Development of a platform for the discovery and practical synthesis of new tetracycline antibiotics

Current Opinion in Chemical Biology

Volumn 32, Issue , 2016, Pages 48-57

  Liu, Fan ^a   Myers, Andrew G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AB ENONE 1; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALDEHYDE; ANTIBIOTIC AGENT; CHLORIDE; DOXYCYCLINE; ERAVACYCLINE; HYDROXYUREA; ISOXAZOLE; LITHIUM CHLORIDE; TETRACYCLINE DERIVATIVE; TIGECYCLINE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ANNULATION REACTION; CLAISEN CONDENSATION; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; DIHYDROXYLATION; DRUG SYNTHESIS; EPIMERIZATION; HYDROXYLATION; MICHAEL CLAISEN CONDENSATION; NONHUMAN; REVIEW; STEREOCHEMISTRY; SWERN OXIDATION; X RAY CRYSTALLOGRAPHY; DRUG DEVELOPMENT; FERMENTATION; SYNTHESIS;

DRUG DISCOVERY; FERMENTATION; TETRACYCLINES;

EID: 84961944302     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2016.03.011     Document Type: Review

References (55)

1. Nguyen F., Starosta A.L., Arenz S., Sohmen D., Dönhöfer A., Wilson D.N. Tetracycline antibiotics and resistance mechanisms. Biol Chem 2014, 395:559-575.
2. Duggar B.M. Aureomycin: a product of the continuing search for new antibiotics. Ann NY Acad Sci 1948, 51:177-181.
3. Finlay A.C., Hobby G., P'an S., Regna P., Routien J., Seeley D., Shull G., Sobin B., Solomons I., Vinson J.W., Kane J. Terramycin, a new antibiotic. Science 1950, 111:85-87.
4. Benitz K.-F., Diermeier H.F. Renal toxicity of tetracycline degradation products. Proc Soc Exp Biol Med 1964, 115:930-935.
5. Boothe J.H., Morton J., Petisi J.P., Wilkinson R.G., Williams J.H. Tetracycline. J Am Chem Soc 1953, 75:4621.
6. Conover L.H., Moreland W.T., English A.R., Stephens C.R., Pilgrim F.J. Terramycin. XI. Tetracycline. J Am Chem Soc 1953, 75:4622-4623.
7. Minieri PP, Sokol H, Firman MC: Process for the preparation of tetracycline and chlortetracycline. US Patent Feb 7, 1956, 2,734,018.
8. Wright P.M., Seiple I.B., Myers A.G. The evolving role of chemical synthesis in antibacterial drug discovery. Angew Chem Int Ed 2014, 53:8840-8869.
9. Blackwood R.K., Beereboom J.J., Rennhard H.H., von Wittenau M.S., Stephens C.R. 6-Methylenetetracyclines. I. A new class of tetracycline antibiotics. J Am Chem Soc 1961, 83:2773-2775.
10. Stephens C.R., Beereboom J.J., Rennhard H.H., Gordon P.N., Murai K., Blackwood R.K., von Wittenau M.S. 6-Deoxytetracyclines. IV. Preparation, C-6 stereochemistry, and reactions. J Am Chem Soc 1963, 85:2643-2652.
11. Stephens C.R., Murai K., Rennhard H.H., Conover L.H., Brunings K.J. Hydrogenolysis studies in the tetracycline series-6-deoxytetracyclines. J Am Chem Soc 1958, 80:5324-5325.
12. McCormick J.R.D., Jensen E.R., Miller P.A., Doerschuk A.P. The 6-deoxytetracyclines. Further studies on the relationship between structure and antibacterial activity in the tetracycline series. J Am Chem Soc 1960, 82:3381-3386.
13. Beereboom JJ, Blackwood RK, Rennhard HH, Stephens JCR: Alpha-6-deoxytetracycline derivatives and process. US Patent Aug 10, 1965, 3,200,149.
14. Villax I, Page PR: Process for the preparation of α-6-deoxytetracyclines. US Patent Feb 19, 1985, 4,500,458.
15. Church R.F.R., Schaub R.E., Weiss M.J. Synthesis of 7-dimethylamino-6-demethyl-6-deoxytetracycline (minocycline) via 9-nitro-6-demethyl-6-deoxytetracycline. J Org Chem 1971, 36:723-725.
16. Martell M.J., Boothe J.H. The 6-Deoxytetracyclines. VII. Alkylated aminotetracyclines possessing unique antibacterial activity. J Med Chem 1967, 10:44-46.
17. Zambrano RT: Reductive alkylation process. US Patent Dec 9, 1969, 3,483,251.
18. Chopra I., Roberts M. Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev 2001, 65:232-260.
19. Cunha B. The atypical pneumonias: clinical diagnosis and importance. Clin Microbiol Infect 2006, 12:12-24.
20. Hercogová J. Lyme borreliosis. European Handbook of Dermatological Treatments 2015, 561-566. Springer, Berlin Heidelberg. A.D. Katsambas, T.M. Lotti, C. Dessinioti, A.M. D'Erme (Eds.).
21. Smilack J.D. The tetracyclines. Mayo Clin Proc 1999, 74:727-729.
22. Stein G.E., Craig W.A. Tigecycline: a critical analysis. Clin Infect Dis 2006, 43:518-524.
23. Sum P.E., Lee V.J., Testa R.T., Hlavka J.J., Ellestad G.A., Bloom J.D., Gluzman Y., Tally F.P. Glycylcyclines. 1. A new generation of potent antibacterial agents through modification of 9-aminotetracyclines. J Med Chem 1994, 37:184-188.
24. Jenner L., Starosta A.L., Terry D.S., Mikolajka A., Filonava L., Yusupov M., Blanchard S.C., Wilson D.N., Yusupova G. Structural basis for potent inhibitory activity of the antibiotic tigecycline during protein synthesis. Proc Natl Acad Sci 2013, 110:3812-3816.
25. Sum P.-E., Petersen P. Synthesis and structure-activity relationship of novel glycylcycline derivatives leading to the discovery of GAR-936. Bioorg Med Chem Lett 1999, 9:1459-1462.
26. Zhanel G.G., Homenuik K., Nichol K., Noreddin A., Vercaigne L., Embil J., Gin A., Karlowsky J.A., Hoban D.J. The glycylcyclines. Drugs 2004, 64:63-88.
27. Kaewpoowat Q., Ostrosky-Zeichner L. Tigecycline: a critical safety review. Expert Opin Drug Saf 2015, 14:335-342.
28. Falagas M.E., Vardakas K.Z., Tsiveriotis K.P., Triarides N.A., Tansarli G.S. Effectiveness and safety of high-dose tigecycline-containing regimens for the treatment of severe bacterial infections. Int J Antimicrob Agents 2014, 44:1-7.
29. Charest M.G., Lerner C.D., Brubaker J.D., Siegel D.R., Myers A.G. A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics. Science 2005, 308:395-398.
30. Sun C., Wang Q., Brubaker J.D., Wright P.M., Lerner C.D., Noson K., Charest M., Siegel D.R., Wang Y.M., Myers A.G. A robust platform for the synthesis of new tetracycline antibiotics. J Am Chem Soc 2008, 130:17913-17927.
31. Xiao X.-Y., Hunt D.K., Zhou J., Clark R.B., Dunwoody N., Fyfe C., Grossman T.H., O'Brien W.J., Plamondon L., Rönn M., et al. Fluorocyclines. 1. 7-Fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: a potent, broad spectrum antibacterial agent. J Med Chem 2012, 55:597-605.
32. Clark R.B., Hunt D.K., He M., Achorn C., Chen C.-L., Deng Y., Fyfe C., Grossman T.H., Hogan P.C., O'Brien W.J., et al. Fluorocyclines. 2. Optimization of the C-9 side-chain for antibacterial activity and oral efficacy. J Med Chem 2012, 55:606-622.
33. Sutcliffe J., O'Brien W., Fyfe C., Grossman T. Antibacterial activity of eravacycline (TP-434), a novel fluorocycline, against hospital and community pathogens. Antimicrob Agents Chemother 2013, 57:5548-5558.
34. Grossman T.H., Starosta A.L., Fyfe C., O'Brien W., Rothstein D.M., Mikolajka A., Wilson D.N., Sutcliffe J.A. Target- and resistance-based mechanistic studies with TP-434, a novel fluorocycline antibiotic. Antimicrob Agents Chemother 2012, 56:2559-2564.
35. Solomkin J.S., Ramesh M.K., Cesnauskas G., Novikovs N., Stefanova P., Sutcliffe J.A., Walpole S.M., Horn P.T. Phase 2, randomized, double-blind study of the efficacy and safety of two dose regimens of eravacycline versus ertapenem for adult community-acquired complicated intra-abdominal infections. Antimicrob Agents Chemother 2014, 58:1847-1854.
36. Korst J.J., Johnston J.D., Butler K., Bianco E.J., Conover L.H., Woodward R.B. The total synthesis of dl-6-demethyl-6-deoxytetracycline. J Am Chem Soc 1968, 90:439-457.
37. Gurevich A.I., Karapetyan M.G., Kolosov M.N., Korobko V.G., Onoprienko V.V., Popravko S.A., Shemyakin M.M. Synthesis of 12a-deoxy-5a,6-anhydrotetracycline. The first total synthesis of the naturally occurring tetracycline. Tetrahedron Lett 1967, 8:131-134.
38. Muxfeldt H., Hardtmann G., Kathawala F., Vedejs E., Mooberry J.B. Tetracyclines. VII. Total synthesis of dl-terramycin. J Am Chem Soc 1968, 90:6534-6536.
39. Muxfeldt H., Haas G., Hardtmann G., Kathawala F., Mooberry J.B., Vedejs E. Tetracyclines. 9. Total synthesis of dl-terramycin. J Am Chem Soc 1979, 101:689-701.
40. Myers A.G., Fraley M.E., Tom N.J., Cohen S.B., Madar D.J. Synthesis of (+)-dynemicin A and analogs of wide structural variability: establishment of the absolute configuration of natural dynemicin A. Chem Biol 1995, 2:33-43.
41. Myers A.G., Tom N.J., Fraley M.E., Cohen S.B., Madar D.J. A convergent synthetic route to (+)-dynemicin A and analogs of wide structural variability. J Am Chem Soc 1997, 119:6072-6094.
42. Brubaker J.D., Myers A.G. A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics. Org Lett 2007, 9:3523-3525.
43. Kummer D.A., Li D., Dion A., Myers A.G. A practical, convergent route to the key precursor to the tetracycline antibiotics. Chem Sci 2011, 2:1710-1718.
44. Zhang W.-Y., Hogan P.C., Chen C.-L., Niu J., Wang Z., Lafrance D., Gilicky O., Dunwoody N., Ronn M. Process research and development of an enantiomerically enriched allyic amine, one of the key intermediates for the manufacture of synthetic tetracyclines. Org Process Res Dev 2015, 19:1784-1795.
45. Ronn M., Zhu Z., Hogan P.C., Zhang W.-Y., Niu J., Katz C.E., Dunwoody N., Gilicky O., Deng Y., Hunt D.K., et al. Process R&D of eravacycline: the first fully synthetic fluorocycline in clinical development. Org Process Res Dev 2013, 17:838-845.
46. Stork G., La Clair J.J., Spargo P., Nargund R.P., Totah N. Stereocontrolled synthesis of (±)-12a-deoxytetracycline. J Am Chem Soc 1996, 118:5304-5305.
47. Myers A.G., Siegel D.R., Buzard D.J., Charest M.G. Synthesis of a broad array of highly functionalized, enantiomerically pure cyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions. Org Lett 2001, 3:2923-2926.
48. Stork G., Hagedorn A.A. 3-Benzyloxyisoxazole system in construction of tetracyclines. J Am Chem Soc 1978, 100:3609-3611.
49. Myers A.G., Movassaghi M., Zheng B. Single-step process for the reductive deoxygenation of unhindered alcohols. J Am Chem Soc 1997, 119:8572-8573.
50. Sun C., Hunt D.K., Clark R.B., Lofland D., O'Brien W.J., Plamondon L., Xiao X.Y. Synthesis and antibacterial activity of pentacyclines: a novel class of tetracycline analogs. J Med Chem 2011, 54:3704-3731.
51. Sun C., Hunt D.K., Chen C.-L., Deng Y., He M., Clark R.B., Fyfe C., Grossman T.H., Sutcliffe J.A., Xiao X.-Y. Design, synthesis, and biological evaluation of hexacyclic tetracyclines as potent, broad spectrum antibacterial agents. J Med Chem 2015, 58:4703-4712.
52. Clark R.B., He M., Fyfe C., Lofland D., O'Brien W.J., Plamondon L., Sutcliffe J.A., Xiao X.Y. 8-Azatetracyclines: synthesis and evaluation of a novel class of tetracycline antibacterial agents. J Med Chem 2011, 54:1511-1528.
53. Wright P.M., Myers A.G. Methodological advances permit the stereocontrolled construction of diverse fully synthetic tetracyclines containing an all-carbon quaternary center at position C5a. Tetrahedron 2011, 67:9853-9869.
54. Riess R., Schön M., Laschat S., Jäger V. Evaluation of protecting groups for 3-hydroxyisoxazoles - short access to 3-alkoxyisoxazole-5-carbaldehydes and 3-hydroxyisoxazole-5-carbaldehyde, the putative toxic metabolite of muscimol. Eur J Org Chem 1998, 1998:473-479.
55. Frey M., Jäger V. Synthesis of N-substituted muscimol derivatives including N-glycylmuscimol. Synthesis 1985, 1985:1100-1104.