Antibiotic compounds DC-92B and DC-92D

Details Antibiotic compounds DC-92B and DC-92D Antibiotic compounds DC-92B and DC-92D

1988-03-17

1989-07-11

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31178

Patent

active

048473871

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to anti-tumor antibiotics DC-92B and DC-92D having the anthraquinone moiety and to a process for producing the same.


BACKGROUND ART

Mitomycins, anthracyclines, anthraquinones, etc. are known as anti-tumor antibiotics having the quinone moiety [CRC Handbook of Antibiotic Compounds, Volume 3, 1981 (CRC Press U.S.A.)]. Of these, the compounds represented by the following formula are illustrative of antraquinone compounds.


______________________________________ ##STR3## R.sub.A R.sub.B ______________________________________ Pluramycin A COCH.sub.3 X Kidamycin H Z Hedamycin H Y Neopluramycin COCH.sub.3 Z ______________________________________ ##STR4## - ##STR5## - ##STR6## -
Mitomycin C, adriamycin, bleomycin and others are known as anti-tumor antibiotics used for chemotherapy against cancers. However, there has been a constant demand for substances with higher anti-tumor activity because these anti-tumor substances presently available are ineffective against some types of cancer and involve the problem of drug resistance.


DISCLOSURE OF THE INVENTION

In accordance with the present invention, novel substances DC-92B and/or DC-92D having anti-tumor and antibacterial activities can be obtained by culturing a microorganism belonging to the genus Actinomadura and capable of producing DC-92B and/or DC-92D.
The physicochemical properties of DC-92B are shown below.
(a) Molecular weight: 776 (Mass spectrometry; SI-MS m/z 777 [M+H].sup.+)
(b) Color: Dark red
(c) Ultraviolet absorption spectra: As shown in FIGS. 1 and 2 [FIG. 1: in methanol, FIG. 2: in alkaline (NaOH) methanol]
(d) Infrared absorption spectrum: As shown in FIG. 5 (measured in CHCl.sub.3)
(e) Solubility: Soluble in methanol, ethanol, acetone, chloroform, ethyl acetate, toluene and dimethylsulfoxide; sparingly soluble in water and hexane
(f) .sup.1 H-NMR spectrum (400 MHz, measured in CDCl.sub.3, internal standard: TMS) .delta.(ppm): 13.88 (1H, br s), ca.9.7 (1H, br), 8.34 (1H, br s), 8.04 (1H, d, J=0.6 Hz), 6.53 (1H, s), 5.50 (1H, br d, J=11.0 Hz), 5.45 (1H, br dd, J=10.2, 1.4 Hz), 3.56 (1H, dq, J=8.6, 6.0 Hz), 3.54 (1H, s), 3.22 (1H, br dd, J=9.8, 8.6 Hz), 3.17 (1H, d, J=4.9 Hz), 3.02 (3H, d, J=0.6 Hz), 2.86 (1H, ddd, J=13.2, 9.8, 3.4 Hz), 2.72 (1H, d, J=4.9 Hz), 2.61 (6H, br s), ca.2.6 (1H), 2.32 (6H, s), 2.19 (1H, m), 1.91 (3H, s), 1.59 (3H, s), 1.44 (3H, d, J=6.0 Hz), 1.38 (1H, br dd, J=11.1, 3.8 Hz), 1.35 (3H, s), 1.12 (3H, s), ca.1.1 (1H, m), 1.08 (3H, s)
(g) .sup.13 C-NMR spectrum (100 MHz measured in CDCl.sub.3, internal standard: TMS) .delta.(ppm): 187.8, 183.2, 178.3, 164.9, 159.3, 156.0, 150.0, 140.0, 138.8, 137.5, 132.6, 126.2, 126.1, 126.0, 119.1, 115.6, 110.9, 100.0, 79.0, 77.5, 75.2, 71.7, 67.3, 63.6, 62.9, 59.9, 59.0, 58.6, 58.2, 43.1, 41.0, 40.4, 28.5, 25.2, 24.2, 24.1, 19.9, 19.7, 18.8, 14.3
(h) Thin layer chromatography: R.sub.f =0.54 [Chemically bonded silica gel thin layer (HPTLC plate Art 15647, E. Merck), developer: toluene/acetone (6:4 V/V)]
(i) Weakly basic substance
The physicochemical properties of DC-92D are shown below.
(a) Molecular weight: 774 (Mass spectrometry; SI-MS m/z 775 [M+H].sup.+)
(b) Color: Dark red
(c) Ultraviolet absorption spectra: As shown in FIGS. 3 and 4 [FIG. 3: in methanol, FIG. 4: in alkaline (NaOH) methanol]
(d) Infrared absorption spectrum: As shown in FIG. 6 (measured in CHCl.sub.3)
(e) Solubility: Soluble in methanol, ethanol, acetone, chloroform, ethyl acetate, toluene and dimethylsulfoxide; sparingly soluble in water and hexane
(f) .sup.1 H-NMR spectrum (400 MHz, measured in CDCl.sub.3, internal standard: TMS) .delta.(ppm): 13.68 (1H, br), ca.9.65 (1H, br), 8.02 (1H, br s), 7.84 (1H, d, J=0.5 Hz), 6.54 (1H, s), 5.46 (1H, br d, J=11.0 Hz), 4.97 (1H, d, J=2.1 Hz), 4.33 (1H, dq, J=9.5, 6.3 Hz), 3.66 (1H, dd, J=9.5, 8.4 Hz), 3.49 (1H, dd, J=8.4, 2.1 Hz), 3.48 (1H, s), 3.17 (1H, d, J=5.0 Hz), 3.02 (3H, d, J=0.5 Hz), 2.74 (1H, d, J=5.0 Hz), ca.2.6 (1H), 2.60 (6H, br s), 2.42 (6H, s), 1.91 (3H, s), 1.55

REFERENCES:
patent: 3334016 (1967-08-01), Schmitz
Tetrahedron Letters, vol. 26, No. 27 (1985), Kawai et al., pp. 3273-3276.
Tetrahedron Letters, vol. 34, No. 24 (1978), Sequin et al., pp. 3623-3629.
CRC Handbook of Antibiotic Compounds, vol. 3 (1981), pp. 167, 9172-9173.

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