Macrocyclic peptoids by selective s-acylation of cysteine esters

Synthesis (Germany)

Volumn 45, Issue 6, 2013, Pages 767-772

  Ibrahim, Mohamed A ^a,b,c   Panda, Siva S ^a   Nhon, Linda ^a   Hamed, Ahmed ^a   El Feky, Said A ^b   Katritzky, Alan R ^a,d  

^a University of Florida   (United States)

^b Zagazig University   (Egypt)

^c Misr University for Science and Technology   (Egypt)

^d KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

acylations; amino acids; heterocycles; macrocycles

Indexed keywords

ACYLATIONS; HETEROCYCLES; MACROCYCLES; MACROCYCLICS; PEPTOIDS;

ACYLATION; ESTERIFICATION; ESTERS;

AMINO ACIDS;

(5 METHYLBENZENE 1,3 DIYL)BIS(1H BENZOTRIAZOL 1 YLMETHANONE); (5 NITROBENZENE 1,3 DIYL)BIS(1H BENZOTRIAZOL 1 YLMETHANONE); CYSTEINE ESTER DERIVATIVE; DIETHY 9,9 DIMETHYL 2,7,11,16 TETRAOXO 6,12 DITHIA 3,15 DIAZABICYCLO[15.3.1]HENICOSA 1(21),17,19 TRIENE 4,14 DICARBOXYLATE; DIETHYL 3,3' [BENZENE 1,2 DIYLBIS(CARBONYLSULFANEDIYL)]BIS(2 AMINOPROPANOATE); DIETHYL 3,3' [METHYLBENZENE 1,2 DIYLBIS(CARBONYLSULFANEDIYL)]BIS(2 AMINOPROPANOATE); DIMETHYL 10 METHYL 2,7,13,18 TETRAOXO 3,17 DITHIA 6,14 DIAZATRICYCLO[17.3.1.1]TETRACOSA 1(23),8(24),9,11,19,21 HEXAENE 5,15 DICARBOXYLATE; DIMETHYL 10 NITRO 2,7,13,18 TETRAOXO 3,17 DITHIA 6,14 DIAZATRICYCLO[17.3.1.1]TETRACOSA 1(23),8(24),9,11,19,21 HEXAENE 5,15 DICARBOXYLATE; DIMETHYL 3,3' [5 NITROBENZENE 1,2 DIYLBIS(CARBONYLSULFANEDIYL)]BIS(2 AMINOPROPANOATE); DIMETHYL 3,3' [BENZENE 1,2 DIYLBIS(CARBONYLSULFANEDIYL)]BIS(2 AMINOPROPANOATE); DIMETHYL 3,3' [METHYLBENZENE 1,2 DIYLBIS(CARBONYLSULFANEDIYL)]BIS(2 AMINOPROPANOATE); DIMETHYL 3,3' [NITROBENZENE 1,2 DIYLBIS(CARBONYLSULFANEDIYL)]BIS(2 AMINOPROPANOATE); ESTER DERIVATIVE; ETHYL (4 METHOXYBENZOYL) LEVO CYSTEINATE; ETHYL (4 METHYLBENZOYL) LEVO CYSTEINATE; ETHYL (4 NITROBENZOYL) LEVO CYSTEINATE; ETHYL 2 NAPHTHOYL LEVO CYSTEINATE; ETHYL 5,15 DIAMINO 4,8,12 TRIOXO 3,10 DIOXA 7,13 DITHIAHEXADECAN 16 OATE; METHYL (4 METHOXYBENZOYL) LEVO CYSTEINATE; METHYL (4 METHYLBENZOYL) LEVO CYSTEINATE; METHYL (4 NITROBENZOYL) LEVO CYSTEINATE; METHYL 4,14 DIAMINO 3,7,11 TRIOXO 2,9 DIOXA 6,12 DITHIAPENTADECAN 15 OATE; PEPTOID; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; PROCESS DEVELOPMENT; PROCESS OPTIMIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 84874729772     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1318148     Document Type: Article

References (24)

1. Zervas L., Photaki I., Ghelis N. J. Am. Chem. Soc.: 1963; 85 1337
2. Katritzky A. R., Tala S. R., Abo-Dya N. E., Gyanda K., El-Gendy B. M., Abdel-Samii Z. K., Steel P. J. J. Org. Chem.: 2009; 74 7165
3. Martine R. B., Hedrick R. I. J. Am. Chem. Soc.: 1962; 84 106
4. Clark D. G., Cordes E. H. J. Org. Chem.: 1973; 38 270
5. Comegna D., Benincasa M., Gennaro R., Izzo I., De Riccardis F. Bioorg. Med. Chem.: 2010; 18 2010
6. Craik D. J., Daly N. L., Waine C. Toxicon: 2001; 39 43
7. Trabi M., Craik D. J. Trends Biochem. Sci.: 2002; 27 132
8. Santiveri C. M., León E., Rico M., Jiménez M. A. Chem. Eur. J.: 2008; 14 488
9. Pakkala M., Hekim C., Soininen P., Leinonen J., Koistinen H., Weisell J., Stenman U. H., Vepsäläinen J., Närvänen A. J. Pept. Sci.: 2007; 13 348
10. Xu S., Li H., Shao X., Fan C., Ericksen B., Liu J., Chi C., Wang C. J. Med. Chem.: 2012; 55 6881
11. Davies J. S. J. Pept. Sci.: 2003; 9 471
12. Khakshoor O., Demeler B., Nowick J. S. J. Am. Chem. Soc.: 2007; 129 5558
13. Blackwell H. E., Sadowsky J. D., Howard R. J., Sampson J. N., Chao J. A., Steinmetz W. E., O'Leary D. J., Grubbs R. H. J. Org. Chem.: 2001; 66 5291
14. Punna S., Kuzelka J., Wang Q., Finn M. G. Angew. Chem. Int. Ed.: 2005; 44 2215
15. Angell Y. L., Burgess K. Chem. Soc. Rev.: 2007; 36 1674
16. Roice M., Johanssen I., Meldal M. QSAR Comb. Sci.: 2004; 23 662
17. Blankenstein J., Zhu J. Eur. J. Org. Chem.: 2005; 1949
18. Li P., Roller P. P., Xu J. Curr. Org. Chem.: 2002; 6 411
19. Meutermans W. D. F, Bourne G. T., Golding S. W., Horton D. A., Campitelli M. R., Craik D., Scanlon M., Smythe M. L. Org. Lett.: 2003; 5 2711
20. Katritzky A. R., Cai C., Singh S. K. J. Org. Chem.: 2006; 71 3375
21. Katritzky A. R., Suzuki K., Singh S. K. Croat. Chem. Acta: 2004; 77 175
22. Katritzky A. R., Meher K. N., Cai C., Singh S. K. Rev. Soc. Quim. Mex.: 2004; 48 275
23. Schneider R. F., Subramanian G., Feld T. A., McAfee J. G., Zapf-Longo C., Palladino E., Thomas F. D. J. Nucl. Med.: 1984; 25 223
24. Katritzky A. R., Tala S. R. Abo-Dya N. E, Ibrahim T. K., El-Feky S. A., Gyanda K., Pandya K. M. J. Org. Chem.: 2011; 76 85