Application of efficient synthetic techniques in drug research

Yaoxue Xuebao

Volumn 48, Issue 7, 2013, Pages 1014-1030

  Zhou, Yu ^a   Zhang, Lei ^a   Li, Zeng ^a   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Cascade reaction; Click chemistry; Combinatorial chemistry; Diversity oriented synthesis; Microwave; Multicomponent reaction

Indexed keywords

CHEMICAL ANALYSIS; CLICK CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DATABASE; DRUG RESEARCH; DRUG SYNTHESIS; METHODOLOGY; REVIEW; DRUG DEVELOPMENT; MICROWAVE RADIATION; PROCEDURES; SYNTHESIS;

DRUG;

CLICK CHEMISTRY; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DISCOVERY; MICROWAVES; PHARMACEUTICAL PREPARATIONS;

EID: 84883611981     PISSN: 05134870     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (49)

1. McCarroll AJ, Bradshaw TD, Westwell AD, et al. Quinols as novel therapeutic agents. 7. Synthesis of antitumor 4-[1-(arylsulfonyl-1H-indol-2-yl)] -4-hydroxycyclohexa-2, 5-dien-1-ones by Sonogashira reactions [J]. J Med Chem, 2007, 50: 1707-1710. (Pubitemid 46564393)
2. Huang H, Liu H, Chen KX, et al. Microwave-assisted rapid synthesis of 2, 6, 9-substituted purines [J]. J Comb Chem, 2007, 9: 197-199.
3. Huang H, Ma JG, Shi JM, et al. Discovery of novel purine derivatives with potent and selective inhibitory activity against c-Src tyrosine kinase [J]. Bioorg Med Chem, 2010, 18: 4615-4624.
4. Chen H, Bai J, Jiao LL, et al. Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2, 6-dihalophenyl)-3-(4, 6-dimethyl-5-(un) substituted-pyrimidin-2-yl)thiazolidin-4-ones [J]. Bioorg Med Chem, 2009, 17: 3980-3986.
5. Shukla NM, Salunke DB, Yoo E, et al. Antibacterial activities of Groebke-Blackburn-Bienaymé-derived imidazo [1,2-a]pyridin-3-amines [J]. Bioorg Med Chem, 2012, 20: 5850-5863.
6. Zhang L, Qiu B, Li X, et al. Preparation of 6-substituted quinoxaline JSP-1 inhibitors by microwave accelerated nucleophilic substitution [J]. Molecules, 2006, 11: 988-999.
7. Zhang L, Qiu B, Xiong B, et al. Quinoxalinylurea derivatives as a novel class of JSP-1 inhibitors [J]. Bioorg Med Chem Lett, 2007, 17: 2118-2122. (Pubitemid 46484320)
8. Meng T, Wang J, Peng H, et al. Discovery of benzhy-drylpiperazine derivatives as CB1 receptor inverse agonists via privileged structure-based approach [J]. Eur J Med Chem, 2010, 45: 1133-1139.
9. Kolb HC, Finn MG, Sharpless KB. Click chemistry: diverse chemical function from a few good reactions [J]. Angew Chem Int Ed, 2001, 40: 2004-2021.
10. Kolb HC, Sharpless KB. The growing impact of click chemistry on drug discovery [J]. Drug Discov Today, 2003, 8: 1128-1137. (Pubitemid 37547919)
11. Li J, Zheng MY, Tang W, et al. Syntheses of triazole-modified zanamivir analogues via click chemistry and anti-AIV activities [J]. Bioorg Med Chem Lett, 2006, 16: 5009-5013. (Pubitemid 44262496)
12. Zhang L, Su M, Li J, et al. Design, synthesis, structure-activity relationships, and docking studies of 1-(γ-1, 2, 3-triazol substituted prolyl)-(S)-3, 3-difluoropyrrolidines as a novel series of potent and selective dipeptidyl peptidase-4 inhibitors [J]. Chem Biol Drug Des, 2013, 81: 198-207.
13. Yermolina MV, Wang JZ, Caffrey M, et al. Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry [J]. J Med Chem, 2011, 54: 765-781.
14. Zhou B, He YT, Zhang X, et al. Targeting mycobacterium protein tyrosine phosphatase B for antituberculosis agents [J]. Proc Natl Acad Sci USA, 2010, 107: 4573-4578.
15. Liu R, Huang ZH, Murray MG, et al. Quinoxalin-2(1H)-one derivatives as inhibitors against hepatitis C virus [J]. J Med Chem, 2011, 54: 5747-5768.
16. Zhang LA, Liu G, Zhang SD, et al. Parallel approach for solution-phase synthesis of 2-quinoxalinol analogues and their inhibition of LPS-induced TNF-alpha release on mouse macrophages in vitro [J]. J Comb Chem, 2004, 6: 431-436. (Pubitemid 38698878)
17. He LY, Zhang L, Liu XF, et al. Discovering potent inhibitors against the beta-hydroxyacyl-acyl carrier protein dehydratase (FabZ) of helicobacter pylori: structure-based design, synthesis, bioassay, and crystal structure determination [J]. J Med Chem, 2009, 52: 2465-2481.
18. Corbett PT, Leclaire J, Vial L, et al. Dynamic combinatorial chemistry [J]. Chem Rev, 2006, 106: 3652-3711. (Pubitemid 44565983)
19. Liénard BMR, Hueting R, Lassaux P, et al. Dynamic combinatorial mass spectrometry leads to metallo-beta-lactamase inhibitors [J]. J Med Chem, 2008, 51: 684-688. (Pubitemid 351252297)
20. Barluenga J, Mendoza A, Rodriguez F, et al. Synthesis of spiroquinolines through a one-pot multicatalytic and multicomponent cascade reaction [J]. Angew Chem Int Ed, 2008, 47: 7044-7047.
21. Magano J. Recent synthetic approaches to oseltamivir phosphate (Tamiflu™) for the treatment of influenza [J]. Tetrahedron, 2011, 67: 7875-7899.
22. Ishikawa H, Suzuki T, Hayashi Y. High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations [J]. Angew Chem Int Ed, 2009, 48: 1304-1307.
23. Vaxelaire C, Winter P, Christmann M. One-pot reactions accelerate the synthesis of active pharmaceutical ingredients [J]. Angew Chem Int Ed, 2011, 50: 3605-3607.
24. Ishikawa H, Suzuki T, Orita H, et al. High-yielding synthesis of the anti-influenza neuraminidase inhibitor (-)-oseltamivir by two "one-pot" sequences [J]. Chem Eur J, 2010, 16: 12616-12626.
25. Pei Z, Li X, von Geldern TW, et al. Discovery of ((4 R, 5S)-5-amino-4-(2, 4, 5-trifluorophenyl)cyclohex-1-enyl)-(3-(trifluoro methyl)-5, 6-dihydro-[1, 2, 4]triazolo[4, 3-a]pyrazin-7(8H)-yl) methanone (ABT-341), a highly potent, selective, orally efficacious, and safe dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes [J]. J Med Chem, 2006, 49: 6439-6442. (Pubitemid 44657439)
26. Ishikawa H, Honma M, Hayashi Y. One-pot high-yielding synthesis of the DPP4-selective inhibitor ABT-341 by a four-component coupling mediated by a diphenylprolinol silyl ether [J]. Angew Chem Int Ed, 2011, 50: 2824-2827.
27. Nicolaou KC, Edmonds DJ, Bulger PG. Cascade reactions in total synthesis [J]. Angew Chem Int Ed, 2006, 45: 7134-7186. (Pubitemid 44748294)
28. Ganem B. Strategies for innovation in multicomponent reaction design [J]. Acc Chem Res, 2009, 42: 463-472.
29. Dömling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry [J]. Chem Rev, 2006, 106: 17-89. (Pubitemid 43159621)
30. Dömling A, Ugi I. Multicomponent reactions with isocyanides [J]. Angew Chem Int Ed, 2000, 39: 3168-3210.
31. Ramon DJ, Yus M. Asymmetric multicomponent reactions (AMCRs): the new frontier [J]. Angew Chem Int Ed, 2005, 44: 1602-1634.
32. Lee D, Sello JK, Schreiber SL. Pairwise use of complexity-generating reactions in diversity-oriented organic synthesis [J]. Org Lett, 2000, 2: 709-712.
33. Macsari I, Besidski Y, Csjernyik G, et al. 3-Oxoisoindoline-1- carboxamides: potent, state-dependent blockers of voltage-gated sodium channel NaV1.7 with efficacy in rat pain models [J]. J Med Chem, 2012, 55: 6866-6880.
34. Salunke DB, Yoo E, Shukla NM, et al. Structure-activity relationships in human Toll-like receptor 8-active 2, 3-diaminofuro[2, 3-c]pyridines [J]. J Med Chem, 2012, 55: 8137-8151.
35. Yang HQ, Li XJ. Chemical proteomics and discovery of drug targets [J]. Acta Pharm Sin, 2011, 46: 877-882.
36. Schreiber SL. Target-oriented and diversity-oriented organic synthesis in drug discovery [J]. Science, 2000, 287: 1964-1969. (Pubitemid 30158663)
37. Thomas GL, Wyatt EE, Spring DR. Enriching chemical space with diversity-oriented synthesis [J]. Curr Opin Drug Discov Dev, 2006, 9: 700-712. (Pubitemid 44759564)
38. Galloway WR, Isidro-Llobet A, Spring DR. Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules [J]. Nat Commun, 2010, 1: 80.
39. Pizzirani D, Kaya T, Clemons PA, et al. Stereochemical and skeletal diversity arising from amino propargylic alcohols [J]. Org Lett, 2010, 12: 2822-2825.
40. Thomas GL, Spandl RJ, Glansdorp FG, et al. Anti-MRSA agent discovery using diversity-oriented synthesis [J]. Angew Chem Int Ed, 2008, 47: 2808-2812.
41. Morton D, Leach S, Cordier C, et al. Synthesis of natural-product-like molecules with over eighty distinct scaffolds [J]. Angew Chem Int Ed, 2009, 48: 104-109.
42. Uchida T, Rodriquez M, Schreiber SL. Skeletally diverse small molecules using a build/couple/pair strategy [J]. Org Lett, 2009, 11: 1559-1562.
43. Nielsen TE, Schreiber SL. Towards the optimal screening collection: a synthesis strategy [J]. Angew Chem Int Ed, 2008, 47: 48-56.
44. Kumagai N, Muncipinto G, Schreiber SL. Short synthesis of skeletally and stereochemically diverse small molecules by coupling Petasis condensation reactions to cyclization reactions [J]. Angew Chem Int Ed, 2006, 45: 3635-3638. (Pubitemid 44105728)
45. Vistoli G, Pedretti A, Testa B. Assessing drug-likeness - what are we missing? [J]. Drug Discov Today, 2008, 13: 285-294.
46. Ursu O, Rayan A, Goldblum A, et al. Understanding drug-likeness [J]. WIREs Comput Mol Sci, 2011, 1: 760-781.
47. Kola I, Landis J. Can the pharmaceutical industry reduce attrition rates? [J]. Nat Rev Drug Discov, 2004, 3: 711-715. (Pubitemid 39173511)
48. Oh S, Park SB. A design strategy for drug-like polyheterocycles with privileged substructures for discovery of specific small-molecule modulators [J]. Chem Commun, 2011, 47: 12754-12761.
49. Ko SK, Jang HJ, Kim E, et al. Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif [J]. Chem Commun (Camb), 2006, 28: 2962-2964. (Pubitemid 44036421)