Regiospecific alkylation of histidine and histamine at N-1 (τ)

Tetrahedron

Volumn 52, Issue 15, 1996, Pages 5363-5370

  Jain, Rahul ^a   Cohen, Louis A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HISTAMINE DERIVATIVE; HISTIDINE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0029920476     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00187-1     Document Type: Article

References (24)

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6. At least 35 cases have been reported: for examples, see Chen, Q.; Rosik, L.O.; Nancarrow, C.D.; Sweet, F. Biochemistry 1989, 28, 8856-8863; Calleman, C.J.; Wachtmeister, C.A. Acta Chem. Scand 1979, 33B, 277-280.
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8. Chillemi, F.; Merrifield, R.B. Biochemistry 1969, 8, 4344-4346; Losse, G.; Krychowski, V.; Tetrahedron Lett. 1971, 4121-4124; Giegel, D.A.; Massey, V.; Williams, C.H. J. Biol. Chem. 1987, 262, 5705-5710; Bambal, R.; Hanzlik, R.P. J. Org. Chem. 1994, 59, 729-732.
9. Chillemi, F.; Merrifield, R.B. Biochemistry 1969, 8, 4344-4346; Losse, G.; Krychowski, V.; Tetrahedron Lett. 1971, 4121-4124; Giegel, D.A.; Massey, V.; Williams, C.H. J. Biol. Chem. 1987, 262, 5705-5710; Bambal, R.; Hanzlik, R.P. J. Org. Chem. 1994, 59, 729-732.
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21. Cf. ref 7a.
22. In previous syntheses of 4 (e.g., ref. 12), the histamine salt was converted to the free base prior to condensation. We have found condensation to occur equally well with the commercial dihydrochloride salt.
23. Prepared by ring opening of 6a, which was obtained according to ref. 12.
24. Hodges, J.C. Synthesis 1987, 20-24.