Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-10-03
1999-10-26
Jones, Dwayne C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549456, A01N 4308
Patent
active
059729970
DESCRIPTION:
BRIEF SUMMARY
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH DEVELOPMENT
Not Applicable
MICROFICHE APPENDIX
Not Applicable
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to compounds which have antitumor activity and are useful as antitumor agents.
2. Description of the Related Art
Several compounds such as anthracycline and the like have been reported as antibiotics which have the anthraquinone nucleus (CRC Handbook of Antibiotic Compounds, CRC Press, U.S.A., 1981).
BRIEF SUMMARY OF THE INVENTION
The present invention relates to UCT1072 compounds.
BRIEF DESCRIPTION OF THE DRAWINGS
Not Applicable
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides UCT1072 compounds represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2 together represent --CH(OH)CH.sub.2 O-- or --CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 --, which has antitumor activity. The compounds can be obtained by culturing a microorganism belonging to the genus Aspergillus.
Among the UCT1072 compounds represented by formula (I), the compound in which R.sup.1 and R.sup.2 together represent --CH(OH)CH.sub.2 -- is called UCT1072M1, and the compounds in which R.sup.1 and R.sup.2 together represent --CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 -- are called UCT1072M2 and UCT1072M3. UCT1072M2 and UCT1072M3 are respective stereoisomers.
The physicochemical properties of UCT1072 compounds are shown below. The physicochemical properties were measured by the following apparatus:
Mass spectrum:
Ultraviolet absorption spectrum:
Infrared absorption spectrum:
Nuclear magnetic resonance spectrum:
Optical rotation:
Melting point:
Color and form of the substance:
Melting point:
Optical rotation:
Ultraviolet absorption spectrum:
Infrared absorption spectrum:
Molecular formula:
Molecular weight:
FAB mass spectrum (positive mode):
High resolution FAB mass spectrum (positive mode): :357.0610)
.sup.1 H NMR spectrum (500 MHz, DMSO-d.sub.6): .delta. ppm
.sup.13 C NMR (125 MHz, DMSO-d.sub.6): .delta. ppm 53.3(d), 72.8(d), 74.9(t), 101.5(d), 108.1(d), 108.5(s), 109.0(d), 110.8(s), 113.0(d), 117.4(s), 134.8(s), 135.6(s), 159.4(s), 164.3(s), 165.28 (s), 165.33(s), 180.9(s), 189.1(s)
Color reagent:
Thin-layer chromatography:
Color and form of the substance:
Melting point:
Optical rotation:
Ultraviolet absorption spectrum:
Infrared absorption spectrum:
Molecular formula:
Molecular weight:
FAB mass spectrum (positive mode):
High resolution FAB mass spectrum (positive mode):
m/z 369.0993 (M+H)+(calculated for C.sub.20 H.sub.17 O.sub.7 :369.0975)
.sup.1 H NMR (400 MHz, DMSO-d.sub.6): .delta. ppm 7.12, 12.12, 12.40
.sup.13 C NMR (100 MHz, DMSO-d.sub.6): .delta. ppm 108.6(s), 108.8(d), 110.8(s), 123.1(s), 134.9(s), 135.2(s), 159.8(s), 164.2(s), 165.2(s), 166.0(s), 181.0(s), 189.3(s)
Color reagent:
Thin-layer chromatography:
Color and form of the substance:
Melting point:
Optical rotation:
Ultraviolet absorption spectrum:
.lambda..sub.max (DMSO) nm 293 (20000), 332 (9300), 459 (4700)
Infrared absorption spectrum:
Molecular formula:
Molecular weight:
FAB mass spectrum (positive mode):
High resolution FAB mass spectrum: :369.0975)
.sup.1 H NMR (400 MHz, DMSO-d.sub.6) .delta. ppm: 7.11, 12.12, 12.31
.sup.13 C NMR (100 MHz, DMSO-d.sub.6) .delta. ppm: 108.6(s), 108.9(d), 110.9(s), 125.9(s), 134.9(s), 135.1(s), 158.9(s), 164.3(s), 165.2(s), 165.5(s), 181.1(s), 189.3(s)
Color reagent:
Thin-layer chromatography:
Biological activities of the UCT1072 compounds are described by the following test examples.
TEST EXAMPLE 1
Human Lung Cancer Lu-65 Cells
Respective cells were dispensed in 3.times.10.sup.3 cells/well portions into a 96 well microtiter plate (produced by Nunc Co., #167008) and pre-cultured at 37.degree. C. for 24 hours in a 5% carbon dioxide incubator. Thereafter, 3 mM solution of UCT1072M1, UCT1072M2 or UCT1072M3 was serially diluted and dispensed in 50 .mu.l portions into the wells. In this example, final concentrations of UCT1072 in each solution are at most 0.013 .mu.M. Culturing was continued at 37.degree. C. for 72 hours in the
REFERENCES:
Anderson et al., "Versicolorin A hemiacetal, hydroxydihydrosterigmatocystin, and aflatoxin G2a reductase activity in extracts from Aspergillus parasiticus", Mycopathologia 111:39-45, 1990.
Sean M. McGuire et al. (J. Am. Chem. Soc.), vol. 111, No. 21, (1989), pp. 8308-8309.
John A. Anderson et al. (Mycopathologia), vol. 111, No. 1, (1990), p. 39-45.
CRC Handbook Of Antibiotic Compounds, Vol. III, Janos Berdy, et al.
Ando Katsuhiko
Asai Akira
Ashizawa Tadashi
Kakita Shingo
Kita Katsunori
Jones Dwayne C.
Kyowa Hakko Kogyo Co. Ltd.
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