Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
1998-01-30
2001-03-06
Shah, Mukund J. (Department: 1611)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
active
06197954
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.
REFERENCES:
patent: 3746705 (1973-07-01), Cavalleri et al.
patent: 4812462 (1989-03-01), Blankley et al.
patent: 5091390 (1992-02-01), Ardecky et al.
patent: 5621099 (1997-04-01), Annoura et al.
patent: 5834609 (1998-11-01), Horne et al.
patent: 2016437 (1990-11-01), None
patent: WO8707274 (1987-12-01), None
Kobayashi et al., Experimentia (1988), 42(9), 1064-1065, 1986.
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. .
Dalkafouki, A., et al., Tetrahedron Letters (1991), “Synthesis of 2-Dimethylaminoimidazole Derivatives: A New Access to Indolyl-imidazole Alkaloids 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 Abstracts 116: 255934p, (1992).
Grimmett, M.R., “imidazoles and their Benzo Derivatives: (ii) Reactivity,” in Comprehensive Heterocyclic Chemistry: The Structure, Reactions, Synthsis and Uses of Heterocyclic Compounds, Potts, K.T., et.; Pergamon Press, New York (1984), vol. 5, pp. 404-405; U.S.A. .
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.
Lancini, G., et al., Journal of Heterocyclic Chemistry (1966), “A New Synthesis of Alkyl and Aryl 2-Amino-imidazoles,” vol. 3, pp. 152-154; U.S.A. .
Ruccia, M., et al, Tetrahedron (1974), “Mononuclear Heterocyclic Rearrangements-VI: Conversion of 1,2,4-Oxadiazoles into Imidazoles,” vol. 30, pp. 3859-3864; U.K. .
Walker, R., et al, Journal of the American Chemical Society (1981), “Sceptrin, an Antimicrobial Agent from the sponge Agelas Sceptrum,” vol. 103, pp. 6772-6773; U.S.A. .
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. .
Supriyono, A. et al. (1995) “Bioactive Alkaloids from the Tropical Marine SpongeAxinella carteri, ”, Naturforsch 50:669-674.
Horne David A.
Yakushijin Kenichi
Cooper & Dunham LLP
Kifle Bruck
Shah Mukund J.
The Trustees of Columbia University in the City of New York
White John P.
LandOfFree
Intermediates for the synthesis of debromohymenialdisine and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Intermediates for the synthesis of debromohymenialdisine and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intermediates for the synthesis of debromohymenialdisine and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2534056