References of Cyclopent[b]oxireno[c]pyridine,7-ethylidene-1a,2,3,7-tetrahydro-, (1aR,7E,7aS)-
Title: Abikoviromycin
CAS Registry Number: 31774-33-1
CAS Name: 7-Ethylidene-1a,2,3,7-tetrahydrocyclopent[
b]oxireno[
c]pyridine
Synonyms: 4,4a-epoxy-5-ethylidene-2,3,4,4a-tetrahydro-5
H-1-pyridine; abicoviromycin; latumcidin
Molecular Formula: C10H11NO
Molecular Weight: 161.20
Percent Composition: C 74.51%, H 6.88%, N 8.69%, O 9.93%
Literature References: Antiviral antibiotic produced by
Streptomyces abikoensis and
Streptomyces rubescens. Chromatographic isoln from broth cultures: Umezawa
et al., Jpn. Med. J. 4, 331 (1951);
C.A. 46, 7167 (1952); Umezawa,
JP 54 6200 (1954 to Nippon). Identity with latumcidin: Sakagami
et al., J. Antibiot. 11A, 231 (1958). Structure: Gurevich
et al., Tetrahedron Lett. 1968, 2209. Stereochemistry: Kono
et al., J. Antibiot. 23, 572 (1970); Gurevich
et al., Khim. Prir. Soedin. 7, 104 (1971),
C.A. 75, 5752e (1971). Crystal and molecular structure of the selenate: Y. Kono
et al., Acta Crystallogr. B27, 2341 (1971).
In vitro antiviral activity: V. M. Roikhel, N. A. Zeitlenok,
Antibiotiki 14, 969 (1969),
C.A. 72, 19394q (1969).
Properties: Highly unstable and polymerizes promptly on isolation even at -50°; however, it can be handled in dilute solutions and in the form of its salts. uv max (neutral ethanol or 0.1
N KOH): 218, 244, 289 nm (log e 3.83, 3.99, 3.94); (0.1
N HCl) 236, 341 nm (log e 3.99, 4.05).
Absorption maximum: uv max (neutral ethanol or 0.1
N KOH): 218, 244, 289 nm (log e 3.83, 3.99, 3.94); (0.1
N HCl) 236, 341 nm (log e 3.99, 4.05)