364 



DESCRIPTI(JX.S OF ANTIBIOTICS 



less (6). Sarkomycin E: LDsn (mice) >600 ing per 

 kg (no route given) (33). 



Utilization: Certain Japanese reports indicate 

 successful use in a variety of neoplastic conditions 

 (5, 7, 12, 14). Others failed to find any objective 

 effect on neoplasms and reported severe side ef- 

 fects, including venous irritation, emesis, and 

 nausea (17, 32). 



Sdrkoiui/rin Analogues and Derivatives 



Produced by: Synthesis. 



Chemical and physical properties: Analogues: 

 (a) 5-Methylenecyclopen.tanone-3-carboxylie acid: 

 Colorless needles; m.p. 67-74°C. Ultraviolet ab- 

 sorption spectrum maximum at 231 m^i (ethanol) 

 (31). Infrared spectrum given in reference 31 

 (Scheme 9). (6) Methyl-5-inethylenecyclopenta- 

 none-S-carbuxylate: Colorless crystals; m.p. (HCl 

 salt) 143-143.5°C (decomposition) (31) (Scheme 

 10). 



Derivatives: (a) Isoniazid-sarkoniycin: Hed sub- 

 stance. More stable than sarkomycin (28). (6) 

 Nicotinic acid hydrazide: Less stable than sarko- 

 mycin (28). 



Biological activity: Analogues a and 6 are active 

 on Staph, aureus. Analogue a has antitumor ac- 

 tivity on HeLa cells, and prolongs survival time 

 of mice with Ehrlich ascites carcinoma (31). 

 Derivative a has antibacterial and antitumor ac- 

 tivity (28). Derivative b is reputed to be "biologi- 

 cally active" (28). 



References: 



1. Umezawa, H. et al. J. Antil)iotics (Japan) 



6A: 101, 1953. 



2. Umezawa, H. et al. J. Antibiotics (Japan) 



6A: 147-152, 1953. 



3. Okami, Y. et al. J. Antibiotics (Japan) 



6A: 153-157, 1953. 



4. Takeuchi, T. J. Antil)iotics (Japan) 7A: 



37^4, 1954. 



5. Ishiyama, S. J. Antibiotics (Jai)an) 7A.' 



82-87, 1954. 



6. Umezawa, H. et al. (ianii 4.5: 543-546, 



1954. 



7. Ishiyama, S. et al. (lann 45: 546-548, 



1954. 



8. Umezawa, H. et al. Antil)iotics & Chemo- 



therapy 4:514-520, 1954. 



9. Hooper, I. R. et al . Antiliiotics & Chemo- 



therapy 5: 585-595, 1955. 



10. Ishiyama, S. et al. J. Antibiotics (Japan) 



8A: 22-25, 1955. 



11. Ishiyama, S. et al. J. Antibiotics (Japan) 



8A: 57-65, 1955. 



12. Fujii, R. et al. J. Antibiotics (Japan) 8A: 



83-88, 1955. 



13. Takeuchi, T. et al. J. Antibiotics (Japan) 



8A: 110-117, 1955. 



14. Momose, Ci. and Kobayashi, T. J. Anti- 



l)iotics (Japan) 8A : 137, 1955. 



15. Oboshi, S. et al. J. Antibiotics (Japan) 



8A: 153-155, 1955. 



16. Oboshi, S. et al. J. Antilnotics (Japan) 



8A: 156-160, 1955. 



17. Alagill, (i. B. et al. Cancer Researcli 16: 



960-964, 1956. 



18. Sugiura, K. Ann. X. Y. Acad. Sci. 63: 



962, 195«). 



19. Hara, T. ('/ rt/. J. Antibiotics (Japan) 9A: 



191-192, 1956. 



20. Umezawa, S. and Kinoshita, M. J. Anti- 



biotics (Japan) 9A: 194, 1956. 



21. Tatsuoka, S. et al . J. Antil)iotics (Japan) 



9B: 110-113, 1956. 



22. Tatsuoka, S. et al. J. Antibiotics (Japan) 



9B: 148-150, 1956. 



23. Kotake, Y. et al. J. Antibiotics (Japan) 



9B: 180-183, 1956. 



24. Hara, T. et al. J. Antibiotics (Japan) 9B: 



184-188, 1956. 



25. Umezawa, H. Giorn. microbiol. 2: 160- 



193, 1956. 



26. Sugiura, K. and Sugiura-Schmid, M. Proc. 



Am. Assoc. Cancer Research 2: 151-152, 

 1956. 



27. Toki, K. ('/«/. J. Antibiotics (Japan) 1(»A : 



35, 1957. 



28. Hara, T. et al. J. Antibiotics (Japan) 



10 A: 66-73, 1957. 



29. Hara, T. et al. J. Antibiotics (Japan) 



lOA: 80-81, 1957. 



30. Toki, K. et al. J. Antibiotics (Japan) 



KtA: 226, 1957. 



31. Umezawa, H. and Kinoshita, Al. Bull. 



Chem. Soc. Japan 30: 267-271, 1957. 



32. Burchenal, J. H. Antibiotics Ann. 1043, 



1957-1958. 



33. Maeda, K. and Kondo, S. J. Antibiotics 



(Japan) llA: 37-56, 1958. 



34. Sugiiu'a, K. et al. Cancer Research 18: 



66-77, 1958. 



35. Japanese Patent 5,748, July 30, 1958. 



36. Japanese Patent 5,749, July 30, 1958. 



37. Tarnowski, (i. S. antl Stock, C. C. Cancer 



Research Sujjpl. I: 26, 1959. 



Seligocidin 



Produced by: Streptomyces sp. resembling S. 

 roseochrouiogenes. 



