Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
2000-12-28
2003-03-04
Kifle, Bruck (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
active
06528646
ABSTRACT:
BACKGROUND OF THE INVENTION
A number of structurally unique C
11
N
5
marine metabolites containing guanidine and either brominated or nonbrominated pyrrole moieties have been isolated from various sponges.
1
Among these are the tricyclic natural products hymenin (1),
2
stevensine (2),
3,4
hymenialdisine (3),
4-8
and debromohymenialdisine (4).
4-9
This group of natural products share in common a fused bicyclic pyrrolo[2,3-c]azepin-8-one ring system that bears either a 2-aminoimidazole (AI) or glycocyamidine appendage. Their structures were elucidated primarily from spectral studies in comparison with biogenetically and structurally related sponge metabolites. The X-ray crystal structure of 3 has been reported by two research groups.
5,6
Hymenialdisine (3) is the only metabolite among the C
11
N
5
and dimerically related natural products that contains a monobromo pyrrole moiety in which the bromine atom is situated in the a position.
10
This invention describes a synthesis of this family of natural products consisting of 1-4.
SUMMARY OF THE INVENTION
The present invention provides a process for producing hymenialdisine and debromohymenialdisine from hymenin via several different pathways for their synthesis.
The present invention further provides the novel compounds which are more fully described and depicted in the Detailed Description, Experimental Details, Claims and Figures. These novel compounds are intermediates or by products of the above pathways. As these compounds are produced in the synthesis of hymenialdisine and debromohymenialdisine, the process for producing these novel compounds is also provided by this invention.
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Xu, Y., et al., “Reactions of 2-Aminoimidazoles with Aldehydes. Hydroxyalkylation and Cycloaddition”, Tetrahedron Letters (1993), 34(44):6981-6984.
Zurita, M., et al., Tetrahedron Letters (1991), “A Diastereoselective Synthesis of Girolline,” vol. 45, pp. 6713-6720; U.K.
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Kobayaski, J., et al., “&agr;-Adrenoceptor blocking action of hymenin, a novel marine alkaloid”, Chemical Abstracts, 108(15): 124371q (1988).
Lancini, G., et al., United Kingdom patent 1,132,013, “Imidazole Derivatives,” published Oct. 30, 1968.
Dalkafouki, A., et al., Tetrahedron Letters (1991), “Synthesis of 2-Dimethylaminoimidazole Derivatives: A New Access to Indoyl-imidazole Alkloids of Marine Origina,” vol. 32 pp. 5325-5328; U.K.
Fernandez-Bolanos, J., et al., “Synthesis of 1-Alkyl (or H)-4-(D-lyxo-tetritol-l-yl)-4-imidazolin-2-ylideneammonium Picrates and Chlorides”, Chemical Abstract 116: 255934p, (1992).
Braun, M., et al., Journal of the American Chemical Society (1978), “Synthesis of Parazoanthoxanthins and Pseudozoanthoxanthins,” vol. 100, pp. 4208-4213; U.S.A.
Braun, M., et al., Journal of the American Chemical Society (1976), “The Synthesis of Zoanthoxanthins,” vol. 32, pp. 3049-3050; U.S.A.
Colson, Genevieve et al., “Mode of Action of the Antitumor Compound Girodazole”, Chemical Abstracts 117: 82994y, (1992).
Commercon, A., et al., Tetrahedron Letters (1991), “A Diastereoselective Synthesis of Girolline,” vol. 32, pp. 1419-1422; U.K.
Horne David A.
Yakushijin Kenichi
Cooper & Dunham LLP
Kifle Bruck
The Trustees of Columbia University in the City of New York
White John P.
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