Stoffwechselprodukte von Actinomyceten 17. MitteilungHolomycin

Abstract

In der vorlicgenden Arbeit wcrden eine neuartige Gruppe basisch substituicrter Hydrazine sowie verschiedene zur Synthese dicscr Verbindungcn ausgearbcitete Wege beschrieben. Diesc Hydrazin-Derivate zcichnen sich zum Teil durch eigene physiologische Eigenschaften aus, anderseits werden sie fur die Synthesc von phy.;lologisch wirksamen Hetcrocyclen verwendct. Pharmazeutisch-chemisches Laboratorium SANDOZ, Base1 (26. I. 59) 17. Mitteilung I) Aus den Kulturen des Actinomyceten, Stamm ETH. 17474, welcher nach seinen artbestimmenden Merkmalen der Species Streptomyces griseus (KRAINSKI) WAKSJIAN et HEXRICI zugeordnet werden muss2), haben wir ein gelbes, lipophiles, neutrales Antibioticum, das mit keinem in der Literatur beschriebenen Actinomyceten-hletaboliten identisch ist , in kristallisierter Form isolieren konnen. Das Antibioticum liess sich aus den Kulturfiltraten mittels Kthylacetat extrahieren und nach chromatographischer Anreicherung durch Kristallisation und Hochvakuumsublimation in reiner Form gewinncn. Es wurde von uns Holomycilz genannt. 440 400 1:ig. 2. I H.-Absor~lionsspektra ,in K B r (PERKTK-ELMER Zweistrahl-Spektrograph Modell 21)

Synthesis of Substituted 6-Amino-4-(2,4-dimethoxyphenyl)-[1,2]dithiolo[4,3-<i>b</i>]pyrrol-5-ones and Their Raising Leukocyte Count Activities

“…In this study, eighteen substituted 6-amino-4-(2,4-dimethoxyphenyl)- [1,2]dithiolo [4,3-b]pyrrol-5-ones were designed and synthesized, and all the newly synthesized compounds were evaluated for their raising leukocyte count activity in normal mice. Among these synthetic compounds, compound 8a, b, d and h showed significant raising leukocyte count activity as comparable to blank control.…”

“…in the 1940s 1) and from other organisms since that time. [2][3][4] This group of compounds includes thiolutin, aureothricin, isobutyropyrrothin, holomycin, xenorhabdins and thiomarinols A-G [5][6][7][8][9] ( Fig.…”

“…Dithiolopyrrolones are a class of natural products that possess the 4H- [1,2]dithiolo [4,3-b]pyrrol-5-one skeleton, which were isolated from the bacteria Streptomyces sp. in the 1940s 1) and from other organisms since that time.…”

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

“…Holomycin (208) is a member of the pyrrothine group and was originally described as antibiotic from Streptomyces griseus [319] and Streptomyces clavuliderus.…”

“…More recently, Kirby has discussed the genetic control of the holomycin biosynthesis by S. clavuligerus [319] . Due to the pronounced activities of holomycin (208) and its analogues thiolutin (209), aureothricin (210) and isobutyropyrrothine (211) against a variety of Gram-positive and Gram-negative bacteria, amoeboid parasites and fungi, many trials to synthesize this type of compounds have been reported [320,321] .…”