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Alicyclic β-amino acids in Medicinal Chemistry

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Summary.

The structural element of alicyclic β-amino acids shows some remarkable biological effects: For some 5- and 6-membered β-amino acids a unique anti fungal activity has been observed, 7-membered β-amino acid derivatives have been investigated for neurological disorders. The application of 5-, 6- and 7-membered alicyclic β-amino acids in Medicinal Chemistry will be reported.

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References

  • VK Aggarwal S Roseblade R Alexander (2003) ArticleTitleThe use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the β-amino acid (−)-cispentacin and the first asymmetric synthesis of cis-(3R, 4R)-4-amino-pyrrolidine-3-carboxylic acid. Org Biomol Chem 1 684–691 Occurrence Handle10.1039/b212719a Occurrence Handle12929455

    Article  PubMed  Google Scholar 

  • Bolm C, Schiffers I, Dinter CL, Defrère L, Gerlach A, Raabe G (2001) Efficient asymmetric synthesis of unnatural β-amino acids. Synthesis: 1719–1730

  • J Booij L Reneman J Lavalaye RJJ Knof K de Bruin JD Speelman AGM Jannssen (2001) ArticleTitleDopamine transporter imaging as an in vivo marker of dopaminergic neurons. Drugs of the Future. 26 271–279 Occurrence Handle10.1358/dof.2001.026.03.858707

    Article  Google Scholar 

  • FI Carroll (2003) ArticleTitle2002 Medicinal chemistry award adress: monoamine transporters and opioid receptors. Targets for addiction therapy. J Med Chem 46 1775–1794 Occurrence Handle10.1021/jm030092d Occurrence Handle12723940

    Article  PubMed  Google Scholar 

  • FI Caroll Y Gao MA Rahman P Abraham K Parham AH Lewin JW Boja MJ Kuhar (1991) ArticleTitleSynthesis, ligand binding, QSAR and CoMFA study of 3β-(p-substituted phenyl)tropane-2β-carboxylic acid methyl esters. J Med Chem 34 2719–2725 Occurrence Handle10.1021/jm00113a008 Occurrence Handle1895292

    Article  PubMed  Google Scholar 

  • FI Caroll AH Lewin JW Boja MJ Kuhar (1992a) ArticleTitleCocaine receptor: biochemical characterisation and structure activity relationship of cocaine analogues at the dopamine transporter. J Med Chem 35 969–981 Occurrence Handle10.1021/jm00084a001

    Article  Google Scholar 

  • FI Carroll P Abraham AH Lewin KA Parham JW Boja MJ Kuhar (1992b) ArticleTitleIsopropyl and phenyl esters of 3.beta.-(4-substituted phenyl)tropan-2.beta.-carboxylic acids. Potent and selective compounds for the dopamine transporter. J Med Chem 35 2497–2500 Occurrence Handle10.1021/jm00091a019

    Article  Google Scholar 

  • Carroll FI, Abraham P, Kuzemko MA, Gray JL, Lewin AH, Boja JW, Kuhar MJ (1993) Synthesis and cocaine receptor affinities of 3-phenyl-2-(3′-methyl-1,2,4-oxadiazole-5-yl)tropane isomers. J Chem Soc Chem Commun: 44–46

  • FI Carroll SW Mascarella MA Kuzemko Y Gao P Abraham AH Lewin JW Boja MJ Kuhar (1994) ArticleTitleSynthesis, ligand binding, and QSAR (CoMFA and classical) study of 3β-(3′-substituted phenyl)-, 3β-(4′-substituted phenyl)-, and 3β-(3′,4′-disubstituted phenyl)-tropane-2β-carboxylic acid methyl esters. J Med Chem 37 2865–2837 Occurrence Handle10.1021/jm00044a007 Occurrence Handle8071935

    Article  PubMed  Google Scholar 

  • FI Caroll LL Howell MJ Kuhar (1999) ArticleTitlePharmacotherapies for treatment of cocaine abuse: preclinical aspects. J Med Chem 42 2721–2736 Occurrence Handle10.1021/jm9706729 Occurrence Handle10425082

    Article  PubMed  Google Scholar 

  • DC Cole (1994) ArticleTitleRecent stereoselective synthetic approaches to β-amino acids. Tetrahedron 50 9517–9582 Occurrence Handle10.1016/S0040-4020(01)85527-7

    Article  Google Scholar 

  • HML Davies E Saikali WB Young (1991) ArticleTitleSynthesis of rac-ferruginine and rac-anhydroecgonine methyl ester by a tandem cyclopropanation/Cope rearrangement. J Org Chem 56 5696–5700

    Google Scholar 

  • Davies SG, Osomu I, Walters Iain AS (1993) An expeditious asymmetric synthesis of (−)-(1R,2S)-cispentacin. Synlett: 461–463

  • HML Davies E Saikali NJS Huby VJ Gilliatt JJ Matasi T Sexton SR Childers (1994) ArticleTitleSynthesis of 2β-acyl-3β-aryl-8-azabicyclo[3.2.1] octanes and their binding affinities at dopamine and seretonin transport sites in rat striatum an frontal cortex. J Med Chem 37 1262–1268 Occurrence Handle10.1021/jm00035a005 Occurrence Handle8176704

    Article  PubMed  Google Scholar 

  • HM Deutsch DM Collard L Zhang KS Burnham AK Deshpande SG Holtzmann MM Schweri (1999) ArticleTitleSynthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-(aminomethyl)-3-phenylbicyclo[2.2.2]- and [2.2.1]alkane dopamine uptake inhibitors. J Med Chem 42 882–895 Occurrence Handle10.1021/jm980566m Occurrence Handle10072685

    Article  PubMed  Google Scholar 

  • DM Dixon MM McNeil ML Cohen BG Gellin JR La Montagne (1996) ArticleTitleFungal infections: a growing threat. Public Health Rep 111 IssueID3 226–235 Occurrence Handle8643813

    PubMed  Google Scholar 

  • MB Edmond SE Wallace DK McClish MA Pfaller RN Jones RP Wenzel (1999) ArticleTitleNosocomial bloodstream infections in United States hospitals: a three-year analysis. Clin Infect Dis 29 239–244 Occurrence Handle10476719

    PubMed  Google Scholar 

  • AE Fleckenstein TA Kopajtic JW Boja FI Caroll MJ Kuhar (1996) ArticleTitleHighly potent cocaine analogues cause long-lasting increase in locomotor activity. Eur J Pharmacol 311 109–114 Occurrence Handle10.1016/0014-2999(96)00423-2 Occurrence Handle8891589

    Article  PubMed  Google Scholar 

  • SP Findlay (1957) ArticleTitleConcerning 2-carbomethoxytropinone. J Org Chem 22 1385–1394 Occurrence Handle10.1021/jo01362a022

    Article  Google Scholar 

  • F Fülöp (2001) ArticleTitleThe chemistry of 2-aminocycloalkanecarboxylic acid. Chem Rev 101 2181–2204 Occurrence Handle11710244

    PubMed  Google Scholar 

  • S Hashimoto T Iwamoto E Tsujii M Ezaki A Fujie M Okuhara M Kohsaka H Imanaka K Kawabata (1990) ArticleTitleFR109615, a new antifungal antibiotic from Streptomyces setonii: taxonomy, fermentation, isolation, physico-chemical properties and biological activity. J Antibiot 43 1–7 Occurrence Handle2307620

    PubMed  Google Scholar 

  • M Hossain MA Ghannoum (2000) ArticleTitleNew investigational antifungal agents for treating invasive fungal infections. Expert Opin Investig Drugs 9 1797–1813 Occurrence Handle11060778

    PubMed  Google Scholar 

  • Juaristi E (ed) (1997) Enantioselective synthesis of β-amino acids. Wiley-VCH, New York Weinheim

  • E Juaristi H López-Ruiz (1999) ArticleTitleRecent advances in the enantioselective synthesis of β-amino acids. Current Medicinal Chemistry 6 983–1004 Occurrence Handle10519909

    PubMed  Google Scholar 

  • K Kawabata Y Inomoto K Sakana T Iwamoto S Hashimoto (1990) ArticleTitleSynthesis and structure determination of FR109615, a new antifungal antibiotic. J Antibiot 43 513–518 Occurrence Handle2193009

    PubMed  Google Scholar 

  • J King (2004) ArticleTitle100 Great investigational drugs. R&D Directions 10 30–33

    Google Scholar 

  • M Konishi M Nishio K Saitoh T Miyaki T Oki H Kawaguchi (1989) ArticleTitleCispentacin, a new antifungal antibiotic I. production, isolation, physico-chemical properties and structure. J Antibiot 42 1749–1755 Occurrence Handle2516082

    PubMed  Google Scholar 

  • T Konosu S Oida (1993) ArticleTitleSynthesis of racemic and optically active cispentacin (FR109615) using intramolecular nitrone-olefin cycloaddition. Chem Pharm Bull 41 1012–1018

    Google Scholar 

  • AP Kozikowski M Roberti KM Johnson JS Bergman RG Ball (1993) ArticleTitleSAR of cocaine: further exploration of structural variations at the C-2 center provides compounds of subnanomolar potency. Biorg Med Chem Lett 3 1327–1332 Occurrence Handle10.1016/S0960-894X(00)80341-8

    Article  Google Scholar 

  • MJ Kuhar MC Ritz J Boja (1991) ArticleTitleThe dopamine hypothesis of the reinforcing properties of cocaine. Trends Neurosci 14 299–302 Occurrence Handle10.1016/0166-2236(91)90141-G Occurrence Handle1719677

    Article  PubMed  Google Scholar 

  • Kunisch F, Babczinski P, Arlt D, Plempel M (1992) Ger. Offen. DE 4028046 A1. Chem Abstr 117: 20486

    Google Scholar 

  • BK Madras MA Fahey J Bergman DR Canfield RD Spealman (1989) ArticleTitleEffects of cocaine and related drugs in nonhuman primates. I. [3H]Cocaine binding sites in the caudate-putamen. J Pharmacol Exp Ther 251 131–141 Occurrence Handle2529364

    PubMed  Google Scholar 

  • PC Meltzer AY Liang BK Madras (1994) ArticleTitleThe discovery of an unusually and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites. J Med Chem 37 2001–2010 Occurrence Handle10.1021/jm00039a014 Occurrence Handle8027983

    Article  PubMed  Google Scholar 

  • Mittendorf J (1997) Eur. Pat. Appli. EP 805145 A1. Chem Abstr 127: 359100

    Google Scholar 

  • Mittendorf J, Kunnisch F, Plempel M (1993a) Ger. Offen. DE 4217776 A1. Chem Abstr 121: 83988

  • Mittendorf J, Kunisch F, Schoenfeld W (1993b) unpublished results

  • Mittendorf J, Kunisch F, Plempel M, Geschke U, Schoenfeld W (1993c) unpublished results

  • Mittendorf J, Arold H, Fey P, Matzke M, Militzer H-C, Mohrs K-H (1995) Ger. Offen. DE 4400749 A1. Chem Abstr 124: 9443

  • J Mittendorf F Kunisch M Matzke H-C Militzer A Schmidt W Schönfeld (2003a) ArticleTitleNovel antifungal β-amino acids: synthesis and activity against Candida albicans. Bioorg Med Chem Lett 13 433–436 Occurrence Handle10.1016/S0960-894X(02)00958-7

    Article  Google Scholar 

  • Mittendorf J, Benet-Buchholz J, Fey P, Mohrs KH (2003b) Efficient asymmetric synthesis of β-amino acid BAY 10-8888/PLD-118, a novel antifungal for the treatment of yeast infections. Synthesis: 136–140

  • GF Morgan DP Nowotnik (1999) ArticleTitleDevelopment of dopamine transporter imaging agents for the diagnosis of Parkinson’s disease. Drugs News Perspect 12 137–145 Occurrence Handle10.1358/dnp.1999.12.3.658764

    Article  Google Scholar 

  • E Nativ P Rona (1972) ArticleTitle2-Azabicyclo[3.2.0]heptane-3-one. Isr J Chem 10 55–58

    Google Scholar 

  • v. Nussbaum F, Spiteller P (2004) Highlights in bioorganic chemistry. Wiley-VCH, New York Weinheim, pp 63–89

  • H Ohki Y Inamoto K Kawabata T Kamimura K Sakane (1991) ArticleTitleSynthesis and antifungal activity of FR109615 analogs: J Antibiot 44 546–549 Occurrence Handle2061196

    PubMed  Google Scholar 

  • MA Pfaller (1995) ArticleTitleEpidemiology of candidiasis. J Hosp Infect 30 329–338 Occurrence Handle10.1016/0195-6701(95)90036-5 Occurrence Handle7560969

    Article  PubMed  Google Scholar 

  • MEA Reith BE Meisler H Sershen A Lajtha (1986) ArticleTitleStructural requirements for cocaine congeners to interact with dopamine and serotonin uptake sites in mouse brain and to induce stereotyped behavior. Biochem Pharmacol 35 1123–1129 Occurrence Handle10.1016/0006-2952(86)90148-6 Occurrence Handle3964292

    Article  PubMed  Google Scholar 

  • H Schoemaker C Pimoule S Arbilla B Scatton F Javoy-Agid SZ Langer (1985) ArticleTitleSodium dependant [3H]cocaine binding associated with dopamine uptake sites in the rat striatum and human putamen decrease after dopaminergic degeneration and in Parkinson’s disease. Naunyn-Schmiedberg’s Arch Pharmacol 329 227–235 Occurrence Handle10.1007/BF00501873

    Article  Google Scholar 

  • Schoenfeld W, Mittendorf J, Schmidt A, Geschke U (2001) Abstracts, 41st Interscience Conference on Antimicrobial Agents and Chemotherapie, Chicago, IL, Sept 22–25, 2001; American Society for Microbiology, Washington, DC; F-2144

  • F Theil S Ballschuh (1996) ArticleTitleChemoenzymatic synthesis of both enantiomers of cispentacin. Tetrahedron Asymmetry 7 3565–3572 Occurrence Handle10.1016/S0957-4166(96)00465-X

    Article  Google Scholar 

  • K Tomatsu T Oki M Hirano K Numamta H Kamei (1989) ArticleTitleCispentacin, a new antifungal antibiotic II. In vitro and in vivo antifungal activities. J Antibiot 42 1756–1762 Occurrence Handle2621158

    PubMed  Google Scholar 

  • J Walsh V Petraitis R Petraitiene AM Kelaher AA Sarafandi T Sein D Mickiene J Bacher AH Groll (2004) ArticleTitleEfficacy of PLD-118, a novel inhibitor of Candida isoleucyl-tRNA synthetase, against experimental oropharyngeal and esophageal candidiasis caused by fluconazole-resistant C. albicans. Antimicrob Agents Chemother 48 3959–3967 Occurrence Handle10.1128/AAC.48.6.2166-2172.2004 Occurrence Handle15388459

    Article  PubMed  Google Scholar 

  • X Zhang W Tang S Wu (2003) ArticleTitleEnantioselective hydrogenation of tetrasubstituted olefins of cyclic β-(acylamino)acrylates. J Am Chem Soc 125 9570–9571 Occurrence Handle10.1021/ja035777h Occurrence Handle12904006

    Article  PubMed  Google Scholar 

  • K Ziegelbauer P Babczinski W Schoenfeld (1998) ArticleTitleMolecular mode of action of the antifungal β-amino acid BAY 10-888. Antimicrob Agents Chemother 42 2197–2205 Occurrence Handle9736535

    PubMed  Google Scholar 

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Kuhl, A., Hahn, M., Dumić, M. et al. Alicyclic β-amino acids in Medicinal Chemistry. Amino Acids 29, 89–100 (2005). https://doi.org/10.1007/s00726-005-0212-y

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