Highly enantioselective catalytic synthesis of neurite growth-promoting secoyohimbanes

Chemistry and Biology

Volumn 20, Issue 4, 2013, Pages 500-509

  Antonchick, Andrey P ^a   López Tosco, Sara ^a   Parga, Juan ^b   Sievers, Sonja ^a   Schürmann, Markus ^c   Preut, Hans ^c   Höing, Susanne ^b   Schöler, Hans R ^b,d   Sterneckert, Jared ^b   Rauh, Daniel ^c   Waldmann, Herbert ^a,c  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b MAX PLANCK INSTITUTE FOR MOLECULAR BIOMEDICINE   (Germany)

^c TU DORTMUND UNIVERSITY   (Germany)

^d INST OF REPRO MED OF THE UNIV   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ISORHYNCHOPHYLLINE; PLANT EXTRACT; RHYNCHOPHYLLINE; SECOYOHIMBANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYONIC STEM CELL; ENANTIOSELECTIVITY; HIPPOCAMPUS; MOTONEURON; NERVE CELL NETWORK; NERVE FIBER GROWTH; PRIORITY JOURNAL; UNCARIA;

ALKALOIDS; ANIMALS; BIOCATALYSIS; CELLS, CULTURED; HIPPOCAMPUS; INDOLE ALKALOIDS; NEURITES; RATS; SPIRO COMPOUNDS; STEREOISOMERISM; UNCARIA;

RATTUS; UNCARIA;

EID: 84876494951     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.03.011     Document Type: Article

References (82)

1. M.S. Airaksinen, and M. Saarma The GDNF family: signalling, biological functions and therapeutic value Nat. Rev. Neurosci. 3 2002 383 394
2. A.P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, and H. Waldmann Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products Nat. Chem. 2 2010 735 740
3. M. Bella, and T. Gasperi Organocatalytic formation of quaternary stereocenters Synthesis 10 2009 1583 1614
4. S. Bertelsen, and K.A. Jørgensen Organocatalysis - after the gold rush Chem. Soc. Rev. 38 2009 2178 2189
5. R.S. Bon, and H. Waldmann Bioactivity-guided navigation of chemical space Acc. Chem. Res. 43 2010 1103 1114
6. M. Bothwell Functional interactions of neurotrophins and neurotrophin receptors Annu. Rev. Neurosci. 18 1995 223 253
7. S. Brandau, A. Landa, J. Franzén, M. Marigo, and K.A. Jørgensen Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes: asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones Angew. Chem. Int. Ed. Engl. 45 2006 4305 4309
8. D.A. Carcache, Y.S. Cho, Z. Hua, Y. Tian, Y.-M. Li, and S.J. Danishefsky Total synthesis of (+/-)-jiadifenin and studies directed to understanding its SAR: probing mechanistic and stereochemical issues in palladium-mediated allylation of enolate-like structures J. Am. Chem. Soc. 128 2006 1016 1022
9. A.P.J. Chen, C.C. Müller, H.M. Cooper, and C.M. Williams Total synthesis of (+/-)-4,5-bis-epi-neovibsanin A and B: a neurite outgrowth comparison study Org. Lett. 11 2009 3758 3761
10. X. Cheng, N. Harzdorf, Z. Khaing, D. Kang, A.M. Camelio, T. Shaw, C.E. Schmidt, and D. Siegel Neuronal growth promoting sesquiterpene-neolignans; syntheses and biological studies Org. Biomol. Chem. 10 2012 383 393
11. M. Clagett-Dame, E.M. McNeill, and P.D. Muley Role of all-trans retinoic acid in neurite outgrowth and axonal elongation J. Neurobiol. 66 2006 739 756
12. A. Deiters, M. Pettersson, and S.F. Martin General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids J. Org. Chem. 71 2006 6547 6561
13. E.W. Dent, and F.B. Gertler Cytoskeletal dynamics and transport in growth cone motility and axon guidance Neuron 40 2003 209 227
14. C.G. Dotti, C.A. Sullivan, and G.A. Banker The establishment of polarity by hippocampal neurons in culture J. Neurosci. 8 1988 1454 1488
15. H. Dückert, V. Pries, V. Khedkar, S. Menninger, H. Bruss, A.W. Bird, Z. Maliga, A. Brockmeyer, P. Janning, and A. Hyman Natural product-inspired cascade synthesis yields modulators of centrosome integrity Nat. Chem. Biol. 8 2012 179 184
16. D. Enders, C. Grondal, and M.R.M. Hüttl Asymmetric organocatalytic domino reactions Angew. Chem. Int. Ed. Engl. 46 2007 1570 1581
17. J. Franzén, and A. Fisher Asymmetric alkaloid synthesis: a one-pot organocatalytic reaction to quinolizidine derivatives Angew. Chem. Int. Ed. Engl. 48 2009 787 791
18. C. Grondal, M. Jeanty, and D. Enders Organocatalytic cascade reactions as a new tool in total synthesis Nat. Chem. 2 2010 167 178
19. Y. Hayashi, M. Toyoshima, H. Gotoh, and H. Ishikawa Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino Michael/Knoevenagel condensation Org. Lett. 11 2009 45 48
20. A. Henriques, C. Pitzer, and A. Schneider Neurotrophic growth factors for the treatment of amyotrophic lateral sclerosis: where do we stand? Front. Neurosci. 4 2010 32
21. M. Inoue, N. Lee, S. Kasuya, T. Sato, M. Hirama, M. Moriyama, and Y. Fukuyama Total synthesis and bioactivity of an unnatural enantiomer of merrilactone a: development of an enantioselective desymmetrization strategy J. Org. Chem. 72 2007 3065 3075
22. M. Ito, C.W. Clark, M. Mortimore, J.B. Goh, and S.F. Martin Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine J. Am. Chem. Soc. 123 2001 8003 8010
23. C.K. Jana, J. Hoecker, T.M. Woods, H.J. Jessen, M. Neuburger, and K. Gademann Synthesis of withanolide A, biological evaluation of its neuritogenic properties, and studies on secretase inhibition Angew. Chem. Int. Ed. Engl. 50 2011 8407 8411
24. S.-W. Jang, X. Liu, C.B. Chan, S.A. France, I. Sayeed, W. Tang, X. Lin, G. Xiao, R. Andero, and Q. Chang Deoxygedunin, a natural product with potent neurotrophic activity in mice PLoS ONE 5 2010 e11528
25. H.J. Jessen, D. Barbaras, M. Hamburger, and K. Gademann Total synthesis and neuritotrophic activity of farinosone C and derivatives Org. Lett. 11 2009 3446 3449
26. H.J. Jessen, A. Schumacher, T. Shaw, A. Pfaltz, and K. Gademann A unified approach for the stereoselective total synthesis of pyridone alkaloids and their neuritogenic activity Angew. Chem. Int. Ed. Engl. 50 2011 4222 4226
27. M. Kaiser, S. Wetzel, K. Kumar, and H. Waldmann Biology-inspired synthesis of compound libraries Cell. Mol. Life Sci. 65 2008 1186 1201
28. T.-H. Kang, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, and K. Matsumoto Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action Life Sci. 76 2004 331 343
29. M.A. Koch, A. Schuffenhauer, M. Scheck, S. Wetzel, M. Casaulta, A. Odermatt, P. Ertl, and H. Waldmann Charting biologically relevant chemical space: a structural classification of natural products (SCONP) Proc. Natl. Acad. Sci. USA 102 2005 17272 17277
30. M.E. Kozisek, D. Middlemas, and D.B. Bylund Brain-derived neurotrophic factor and its receptor tropomyosin-related kinase B in the mechanism of action of antidepressant therapies Pharmacol. Ther. 117 2008 30 51
31. K. Kumar, and H. Waldmann Synthesis of natural product inspired compound collections Angew. Chem. Int. Ed. Engl. 48 2009 3224 3242
32. H. Lachance, S. Wetzel, K. Kumar, and H. Waldmann Charting, navigating, and populating natural product chemical space for drug discovery J. Med. Chem. 55 2012 5989 6001
33. G. Laus Kinetics of isomerization of tetracyclic spiro oxindole alkaloids J. Chem. Soc., Perkin Trans. 2 1998 315 318
34. G. Laus, D. Brössner, G. Senn, and K. Wurst Analysis of the kinetics of isomerization of spiro oxindole alkaloids J. Chem. Soc., Perkin Trans. 2 1996 1931 1936
35. A. Lerchner, and E.M. Carreira First total synthesis of (+/-)-strychnofoline via a highly selective ring-expansion reaction J. Am. Chem. Soc. 124 2002 14826 14827
36. A. Lerchner, and E.M. Carreira Synthesis of (+/-)-strychnofoline via a highly convergent selective annulation reaction Chemistry 12 2006 8208 8219
37. J.W.H. Li, and J.C. Vederas Drug discovery and natural products: end of an era or an endless frontier? Science 325 2009 161 165
38. M. Marigo, S. Bertelsen, A. Landa, and K.A. Jørgensen One-pot organocatalytic domino Michael-aldol and intramolecular SN2 reactions. Asymmetric synthesis of highly functionalized epoxycyclohexanone derivatives J. Am. Chem. Soc. 128 2006 5475 5479
39. E. Marqués-López, R.P. Herrera, and M. Christmann Asymmetric organocatalysis in total synthesis - a trial by fire Nat. Prod. Rep. 27 2010 1138 1167
40. S.F. Martin, and M. Mortimore New methods for the synthesis of oxindole alkaloids. Total syntheses of isopteropodine and pteropodine Tetrahedron Lett. 31 1990 4557 4560
41. G. Masi, and P. Brovedani The hippocampus, neurotrophic factors and depression: possible implications for the pharmacotherapy of depression CNS Drugs 25 2011 913 931
42. G. Mehta, R. Samineni, P. Srihari, R.G. Reddy, and S. Chakravarty Diverted organic synthesis (DOS): accessing a new, natural product inspired, neurotrophically active scaffold through an intramolecular Pauson-Khand reaction Org. Biomol. Chem. 10 2012 6830 6833
43. P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli Asymmetric aminocatalysis - gold rush in organic chemistry Angew. Chem. Int. Ed. Engl. 47 2008 6138 6171
44. F.Y. Miyake, K. Yakushijin, and D.A. Horne Preparation and synthetic applications of 2-halotryptophan methyl esters: synthesis of spirotryprostatin B Angew. Chem. Int. Ed. Engl. 43 2004 5357 5360
45. H. Miyamoto, Y. Okawa, A. Nakazaki, and S. Kobayashi Highly diastereoselective one-pot synthesis of spirocyclic oxindoles through intramolecular Ullmann coupling and Claisen rearrangement Angew. Chem. Int. Ed. Engl. 45 2006 2274 2277
46. D.J. Newman, and G.M. Cragg Natural products as sources of new drugs over the last 25 years J. Nat. Prod. 70 2007 461 477
47. A. Nören-Müller, I. Reis-Corrêa Jr., H. Prinz, C. Rosenbaum, K. Saxena, H.J. Schwalbe, D. Vestweber, G. Cagna, S. Schunk, and O. Schwarz Discovery of protein phosphatase inhibitor classes by biology-oriented synthesis Proc. Natl. Acad. Sci. USA 103 2006 10606 10611
48. A. Nören-Müller, W. Wilk, K. Saxena, H. Schwalbe, M. Kaiser, and H. Waldmann Discovery of a new class of inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B by biology-oriented synthesis Angew. Chem. Int. Ed. Engl. 47 2008 5973 5977
49. R.W. Oppenheim The neurotrophic theory and naturally occurring motoneuron death Trends Neurosci. 12 1989 252 255
50. B. Over, S. Wetzel, C. Grütter, Y. Nakai, S. Renner, D. Rauh, and H. Waldmann Natural-product-derived fragments for fragment-based ligand discovery Nat. Chem. 5 2013 21 28
51. J.D. Phillipson, and S.R. Hemingway Indole and oxindole alkaloids from Uncaria bernaysia Phytochemistry 12 1973 1481 1487
52. J.D. Phillipson, and S.R. Hemingway Oxindole alkaloids from Uncaria macrophylla Phytochemistry 12 1973 2795 2798
53. V. Praveen Kumar, R. Gajendra Reddy, D.D. Vo, S. Chakravarty, S. Chandrasekhar, and R. Grée Synthesis and neurite growth evaluation of new analogues of honokiol, a neolignan with potent neurotrophic activity Bioorg. Med. Chem. Lett. 22 2012 1439 1444
54. M. Rawat, C.I. Gama, J.B. Matson, and L.C. Hsieh-Wilson Neuroactive chondroitin sulfate glycomimetics J. Am. Chem. Soc. 130 2008 2959 2961
55. K. Schindowski, K. Belarbi, and L. Buée Neurotrophic factors in Alzheimer's disease: role of axonal transport Genes Brain Behav. 7 Suppl 1 2008 43 56
56. F. Schmidt, P. Champy, B. Séon-Méniel, X. Franck, R. Raisman-Vozari, and B. Figadère Chemicals possessing a neurotrophin-like activity on dopaminergic neurons in primary culture PLoS ONE 4 2009 e6215
57. J.C. Seaton, M.D. Nair, O.E. Edwards, and L. Marion The structure and stereoisomerism of three mitragyna alkaloids Can. J. Chem. 38 1960 1035 1042
58. E.J. Shellard, and P.K. Lala The alkaloids of Mitragyna rubrostipulata (Schum.) Havil Planta Med. 33 1978 63 69
59. E.J. Shellard, J.D. Phillipson, and D. Gupta The Mitragyna species of Asia. XV. The alkaloids from the bark of Mitragyna parvifolia (Roxb.) Korth and a possible biogenetic route for the oxindole alkaloids Planta Med. 17 1969 146 163
60. Y. Shimada, H. Goto, T. Itoh, I. Sakakibara, M. Kubo, H. Sasaki, and K. Terasawa Evaluation of the protective effects of alkaloids isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death in cultured cerebellar granule cells from rats J. Pharm. Pharmacol. 51 1999 715 722
61. R. Stahl, H.J. Borschberg, and P. Acklin A reinvestigation of the oxidative rearrangement of yohimban-type alkaloids. Part B. Formation of oxindole (1,3-dihydro-2H-indol-2-one) derivatives Helv. Chim. Acta 79 1996 1361 1378
62. A. Steven, and L.E. Overman Total synthesis of complex cyclotryptamine alkaloids: stereocontrolled construction of quaternary carbon stereocenters Angew. Chem. Int. Ed. Engl. 46 2007 5488 5508
63. M.H. Theus, L. Wei, K. Francis, and S.P. Yu Critical roles of Src family tyrosine kinases in excitatory neuronal differentiation of cultured embryonic stem cells Exp. Cell Res. 312 2006 3096 3107
64. B.M. Trost, and C. Jiang Catalytic enantioselective construction of all-carbon quaternary stereocenters Synthesis 3 2006 369 396
65. B.M. Trost, and M.K. Brennan Asymmetric syntheses of oxindole and indole spirocyclic alkaloid natural products Synthesis 18 2009 3003 3025
66. G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, and R. Rios Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-paroxetine Tetrahedron Lett. 50 2009 1943 1946
67. H. Waldmann, V. Khedkar, H. Dückert, M. Schürmann, I.M. Oppel, and K. Kumar Asymmetric synthesis of natural product inspired tricyclic benzopyrones by an organocatalyzed annulation reaction Angew. Chem. Int. Ed. Engl. 47 2008 6869 6872
68. E. Wenkert, J.H. Udelhofen, and N.K. Bhattacharyya 3- hydroxymethyleneoxindole and its derivatives J. Am. Chem. Soc. 81 1959 3763 3768
69. S. Wetzel, R.S. Bon, K. Kumar, and H. Waldmann Biology-oriented synthesis Angew. Chem. Int. Ed. Engl. 50 2011 10800 10826
70. W. Wilk, T.J. Zimmermann, M. Kaiser, and H. Waldmann Principles, implementation, and application of biology-oriented synthesis (BIOS) Biol. Chem. 391 2010 491 497
71. R.M. Wilson, and S.J. Danishefsky Applications of total synthesis to problems in neurodegeneration: Fascinating chemistry along the way Acc. Chem. Res. 39 2006 539 549
72. X. Wu, Q. Liu, H. Fang, J. Chen, W. Cao, and G. Zhao Enantioselective organocatalyzed cascade reactions to highly functionalized spirotetracyclic indolenines and oxindoles Chemistry 18 2012 12196 12201
73. D.D. Xu, R. Hoeven, R. Rong, and W.C.-S. Cho Rhynchophylline protects cultured rat neurons against methamphetamine cytotoxicity Evid. Based Complement. Alternat. Med. 2012 2012 636091
74. M. Yamamoto, Y. Kobayashi, M. Li, H. Niwa, N. Mitsuma, Y. Ito, T. Muramatsu, and G. Sobue In vivo gene electroporation of glial cell line-derived neurotrophic factor (GDNF) into skeletal muscle of SOD1 mutant mice Neurochem. Res. 26 2001 1201 1207
75. M. Yasuda, M. Fukuchi, A. Tabuchi, M. Kawahara, H. Tsuneki, Y. Azuma, Y. Chiba, and M. Tsuda Robust stimulation of TrkB induces delayed increases in BDNF and Arc mRNA expressions in cultured rat cortical neurons via distinct mechanisms J. Neurochem. 103 2007 626 636
76. D. Yuan, B. Ma, C. Wu, J. Yang, L. Zhang, S. Liu, L. Wu, and Y. Kano Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia J. Nat. Prod. 71 2008 1271 1274
77. W. Zhang, and J. Franzén Diverse asymmetric quinolizidine synthesis: a stereodivergent one-pot approach Adv. Synth. Catal. 352 2010 499 518
78. H. Zhang, X. Ma, H. Kang, L. Hong, and R. Wang The enantioselective formal synthesis of rhynchophylline and isorhynchophylline Chem. Asian J. 8 2013 542 545
79. J.Y. Zhou, and S.W. Zhou Antihypertensive and neuroprotective activities of rhynchophylline: the role of rhynchophylline in neurotransmission and ion channel activity J. Ethnopharmacol. 132 2010 15 27
80. J.Y. Zhou, and S.W. Zhou Isorhynchophylline: A plant alkaloid with therapeutic potential for cardiovascular and central nervous system diseases Fitoterapia 83 2012 617 626
81. F. Zhou, Y.-L. Liu, and J. Zhou Catalytic asymmetric synthesis of oxindoles bearing a tetrasubstituted stereocenter at the C-3 position Adv. Synth. Catal. 352 2010 1381 1407
82. A.D. Zurn, L. Winkel, A. Menoud, K. Djabali, and P. Aebischer Combined effects of GDNF, BDNF, and CNTF on motoneuron differentiation in vitro J. Neurosci. Res. 44 1996 133 141