A novel scaffold for the modular assembly of receptor models

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7035-7038

  Mink, Daniel ^a   Deslongchamps, Ghislain ^a  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

9 ETHYLADENINE; ADENINE DERIVATIVE; DRUG RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG BINDING; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; MODEL; NUCLEAR MAGNETIC RESONANCE;

EID: 0030599274     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01542-0     Document Type: Article

References (18)

1. 1 Zimmerman, S. C.; Kwan, W. S. Angew. Chem. Int. Ed. Engl. 1995, 34, 2404-2406, and refs. therein.
2. 2 (a) Diederich, F. Cyclophanes; Monographs in Supramolecular Chemistry; the Royal Society of Chemistry: London, 1991.
3. (b) For a chloroform-soluble example, see Whitlock, B. J.; Whitlock, H. W. J. Am. Chem. Soc. 1994, 116, 2301-2311.
4. 3. Ref. 2(a), Chapter 7.
5. 4. (a) Camps, P.; Figueredo, M. Can. J. Chem. 1984, 62, 1184-1192.
6. (b) Deslongchamps, G.; Mink, D.; Boyle, P. D.; Singh, N. Can. J. Chem., 1994 72, 1162-1164.
7. 5. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109-1112.
8. 6. For example, irradiation of the methylene and aryl signals of the PMB protecting group gave enhancements to the methyl ester singlet in 6.
9. 7. For this discussion, "endo" refers to the conformation of the individual cyclopentane units where the ester is quasi-axial and closest to the imide while "exo" refers to the other envelope conformation where the ester is quasi-equatorial, pointing away from the imide.
10. 8. This is also consistent with the observed chemical shift for the methyl esters in the other two alkylation isomers: exo-exo (3.65 ppm), exo-endo (3.33 and 3.68 ppm).
11. 9. Gardette, D.; Gramain, J.-C.; Lhomme, J.; Pascard, C.; Prangé, T. Bull. Soc. Chim. Fr. 1984, 404-408.
12. 10. MM2 * force field with GB/SA chloroform model using MacroModel 4.5: Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liscamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-449.
13. 11. (a) Rebek Jr., J.; Askew, B.; Ballester, P.; Buhr, C.; Jones, S.; Nemeth, D.; Williams K. J. Am. Chem. Soc. 1987, 109, 5033-5035.
14. (b) Rebek Jr., J.; Askew, B.; Ballester, P.; Buhr, C.; Costero, A.; Jones, S.; Williams K. J. Am. Chem. Soc. 1987, 109, 6866-6867
15. (c) Askew, B.; Ballester, P.; Buhr, C.; Jeong, K.S.; Jones, S.; Parris, K.; Williams, K.; Rebek Jr., J., J. Am. Chem. Soc. 1989, 111, 1082-1090.
16. (d) Williams, K.; Askew, B.; Ballester, P.; Buhr, C.; Jeong, K.S.; Jones, S.; Rebek Jr., J., J. Am. Chem. Soc. 1989, 111, 1090-1094.
17. 3 (<1mM) proved to be too low for a statistically useful determination of the association constant. See: Deranleau, D. J. Am. Chem. Soc. 1969, 91, 4044-4049.
18. 13. Quenching the dienolate of 6 with bromohexane gave a 57% yield of the desired dihexyl isomer, D. Mink, D. Shannon, G. Deslongchamps, unpublished results.