DOCSLIB.ORG

Download Article (PDF)

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Download Article (PDF) Synthesis of New Furobenzoxazole and Furoflavone Derivatives Orchidee H. Hishmat, Khairia M. Khalil, Nabila M. A. El-Ebrashi, and Mohamed N. M. Khodeir National Research Centre, Dokki, Cairo, Egypt Z. Naturforsch. 33b, 1491-1495 (1978); received July 4, 1978 Furobenzoxazoles, Furoflavones The synthesis of visnaginone-oxime (2 a) and khellinone-oxime (2 b) is reported. Beck- mann rearrangement of 2 a and 2b using different cyclising agents was studied. Structure assignement for the produced benzoxazole derivatives and benzisoxazole derivatives was confirmed by chemical and spectral evidences. Utilization of visnaginone (la) and khelli- none (lb) for the synthesis of new furoflavone derivatives was also undertaken. It is well known that both nitrogen [1] and oxy- was obtained upon using hydrogen chloride gas in gen [2] heterocycles are eminent in the field of glacial acetic acid in the cyclization of visnaginone pharmaceutical chemistry. Compounds containing oxime (2 a). Similar treatment of the khellinone both types of heterocycles, particularly the furo- oxime (2 b) yielded the benzoxazole (3 b), however, benzoxazoles, and furobenzisoxazoles are of high as the sole reaction product. biological importance and find wide applications as 0CH3 OCH3 analgesic, antiinflammatory, muscle relaxant, bac- n—A,—N ^J^nhcoch3 tericide as well as fungicide [3]. During our in- vestigations in the benzofuran series [4], it appeared oux ncr now of interest to undertake the synthesis of some R new furobenzoxazole (3) and furobenzisoxazoles (5) 3a: R = H 4 derived from visnaginone (la) and khellinone (lb) 3b: R = 0CH respectively. This was achieved by condensing la 3 and lb with hydroxylamine, followed by cyclizing The structure of the oxazole (3 a) was confirmed the oximes 2 a and 2 b so formed, under the condi- by: (a) it is insoluble in dilute aqueous alkali and tions of Beckmann rearrangement. Thus, treatement gives no colour reaction with alcoholic ferric chloride of the oximes 2 a and 2 b with pyridine hydro- solution, (b) The IR spectrum of 3 a showed two chloride at 100 °C for 20 min, gave rise to 4-methoxy- bands at 1160 cm-1 and 1060 cm-1 due to the in- plane bending vibrations of the a- and ^-hydrogen N.OH atoms of the furan ring [5]. The bands in the 1625-1510 cm-1 region are associated with the C=C (aromatic) and C=N (oxazole) vibrations [6, 7]. The band at 1375 cm-1 is caused by the symmetrical R R deformation mode of the C-CH3 group [8]. The 1 2 absorption at 1330 cm-1 can be attributed to the a: R = R' = H, vibrations of the oxazole heterocycles [3, 6, 7]. b: R = OCH3; R' = H, The anilide (4) is soluble in sodium hydroxide c: R = H; R' = CH3. solution and gives a green colour with ferric chloride 2-methylfuro[3,2-f]benzoxazole (3 a) and 4,8-di- solution. The IR spectrum of 4 reveals beside the methoxy-2-methylfuro[3,2-f]benzoxazole (3b), re- normal bands for a- and ^-hydrogen atoms of the spectively. Compound 3 a was also obtained upon furan ring and the C=C stretching modes of the treatement of the oxime (2c), derived from visnagi- benzene ring, the amide I band at 1645 cm-1 and none methyl ether (lc) with pyridine hydrochloride. the amide II band at 1553 cm-1. An amide III band A mixture of the oxazole (3 a) and the anilide (4) occurs at 1280 cm-1. A broad band appears in the 3110-3205 cm-1 region probably arising from a chelated OH group. Requests for reprints should be sent to Prof. Dr. O. H. Cyclization of the oxime (2 a) with acetic an- Hishmat, National Research Centre, Dokki, Cairo, Egypt. hydride, gave rise to 4-methoxy-3-methylfuro- 1492 O. H. Hishmat et al. • Synthesis of New Furobenzoxazole and Furoflavone Derivatives [3,2-f]benzisoxazole (5a). This reaction recalls the and a singlet at 12.75 ppm (for the exchangeable OH observation that cyclization of khellinone oxime proton at C5). (2 b) with acetic anhydride furnishes the correspond- ing benzisoxazole (5 b) [9]. Under the same experi- OR 0 ,COCH=CHC6H5 mental conditions, on the other hand, cyclization of the oxime of visnaginone methyl ether (2 c) led only, C6H5 to the formation of the respective acetyl deriva- tive (6). 7a: R = CH3; R' = H, 8a:R = R' = H, N.O.COCH3 OCH OCH3 || 7b: R = CH3; R' = OCH3, 8b: R = H; R' = OCH3, C-CH3 7c: R = R' = H, 8c: R = CH3; R' = OCH3. 7d: R = H; R' = OCH3. OCH3 In a similar manner, treatment of 7 b with pyridine hydrochloride yielded a mixture of 4,6-dihydroxy- &A:R=H • 5-cinnamoyl-7-methoxybenzofuran (7d) and 2- 5 b: R • OCH3 phenyl-5-hydroxy-9-methoxy-4H-furo[3,2-g][l]- benzopyran-4-one (8b). Methylation of 8b with Structure of the benzisoxazole (5 b), is now further dimethyl sulphate in acetone in presence of potas- confirmed by the study of its NMR spectrum. Its sium iodide and anhydrous potassium carbonate H NMR spectrum (CDCI3) showed the following yielded the already known 2-phenyl-5,9-dimethoxy- assignments: two doublets at 7.65 and 7.05 ppm 4H-furo[3,2-g][l]benzopyran-4-one (8c) (m.p. and 1/5,6 =1.4 c/s (for the furan ring protons), the mixed m.p. with an authentic specimen prepared by singlets at 4.30 and at 4.20 ppm (two OCH3 at C-4 Stener's method [12] gave no depression). and C-8) and a singlet at 2.65 ppm (CH3 group at It is of interest to note that whereas Brule and C-3). Mentzer [13] have obtained a partially demethylated The McConnell equation gives a ratio of distance flavanone derivative by cyclization of the chalcone = 0.95 (angle factor neglected), if the methoxyl using pyridine hydrochloride at 155 °C or completely groups are freely rotating, this is in good agreement demethylated flavanone by heating at 180 °C, in with the isoxazolic structure. (For an oxazolic the present investigation the flavone 8 was obtained structure the shift ratio would lie around 3-4 with directly as confirmed by the presence of a singlet at the same condition for the methoxyl groups to 6.60 ppm characteristic for the vinyl proton at C3 rotate freely). The 13C NMR spectrum of 5b, proved in the NMR spectrum of 8 a. the isoxazole structure exclusively. (154 ppm for When either visnaginone (la) or khellinone (lb) the isoxazolic C whilst it would be 164 ppm for an was treated with pyridine hydrochloride under the oxazolic one) [10]. same experimental conditions, demethylation of Utilization of visnaginone (la) and khellinone (lb) the methoxyl group at C4 took place leading to the for the synthesis of new furoflavone derivatives was formation of 4,6-dihydroxy- (9 a) or 4,6-dihydroxy- also undertaken. Compounds la and lb condense 7-methoxy-5-benzofuranyl methyl ketone (9b) [11]. with benzaldehyde in presence of alkali to give the When the latter compound was treated with benz- respective chalcones (7a) and (7b). aldehyde in the presence of alcoholic sodium When 7 a was treated with pyridine hydrochloride hydroxide solution 4,6-dihydroxy-5-cinnamoyl-7- at 100-120 °C for 1 h a mixture of about 30% of methoxybenzofuran (7d) was produced. Cyclization 4,6-dihydroxy-5-cinnamoylbenzofuran (7 c) and 70% of 7d was effected using pyridine hydrochloride to of 2-phenyl-5-hydroxy-4H-furo[3,2-g][l]benzopyran- form 8 b in good yield. 4-one (8 a) was obtained. The H NMR spectrum (CDCI3) of compound 8 a showed the following assignements: Two doublets at 7.40 and 6.80 ppm COCH, (J6>7= 1.8 c/s) (for the furan ring protons), a sharp singlet at 6.60 ppm (for the vinyl proton at C3), a multiplet in the region 7.80-7.30 ppm (due to the 9a: R = H five phenyl ring protons at C2 and the proton at C9) 9b: R = OCH3 1493 O. H. Hishmat et al. • Synthesis of New Furobenzoxazole and Furoflavone Derivatives Experimental The alkaline filterate was treated with concen- Melting points are not corrected. The infrared trated hydrochloric acid till pH 5, extracted with spectra were carried out in potassium bromide on ether, washed with water, dried over anhydrous a Carl Zeiss Infrared spectrophotometer, model sodium sulphate then evaporated to give a solid. "UR 10". The NMR spectra were carried out in Crystallize from ethanol as pale yellowish crystals CDCI3 on a Hitachi Perkin-Elmer and an XL 100. of 4, m.p. 152 °C; yield is ea. 12%. It gives a green colour with aqueous ferric chloride solution. 4-Methoxy-6-hydroxy- 5-benzofuranylmethyl ketone CuHuNO* oxime (2 a) Calcd C 59.73 H 4.98 N 6.34, A mixture of visnaginone (la) (0.5 g), hydroxyl- Found C 59.67 H 5.14 N 5.99. amine hydrochloride (0.5 g) in ethanol (5 ml) and pyridine (0.5 ml) is refluxed for 1 h. After evapo- 4,8-Dimethoxy-2-methylfuro[3,2-f Jbenzoxazole (3b) rating the volatile materials, water is added (5 ml) Treatment of 2 b (2 g) with pyridine hydrochloride while stirring. The solid that separated after cooling as in the case of 3 a yielded colourless needles from is filtered, washed with water and dried. Crystallize petroleum ether (b.p. 60-80 °C), m.p. 135 °C; yield from benzene as white needles m.p. 142 °C (78%). is ea. 47%. It gives no colour with ferric chloride solution.
Load more

Recommended publications
  • Retention Indices for Frequently Reported Compounds of Plant Essential Oils
    Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5.
    [Show full text]
  • Electrooxidation Enables Highly Regioselective Dearomative Annulation of Indole and Benzofuran Derivatives
    ARTICLE https://doi.org/10.1038/s41467-019-13829-4 OPEN Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives Kun Liu1, Wenxu Song1, Yuqi Deng1, Huiyue Yang1, Chunlan Song1, Takfaoui Abdelilah1, Shengchun Wang 1, Hengjiang Cong 1, Shan Tang1 & Aiwen Lei1* 1234567890():,; The dearomatization of arenes represents a powerful synthetic methodology to provide three-dimensional chemicals of high added value. Here we report a general and practical protocol for regioselective dearomative annulation of indole and benzofuran derivatives in an electrochemical way. Under undivided electrolytic conditions, a series of highly functio- nalized five to eight-membered heterocycle-2,3-fused indolines and dihydrobenzofurans, which are typically unattainable under thermal conditions, can be successfully accessed in high yield with excellent regio- and stereo-selectivity. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in large-scale synthesis under oxidant-free conditions. In addition, cyclic voltammetry, electron paramagnetic resonance (EPR) and kinetic studies indicate that the dehydrogenative dearomatization annulations arise from the anodic oxidation of indole into indole radical cation, and this process is the rate- determining step. 1 College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China. *email: aiwenlei@whu. edu.cn NATURE COMMUNICATIONS | (2020) 11:3 | https://doi.org/10.1038/s41467-019-13829-4 | www.nature.com/naturecommunications 1 ARTICLE NATURE COMMUNICATIONS | https://doi.org/10.1038/s41467-019-13829-4 reaking the aromatic systems of electron-rich arenes or fused indolines (Fig. 1a)39–44. Therefore, it is highly appealing to heteroarenes provides three-dimensional chemicals of high develop efficient approaches to allow for their preparation.
    [Show full text]
  • Benzofuran Synthesis Through Iodocyclization Reactions: Recent Advances
    MOJ Bioorganic & Organic Chemistry Mini Review Open Access Benzofuran synthesis through iodocyclization reactions: recent advances Abstract Volume 1 Issue 7 - 2017 Recent advancements (2014-17) in the benzofuran synthesis through iodocyclization Saurabh Mehta have been summarized. The successful use of various iodinating agents, bases, additives Department of Applied Chemistry, Delhi Technological etc. make iodocyclization a versatile and efficient methodology. The methodology has University, India been applied for the synthesis of more complex benzofuran derivatives, and may open interesting avenues in the area of heterocyclic chemistry (Figure 1). Correspondence: Saurabh Mehta, Department of Applied O-LG Chemistry, Delhi Technological University, Bawana Road, Delhi, + O R1 I 1 2 110042 India, Tel +9188 0066 5868, R R Email [email protected], [email protected] R2 I Received: December 17, 2017 | Published: December 29, 2017 LG = H, Me or other Protecting group 1 R = H, Me, OMe, I, CO2Me, etc. R2 = H, aryl, alkyl, alkenyl, etc. Figure 1 Keywords: annulations, alkyne, benzofuran, iodocyclization, heterocycle Introduction derivatives were obtained in high yields (84%−100%) under mild conditions. The authors demonstrated that the choice of bis(2,4,6- Benzo[b]furan is a privileged heterocyclic scaffold. Several collidine)iodonium hexafluorophosphate [I(coll)2PF6] as the compounds containing this scaffold have interesting biological iodinating agent was necessary for the success of the reaction. Also, 1 activities, such as anti-cancer, anti-viral, anti-inflammatory, etc. Few the ethoxyethyl ether group acted as a protecting group as well as a 2 derivatives are even used as commercial drugs, such as Amiodarone, good leaving group.
    [Show full text]
  • Last Decade of Unconventional Methodologies for the Synthesis Of
    Review molecules Last Decade of Unconventional Methodologies for theReview Synthesis of Substituted Benzofurans Last Decade of Unconventional Methodologies for the Lucia Chiummiento *, Rosarita D’Orsi, Maria Funicello and Paolo Lupattelli Synthesis of Substituted Benzofurans Department of Science, Via dell’Ateneo Lucano, 10, 85100 Potenza, Italy; [email protected] (R.D.); [email protected] (M.F.); [email protected] (P.L.) Lucia Chiummiento * , Rosarita D’Orsi, Maria Funicello and Paolo Lupattelli * Correspondence: [email protected] Department of Science, Via dell’Ateneo Lucano, 10, 85100 Potenza, Italy; [email protected] (R.D.); Academic Editor: Gianfranco Favi [email protected] (M.F.); [email protected] (P.L.) Received:* Correspondence: 22 April 2020; [email protected] Accepted: 13 May 2020; Published: 16 May 2020 Abstract:Academic This Editor: review Gianfranco describes Favi the progress of the last decade on the synthesis of substituted Received: 22 April 2020; Accepted: 13 May 2020; Published: 16 May 2020 benzofurans, which are useful scaffolds for the synthesis of numerous natural products and pharmaceuticals.Abstract: This In review particular, describes new the intramolecular progress of the and last decadeintermolecular on the synthesis C–C and/or of substituted C–O bond- formingbenzofurans, processes, which with aretransition-metal useful scaffolds catalysi for thes or synthesis metal-free of numerous are summarized. natural products(1) Introduction. and (2) Ringpharmaceuticals. generation via In particular, intramolecular new intramolecular cyclization. and (2.1) intermolecular C7a–O bond C–C formation: and/or C–O (route bond-forming a). (2.2) O– C2 bondprocesses, formation: with transition-metal (route b).
    [Show full text]
  • An Update on Natural Occurrence and Biological Activity of Benzofurans
    Acta Scientific MEDICAL SCIENCES (ISSN: 2582-0931) Volume 4 Issue 10 October 2020 Review Article An Update on Natural Occurrence and Biological Activity of Benzofurans Kavita Khatana* and Anjali Gupta Received: June 28, 2020 Department of Chemistry, School of Basic and Applied Sciences, Galgotias Published: September 21, 2020 University, Greater Noida, UP, India © All rights are reserved by Kavita Khatana. *Corresponding Author: Kavita Khatana, Department of Chemistry, School of Basic and Applied Sciences, Galgotias University, Greater Noida, UP, India. Graphical Abstract Figure a Abstract Benzofuran and its derivatives are the major group amongst the natural collection of biologically active heterocyclic compounds. Their wide range of pharmacological activities and imaginable applications in medicinal and pharmaceutical chemistry have at- tracted various research scholars, medicinal chemists and pharmacologists. This review emphasizes the progress and development . ofKeywords: benzofuran Benzofuran; derivatives Antioxidant; in various biological Antiviral; activities Antimicrobial; with an Anticancer update of current research findings during a decade Introduction physiological and industrial world. In reference to pharmaceutical Heterocyclic ring systems have emerged as powerful scaf- industry, over 60% of the top retailing drugs contain at least one folds for many biological evaluations. Heterocyclic compounds heterocyclic motif as a part of overall topography of the compound. Benzofurans and its derivatives are important class of heterocyclic have significant role in medicinal and pharmacological chemistry, Citation: Kavita Khatana and Anjali Gupta. “An Update on Natural Occurrence and Biological Activity of Benzofurans”. Acta Scientific Medical Sciences 4.10 (2020): 114-123. An Update on Natural Occurrence and Biological Activity of Benzofurans 115 compounds, which are known to possess various biological proper- 3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzo furan-5-yl) ties.
    [Show full text]
  • Synthesis of Benzo-Fused Heterocycles Using Isomerization and Ring-Closing Metathesis Reactions
    I Synthesis of benzo-fused heterocycles using isomerization and ring-closing metathesis reactions Lee Gavin Madeley Supervised by Prof. W.A.L. van Otterlo A dissertation submitted in the School of Chemistry to the Faculty of Science, University of the Witwatersrand, in fulfilment of the requirements for the Degree of Master of Science March 2010 II Declaration I declare that the work presented in this dissertation is my own, unaided work and was carried out under the supervision of Prof. W.A.L. van Otterlo. It is being submitted for the Degree of Master of Science in the University of the Witwatersrand, Johannesburg. It has not been submitted before for any degree or examination in any other University. __________________________ Lee Gavin Madeley March 2010 III Abstract The first part of the dissertation involves the use of ruthenium mediated isomerization (RMI) followed by ring-closing metathesis (RCM) on a selection of phenols and naphthol-1-ol precursors – that had been subjected to allylation; followed by a heat initiated Claisen rearrangement; followed by re-allylation – to form a selection of benzofurans. This procedure, to the best of our knowledge, represents a novel method for the synthesis of benzofurans, with very good average yields of around 90% overall for the RMI/RCM and allylation steps. The lowest yield of the five synthetic steps, were for the Claisen rearrangements with a range of yields between 50% and 86%, indicating the potential to optimise the yields of these reactions, which were carried out using both conventional and microwave heating. The following five-membered oxygen-containing heterocycles were thus obtained: 4,7-dimethoxybenzofuran, 5-bromobenzofuran, 5-tert-butyl-benzofuran, 7- phenyl-1-benzofuran and naphtho[1,2-b]furan.
    [Show full text]
  • Aromaticity of Anthranil and Its Isomers, 1,2-Benzisoxazole and Benzoxazole Carmen Domene,A Leonardus W
    Tetrahedron Letters Tetrahedron Letters 46 (2005) 4077–4080 Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole Carmen Domene,a Leonardus W. Jenneskensb,* and Patrick W. Fowlerc aPhysical and Theoretical Chemistry Laboratory, Oxford University, South Parks Road, Oxford OX1 3QZ, UK bDebye Institute, Organic Chemistry and Catalysis, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands cDepartment of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK Received 14 February 2005; revised 28 March 2005; accepted 5 April 2005 Available online 19 April 2005 Abstract—Direct computation of the p-current density, that is, the Ôring currentÕ, of anthranil (1) and its isomers 1,2-benzisoxazole (2) and benzoxazole (3) reveals different patterns of current flow: isomers 2 and 3 sustain strong benzene-like currents in the six- membered and bifurcated flow in the five-membered ring, whereas, in keeping with its lower thermodynamic stability, 1 has only a perimeter circulation without separate monocycle currents. Although the ring current criterion does not offer a sharp distinction between 2 and 3, their difference in thermodynamic stability is identical to that between isoxazole (4) and oxazole (5) suggesting an aromaticity order 1 < 2 3. Ó 2005 Elsevier Ltd. All rights reserved. The extent to which energetic, reactivity and magnetic property underlying NICS: the current density induced criteria of aromaticity are descriptions of a single, unify- by a perpendicular magnetic field, that is, the Ôring ing property of molecules remains a matter of debate.1 currentÕ, which gives an insight into the essential differ- Anthranil (1) and its isomers 1,2-benzisoxazole (2) and ence between anthranil (1) on the one hand and its benzoxazole (3) offer a series of bicyclic molecules with two isomers 2 and 3 on the other.
    [Show full text]
  • Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System
    molecules Article Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System Ernestine Nicaise Djuidje 1, Elisa Durini 1, Sabrina Sciabica 2, Elena Serra 3, Jan Balzarini 4, Sandra Liekens 4, Stefano Manfredini 1 , Silvia Vertuani 1 and Anna Baldisserotto 1,* 1 Department of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, 44121 Ferrara, Italy; [email protected] (E.N.D.); [email protected] (E.D.); [email protected] (S.M.); [email protected] (S.V.) 2 Department of Chemical and Pharmaceutical Sciences, University of Ferrara, 44121 Ferrara, Italy; [email protected] 3 Aptuit, An Evotec Company, 37135 Verona, Italy; [email protected] 4 Department of Microbiology and Immunology, KU Leuven, University of Leuven, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, B-3000 Leuven, Belgium; [email protected] (J.B.); [email protected] (S.L.) * Correspondence: [email protected]; Tel.: +39-0532-455258 Academic Editor: György Szöllösi Received: 31 August 2020; Accepted: 17 September 2020; Published: 21 September 2020 Abstract: In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position of the benzimidazole ring (-H, -COOH or –SO3H) and different heterocycle at position 2 (thiophene, furan or pyrrole). All the derivatives were synthesized and tested to determine their photoprotective profile against UV rays, in vitro antioxidant capacity against different radicals (DPPH and FRAP test), antifungal inhibitory activity (dermatophytes and Candida albicans), antiviral and antiproliferative activity.
    [Show full text]
  • Synthesis of New Benzofuran-2-Carboxylic Acid Derivatives
    Hindawi Publishing Corporation Journal of Chemistry Volume 2013, Article ID 183717, 7 pages http://dx.doi.org/10.1155/2013/183717 Research Article Synthesis of New Benzofuran-2-Carboxylic Acid Derivatives M. Kowalewska, H. Kwiecień, M. Śmist, and A. Wrześniewska Institute of Organic Technology, West Pomeranian University of Technology, 42 Aleja Piastów, 71-065 Szczecin, Poland Correspondence should be addressed to H. Kwiecień; [email protected] Received 20 June 2012; Revised 4 September 2012; Accepted 14 September 2012 Academic Editor: Aleš Imramovsky Copyright © 2013 M. Kowalewska et al. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Novel ethyl ester and methylamide of 5-[bis(2-chloroethyl)amino]-7-methoxybenzofuran-2-carboxylic acid as well as (2-hydroxy- 1,1-dimethylethyl)amides of 5-bromo- and 5,7-dichlorobenzofuran-2-carboxylic acid were synthesized and characterized. 1. Introduction cyclocondensation of 2-hydroxy-5-nitrobenzaldehyde with bromomalonic acid [18] as well as palladium catalysed Derivatives of benzofuran-2-carboxylic acid are known for carbonylative cyclization of o-alkynylphenols [19–21]. exhibiting various pharmacological activities. Such Most of these methods are restricted by the requirement compounds were found to be selective adenosine A A of relatively long reaction time to obtain the expected product receptor antagonists [1], anti-in�ammatory agents [2], and in low to moderate yields. local anaesthetics [3]. Variously substituted 2-benzofuran-2 We present herein a short synthetic route to obtain carboxylic acid derivatives show selective cytotoxicity against halogen-substituted benzofuran-2-carboxylic acid deriva- human cancer cell line [4].
    [Show full text]
  • Review of Pharmacokinetics and Pharmacogenetics in Atypical Long-Acting Injectable Antipsychotics
    pharmaceutics Review Review of Pharmacokinetics and Pharmacogenetics in Atypical Long-Acting Injectable Antipsychotics Francisco José Toja-Camba 1,2,† , Nerea Gesto-Antelo 3,†, Olalla Maroñas 3,†, Eduardo Echarri Arrieta 4, Irene Zarra-Ferro 2,4, Miguel González-Barcia 2,4 , Enrique Bandín-Vilar 2,4 , Victor Mangas Sanjuan 2,5,6 , Fernando Facal 7,8 , Manuel Arrojo Romero 7, Angel Carracedo 3,9,10,* , Cristina Mondelo-García 2,4,* and Anxo Fernández-Ferreiro 2,4,* 1 Pharmacy Department, University Clinical Hospital of Ourense (SERGAS), Ramón Puga 52, 32005 Ourense, Spain; [email protected] 2 Clinical Pharmacology Group, Institute of Health Research (IDIS), Travesía da Choupana s/n, 15706 Santiago de Compostela, Spain; [email protected] (I.Z.-F.); [email protected] (M.G.-B.); [email protected] (E.B.-V.); [email protected] (V.M.S.) 3 Genomic Medicine Group, CIMUS, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain; [email protected] (N.G.-A.); [email protected] (O.M.) 4 Pharmacy Department, University Clinical Hospital of Santiago de Compostela (SERGAS), Citation: Toja-Camba, F.J.; 15706 Santiago de Compostela, Spain; [email protected] Gesto-Antelo, N.; Maroñas, O.; 5 Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Echarri Arrieta, E.; Zarra-Ferro, I.; 46100 Valencia, Spain González-Barcia, M.; Bandín-Vilar, E.; 6 Interuniversity Research Institute for Molecular Recognition and Technological Development,
    [Show full text]
  • The Synthesis of Tryptophan Derivatives, 2
    Graduate Theses, Dissertations, and Problem Reports 2009 The synthesis of tryptophan derivatives, 2- and/or 3-substituted indoles, progress toward dilemmaones A-C, and synthetic studies towards fistulosin via palladium-catalyzed reductive N- heteroannulation Christopher Andrew Dacko West Virginia University Follow this and additional works at: https://researchrepository.wvu.edu/etd Recommended Citation Dacko, Christopher Andrew, "The synthesis of tryptophan derivatives, 2- and/or 3-substituted indoles, progress toward dilemmaones A-C, and synthetic studies towards fistulosin via palladium-catalyzed reductive N-heteroannulation" (2009). Graduate Theses, Dissertations, and Problem Reports. 4454. https://researchrepository.wvu.edu/etd/4454 This Dissertation is protected by copyright and/or related rights. It has been brought to you by the The Research Repository @ WVU with permission from the rights-holder(s). You are free to use this Dissertation in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you must obtain permission from the rights-holder(s) directly, unless additional rights are indicated by a Creative Commons license in the record and/ or on the work itself. This Dissertation has been accepted for inclusion in WVU Graduate Theses, Dissertations, and Problem Reports collection by an authorized administrator of The Research Repository @ WVU. For more information, please contact [email protected]. The Synthesis of Tryptophan Derivatives, 2- and/or 3- Substituted Indoles, Progress Toward Dilemmaones A-C, and Synthetic Studies Towards Fistulosin via Palladium-Catalyzed Reductive N-Heteroannulation Christopher Andrew Dacko Dissertation submitted to the Eberly College of Arts and Sciences at West Virginia University in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry Björn C.
    [Show full text]
  • Coal Tar Creosote
    This report contains the collective views of an international group of experts and does not necessarily represent the decisions or the stated policy of the United Nations Environment Programme, the International Labour Organization, or the World Health Organization. Concise International Chemical Assessment Document 62 COAL TAR CREOSOTE Please note that the layout and pagination of this pdf file are not identical to the document being printed First draft prepared by Drs Christine Melber, Janet Kielhorn, and Inge Mangelsdorf, Fraunhofer Institute of Toxicology and Experimental Medicine, Hanover, Germany Published under the joint sponsorship of the United Nations Environment Programme, the International Labour Organization, and the World Health Organization, and produced within the framework of the Inter-Organization Programme for the Sound Management of Chemicals. World Health Organization Geneva, 2004 The International Programme on Chemical Safety (IPCS), established in 1980, is a joint venture of the United Nations Environment Programme (UNEP), the International Labour Organization (ILO), and the World Health Organization (WHO). The overall objectives of the IPCS are to establish the scientific basis for assessment of the risk to human health and the environment from exposure to chemicals, through international peer review processes, as a prerequisite for the promotion of chemical safety, and to provide technical assistance in strengthening national capacities for the sound management of chemicals. The Inter-Organization Programme for the Sound Management of Chemicals (IOMC) was established in 1995 by UNEP, ILO, the Food and Agriculture Organization of the United Nations, WHO, the United Nations Industrial Development Organization, the United Nations Institute for Training and Research, and the Organisation for Economic Co-operation and Development (Participating Organizations), following recommendations made by the 1992 UN Conference on Environment and Development to strengthen cooperation and increase coordination in the field of chemical safety.
    [Show full text]