UCF116 compounds

Details UCF116 compounds UCF116 compounds

1996-07-12

1997-11-11

Bond, Robert T.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

514183, C07D22506, A61K 31415

Patent

active

056866062

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP45/02325 filed Nov. 14, 1995, which claims the priority of Japanese Application 6 280,271, filed 15 Nov. 1994.


TECHNICAL FIELD

The present invention relates to UCF116 compounds which have antibacterial and antitumor activity and are useful as antibacterial and antitumor agents.


BACKGROUND ART

Mycotrienin II having antibacterial and antitumor activity which is represented by the following formula (A) and Mycotrienin I having antibacterial and antitumor activity which is represented by the following Tetrahedron Letters, 32, 841 (1991)!. ##STR4##
Further, the following compounds are known: Trienomycin A having antibacterial and antitumor activity which is represented by the formula (C): ##STR5## of Antibiotics, 42, 479 (1989)!; and Trienomycin F which is represented by the formula (D): ##STR6##


DISCLOSURE OF THE INVENTION

The present invention provides UCF116 compounds having antibacterial and antitumor activity which are represented by the formula (I): ##STR7## wherein when Q.sup.1 is ##STR8## Q.sup.2 represents ##STR9## and when Q.sup.1 is ##STR10## Q.sup.2 represents ##STR11##
UCF116 compounds can be produced by cultivating a microorganism belonging to the genus Streptomyces.
The present invention is described in detail below.
UCF116 compounds include compounds represented by the formulae (1a), (1b) and (1c), respectively. The compound represented by the formula (1a): ##STR12## is referred to as UCF116-B, the compound represented by the formula (1b): ##STR13## is referred to as UCF116-D, and the compound represented by the formula (1c): ##STR14## is referred to as UCF116-A3.
The physicochemical properties of UCF116 compounds are shown below.
White powder
(calculated for C.sub.36 H.sub.49 N.sub.2 O.sub.8 :637.3489) 271(40,900), 260(31,600), 206(42,100) 6.52(1H), 6.28(1H), 6.24(1H), 6.23(1H), 6.04(1H), 6.03(1H), 5.65(1H), 5.49(1H), 5.15(1H), 4.93(1H), 4.71(1H), 4.49(1H), 4.19(1H), 3.35(3H), 2.94(1H), 2.89(1H), 2.58(1H), 2.52(1H), 2.3(1H), 2.25(1H), 2.20(2H), 2.2(1H), 2.15(2H), 2.05(1H), 1.87(1H), 1.73(3H), 1.65(2H), 1.55(2H), 1.47(3H), 0.82(3H) 141.2(s), 138.0(s), 135.8(d), 134.9(d), 134.4(d), 133.8(d), 132.8(s), 132.0(s), 129.5(d), 129.5(d), 129.2(d), 125.4(s), 124.0(d), 115.8(d), 107.4(d), 79.6(d), 75.8(d), 68.6(d), 56.7(q), 49.0(d), 43.1(t), 39.0(d), 33.7(t), 31.7(t), 26.5(t), 25.5(t), 24.1(t), 22.0(t), 21.4(t), 20.4(q), 17.8(q), 9.7(q) insoluble in water and hexane.
After the development, the spot of UCF116-B can be detected with the iodine reagent. H.sub.47 O.sub.8 N.sub.2 : 611.3333) 271(13,300), 260(11,200), 204(21,900) 6.49(1H), 6.32(1H), 6.3(1H), 6.2(1H), 6.1(1H), 6.0(1H), 5.64(1H), 5.48(1H), 5.16(1H), 4.93(1H), 4.72(1H), 4.48(1H), 4.18(1H), 3.34(3H), 2.92(1H), 2.87(1H), 2.58(1H), 2.52(1H), 2.3(1H), 2.25(1H), 2.2(1H), 2.07(1H), 1.9(1H), 1.82(3H), 1.74(3H), 1.73(3H), 1.48(3H), 0.82(3H) 141.1(S), 137.9(s), 135.0(d), 134.4(d), 33.8(d), 132.9(d), 132.8(s), 130.6(s), 129.6(d), 29.5(d), 129.2(d), 125.4(s), 124.0(d), 115.8(d), 07.5(d), 79.7(d), 75.7(d), 68.5(d), 56.6(q), 49.1(d), 3.0(t), 38.8(d), 33.7(t), 31.7(t), 26.5(t), 20.5(q), 7.7(q), 14.1(q), 12.2(q), 9.7(q) and hexane. Inc.)
After the development, the spot of UCF116-D can be detected with the iodine reagent. H.sub.49 N.sub.2 O.sub.8 : 649.3489) 262(26,800), 227(21,500), 203(25,900) .sup.1 H-NMR spectrum (CDCl.sub.3): 6.1(1H), 6.1(1H), 6.1(1H), 6.0(1H), 5.58(1H), 5.50(1H), 5.18(1H), 4.86(1H), 4.48(1H), 4.03(1H), 3.37(3H), 2.84(1H), 2.6(1H), 2.5(1H), 2.4(1H), 2.3(1H), 2.3(1H), 2.1(1H), 2.0(2H), 1.85(3H), 1.80(3H), 1.75(2H), 1.7(1H), 1.5(2H), 1.35(3H), 1.25(2H), 1.12(2H), 0.89(3H) 169.5(s), 145.5(s), 139.8(s), 138.0(s), 134.0(d), 133.9(d), 133.3(d), 133.1(d), 131.2(d), 129.8(d), 129.4(d), 122.7(d), 114.6(d), 79.1(d), 75.9(d), 68.0(d), 56.8(q), 45.2(d), 44.9(t), 40.3(d), 33.7(s), 33.2(t), 29.8(t), 29.7(t), 29.6(t), 29.3(t), 25.70(t), 25.67(t), 25.65(t), 20.7(q), 18.2(t), 17.8 (t), 9.7 (q)
After the development, the spot of UCF116-A3 can be detected with the iodine reagent.
The above data were obtained by using

REFERENCES:
Journal of Antibiotics, vol.XLII, No. 3 by Hisayo Nomoto, et al pp. 479-481 (1988).
The Journal of Antibiotics, vol.XXXV, No.11, by Masanori Sugita, et al pp. 1474-1479.
The Journal of Antibiotics, vol. XXXVII, No.6, by Iwao Umezawa, et al pp. 699-698 (1985).
The Journal of Antibiotics, vol. XXXVIII, No. 12, by Shinji Funayama, et al. pp. 1677-1683.
The Journal of Antibiotics, vol. XXXVIII, No.8, pp. 1107-1109 (1985).
The Journal of Antibiotics,vol. XXXV, No.11, by Masanori Sugita, et al. pp. 1460-1473.
Journal of Antibiotics, vol.XLI, No.9, by Shinji Funayama, et al pp. 1223-1231 (1988).
Tetrahedron Letters, vol.32, No.7, pp. 841-842 (1991).
Tetrahedron Letters, vol.32, No.13, pp. 1627-1630 (1991).

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