A modular synthetic route to dimeric calixarenes: A new family of DNA major groove binders

Synthesis

Volumn , Issue 8, 2011, Pages 1193-1204

  Blecking, C J ^a   Hu, W ^a   Zadmard, R ^b   Dasgupta, A ^a   Schrader, T ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

Author keywords

binding affinity; calixarenes; DNA; major groove; oligopyrroles; sequence selectivity

Indexed keywords

BINDING AFFINITIES; CALIXARENES; MAJOR GROOVE; OLIGOPYRROLES; SEQUENCE SELECTIVITY;

BINDING ENERGY; DNA; PHENOLS;

NUCLEIC ACIDS;

4 (4 CARBOXYBUTANAMIDO) 1 METHYL 1H PYRROLE 2 CARBOXYLIC ACID N.N' BIS(11,17,23 TRIAMINO 25,26,27,28 TETRABUTOXYCALIX[4]AREN 5 YL)DIAMIDE; 4 (4 CARBOXYBUTANAMIDO) 1 METHYL 1H PYRROLE 2 CARBOXYLIC ACID N.N' BIS[25,26,27,28 TETRABUTOXY 11,17,23 TRIS[(TERT BUTOXYCARBONYL)AMINO]CALIX[4]AREN 5 YL]DIAMIDE; 4 [4 [4 (2 CARBOXYACETAMIDO) 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXYLIC ACID N.N' BIS(11,17,23 TRIAMINO 25,26,27,28 TETRABUTOXYCALIX[4]AREN 5 YL)DIAMIDE; 4 [4 [4 (2 CARBOXYACETAMIDO) 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXYLIC ACID N.N' BIS[25,26,27,28 TETRABUTOXY 11,17,23 TRIS[(TERT BUTOXYCARBONYL)AMINO]CALIX[4]AREN 5 YL]DIAMIDE; 4 [4 [4 (3 CARBOXYBENZAMIDO) 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXYLIC ACID N.N' BIS(11,17,23 TRIAMINO 25,26,27,28 TETRABUTOXYCALIX[4]AREN 5 YL)DIAMIDE; 4 [4 [4 (3 CARBOXYBENZAMIDO) 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXAMIDO] 1 METHYL 1H PYRROLE 2 CARBOXYLIC ACID N.N' BIS[25,26,27,28 TETRABUTOXY 11,17,23 TRIS[(TERT BUTOXYCARBONYL)AMINO]CALIX[4]AREN 5 YL]DIAMIDE; ANILINIUM DERIVATIVE; CALIXARENE; DOUBLE STRANDED DNA; GUANIDINE; N.N' BIS(25,26,27,28 TETRABUTOXY 11,17,23 TRIGUANIDINIUM CALIX[4]AREN 5 YL)HEXANEDIAMINE; N.N' BIS[11,17,23 TRIS[2,3 BIS(TERT BUTOXYCARBONYL)GUANIDINO] 25,26,27,28 TETRABUTOXYCALIX[4]AREN 5 YL]HEXANEDIAMINE; N.N' BIS[11,17,23 TRIS[[2,3 BIS(TERT BUTOXYCARBONYL)GUANIDINO]METHYL] 25,26,27,28 TETRABUTOXYCALIX[4]AREN 5 YLMETHYL]HEXANEDIAMINE; N.N' BIS[[11,17,23 TRIS(AMINOMETHYL) 25,26,27,28 TETRABUTOXYCALIX[4]AREN 5 YL]METHYL]HEXANEDIAMINE; N.N' BIS[[25,26,27,28 TETRABUTOXY 11,17,23 TRIS[(GUANIDINIUM)METHYL]CALIX[4]AREN 5 YL]METHYL]HEXANEDIAMINE; N.N' BIS[[25,26,27,28 TETRABUTOXY 11,17,23 TRIS[[(TERT BUTOXYCARBONYL)AMINO]METHYL]CALIX[4]AREN 5 YL]METHYL]HEXANEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BOND; DIMERIZATION; DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 79953779597     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1259980     Document Type: Article

References (36)

1. Cragg G M., Newman D J., Snader K M. J., J. Nat. Prod. 1997 60 52
2. Zadmard R, Schrader T, Angew. Chem. Int. Ed. 2006 45 2703
3. Aoyama Y, Kanamori T, Nakai T, Sasaki T, Horiuchi S, Sando S, Niidome T, J. Am. Chem. Soc. 2003 125 3455
4. Horiuchi S, Aoyama Y, J. Controlled Release 2006 116 107
5. Sansone F, Dudic M, Donofrio G, Rivetti C, Baldini L, Casnati A, Cellai S, Ungaro R, J. Am. Chem. Soc. 2006 128 14528
6. Bagnacani V, Sansone F, Donofrio G, Baldini L, Casnati A, Ungaro R, Org. Lett. 2008 10 3953
7. Galindo M A., Olea D, Romero M A., Gomez J, del Castillo P, Hannon M J., Rodger A, Zamora F, Navarro J A. R., Chem. Eur. J. 2007 13 5075
8. Lalor R, DiGesso J L., Mueller A, Matthews S E., Chem. Commun. 2007 4907
9. Shahgaldian P, Sciotti M A., Pieles U, Langmuir 2008 24 8522
10. Zadmard R, Junkers M, Schrader T, Grawe T, Kraft A, J. Org. Chem. 2003 68 6511
11. Elrod-Erickson M, Benson T E., Pabo C O., Structure 1998 6 451
12. Landschultz W H., Johnson P F., McKnight S L., Science 1998 240 1759
13. Gutsche C D., Iqbal M, Org. Synth. 1990 68 234
14. Gutsche C D., Iqbal M, Stewart D, J. Org. Chem. 1986 51 742
15. Simaan S, Biali S E., J. Org. Chem. 2003 68 7685
16. Conner M, Janout V, Regen S L., J. Org. Chem. 1992 57 3744
17. Jakobi R A., Böhmer V, Grttner C, Kraft D, Vogt W, New J. Chem. 1996 20 493
18. Dudi M, Colombo A, Sansone F, Casnati A, Donofrio G, Ungaro R, Tetrahedron 2004 60 11613
19. Zadmard R, Schrader T, Grawe T, Kraft A, Org. Lett. 2002 4 1687
20. Reinhoudt D N., J. Org. Chem. 1996 61 3476
21. Saadioui M, Shivanyuk A, Böhmer V, Vogt W, J. Org. Chem. 1999 64 3774
22. Evans D. R, Huang M, Fettinger J. C, Williams T. L, Inorg. Chem. 2002 41 5986
23. Ikeda A, Sbinka S, J. Am. Chem. Soc. 1994 116 3102
24. Zadmard R, Junkers M, Schrader T, Grawe T, Kraft A, J. Org. Chem. 2003 68 6511
25. Zadmard R, Taghvaei-Ganjali S, Gorji B, Schrader T, Chem. Asian J. 2009 4 1458
26. Breitkreuz C J., Zadmard R, Schrader T, Supramol. Chem. 2008 20 109
27. Maji S K., Banerjee R, Velmurugan D, Razak A, Fun H K., Banerjee A, J. Org. Chem. 2002 67 633
28. Mukaiyama T, Angew. Chem. 1979 91 798
29. Wade W S., Mrksich M, Dervan P B., J. Am. Chem. Soc. 1992 114 8783
30. White S, Turner J M., Szewczyk J W., Baird E E., Dervan P B., J. Am. Chem. Soc. 1999 121 260
31. Urbach A R., Szewczyk J W., White S, Turner J M., Baird E E., Dervan P B., J. Am. Chem. Soc. 1999 121 11621
32. Melander C, Herman D M., Dervan P B., Chem. Eur. J. 2000 6 4487
33. Ellervik U, Wang C C. C., Dervan P B., J. Am. Chem. Soc. 2000 122 9354
34. See also:, Boger D L., Fink B E., Hedrick M P., J. Am. Chem. Soc. 2000 122 6382
35. Bremer R E., Wurtz N R., Szewczyk J W., Dervan P B., Bioorg. Med. Chem. 2001 9 2093
36. Brown T, Pritchard C E., Turner G, Salisbury S A., J. Chem. Soc., Chem. Commun. 1989 891