One-pot syntheses of isoquinolin-3-ones and benzo-1,4-diazepin-2,5-diones utilizing Ugi-4CR post-transformation strategy

ACS Combinatorial Science

Volumn 15, Issue 4, 2013, Pages 202-207

  Che, Chao ^a,b,c   Li, Song ^a,c   Yu, Zhixiong ^b   Li, Fangfang ^a   Xin, Shengchang ^a   Zhou, Liyan ^a   Lin, Shuo ^a,d   Yang, Zhen ^a,e  

^a PEKING UNIVERSITY   (China)

^b South China Center for Innovative Pharmaceuticals   (China)

^c Shenzhen Shengjie Biotech Co Ltd   (China)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e Peking University   (China)

Author keywords

benzo 1,4 diazepin 2,5 diones; diversity oriented synthesis; isoquinolin 3 ones; multicomponent reaction; one pot synthesis; Ugi 4CR

Indexed keywords

AMIDE; BENZODIAZEPINE DERIVATIVE; BZ 423; BZ-423; CARBOXYLIC ACID; ISOQUINOLINE DERIVATIVE; NITRILE; PHTHALALDEHYDE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; METHODOLOGY; SYNTHESIS;

AMIDES; BENZODIAZEPINES; CARBOXYLIC ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; ISOQUINOLINES; NITRILES; O-PHTHALALDEHYDE;

EID: 84876007433     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co400001h     Document Type: Article

References (53)

1. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Multiple-Component Condensation Strategies for Combinatorial Library Synthesis Acc. Chem. Res. 1996, 29, 123-131
2. Dömling, A.; Ugi, I. Multicomponent Reactions with Isocynides Angew. Chem., Int. Ed. 2000, 39, 3168-3210
3. Dömling, A. Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry Chem. Rev. 2006, 106, 17-89
4. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Cascade Reactions in Total Synthesis Angew. Chem., Int. Ed. 2006, 45, 7134-7186
5. Enders, D.; Grondal, C.; Hüttl, M. R. M. Asymmetric Organocatalytic Domino Reactions Angew. Chem., Int. Ed. 2007, 46, 1570-1581
6. Toure, B. B.; Hall, D. G. Natural Product Synthesis Using Multicomponent Reaction Strategies Chem. Rev. 2009, 109, 4439-4486
7. Blackwell, H. E. Hitting the SPOT: Small-molecule Macroarrays Advance Combinatorial Synthesis Curr. Opin. Chem. Biol. 2006, 10, 203-212
8. Akritopoulou-Zanze, I. Isocyanide-based Multicomponent Reactions in Drug Discovery Curr. Opin. Chem. Biol. 2008, 12, 324-331
9. Bräuer, S.; Almstetter, M.; Antuch, W.; Behnke, D.; Taube, R.; Furer, P.; Hess, S. Evolutionary Chemistry Approach toward Finding Novel Inhibitors of the Type 2 Diabetes Target Glucose-6-phosphate Translocase J. Comb. Chem. 2005, 7, 218-226
10. Weber, L. The Application of Multi-component Reactions in Drug Discovery Curr. Med. Chem. 2002, 9, 205-2093
11. Hulme, C.; Gore, V. Multi-component Reactions: Emerging Chemistry in Drug Discovery 'From Xylocain to Crixivan' Curr. Med. Chem. 2003, 10, 51-80
12. Dömling, A. The Discovery of New Isocyanide-based Multi-component Reactions Curr. Opin. Chem. Biol. 2000, 4, 318-323
13. Roth, J.; Madoux, F.; Hodder, P.; Roush, W. R. Synthesis of Small Molecule Inhibitors of the Orphan Nuclear Receptor Steroidogenic Factor-1 (NR5A1) Based on Isoquinolinone Scaffolds Bioorg. Med. Chem. Lett. 2008, 18, 2628-2632
14. Hu, J.; Zhang, W. D.; Liu, R. H.; Zhang, C.; Shen, Y. H.; Li, H. L.; Liang, M. J.; Xu, X. K. Benzophenanthridine Alkaloids from Zanthoxylum nitidum (Roxb.) DC, and Their Analgesic and Anti-Inflammatory Activities Chem. Biodiversity 2006, 3, 990-995
15. Micale, N.; Ettari, R.; Schirmeister, T.; Evers, A.; Gelhaus, C.; Leippe, M.; Zappalà, M.; Grasso, S. Novel 2 H -Isoquinolin-3-ones as Antiplasmodial Falcipain-2 Inhibitors Bioorg. Med. Chem. 2009, 17, 6505-6511
16. Trotter, B. W.; Nanda, K. K.; Kett, N. R.; Regan, C. P.; Lynch, J. J.; Stump, G. L.; Kiss, L.; Wang, J.; Spencer, R. H.; Kane, S. A.; White, R. B.; Zhang, R.; Anderson, K. D.; Liverton, N. J.; McIntyre, C. J.; Beshore, D. C.; Hartman, G. D.; Dinsmore, C. J. Design and Synthesis of Novel Isoquinoline-3-nitriles as Orally Bioavailable Kv1.5 Antagonists for the Treatment of Atrial Fibrillation J. Med. Chem. 2006, 49, 6954-6957
17. Hutchinson, J. H.; Cook, J. J.; Brashear, K. M.; Breslin, M. J.; Glass, J. D.; Gould, R. J.; Halczenko, W.; Holahan, M. A.; Lynch, R. J.; Sitko, G. R.; Stranieri, M. T.; Hartman, G. D. Non-Peptide Glycoprotein IIb/IIIa Antagonists. 11. Design and in Vivo Evaluation of 3,4-Dihydro-1(1 H)-isoquinolinone-Based Antagonists and Ethyl Ester Prodrugs J. Med. Chem. 1996, 39, 4583-4591
18. Ontoria, J. M.; Rydberg, E. H.; Di Marco, S.; Tomei, L.; Attenni, B.; Malancona, S.; Martin Hernando, J. I.; Gennari, N.; Koch, U.; Narjes, F.; Rowley, M.; Summa, V.; Olsen, D. B.; De Francesco, R.; Altamura, S.; Migliaccio, G.; Carfì, A. Identification and Biological Evaluation of a Series of 1 H -Benzo[ de ]isoquinoline-1,3(2 H)-diones as Hepatitis C Virus NS5B Polymerase Inhibitors J. Med. Chem. 2009, 52, 5217-5227
19. Malancona, S.; Donghi, M.; Ferrara, M.; Hernando, J. I. M.; Pompei, M.; Pesci, S.; Ontoria, J. M.; Koch, U.; Rowley, M.; Summa, V. Allosteric Inhibitors of Hepatitis C Virus NS5B Polymerase Thumb Domain Site II: Structure-Based Design and Synthesis of New Templates Bioorg. Med. Chem. 2010, 18, 2836-2848
20. Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamoto, Y.; Moritani, Y.; Saruta, K.; Higashijima, T.; Kotera, J.; Takagi, M.; Kikkawa, K.; Omori, K. Novel, Potent, and Selective Phosphodiesterase 5 Inhibitors: Synthesis and Biological Activities of a Series of 4-Aryl-1-isoquinolinone Derivatives J. Med. Chem. 2001, 44, 2204-2218
21. Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamoto, Y.; Moritani, Y.; Saruta, K.; Higashijima, T.; Kotera, J.; Fujishigeb, K.; Takagi, M.; Kikkawa, K.; Omori, K. 1,7- and 2,7-Naphthyridine Derivatives as Potent and Highly Specific PDE5 Inhibitors Bioorg. Med. Chem. Lett. 2003, 13, 2341-2345
22. Rhee, H. K.; Lim, S. Y.; Jung, M. J.; Kwon, Y.; Kim, M. H.; Choo, H. Y. Synthesis of Isoquinolinone-Based Tetracycles as Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors Bioorg. Med. Chem. 2009, 17, 7537-7541
23. Jagtap, P. G.; Baloglu, E.; Southan, G. J.; Mabley, J. G.; Li, H.; Zhou, J.; Duzer, J.; Salzman, A. L.; Szabo, C. Discovery of Potent Poly(ADP-ribose) Polymerase-1 Inhibitors from the Modification of Indeno[1,2- c ]isoquinolinone J. Med. Chem. 2005, 48, 5100-5103
24. Lin, L. Z.; Cordell, G. A. Quinoline alkaloids from Camptotheca acuminata Phytochemistry 1989, 28, 1295-1297
25. Wang, S. Q.; Wang, G. Q.; Huang, B. K.; Zhang, Q. Y.; Qin, L. P. Isoquinoline Alkaloids from Broussonetia Papyrifera Fruits Chem. Nat. Compd. 2007, 43, 100-102
26. Wright, W. B.; Brabander, H. J.; Greenblatt, E. N.; Day, I. P.; Hardy, R. A. Derivatives of 1,2,3,11a-Tetrahydro-5H-Pyrrolo[2,1-C][1,4]Benzodiazepine-5, 11(10H)-Dione as Anxiolytic Agents J. Med. Chem. 1978, 21, 1087-1089
27. Li, X.; Yu, J.; Atack, J. R.; Cook, J. M. Development of Selective Ligands for Benzodiazepine Receptor Subtypes by Manipulating the Substituents at Positions 3- and 7- of Optically Active BzR Ligands Med. Chem. Res. 2004, 13, 259-281
28. Leimgruber, W.; Stefanovic, V.; Schenker, F.; Karr, A.; Berger, J. Isolation and Characterization of Anthramycin, a New Antitumor Antibiotic J. Am. Chem. Soc. 1965, 87, 5791-5793
29. Leimgruber, W.; Batcho, A. D.; Schenker, F. The Structure of Anthramycin J. Am. Chem. Soc. 1965, 87, 5793-5795
30. Cooper, N.; Hagan, D. R.; Tiberghien, A.; Ademefun, T.; Mattews, C. S.; Howard, P. W.; Thurston, D. E. Synthesis of Novel C2-Aryl Pyrrolobenzodiazepines (Pbds) as Potential Antitumour Agents Chem. Commun. 2002, 1764-1765
31. Kamal, A.; Reddy, K. L.; Devaiah, V.; Shankaraiah, N.; Reddy, G.; Raghavan, S. Solid-Phase Synthesis of a Library of Pyrrolo[2,1- c ][1,4]benzodiazepine-5,11-diones with Potential Antitubercular Activity J. Comb. Chem. 2007, 9, 29-42
32. Hsu, M. C.; Schutt, A. D.; Holly, M.; Slice, L. W.; Sherman, M. L.; Richman, D. D.; Potash, M. J.; Volsky, D. J. Inhibition of HIV Replication in Acute and Chronic Infections in Vitro by A Tat Antagonist Science 1991, 254, 1799-1802
33. Araújo, A. C.; Nicotra, F.; Airoldi, C.; Costa, B.; Giagnoni, G.; Fumagalli, P.; Cipolla, L. Synthesis and Biological Evaluation of Novel Rigid 1,4-Benzodiazepine-2,5-dione Chimeric Scaffolds Eur. J. Org. Chem. 2008, 635-639
34. Li, X.; Yu, J.; Atack, J. R.; Cook, J. M. Development of Selective Ligands for Benzodiazepine Receptor Subtypes by Manipulating the Substituents at Positions 3- and 7- of Optically Active BzR Ligands Med. Chem. Res. 2004, 13, 259-281
35. Loudni, L.; Roche, J.; Potiron, V.; Clarhaut, J.; Bachmann, C.; Gesson, J.; Tranoy-Opalinski, I. Design, synthesis and biological evaluation of 1,4-benzodiazepine-2,5-dione-based HDAC inhibitors Bioorg. Med. Chem. Lett. 2007, 17, 4819-4823
36. Mondraǵn, L.; Orzáez, M.; Sanclimens, G.; Moure, A.; Armiñán, A.; Sepúlveda, P.; Messeguer, A.; Vicent, M. J.; Pérez-Payá, E. Modulation of Cellular Apoptosis with Apoptotic Protease-Activating Factor 1 (Apaf-1) Inhibitors J. Med. Chem. 2008, 51, 521-529
37. Marugan, J. J.; Leonard, K.; Raboisson, P.; Gushue, J. M.; Calvo, R.; Koblish, H. K.; Lattanze, J.; Zhao, S. Y.; Cummings, M. D.; Player, M. R.; Schubert, C.; Maroney, A. C.; Lu, T. Enantiomerically Pure 1,4-Benzodiazepine-2, 5-diones as Hdm2 Antagonists Bioorg. Med. Chem. Lett. 2006, 16, 3115-3120
38. Leonard, K.; Marugan, J. J.; Raboisson, P.; Calvo, R.; Gushue, J. M.; Koblish, H. K.; Lattanze, J.; Zhao, S. Y.; Cummings, M. D.; Player, M. R.; Maroney, A. C.; Lu, T. Novel 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists with improved cellular activity Bioorg. Med. Chem. Lett. 2006, 16, 3463-3468
39. Che, C.; Xiang, J.; Wang, G. X.; Fathi, R.; Quan, J. M.; Yang, Z. One-Pot Synthesis of Functionalized Quinoline-based Poly-Heterocycles by a Tandem Three-Component Reaction J. Comb. Chem. 2007, 9, 982-989
40. Xiang, J.; Yang, H.; Che, C.; Zou, H.; Yang, H.; Wei, Y.; Quan, J.; Zhang, H.; Yang, Z.; Lin, S. Identifying Tumor Cell Growth Inhibitors by Combinatorial Chemistry and Zebrafish Assays PLoS One 2009, 4, e4361
41. Zhong, H.; Zou, H.; Semenov, M. V.; Moshinsky, D.; He, X.; Huang, H.; Li, S.; Quan, J.; Yang, Z.; Lin, S. Characterization and Development of Novel Small-Molecules Inhibiting GSK3 and Activating Wnt Signaling Mol. BioSyst. 2009, 5, 1356-1360
42. Zou, H.; Zhou, L.; Li, Y.; Cui, Y.; Zhong, H.; Pan, Z.; Yang, Z.; Quan, J. Benzo[ e ]isoindole-1,3-diones as Potential Inhibitors of Glycogen Synthase Kinase-3 (GSK-3). Synthesis, Kinase Inhibitory Activity, Zebrafish Phenotype, and Modeling of Binding Mode J. Med. Chem. 2010, 53, 994-1003
43. 2Cl-Mediated Ring-Opening Reaction of Oxacycles Org. Lett. 2010, 12, 488-491
44. Che, C.; Li, S.; Jiang, X. L.; Quan, J. M.; Lin, S.; Yang, Z. One-Pot Synthesis of Chromeno[3,4-c]pyrrole-3,4-diones via Ugi-4CR and Intramolecular Michael Addition Org. Lett. 2010, 12, 4682-4685
45. Che, C.; Li, S.; Yang, B.; Xin, S. C.; Yu, Z. X.; Shao, T. F.; Tao, C. Y.; Lin, S.; Yang, Z. Synthesis and Characterization of Sant-75 Derivatives as Hedgehog Pathway Inhibitors Beilstein J. Org. Chem. 2012, 8, 841-849
46. Xiang, Z.; Luo, T. P.; Lu, K.; Cui, J. Y.; Shi, X. M.; Fathi, R.; Chen, J. H.; Yang, Z. Concise Synthesis of Isoquinoline via the Ugi and Heck Reactions Org. Lett. 2004, 6, 3155-3158
47. Kaüm, L. E.; Grimaud, L.; Oble, J. Phenol Ugi-Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols Angew. Chem., Int. Ed. 2005, 44, 7961-7964
48. Ramazani, A.; Rezaei, A. Novel One-Pot, Four-Component Condensation Reaction: An Efficient Approach for the Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives by a Ugi-4CR/ aza -Wittig Sequence Org. Lett. 2009, 11, 995-997
49. Lee, D.; Sello, J. K.; Schreiber, S. L. Pairwise Use of Complexity-Generating Reactions in Diversity-Oriented Organic Synthesis Org. Lett. 2000, 2, 709-712
50. Wang, W.; Ollio, S.; Herdtweck, E.; Dömling, A. Polycyclic Compounds by Ugi-Pictet-Spengler Sequence J. Org. Chem. 2011, 76, 637-644
51. N2′-Heck Double Cyclization J. Org. Chem. 2010, 75, 5134-5143
52. Bienaymé, H.; Bouzi, K. Synthesis of Rigid Hydrophobic Tetrazoles Using an Ugi Multi-Component Heterocyclic Condensation Tetrahedron Lett. 1998, 39, 2735-2738
53. Bonnaterre, F.; Bois-Choussy, M.; Zhu, J. P. Rapid Access to Oxindoles by the Combined Use of an Ugi Four-Component Reaction and a Microwave-Assisted Intramolecular Buchwald-Hartwig Amidation Reaction Org. Lett. 2006, 8, 4351-4354