Sch 53823 and Sch 53825, novel fungal metabolites with phospholipase D inhibitory activity

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 5, 1996, Pages 579-584

  Chu, Min ^a   Patel, Mahesh G ^a   Pai, Jin Keon ^a   Das, Pradip R ^a   Puar, Mohindar S ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; EPOXIDE; NAPHTHALENE DERIVATIVE; PHOSPHOLIPASE D; PHOSPHOLIPASE INHIBITOR; SCH 53823; SCH 53825; SCH 53827; SCH 53829; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FUNGUS; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029670483     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00074-1     Document Type: Article

References (17)

1. Chu, M.; Gullo, V. P.; Horan A. C.; Patel, M. G. WO93/20081, 1993.
2. Chu, M.; Truumees, I.; Patel, M. G.; Gullo, V. P.; Blood, C.; King, I.; Pai J.-K.; Puar, M. S. Tetrahedron Lett. 1994, 1343.
3. Chu, M.; Truumees, I.; Patel, M. G.; Gullo, V. P.; Puar, M. S. J. Org. Chem. 1994, 59, 1222.
4. Ogishi, H.; Chiba, N.; Mikawa, T.; Sakaki, T.; Miyaji, S.; Seraki, M. J. Patent 01 294 686, 1989, Chem. Abstract 1990, 113, 38906 q.
5. Ogishi, H.; Chiba, N.; Mikawa, T.; Sakaki, T.; Miyaji, S.; Seraki, M. J. Patent 01 294 686, 1989, Chem. Abstract 1990, 113, 38906 q.
6. Schlingmann, G.; West, R. R.; Milne, L.; Pearce, C. J.; Carter, G. T. Tetrahedron Lett. 1993, 7225.
7. Thiergardt, R.; Hug, P.; Rihs, G.; Peter, H. H. Tetrahedron Lett. 1994, 1043.
8. Krohn, K.; Michel, A.; Florke, U.; Aust, H.-J.; Draeger, S.; Schulz, B. Liebigs Ann. Chem. 1994, 11, 1093.
9. Sakagami, Y.; Sano, A.; Hara, O.; Mikawa, T.; Marumo, S. Tetrahedron Lett. 1995, 1469.
10. The fungus was supplied by Dr. B. Katz from MYCOsearch.
11. 11 and 1 are different stereoisomer.
12. -1 3520, 3280, 1605, 1410, 1380, 1270, 1115, 1030, 980, 960, 810, 780, 720.
13. -1 3430, 3310, 1610, 1415, 1370, 1280, 1110, 1040, 980, 955, 815, 770.
14. 3) δ 170.2, 169.1, 149.3, 147.3, 147.2 134.1, 133.8, 130.8, 127.7, 127.5, 125.3, 124.6, 123.1, 121.1, 121.0, 112.9, 110.0, 109.1, 97.0, 61.8, 50.6, 50.0, 20.9, 20.9.
15. 3) δ 170.1, 167.8, 147.2, 147.0, 134.1, 132.4, 131.5, 129.9, 127.7, 127.5, 126.3, 125.8, 121.2, 121.1, 112.8, 110.0, 109.2, 96.8, 61.8, 50.6, 49.9, 29.7, 20.8, 20.4.
16. 3H]-choline in the water phase indicates the induction of PLD activity. fMLP and testing compounds were initially dissolved in dimethylsulfoxide and then diluted with buffer to appropriate concentrations. The final concentration of dimethylsulfoxide in assay did not exceed 0.1%, which had no discernible effects on the parameter measured.
17. 3H]-choline in the water phase indicates the induction of PLD activity. fMLP and testing compounds were initially dissolved in dimethylsulfoxide and then diluted with buffer to appropriate concentrations. The final concentration of dimethylsulfoxide in assay did not exceed 0.1%, which had no discernible effects on the parameter measured.