Flustramina

Las flustraminas son alcaloides pirroloindólicos aislados de Flustra foliacea (Bryozoa).

Flustra foliacea

Síntesis

Se han reportado diversos métodos de síntesis para las frustramidas.

Fuchs y colaboradores sintetizaron la flustramina A por medio del acoplamiento de una 3-bromoindolin-2-ona con prenilestannano.[1]​ Fuchs synthesis of flustramine A

Austin y colaboradores propusieron la síntesis total de la flustramina B a partir de N-{2-[6-bromo-1-(3-metilbut-2-en-1-il)-1H-indol-3-il]etil}-2,2-dimetilpropanamida y acroleína.[2]​

Propiedades

A continuación se muestran las propiedades de las flustraminas:

 Nombre    Estructura    Fórmula molecular    CAS   Masa molecular (g/mol)   Estado   Otras propiedades  
Flustramina A
C21H29BrN2 71239-64-0 389.377 Líquido Relajante muscular. [a]20D = -76.9 (c, 6.6 en EtOH). Soluble en metanol, benceno y cloroformo. UV: [ácido]λmax219 (e21000) ;253 (e7700) ;305 (e3500) ( EtOH/HCl) [neutral]λmax218 (e20000) ;262 (e9200) ;317 (e3500) ( EtOH)[3]​
Flustramina B
C21H29BrN2 71239-65-1 389.377 Relajante muscular.[4]​ Soluble en metanol, benceno y cloroformo. UV: [ácido]λmax219 (e21000) ;253 (e7700) ;305 (e3500) ( EtOH/HCl) [neutral]?max218 (e20000) ;262 (e9200) ;317 (e3500) (EtOH)
Flustramina C
C16H19BrN2 78127-86-3 319.243 Líquido oleoso UV: [ácido]λmax210 (e13000) ;230 (e23000) ;280 (e4600) ( EtOH/HCl) [neutro]λmax210 (e10000) ;232 (e27000) ;290 (e9400) ;307 (e4300) ( EtOH)[5]​
Flustramina D
C21H29BrN2 104387-12-4 389.377 Líquido oleoso [a]25D = -86.5 (c, 1.03 en diclorometano); UV:[neutro]λmax231 (e7100) ;292 (e3100) (MeOH)[6]​
Flustramina E[7]​
C16H21BrN2 158642-05-8 321.259 [a]20D = -1136 (c, 0.0088 en EtOH); UV: [neutro]λmax210;250;308 (MeOH)
Flustramina F
C18H23BrN2O 1187956-19-9 363.297 Líquido oleoso [a]D = -22 (c, 0.2 en cloroformo) UV: [neutro]λmax219 (log e4.41) ;252 (log e3.98) ;287 (log e3.39) ( MeOH)[8]​
Flustramina G
C16H20Br2N2 1187956-20-2 400.155 Líquido aceitoso [a]D = -80 (c, 0.21 en cloroformo); UV: [neutro]λmax212;247;310 (MeOH)
Flustramina H[9]​
C21H29BrN2O 1187956-21-3 405.377 Líquido oleoso [a]D = -58 (c, 0.3 en cloroformo); UV: [neutro]λmax217 (log e4.77) ;246 (log e4.2) ;295 (log e3.84) (MeOH)
Flustramina I
C16H21BrN2O 1187956-23-5 337.259 Líquido oleoso [a]D = -87 (c, 0.18 en cloroformo); UV: [neutro]λmax217 (log e4.79) ;297 (log e3.65) (MeOH)
Flustramina J
C21H28Br2N2O 1187956-24-6 484.273 Líquido oleoso [a]D = -40 ( c, 0.15 en cloroformo); UV: [neutro]λmax217;293 (MeOH)
Flustramina K
C16H20Br2N2O 1187956-25-7 416.155 Líquido oleoso [a]D = -29 (c, 0.05 en cloroformo)
Flustramina L
C21H29BrN2O 1187956-26-8 405.377 Líquido oleoso [a]D = -53 (c, 0.3 en cloroformo); UV: [neutro]λmax218 (log e4.82) ;302 (log e3.83) (MeOH)[9]​
Flustramina M
C21H27BrN2O2 1187956-27-9 419.361 Líquido oleoso [a]D = -159 (c, 0.08 en cloroformo); UV: [neutro]λmax218 (log e4.5) ;299 (log e4.06) ;318 (log e3.85) (MeOH)
Flustramina N
C21H29BrN2O 1187956-29-1 405.377 Líquido oleoso [a]D = -61 (c, 0.28 en cloroformo); UV: [neutro]λmax217 (log e4.73) ;299 (log e3.79) ( MeOH)
Flustramina O
C21H27BrN2O2 1187956-31-5 654.530 Líquido oleoso [a]D = -211 (c, 0.63 en cloroformo); UV: [neutro]λmax215 (log e4.82) ;259 (log e4.32) ;312 (log e3.89) ( MeOH)
Flustramina P
C38H50Br2N4O 1187956-33-7 738.647 Líquido oleoso [a]D = -5 (c, 0.44 en cloroformo); UV: [neutro]λmax213 (log e5.06) ;259 (log e4.53) ;305 (log e4.07) ( MeOH)

Referencias

  1. ↑ Fuchs, J.R. et al., Org. Lett., 2005, 7, 677- 680
  2. ↑ Austin J. F. et al. PNAS 2004;101:5482-5487
  3. ↑ Morales-Rios, M.S. et al., Magn. Reson. Chem., 2002, 40, 677- 682
  4. ↑ Carlé, J.S. et al., JOC, 1980, 45, 1586- 1589
  5. ↑ Carlé, J.S. et al., JOC, 1981, 46, 3440- 3443
  6. ↑ Laycock, M.V. et al., Can. J. Chem., 1986, 64, 1312- 1316
  7. ↑ Carlé, J.S. et al., JACS, 1979, 101, 4012- 4013
  8. ↑ Rochfort, S.J. et al., J. Nat. Prod., 2009, 72, 1773- 1781
  9. ↑ a b Rochfort, S.J. et al., J. Nat. Prod., 2009, 72, 1773- 1781


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