Chemoenzymatic approach to optically active 1,4-dihydropyridine derivatives

Tetrahedron

Volumn 71, Issue 23, 2015, Pages 3976-3984

  Torres, Susana Y ^a,b   Verdecia, Yamila ^b   Rebolledo, Francisca ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF HAVANA   (Cuba)

Author keywords

1,4 Dihydropyridine; 2 Methylpropanoyloxymethyl esters; Hydrolysis; Lipase; Resolution

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; ACID LIPASE; ENZYME; ESTERASE; SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; [2 (METHYL)PROPANOYLOXY]METHYL 4 (4 BROMOPHENYL) 6 CHLORO 5 METHANOYL 2 METHYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 4 (2 CHLORO 5 NITROPHENYL) 5 METHANOYL 2 METHYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 5 METHANOYL 2 METHYL 4 (1 NAPHTHYL) 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 5 METHANOYL 2 METHYL 4 (2 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 5 METHANOYL 2 METHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 5 METHANOYL 2 METHYL 4 (4 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 5 METHANOYL 2 METHYL 4 PHENYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID; [2 (METHYL)PROPANOYLOXY]METHYL 6 CHLORO 5 METHANOYL 4 ( METHOXYPHENYL) 2 METHYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLIC ACID;

ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; CANDIDA RUGOSA; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HANTZSCH REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OPTICAL ROTATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SOLVENT EFFECT; VILSMEIER HAACK REACTION;

CANDIDA ANTARCTICA; CANDIDA RUGOSA;

EID: 84929999149     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.04.047     Document Type: Article

References (45)

1. P. Ioan, E. Carosati, M. Micucci, G. Cruciani, F. Broccatelli, B.S. Zhorov, A. Chiarini, and R. Budriesi Curr. Med. Chem. 18 2011 4901 4922
2. E. Carosati, P. Ioan, M. Micucci, F. Broccatelli, G. Cruciani, B.S. Zhorov, A. Chiarini, and R. Budriesi Curr. Med. Chem. 19 2012 4306 4323
3. G. Tenti, E. Parada, R. León, J. Egea, S. Martínez-Revelles, A.M. Briones, V. Sridharan, M.G. López, M.T. Ramos, and J.C. Menéndez J. Med. Chem. 57 2014 4313 4323
4. R. León, and J. Marco-Contelles Curr. Med. Chem. 18 2011 552 576
5. J.A.M. Christiaans, and H. Timmerman Eur. J. Pharm. Sci. 4 1996 1 22
6. K.V. Sashidhara, M. Kumar, V. Khedgikar, P. Kushwaha, R.K. Modukuri, A. Kumar, J. Gautam, D. Singh, B. Sridhar, and R. Trivedi J. Med. Chem. 56 2013 109 122
7. A. Locatelli, S. Cosconati, M. Micucci, A. Leoni, L. Marinelli, A. Bedini, P. Ioan, S.M. Spampinato, E. Novellino, A. Chiarini, and R. Budriesi J. Med. Chem. 56 2013 3866 3877
8. Y. Nuñez-Figueredo, J. Ramírez-Sánchez, R. Delgado-Hernández, M. Porto-Verdecia, E. Ochoa-Rodríguez, Y. Verdecia-Reyes, J. Marin-Prida, M. González-Durruthy, S.A. Uyemura, F.P. Rodrigues, C. Curti, D.O. Souza, and G.L. Pardo-Andreu Eur. J. Pharmacol. 726 2014 57 65
9. C.E. Paul, I.W.C.E. Arends, and F. Hollmann ACS Catal. 4 2014 788 797
10. M.-W. Chen, X.-F. Cai, Z.-P. Chen, L. Shi, and Y.-G. Zhou Chem. Commun. 2014 12526 12529
11. Z. Wang, F. Ai, Z. Wang, W. Zhao, G. Zhu, Z. Lin, and J. Sun J. Am. Chem. Soc. 137 2015 383 389
12. S.-L. You Chem. Asian J. 2 2007 820 827
13. M. Rueping, E. Sugiono, and F.R. Schoepke Synlett 2010 852 865
14. M. Rueping, J. Dufour, and F.R. Schoepke Green Chem. 13 2011 1084 1105
15. C. Zheng, and S.-L. You Chem. Soc. Rev. 41 2012 2498 2518
16. P.T. Franke, R.L. Johansen, S. Bertelsen, and K.A. Jørgensen Chem. Asian J. 3 2008 216 224
17. Y. Murakami, J.-i. Kikuchi, Y. Hisaeda, and O. Hayashida Chem. Rev. 96 1996 721 758
18. S. Fustero, S. Catalán, M. Sánchez-Roselló, A. Simón-Fuentes, and C. del Pozo Org. Lett. 12 2010 3484 3487
19. K. Kwon, J.A. Shin, and H.-Y. Lee Tetrahedron 67 2011 10222 10228
20. J.A. Bull, J.J. Mousseau, G. Pelletier, and A.B. Charette Chem. Rev. 112 2012 2642 2713
21. A. Noole, M. Borissova, M. Lopp, and T. Kanger J. Org. Chem. 76 2011 1538 1545
22. J. Yu, F. Shi, and L.-Z. Gong Acc. Chem. Res. 44 2011 1156 1171
23. N. Molleti, S. Allu, S.K. Ray, and V.K. Singh Tetrahedron Lett. 54 2013 3241 3244
24. F. Dollé, F. Hinnen, H. Valette, C. Fuseau, R. Duval, J.-L. Péglion, and C. Crouzel Bioorg. Med. Chem. 5 1997 749 764
25. B.-l. Zhang, W. He, X. Shi, M.-l. Huan, Q.-j. Huang, and S.-y. Zhou Bioorg. Med. Chem. Lett. 20 2010 805 808
26. D.M. Gotrane, R.D. Deshmukh, P.V. Ranade, S.P. Sonawane, B.M. Bhawal, M.M. Gharpure, and M.K. Gurjar Org. Process Res. Dev. 14 2010 640 643
27. A. Sobolev, M.C.R. Franssen, G. Duburs, and A.E. de Groot Biocatal. Biotransform. 22 2004 231 252
28. S. Marchalín, M. Chudík, V. Mastihuba, and B. Decroix Heterocycles 48 1998 1943 1958
29. A. Sobolev, R. Zhalubovskis, M.C.R. Franssen, B. Vigante, B. Chekavichus, G. Duburs, and A.E. de Groot Chem. Heterocycl. Compd. 40 2004 931 937
30. Z. Andzans, I. Adlere, A. Versilovskis, L. Krasnova, S. Grinberga, G. Duburs, and A. Krauze Heterocycles 89 2014 43 58
31. D. Vo, W.C. Matowe, M. Ramesh, N. Iqbal, M.W. Wolowyk, S.E. Howlett, and E.E. Knaus J. Med. Chem. 38 1995 2851 2859
32. R. Shan, S.E. Howlett, and E.E. Knaus J. Med. Chem. 45 2002 955 961
33. Kobayashi, T.; Sada, T. U.S. Patent US 20,050,272,715 A1, 2005; CAN 2005:1291987.
34. S.Y. Torres, E. Ochoa, Y. Verdecia, and F. Rebolledo Tetrahedron 70 2014 4675 4684
35. A.P. Rajput, and P.D. Girase IJPCBS 3 2012 25 43
36. W. Su, Y. Weng, L. Jiang, Y. Yang, L. Zhao, Z. Chen, Z. Li, and J. Li Org. Prep. Proced. Int. 42 2010 503 555
37. W. Ziegenbein, and W. Lang Chem. Ber. 93 1960 2743 2749
38. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
39. Faber, K.; Hoenig, H. Program "Selectivity". http://www.cis.TUGraz.at/orgc/.
40. Esterase-catalyzed hydrolyses of (±)-5c were carried out at 28 °C in phosphate buffer pH 7.5 (100 mM, 100 μL/mg of substrate) using DMSO as a co-solvent (10 μL/mg of substrate). The amount of esterase was 1.0-0.25 mg/mg of substrate, depending of the activity provided by the supplier.
41. M. Suárez, E. Ochoa, B. Pita, R. Espinosa, L. González, N. Martín, M. Quinteiro, C. Seoane, and J.L. Soto J. Heterocycl. Chem. 34 1997 931 935
42. Y. Verdecia, M. Suárez, A. Morales, E. Rodríguez, E. Ochoa, L. González, N. Martín, M. Quinteiro, C. Seoane, and J.L. Soto J. Chem. Soc., Perkin Trans. 1 1996 947 951
43. Carboxylic acids (R)- and/or (S)-6 were used, the last being previously prepared from the optically active remaining substrates (S)-5 such as was described for the synthesis of (±)-6 (Section 4.3).
44. H. Rodríguez, O. Martin, M. Suárez, N. Martín, and F. Albericio Molecules 16 2011 9620 9635
45. M. Suárez, N. Martín, R. Martínez, Y. Verdecia, D. Molero, L. Alba, C. Seoane, and E. Ochoa Magn. Reson. Chem. 40 2002 303 306