleavage in vitro were investigated. We found that the antimicrobial and cytotoxic activity of indolo[2,3-b]quinolines was strongly influenced by the position, and the number of methyl substituents and the presence of methyl group at pyridine nitrogen was essential for the cytotoxicity of these compounds. All indolo[2,3-b]quinolines belonging to the 5H series, i.e., bearing a methyl group on the pyridine nitrogen, showed significant activity against procaryotic and eucaryotic organisms. They inhibited the growth of Gram-positive bacteria and pathogenic fungi at MIC range 3 x 10-2 to 2.5 x 10-1 μmol/mL, displayed cytotoxicity against KB cells ID50 in the range 2 x 10-3 to 9 x 10-3 μmol/mL, and stimulated the formation of calf thymus topoisomerase II mediated DNA cleavage at concentration between 0.4 and 10 μM. None of the indolo[2,3-b]quinolines belonging to the 6H series, i.e., lacking a methyl group on the pyridine nitrogen, was active in analogous tests. Of the investigated compounds, the most active was 2,5,9,11-tetramethyl-5H-indolo[2,3-b]quinoline, a compound bearing the highest number of symmetrically distributed methyl groups. The interaction of indolo[2,3-b]quinolines with DNA was studied by measuring the increase of calf thymus DNA denaturating temperature (T(m)). The ΔT(m) values for the 5H series were found to be about 10 times as high as those for the 6H compounds. Indolo[2,3-b]quinolines with the highest number of methyl groups had the greatest contribution to the increase in the T(m) of calf thymus DNA. The values of ΔT(m) reached 19 °C and 1.6 °C for the most substituted compounds of both series.
- Peczynska-Czoch,Pognan,Kaczmarek,Boratynski
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p. 3503 - 3510
(2007/10/02)
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