Một phương pháp tổng hợp mới cho các dẫn xuất $$\upalpha $$ -axit amino bất tự nhiên dựa trên chromone

Nian-Guang Li, Zhi-Hao Shi, Yu-Ping Tang, Hong-Yue Ma, Jian-Ping Yang, Bao-Quan Li, Zhen-Jiang Wang, Shu-Lin Song and Jin-Ao Duan 2010 Synthetic strategies in the construction of chromones J. Heterocycl. Chem. 47 785 Leaby J J J, Golding B T, Griffin R J, Hardcastle I R, Richardson C, Rigoreau L and Smith G C M 2004 Identification of a highly potent and selective DNA-dependent protein kinase (DNA-PK) inhibitor (NU7441) by screening of chromenone libraries Biorg. Med. Chem. Lett. 14 6083 Griffin R J, Fontana G, Golding B T, Guird S, Hardcastle I R, Leahy J J J, Martin N, Richardson C, Rigoreau L, Stockley M and Smith G C M 2005 Selective Benzopyranone and Pyrimido[2,1-\(a\)]isoquinolin-4-one Inhibitors of DNA-Dependent Protein Kinase: Synthesis, Structure-Activity Studies and Radio-sensitization of a Human Tumor Cell Line in Vitro J. Med. Chem. 48 569 Kim H P, Son K H, Chang H W and Kang S S 2004 Anti-inflammatory Plant Flavonoids and Cellular Action Mechanisms J. Pharmacol. Sci. 96 229 Bhatt A S, Whetstone J L and Btueggemeier R W 1999 Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries Tetrahedron Lett. 40 2469 (a) Marie-Laure L, Mahesh U, Grace Y.J C and Shao Q Y 2004 Developing site-Specific immobilization strategies of peptides in a microarray Bioorg. Med. Chem. 12 2079; (b) Krisnamachari V, Levin L H, Zhou C and Pare P W 2004 In Vitro Flavon-3-ol Oxidation Mediated by a B Ring Hydroxylation Pattern Chem. Res. Toxicol. 17 795 Marder M, Viola H, bacigaluppo J A, Colombo M I, Wasowski C, Wolfman C, Medina V, Ruveda V and Paladini A C 1998 Detection of benzodiazepine receptor ligands in small libraries of flavone derivatives synthesized by solution phase combinatorial chemistry Biochem. Biophys. Res. Commun. 249 481 Hoult J R S, Moroney M A and Paya M 1994 Actions of flavonoids and coumarins on lipoxygenase and cyclooxygenase Methods. Enzymol. 234 443 Parmar V S, Bracke M E, Philippe J, Wengel J, Jain S C, Olsen C E, Bisht K S, Sharma N K, Courtens A, Sharma S K, Vennekens K, Van Marck V, Singh S K, Kumar N, Kumar A, Malhothra S, Kumar R, Rajwanshi V K, Jain R and Mareel M M 1997 Anti-invasive activity of alkaloids and polyphenolics in vitro Bioorg. Med. Chem. 5 1609 Galietta L J V, Springsteel M F, Eda M, Neidzinsk E J, By K, Haddadin M J, Nantz M H and Verkman A S 2001 Novel CFTR Chloride Channel Activators Identified by Screening of Combinatorial Libraries Based on Flavone and Benzoquinolizinium Lead Compounds J. Biol. Chem. 276 19723 Horton D A, Bourne G T and Smythe M L 2003 The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures Chem. Rev. 103 893 Protti S, Mezzetti A, Lapouge C and Cornard J P 2008 Photochemistry of metal complexes of 3-hydroxyflavone: towards a better understanding of the influence of solar light on the metal–soil organic matter interactions Photochem. Photobiol. Sci. 7 109 Kotha S 2003 The Building Block Approach to Unusual \(\upalpha \)-Amino Acid Derivatives and Peptides Acc. Chem. Res. 36 342 Dougherty D A 2000 Unnatural amino acids as probes of protein structure and function Curr. Opin. Chem. Biol. 4 645 Rossi E, Pirovano V, Negrato M, Abbiati G and Dell’Acqua M 2015 Synthesis of constrained analogues of tryptophan Beilstein J. Org. Chem. 11 1997 Craik D J, Fairlie D P, Liras S and Price D 2013 The future of peptide-based drugs Chem. Biol. Drug Des. 81 136 Góngora-Benítez M, Tulla-Puche J and Albericio F 2014 Multifaceted Roles of Disulfide Bonds. Peptides as Therapeutics Chem. Rev. 114 901 Vagner J, Qu H and Hruby V J 2008 Peptidomimetics, a synthetic tool of drug discovery Curr. Opin. Chem. Biol. 12 292 Liskamp R M J, Rijkers D T, Kruijtzer J A and Kemmink J 2011 Peptides and proteins as a continuing exciting source of inspiration for peptidomimetics Chem. Bio. Chem. 12 1626 Hanessian S and Auzzas L 2008 The practice of ring constraint in peptidomimetics using bicyclic and polycyclic amino acids Acc. Chem. Res. 41 1241 Stevenazzi A, Marchini M, Sandrone G, Vergani B and Lattanzio M 2014 Amino acidic scaffolds bearing unnatural side chains: an old idea generates new and versatile tools for the life sciences Biorg. Med. Chem. Lett. 24 5349 O’Donnell M J 2001 The preparation of optically active \(\upalpha \)-amino acids from the benzophenone imines of glycine derivatives Aldrichimica Acta 34 3 Hashimoto T and Maruoka K 2007 Recent development and application of chiral phase-transfer catalysts Chem. Rev. 107 5656 Kotha S, Goyal D and Chavan A S 2013 Diversity-Oriented Approaches to Unusual \(\upalpha \)-Amino Acids and Peptides: Step Economy, Atom Economy, Redox Economy, and Beyond J. Org. Chem. 78 12288 Ball J B, Hughes R A, Alewood P F and Andrews P R 1993 \(\upbeta \)-turn topography Tetrahedron 49 3467 Lesma G, Colombo A, Sacchetti A and Silvani V 2008 A new spirocyclic proline-based lactam as efficient type \(\text{ II }^{\prime }\,\upbeta \)-turn inducing peptidomimetic Tetrahedron Lett. 49 7423 Mercelino A M C and Gierasch L M 2008 Roles of beta-turns in protein folding: from peptide models to protein engineering Biopolymers 89 380 Wallen E A A, Dahlen K, Grotli M and Luthman K 2007 Synthesis of 3-Aminomethyl-2-aryl-8-bromo-6-chlorochromones Org. Lett. 9 389 Friden-Saxin M, Seifert T, Malo M, Anderson K, Pemberton N, Dyrager C, Friberg A, Dahlen A, Wallen E A A, Grotli M and Luthman K 2016 Chroman-4-one and chromone based somatostatin \(\upbeta \)-turn mimetics Eur. J. Med. Chem. 114 59 Friden-Saxin M, Seifert T, Hansen L K, Grotli M, Erdelyi M and Luthman K 2012 Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines Tetrahedron 68 7035 Teimouri M B, Moghaddam P A and Golbaghi G 2011 Pseudo-Five-Component Reaction between 3-Formylchromones, Meldrum’s Acid, Isocyanides and Primary Arylamines: Diversity-Oriented Synthesis of Novel Chromone-Containing Peptidomimetics ACS Comb. Sci. 13 659 Tietze L F, Bell H P and Chandrasekhar S 2003 Natural product hybrids as new leads for drug discovery Angew Chem. Int. Ed. Eng. 42 3996 Mehta G and Singh V 2002 Hybrid systems through natural product leads: An approach towards new molecular entities Chem. Soc. Rev. 31 324 Decker M 2011 Hybrid molecules incorporating natural products: applications in cancer therapy, neurodegenerative disorders and beyond Curr. Med. Chem. 18 1464 Jones W D 1981 Aminolysis and hydrolysis of chromonyl oxazolones and some condensation reactions of 2-methylchromone leading to novel chromones J. Chem. Soc. Perkin Trans. 1 344 (a) Ravi Kumar P, Behera M, Raghavulu K, Jaya Shree A and Yennam S 2012 Synthesis of novel isoxazole-benzoquinone hybrids via 1,3-dipolar cycloaddition reaction as key step Tetrahedron Lett. 53 4108; (b) Ravi Kumar P, Behera M, Sambaiah M, Venu K, Nagaraju P, Jaya Shree A and Yennam S 2014 Design and Synthesis of Novel Isoxazole Tethered Quinone-Amino Acid Hybrids Journal of Amino Acids. Article ID 2014 721291; (c) Balakrishna C, Nagaraju P, Yennam S, Uma Devi P and Behera M 2015 Synthesis of new kojic acid based unnatural \(\upalpha \)-amino acid derivatives Bioorg. Med. Chem. Lett. 25 4753 China Raju B, Nagaswara Rao R, Suman P, Yogeeswari P, Sriram D, Thokhir B S and Shasi V K 2011 Synthesis, structure–activity relationship of novel substituted \(4H\)-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates as potential anti-mycobacterial and anticancer agents Biorg. Med. Chem. Lett. 21 2855 Theodora W G and Peter G M W 1999 In Protective Group in Organic Synthesis 3rd edn. (New York: John Wiley) p. 494