OxymaPure/DIC: An efficient reagent for the synthesis of a novel series of 4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino] benzoyl amino acid ester derivatives

Molecules

Volumn 18, Issue 12, 2013, Pages 14747-14759

  El Faham, Ayman ^a,b   Al Marhoon, Zainab ^a   Abdel Megeed, Ahmed ^a,c   Albericio, Fernando ^d,e,f  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b Alexandria University Faculty Of Science   (Egypt)

^c ALEXANDRIA UNIVERSITY   (Egypt)

^d INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^e UNIVERSITY OF BARCELONA   (Spain)

^f UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

ketoamide; 4 aminobenzoic acid; Amino acid esters; DIC; N acetylisatin; OxymaPure

Indexed keywords

ACETIC ACID DERIVATIVE; AMINO ACID; DACARBAZINE; ESTER; ETHYL 2 CYANO 2 (HYDROXYIMINO)ACETATE; ETHYL 2-CYANO-2-(HYDROXYIMINO)ACETATE; OXIME;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ACETATES; AMINO ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; DACARBAZINE; ESTERS; OXIMES;

EID: 84890930334     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181214747     Document Type: Article

References (44)

1. Li, Z.; Ortega-Vilain, A.C.; Patil, G.S.; Chu, D.L.; Foreman, J.E.; Eveleth, D.D.; Powers, J.C. Novel peptidyl α-Keto amide inhibitors of calpains and other cysteine proteases. J. Med. Chem. 1996, 39, 4089-4098.
2. James, D.A.; Koya, K.; Li, H.; Liang, G.; Xia, Z.; Ying, W.; Wu, Y.; Sun, L. Indole- and indolizine-glyoxylamides displaying cytotoxicity against multidrug resistant cancer cell lines. Bioorg. Med. Chem. Lett. 2008, 18, 1784-1787.
3. Montalban, A.G.; Boman, E.; Chang, C.D.; Ceide, S.C.; Dahl, R.; Dalesandro, D.; Delaet, N.G.J.; Erb, E.; Ernst, J.T.; Gibbs, A.; et al. The design and synthesis of novel α-ketoamide-based p38 MAP kinase inhibitors. J. Bioorg. Med. Chem. Lett. 2008, 18, 1772-1777.
4. Yu, P.-F.; Chen, H.; Wang, J.; He, C.-X.; Cao, B.; Li, M.; Yang, N.; Lei, Z.Y.; Cheng, M.-S. Design, synthesis and cytotoxicity of novel podophyllotoxin derivatives. Chem. Pharm. Bull. 2008, 56, 831-834.
5. Perni, R.B.; Farmer, L.J.; Cottrell, K.M.; Court, J.J.; Courtney, L.F.; Deininger, D.D.; Gates, C.A.; Harbeson, S.L.; Kim, J.L.; Lin, C.; et al. Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants. Bioorg. Med. Chem. Lett. 2004, 14, 1939-1942.
6. Victor, F.; Lamar, J.; Snyder, N.; Yip, Y.; Guo, D.; Yumibe, N.; Johnson, R.B.; Wang, Q.M.; Glass, J.I.; Chen, S.H. P1 and P3 optimization of novel bicycloproline P2 bearing tetrapeptidyl α-ketoamide based HCV protease inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 257-261.
7. Banfi, L.; Guanti, G.; Riva, R. Passerini multicomponent reaction of protected alpha-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors. J. Chem. Soc. Chem. Commun. 2000, 985-986.
8. Nakamura, M.; Inoue, J.; Yamada, T. A two-step, one-pot synthesis of diverse N-pyruvoyl amino acid derivatives using the Ugi reaction. Bioorg. Med. Chem. Lett. 2000, 10, 2807-2810.
9. Xu, P.; Lin, W.; Zhou, X. Synthesis of a peptidomimetic HCMV protease inhibitor library. Synthesis 2002, 8, 1017-1026.
10. Chen, J.J.; Deshpande, V. Rapid synthesis of α-ketoamides using microwave irradiation simultaneous cooling method. Tetrahedron Lett. 2003, 44, 8873-8876.
11. Faggi, C.; Neo, A.G.; Marcaccini, S.; Menchi, G.; Revuelta, J. Ugi four-component condensation with two cleavable components: The easiest synthesis of 2,N-diarylglycines. Tetrahedron Lett. 2008, 49, 2099-2102.
12. Grassot, J.M.; Masson, G.; Zhu, J. Synthesis of α-ketoamides by a molecular-sieves-promoted formal oxidative coupling of aliphatic aldehydes with isocyanides. Angew. Chem. Int. Ed. 2008, 47, 947-950.
13. Chen, Y.H.; Zhang, Y.H.; Zhang, H.J.; Liu, D.Z.; Gu, M.; Li, J.Y.; Wu, F.; Zhu, X.Z.; Li, J.; Nan, F.J. Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent Caspase-3 inhibitors. J. Med. Chem. 2006, 49, 1613-1623.
14. Song, B.; Wang, S.; Sun, C.; Deng, H.; Xu, B. Cesium carbonate promoted aerobic oxidation of arylacetamides: An efficient access to N-substituted α-keto amides. Tetrahedon Lett. 2007, 48, 8982-8986.
15. Chen, C.T.; Bettigeri, S.; Weng, S.S.; Pawar, V.D.; Lin, Y.H.; Liu, C.Y.; Lee, W.Z. Asymmetric aerobic oxidation of α-hydroxy acid derivatives by C4-Symmetric, Vanadate-Centered, Tetrakisvanadyl(V) clusters derived from N-Salicylidene-a-aminocarboxylates. J. Org. Chem. 2007, 72, 8175-8185.
16. Lamberth, C.; Jeanguenat, A.; Cederbaum, F.; de Mesmaecker, A.; Zeller, M.; Kempf, H.J.; Zeun, R. Multicomponent reactions in fungicide research: The discovery of mandipropamid. Bioorg. Med. Chem. 2008, 16, 1531-1545.
17. Sanz, R.; Castroviejo, M.P.; Guilarte, V.; Pérez, A.; Fananás, F.J. Regioselective synthesis of 4- and 7-Alkoxyindoles from 2,3-Dihalophenols: Application to the preparation of indole inhibitors of phospholipase A2. J. Org. Chem. 2007, 72, 5113-5118.
18. Maresh, J.J.; Giddings, L.-A.; Friedrich, A.; Loris, E.A.; Panjikar, S.; Trout, B.L.; Stockigt, J.; Peters, B.; O'Connor, S.E. Strictosidine synthase: Mechanism of a pictet-spengler catalyzing enzyme. J. Am. Chem. Soc. 2008, 130, 710-723.
19. Hua, R.; Takeda, H.A.; Abe, Y.; Tanaka, M. Reactions of a carbamoylstannane with acid chlorides: Highly efficient synthesis of α-Oxo amides. J. Org. Chem. 2004, 69, 974-976.
20. Arasappan, A.; Venkatraman, S.; Padilla, A.I.; Wu, W.; Meng, T.; Jin, Y.; Wong, J.; Prongay, A.; Girijavallabhan, V.; Njoroge, F.G. Practical and efficient method for amino acid derivatives containing β-quaternary center: Application toward synthesis of hepatitis C virus NS3 serine protease inhibitors. Tetrahedron Lett. 2007, 48, 6343-6347.
21. Zhang, L.; Sun, F.; Li, Y.; Sun, X.; Liu, X.; Huang, Y.; Zhang, L.-H.; Ye, X.-S.; Xiao, J. Rapid synthesis of iminosugar derivatives for cell-based in situ screening: Discovery of "Hit" compounds with anticancer activity. ChemMedChem 2007, 2, 1594-1597.
22. González, J.F.; de la Cuesta, E.; Avendano, C. Atom-efficient synthesis of 2,6-diazacyclophane compounds through alcoholysis/reduction of 3-nitroarylmethylene-2,5-piperazinediones. Tetrahedron 2008, 64, 2762-2771.
23. Popp, F.D.; Piccirilli, M. The reaction of N-acetylisatin with amines. J. Heterocycl. Chem. 1971, 8, 473-475.
24. Obafemi, C.A.; Taiwo, F.O.; Iwalewai, E.O.; Akinpelu, D.A. Synthesis, antibacterial and anti-inflammatory activities of some 2-phenylglyoxylic acid derivatives. Int. J. Life Sci. 2013, 2, 22-36.
25. Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Cremonini, M.A.; Placucci, G.; et al. New isatin derivatives with antioxidant activity. Eur. J. Med. Chem. 2010, 45, 1374-1378.
26. Boechat, N.; Kover, W.B.; Bastos, M.M.; Pinto, A.C.; Maciel, L.C.; Mayer, L.M.U.; da Silva, F.S.Q.; Sá, P.M.; Mendonça, J.S.; Wardella, S.M.S.V.; et al. N-Acyl-3,3-difluoro-2-oxoindoles as versatile intermediates for the preparation of different 2,2-difluorophenylacetic derivatives. J. Braz. Chem. Soc. 2008, 19, 445-457.
27. Ghazzali, M.; El-Faham, A.; Abdel-Megeed, A.; Al-Farhan, K. Microwave-assisted synthesis, structural elucidation and biological assessment of 2-(2-acetamidophenyl)-2-oxo-N phenyl acetamide and N-(2-(2-oxo-2(phenylamino) acetyl)phenyl)propionamide derivatives. J. Mol. Struct. 2012, 1013, 163-167.
28. Cheah, W.C.; Black, D.S.; Goh, W.K.; Kumar, N. Synthesis of anti-bacterial peptidomimetics derived from N-acylisatins. Tetrahedron Lett. 2008, 49, 2965-2968.
29. Cheah, W.C.; Wood, K.; Black, D.S.; Kumar, N. Facile ring-opening of N-acylisatins for the development of novel peptidomimetics. Tetrahedron 2011, 67, 7603-7610.
30. Hossain, M.M.; Islam, R.M.; Saha, S.K.; Islam, M.K. An efficient microwave-assisted synthesis of dihydropyrazinones and bis-benzoylketones. Tetrahedron Lett. 2010, 51, 1155-1157.
31. Somogy, L. Transformation of Isatin 3-Acylhydrazones under acetylating conditions: Synthesis and structure elucidation of 1,5′-Disubstituted 3′-Acetylspiro[oxindole-3,2′-[1,3,4]oxadiazolines]. Bull. Chem. Soc. Jpn. 2001, 74, 873-881.
32. Pandey, S.K. Synthesis and evaluation of anti-inflammatory activity of 3-substituted indole derivatives. J. Pharm. Res. 2010, 3, 2738-2741.
33. Verma, M.; Pandeya, S.N.; Singh, K.N.; Stables, J. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm. 2004, 54, 49-56.
34. Subirós-Funosas, R.; Prohens, R.; Barbas, R.; El-Faham, A.; Albericio, F. Oxyma: An efficient additive for peptide synthesis to replace benzotriazole-based HOBt and HOAt with a lower risk of explosion. Chem. Eur. J. 2009, 15, 9394-9403.
35. Subirós-Funosas, R.; Khattab, S.N.; Nieto-Rodriguez, L.; El-Faham, A.; Albericio, F. Oxyma as cyanooxime building block for the construction of versatile reagents assisting acylation reactions in peptide and organic chemistry. Aldrichimica Acta 2013, 40, 21-40.
36. Jad, Y.E.; Khattab, S.N.; El-Faham, A.; Albericio, F. Oxime-based carbonates as useful reagents for both N-protection and peptide coupling. Molecules 2012, 17, 14361-14376.
37. Khattab, S.N.; Subirós-Funosas, R.; El-Faham, A.; Albericio, F. Screening of N-alkyl-cyanoacetamido oximes as substitutes for N-Hydroxysuccinimide. ChemistryOpen 2012, 1, 147-152.
38. Subiros-Funosas, R.; El-Faham, A.; Albericio, F. Use of Oxyma as pH modulatory agent to be used in the prevention of base-driven side reactions and its effect on 2-chlorotrityl chloride resin. Biopolymer 2012, 98, 89-97.
39. El-Faham, A.; Albericio, F. Peptide coupling reagents, more than a letter soup. Chem. Rev. 2011, 111, 6557-6602.
40. Subiros-Funosas, R.; El-Faham, A.; Albericio, F. Aspartimide formation in peptide chemistry: Occurrence, prevention strategies and the role of N-hydroxylamines. Tetrahedron 2011, 67, 8595-8606.
41. El-Faham, A.; Subiros-Funosas, R.; Albericio, F. A novel family of onium salts based upon isonitroso Meldrum's acid proves useful as peptide coupling reagents. Eur. J. Org. Chem. 2010, 2010, 3641-3649.
42. Subiros-Funosas, R.; Acosta, G.A.; El-Faham, A.; Albericio, F. Microwave irradiation and COMU: A superior tool for solid phase peptide synthesis. Tetrahedron Lett. 2009, 50, 6200-6202.
43. Kudelko, A.; Zielinski, W. An efficient synthesis of new 2-aminomethyl-1,3,4-oxadiazoles from enantiomeric phenylglycine hydrazides. Tetrahedron 2009, 65, 1200-1206.
44. Li, J.; Sha, Y. A convenient synthesis of amino acid methyl esters. Molecules 2008, 13, 1111-1119.