Dimeric arylisoquinoline alkaloid compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D40110

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055787290

ABSTRACT:
The present invention provides a method of preparing dimeric arylisoquinoline alkaloids by coupling two isoquinoline building blocks, each of which may be the same or different, together with a symmetrical or nonsymmetrical biaryl building block to form homodimers or heterodimers, including the antiviral michellamines. The present invention also provides new, medically useful homodimeric and heterodimeric arylisoquinoline compounds and derivatives thereof.

REFERENCES:
patent: 5260315 (1993-11-01), Bringmann et al.
patent: 5409938 (1995-04-01), Boyd et al.
Bringmann et al.,"First total synthesis of korupensamines A and B," Heterocycles, 39(2), 503-508 (1994).
Bringmann et al., "Biomimetic oxidative dimerization of korupensamine A: Completion of the first total synthesis of michellamines A, B, and C," Tetrahedron, 50(32), 9643-9648 (1994).
Bringmann et al., "Ancistrobrevine B, the first naphthylisoquinoline alkaloid with a 5,8'-coupling site, and related compounds from ancistrocladus abbreviatus," Phytochemistry, 31(11), 4011-4014 (1992).
Bringmann et al., "Regioselective and atropoisomeric-selective aryl coupling to give naphthyl isoquinoline alkaloids," Angewandte Chemi Int'l Edition, 25(10), 913-915 (1986).
Hoye et al., "Total synthesis of michellamines A-C: Important anti-HIV agents," Tetrahedron Letters, 35(47), 8747-8750 (1994).
Kelly et al., "Convergent total synthesis of the michellamines," Tetrahedron Letters, 35(41), 7621-7624 (1994).
Manfredi et al., "Novel alkaloids from the tropical plant Ancistrocladus abbreviatus inhibit cell killing by HIV-1 and HIV-2," Journal of Med. Chem., 34(12), 3402-3405 (1991).
Bringmann et al., Tetrahedron, vol. 50, No. 26, Jun. 1994 pp. 7807-7814.
Chemical Abstracts, vol. 117, No. 11, Abstract No. 104,239k, Sep. 14, 1992, p. 98, Boyd et al.

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