Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes

Molecular Diversity

Volumn 16, Issue 3, 2012, Pages 607-612

  Xu, Zhigang ^a   Shaw, Arthur Y ^a   Nichol, Gary S ^b   Cappelli, Alexandra P ^b   Hulme, Christopher ^a,b  

^a UNIVERSITY OF ARIZONA   (United States)

^b University of Arizona   (United States)

Author keywords

Benzimidazole quinoxalines; Bis benzimidazoles; Dihydroquinoxalinone; Multi component reactions (MCRs)

Indexed keywords

2 N BOC ANILINE; 2 PHENYLISONITRILE; ANILINE DERIVATIVE; BENZIMIDAZOLE; CYANIDE; ELEMENT; GLYOXYLIC ACID; ISOCYANIDE; ISONITRILE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; MICROWAVE IRRADIATION; POLYMERIZATION; PRIORITY JOURNAL;

ANILINE COMPOUNDS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRILES;

EID: 84869398408     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-012-9374-1     Document Type: Article

References (39)

1. Mavrova ATS, Anichina KK, Vuchev DI (2005) Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a] benzimidazol-3(2H)-ones. Bioorg Med Chem 13:5550-5559. doi:10.1016/j.bmc.2005. 06.046 (Pubitemid 41187918)
2. Göker H, Kus C, Boykin DW, Yildiz S, Altanlar N (2002) Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorg Med Chem 10:2589-2596. doi:10.1016/S0968-0896(02)00103-7 (Pubitemid 34626222)
3. Richards ML, Lio SC, Sinha A, Tieu KK, Sircar JC (2004) Novel 2-(substituted phenyl)benzimidazole derivatives with potent activity against IgE, cytokines, and CD23 for the treatment of allergy and asthma. J Med Chem 47:6451-6454. doi:10.1021/jm049288j (Pubitemid 39657305)
4. Göker H, Ozden S, Yildiz S, Boykin DW (2005) Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H- benzimidazole-N-alkylated-5-carboxamidines. Eur J Med Chem 40:1062-1069. doi:10.1016/j.ejmech. 2005.05.002 (Pubitemid 41421112)
5. Prichard MN, Frederick SL, Daily S, Borysko KZ, Townsend LB, Drach JC, Kern ER (2011) Benzimidazole analogs inhibit human herpesvirus 6. Antimicrob Agents Chemother 55:2442-2445. doi:10.1128/AAC.01523-10
6. Li Y, Tan C, Gao C, Zhang C, Luan X, Chen X, Liu H, Chen Y, Jiang Y (2011) Discovery of benzimidazole derivatives as novel multi-target EGFR, VEGFR-2 and PDGFR kinase inhibitors. Bioorg Med Chem 19:4529-4535. doi:10.1016/j.bmc.2011.06.022
7. Li X, Yang KH, Li WL, Xu WF (2006) Recent advances in the research of quinoxalinone derivatives. Drug Future 31:979-989. doi:10.1358/dof.2006.031.11. 1037128 (Pubitemid 46165991)
8. Sanna P, Carta A, Loriga M, Zanetti S, Sechi L (1999) Synthesis of 3,6,7-substituted-quinoxalin-2-ones for evaluation of antimicrobial and anticancer activity. Part 2. IL Farmaco 54:161-168. doi:10.1016/S0014-827X(99) 00010-5 (Pubitemid 29237563)
9. Sanna P, Carta A, Loriga M, Zanetti S, Sechi L (1999) Preparation and biological evaluation of 6/7-trifluoromethyl(nitro)-6,7-difluoro-3-alkyl (aryl)-substituted-quinoxalin-2-ones. Part 3. IL Farmaco 54:169-177. doi:10.1016/S0014-827X(99)00011-7 (Pubitemid 29237564)
10. Ali MMM, Ismail MF, El-Gaby MS, Zahran MA, Ammar YA (2000) Synthesis and antimicrobial activities of some novel quinoxalinone derivatives. Molecules 5:864-873. doi:10.3390/50600864 (Pubitemid 38994441)
11. El-Sabbagh OI, El-Sadek ME, Lashine SM, Yassin SHS, El-Nabtity M (2009) Synthesis of new 2(1H)-quinoxalinone derivatives for antimicrobial and antiinflammatory evaluation. Med Chem Res 18:782-797. doi:10.1007/s00044-009- 9203-y
12. Carta A, Sanna P, Gherardini L, Usai D, Zanetti S (2001) Novel functionalized pyrido[2,3-g]quinoxalinones as antibacterial, antifungal and anticancer agents. IL Farmaco 56:933-938. doi:10.1016/S0014-827X(01)01161-2 (Pubitemid 34017400)
13. Gupta D, Ghosh NN, Chandra R (2005) Synthesis and pharmacological evaluation of substituted 5-[4-[2-(6,7-dimethyl-1,2,3,4-tetrahydro-2-oxo-4- quinoxalinyl)ethoxy]phenyl]methylene] thiazolidine-2,4-dione derivatives as potent euglycemic and hypolipidemic agents. Bioorg Med Chem Lett 15:1019-1022. doi:10.1016/j.bmcl.2004.12.041 (Pubitemid 40458641)
14. Patel M, McHugh RJ Jr, Cordova BC, Klabe RM, Erickson-Viitanen S, Trainor GL, Rodgers JD (2000) Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem Lett 10:1729-1731. doi:10.1016/S0960-894X(00)00321-8 (Pubitemid 30495249)
15. Carta A, Sanna P, Loriga M, Setzu MG, Colla PL, Loddo R (2002) Synthesis and evaluation for biological activity of 3-alkyl and 3-halogenoalkyl- quinoxalin-2-ones variously substituted. Part 4. IL Farmaco 57:19-25. doi:10.1016/S0014-827X(01)01153-3 (Pubitemid 34143134)
16. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17-89. doi:10.1021/cr0505728 (Pubitemid 43159621)
17. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168-3210. doi:10.1002/1521-3773(20000915)39:18<3168:: AID-ANIE3168>3.0.CO;2-U
18. Humphrey GR, Kuethe JT (2006) Practical methodologies for the synthesis of indoles. Chem Rev 106:2875-2911. doi:10.1021/cr0505270 (Pubitemid 44193050)
19. Hulme C, Gore VJ (2003) "Multi-component reactions: emerging chemistry in drug discovery" 'from xylocain to crixivan'.CurrMed Chem 10:51-80. doi:10.2174/0929867033368600 (Pubitemid 36131649)
20. Hulme C, Dietrich J (2009) Emerging molecular diversity from the intra-molecular Ugi reaction: iterative efficiency in medicinal chemistry. Mol Divers 13:195-207. doi:10.1007/s11030-009-9111-6
21. Sisko J,MellingerM (2002) Development of a general process for the synthesis of highly substituted imidazoles. Pure Appl Chem 74:1349-1357. doi:10.1351/pac200274081349
22. Dolle RE, La Bourdonnec B, Goodman AJ, Morales GA, Thomas CJ, Zhang W (2009) Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2008. J Comb Chem 11:739-790. doi:10.1021/cc9000828
23. Hulme C, Nixey T (2003) Rapid assembly of molecular diversity via exploitation of isocyanide based multi-component reactions. Curr Opin Drug Discov Dev 6:921-929. doi:10.1002/chin.200413254 (Pubitemid 38084088)
24. Bräuer S, Almstetter M, Antuch W, Behnke D, Taube R, Furer P, Hess S (2005) Evolutionary chemistry approach toward finding novel inhibitors of the type 2 diabetes target glucose-6-phosphate translocase. J Comb Chem 7:218-226. doi:10.1021/cc049867+ (Pubitemid 40522004)
25. Hulme C, Morrissette M, Volz F, Burns C (1998) The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile. Tetrahedron Lett 39:1113-1116. doi:10.1016/S0040-4039(97)10795-X (Pubitemid 28076183)
26. Hulme C, Peng J, Morton G, Salvino JM, Herpin T, Labaudiniere R (1998) Novel safety-catch linker and its application with a Ugi/De-BOC/Cyclization (UDC) strategy to access carboxylic acids, 1,4-benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones. Tetrahedron Lett 39:7227-7230. doi:10.1016/S0040-4039(98)01593-7 (Pubitemid 28545030)
27. Xu Z, Dietrich J, ShawAY,Hulme C (2010) Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines. Tetrahedron Lett 51:4566-4569. doi:10.1016/j.tetlet.2010.06.116
28. Hulme C, Chappeta S, Griffith C, Lee YS, Dietrich J (2009) An efficient solution phase synthesis of triazadibenzoazulenones: 'designer isonitrile free' methodology enabled bymicrowaves. Tetrahedron Lett 50:1939-1942. doi:10.1016/j.tetlet.2009.02.099
29. Tempest P, Ma V, Thomas S, Hua Z, Kelly MG, Hulme C (2001) Two-step solution-phase synthesis of novel benzimidazoles utilizing a UDC (Ugi/de-Boc/cyclize) strategy. Tetrahedron Lett 42:4959-4962. doi:10.1016/S0040-4039(01)00919-4 (Pubitemid 32607371)
30. Tempest P, Pettus L, Gore V, Hulme C (2003) MCC/SNAr methodology. Part 2: Novel three-step solution phase access to libraries of benzodiazepines. Tetrahedron Lett 44:1947-1950. doi:10.1016/S0040-4039(03)00084-4 (Pubitemid 36183439)
31. Liu A, Zhou H, Su G, ZhangW, Yan B (2009) Microwave-assisted fluorous synthesis of a 1,4-benzodiazepine-2,5-dione library. J Comb Chem 11:1083-1093. doi:10.1021/cc900109e
32. Cuny G, Bois-Choussy M, Zhu J (2004) Palladium-and coppercatalyzed synthesis of medium-and large-sized ring-fused dihydroazaphenanthrenes and 1,4-benzodiazepine-2,5-diones. Control of reaction pathway by metal-switching. J Am Chem Soc 126: 14475-14484. doi:10.1021/ja047472o (Pubitemid 39463631)
33. Kennedy AL, Fryer AM, Josey JA (2002) A new resin-bound universal isonitrile for the Ugi 4CC reaction: preparation and applications to the synthesis of 2,5-diketopiperazines and 1,4-benzodiazepine-2,5-diones. Org Lett 4:1167-1170. doi:10.1021/ol0256015
34. Xu Z, Shaw AY, Dietrich J, Cappelli AP, Nichol G, Hulme C (2012) Facile, novel two-step syntheses of benzimidazoles, bisbenzimidazoles, and bis-benzimidazole-dihydroquinoxalines. Mol Divers 16:73-79. doi:10.1007/s11030- 011-9354-x
35. Park SJ, Keum G, Kang SB, Koh HY, Kim Y (1998) A facile synthesis of N-carbamoylmethyl-α-aminobutyrolactones by the Ugi multicomponent condensation reaction. Tetrahedron Lett 39:7109- 7112. doi:10.1016/S0040- 4039(98)01509-3 (Pubitemid 28414795)
36. Zhu D, Chen R, Liang H, Li S, Pan L, Chen X (2010) An efficient procedure for the synthesis of morpholin-2-one-3-carboxamide derivatives in good diastereoselectivity by the Ugi reaction. Synlett 6:897-900. doi:10.1055/s-0029-1219533
37. Cristau P, Vors JP, Zhu J (2003) Solid-phase synthesis of natural product-like macrocycles by a sequence of Ugi-4CR and SNArbased cycloetherification. Tetrahedron Lett 44:5575. doi:10.1016/S0040-4039(03)01378-9 (Pubitemid 36782582)
38. Shaw AY, Xu Z, Hulme C (2012) Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles. Tetrahedron Lett 53:1998-2000. doi:10.1016/j.tetlet.2012.02.030
39. Shaw AY, McLaren JA, Nichol GS, Hulme C (2012) Hydrazinemediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles. Tetrahedron Lett 53:2592-2594. doi:10.1016/j.tetlet.2012.03.033