Synthesis and preliminary pharmacological evaluation of analogues of caracasanamide, a hypotensive natural product

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 6, 1996, Pages 653-658

  Corelli, Federico ^a   Dei, Donate ^a   Delle Monache, Giuliano ^b   Botta, Bruno ^c   De Luca, Carlo ^d   Carmignani, Marco ^e   Volpe, Anna Rita ^b   Botta, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b CATHOLIC UNIVERSITY   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

^d Ctro Elettrochimica Chim Fis I   (Italy)

^e UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIHYPERTENSIVE AGENT; CARACASANAMIDE; CARACASANAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BLOOD PRESSURE; CONTROLLED STUDY; DRUG SYNTHESIS; HEART RATE; INTRAVENOUS DRUG ADMINISTRATION; MASS SPECTROMETRY; NONHUMAN; RAT; RESPIRATORY FUNCTION; STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 0029981644     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00079-0     Document Type: Article

References (15)

1. Part 4 in the series "Hypertensive Agents from Verbesina Caracasana". For part 3, see: Delle Monache, G.; Botta, B.; Delle Monache, F.; Espinal, R.; De Bonnevaux, S.C.; De Luca, C.; Botta, M.; Corelli, F.; Dei, D.; Gacs-Baitz, E.; Carmignani, M. Bioorg. Med. Chem. Lett., in press.
2. Part 4 in the series "Hypertensive Agents from Verbesina Caracasana". For part 3, see: Delle Monache, G.; Botta, B.; Delle Monache, F.; Espinal, R.; De Bonnevaux, S.C.; De Luca, C.; Botta, M.; Corelli, F.; Dei, D.; Gacs-Baitz, E.; Carmignani, M. Bioorg. Med. Chem. Lett., in press.
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10. Studies on lower homologues of caracasanamide are in progress and will be reported in the due course.
11. Acid chlorides 6a-c are commercially available, while 6d-g were prepared by standard methods from the corresponding acids. 3,4-Dimethoxycinnamic acid and 3-(3′,4′-dimethoxyphenyl)propionic acid were purchased from Aldrich Chemical Co., while 3-(3′,4′-dimethoxyphenyl)propiolic acid and trans-2-(3′,4′-dimethoxyphenyl)cyclopropane-1-carboxylic acid were prepared as reported in the two following references, respectively: a) Adler, E.; Gustaffson, B. Acta Chem. Scand. 1963, 17, 27;
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13. 3OD) δ 1.55-1.70 (2s + m, 10H), 2.72 (s, 3H), 3.20-3.30 (m, 2H), 3.38-3.45 (m, 2H), 3.78-3.85 (s + d, 5H), 5.12-5.20 (t, 1H), 6.85-6.90 (d, 2H), 7.85-7.90 (d, 2H).
14. Carmignani, M.; Finelli, V.N.; Boscolo, P. Toxicol. Appl. Pharmacol. 1983, 69, 442.
15. Delle Monache, G.; Delle Monache, F.; Botta, B.; De Bonnevaux, S.C.; Espinal, R.; De Luca, C.; Carmignani, M. Eur. Pat. n. 0330629 A3., Feb 17, 1989; U. S. Pat. n. 5,059,624, Oct 22, 1991.