Folifine (Ribalinine)

Reference work entry

CAS Registry Number: 62928-56-7 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum bucharicum, H. foliosum

C15H17NO3: 259.1208

Mp: 232–233°C (EtOH) [1, 2]; 231 (hydrochloride), 190°C (picrate), 149°C (nitrate), 155°C (Ac) [1]

[α]D +14° (MeOH) [1]

Solubility: very sol. MeOH; sol. CHCl3, EtOH [1]

UV: 238, 316, 328 (4.40, 4.00, 3.98) [1]

IR: 3180, 1630, 1605, 1580, 1555, 1510 [2]

MSm/z: 259(M+, 37), 242(4), 230(4), 226(4), 216(4), 200(5), 189(45), 188(100), 135(12), 134(8), 72(12) [2, 3]

1H NMR: 1.23, 1.47(each 3H, 2 × CH3), 2.88(2H, d, J = 6.5, H-9). 3.36(3H, s, NCH3), 3.86(1H, t, H-10), 6.95–7.60(3H, m, H–Ar), 8.15(1H, dd, J = 9, 2.5, H-5) [4]

13 C NMR: [ 5]

Table 1

C-2

154.0

C-6

125.2

C-10

67.3

 3

96.3

 7

131.3

 11

82.1

 4

175.1

 8

115.4

 12

20.9

 4a

123.2

 8a

138.9

 13

25.0

 5

122.0

 9

25.7

NCH3

30.1

References

  1. 1.
    Z.Sh. Faizutdinova, I.A. Bessonova, S.Yu. Yunusov, Chem. Nat. Comp. 3, 215 (1967)Google Scholar
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    R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Vinogradova, V.I. Akhmedzhanova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. Comp. 32, 932 (1996)Google Scholar
  3. 3.
    Ya.V. Rashkes, Z.Sh. Faizutdinova, S.Yu. Yunusov, Chem. Nat. Comp. 6, 100 (1970)Google Scholar
  4. 4.
    M.R. Yagudaev, S.Yu. Yunusov, Chem. Nat. Comp. 12, 608 (1976)Google Scholar
  5. 5.
    N.M.D. Brown, M.F. Grundon, D.M. Harrison, S.A. Surgenor, Tetrahedron 36, 3579 (1980)Google Scholar

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