Thiarubrines
Title: Thiarubrines
Molecular Formula: C13H8S2
Molecular Weight: 228.33
Percent Composition: C 68.38%, H 3.53%, S 28.09%
Literature References: Class of dark red bioactive dithiacyclohexadiene polyacetylenes found in various Asteraceae; A and B forms are most common. Used medicinally in Africa: J. M. Watt, M. G. Breyer-Brandwijk, The Medicinal and Poisonous Plants of Southern and Eastern Africa (E. & S. Livingstone Ltd., Edinburgh, 2nd edition, 1962) pp 202-205; leaves are consumed by chimpanzees possibly as a pharmaceutic: E. Rodriguez et al., Experientia 41, 419 (1985). Isoln: F. Bohlmann, K.-M. Kleine, Ber. 98, 3081 (1965); and separation by HPLC: R. A. Norton et al., Phytochemistry 24, 356 (1985); from Ambrosia chamissonis: S. Ellis et al., ibid. 33, 224 (1993). NMR spectra and biosynthetic study of A: M. L. Gomez-Barrios et al., ibid. 31, 2703 (1992). Synthesis of A: M. Koreeda, W. Yang, J. Am. Chem. Soc. 116, 10793, (1994); of B: E. Block et al., ibid. 9403. Antibiotic properties of A: G. H. N. Towers et al., Planta Med. 51, 225 (1985); photo-enhancement of activity: G. P. Constabel, G. H. N Towers, ibid. 55, 35 (1989). Antiviral properties of A: J. B. Hudson et al., ibid. 52, 51 (1986); photo-enhancement of activity against HIV: J. B. Hudson et al., Photochem. Photobiol. 57, 675 (1993).
 
Derivative Type: Thiarubrin(e) A
CAS Registry Number: 63543-09-9
CAS Name: 3-(5-Hexene-1,3-diynyl)-6-(1-propynyl)-1,2-dithiin
Properties: Red liquid. lmax (EtOH): 490 nm. uv max (EtOH): 345, 233 nm.
Absorption maximum: uv max (EtOH): 345, 233 nm
 
Derivative Type: Thiarubrin(e) B
CAS Registry Number: 71539-72-5
CAS Name: 3-(3-Buten-1-ynyl)-6-(1,3-pentadiynyl)-1,2-dithiin
Properties: lMax (EtOH): 490 nm. uv max (EtOH): 345, 243 nm.
Absorption maximum: uv max (EtOH): 345, 243 nm

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