Studies on chemical modification of monensin. Part 7: Synthesis and Ca2+ ion transport activity of 25-carboxylmonensin

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2629-2632

  Nagatsu, Akito ^a   Tanaka, Rie ^a   Hashimoto, Masayo ^a   Mizukami, Hajime ^a   Ogihara, Yukio ^a   Sakakibara, Jinsaku ^b  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b MEIJO UNIVERSITY   (Japan)

Author keywords

25 carboxylmonensin; Calcium ionophore; Ion transport activity; Monensin

Indexed keywords

25 CARBOXYLMONENSIN; CALCIUM ION; CALCIUM IONOPHORE; CHLOROFORM; LASALOCID; MONENSIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM TRANSPORT; CHEMICAL MODIFICATION; DRUG CONFORMATION; DRUG SYNTHESIS; LIQUID MEMBRANE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034620919     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00233-1     Document Type: Article

References (13)

1. For Part 6, see: Nagatsu (née Nakamura), A.; Tabunoki, Y.; Nagai, S.; Ueda, T.; Sakakibara, J.; Hidaka, H. Chem. Pharm. Bull. 1997, 45, 966-970.
2. (a) Taylor, R. W.; Kauffman, R. F.; Pfeiffer, D. R. Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vol. 1, pp. 157-170.
3. (b) Duelsler, E. N.; Paul, I. C. Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vol. 2, pp. 170-178.
4. (a) Cram, D. J.; Helgeson, R. C.; Koga, K.; Kyba, E. P.; Madan, K.; Sausa, L. R.; Siegel, M. G.; Moreau, P.; Gokel, G. W.; Timko, J. M.; Sogah, G. D. Y. J. Org. Chem. 1978, 43, 2758-2772.
5. (b) Behr, J. P.; Lehn, J. M.; Moras, D.; Thierry, J. C. J. Am. Chem. Soc. 1981, 103, 701-703.
6. 12: C, 64.84; H, 9.25; found: C, 64.59; H, 9.29.
7. 3): 169.0, 170.8, 175.9 (CO).
8. Lindgren, M.; Nilsso, T. Acta Chem. Scand. 1973, 27, 888-890.
9. 3): 180.4 (C-1), 41.0 (C-2), 81.9 (C-3), 37.1 (C-4), 67.6 (C-5), 34.9 (C-6), 70.5 (C-7), 33.5 (C-8), 107.0 (C-9), 39.1 (C-10), 33.2 (C-11), 85.3 (C-12), 82.5 (C-13), 27.4 (C-14), 29.9 (C-15), 86.0 (C-16), 85.1 (C-17), 34.1 (C-18), 33.3 (C-19), 76.5 (C-20), 74.8 (C-21), 31.5 (C-22), 35.9 (C-23), 34.8 (C-24), 97.5 (C-25), 173.6 (C-26), 15.9 (C-27), 58.1 (C-28), 10.8 (C-29), 10.4 (C-30), 27.4 (C-31), 30.7 (C-32), 8.2 (C-33), 14.6 (C-34), 16.9 (C-35), 16.7 (C-36).
10. (a) Koenig, K. E.; Lein, G. M.; Stuckler, P.; Kaneda, T.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3553-3566.
11. (b) Desroches, J.; Dugas, H.; Bouchard, M.; Fyles, T. M.; Robertson, G. D. Can. J. Chem. 1987, 65, 1513-1520.
12. (c) Bartsch, R. A.; Eley, M. D. Tetrahedron Lett. 1993, 34, 5377-5380.
13. + ion.