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Sophoranol

Reference work entry

CAS Registry Number: 3411-37-8 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Sophora flavescens

C15H24N2O2: 264.1838

Mp: 172°C (Me2CO) [1], 232°C (hydrochloride) [2]

[α]D +60° (H2O) [1]

UV: 220 [3]

IR: 3340, 2800–2700, 1645 [2, 4]

IR(KBr): 3236(OH), 2933, 2857, 2796, 2747(trans-quinolizidine), 1629(C = O) [5]

EI-MS: 264.1840(M+, 87), 263.1761(29), 247.1815 (C15H23N2O, 100), 246.1728(C15H22N2O, 24), 222.1850(C14H24NO, 6), 221.1289(C12H17N2O2, 26), 208.1569(C21H20N2O, 4), 193.1345 (C11H17N2O, 10), 166.1235(C10H16NO, 15), 112.1129(C7H14N, 3), 120.0768(C6H10NO, 35), 98.0962(C6H12N, 4), 98.0606(C5H8NO, 6), 96.0813(C6H10N, 36) [5]

1H NMR(C5D5N, 100 MHz): [6]

1H NMR(CDCl3, 100 MHz): 4.34(1H, dd, Heq-17), 3.77(1H, m, H-11), 3.21(1H, d, Hax-17), 2.86(1H, bd, Heq-10), 2.75(1H, bd, Heq-2) [6]

13 C NMR: [ 7, 8]

Table 1

C-2

56.8

C-7

37.1

C-12

26.6

 3

22.4

 8

25.8

 13

18.7

 4

37.1

 9

20.4

 14

32.6

 5

65.5

 10

References

  1. 1.
    A.M. Abdel’-Baki, K.F. Blinova, Khim. Prirod. Soedin. 427 (1980)Google Scholar
  2. 2.
    F. Bohlmann, D. Rahtz, C. Arndt, Chem. Ber. 91, 2189 (1958)CrossRefGoogle Scholar
  3. 3.
    F. Wiewiorowski, F. Galinovsky, M.D. Brateck, Monatsh. Chem. 88, 663 (1957)CrossRefGoogle Scholar
  4. 4.
    A.S. Sadykov, Kh.A. Aslanov, Yu.K. Kushmuradov, Alkaloids of the Quinolizidine Series [in Russian] (Nauka, Moscow, 1975), p. 217Google Scholar
  5. 5.
    R. Negrete, B.K. Cassels, G. Eckhardt, Phytochemistry 22, 2069 (1983)CrossRefGoogle Scholar
  6. 6.
    S. Ohmiya, K. Higashiyama, H. Otomasu, I. Murakoshi, J. Haginiwa, Phytochemistry 18, 645 (1979)CrossRefGoogle Scholar
  7. 7.
    A.S. Sadykov, Izv. AN SSSR, Ser. Khim. 2432 (1983)Google Scholar
  8. 8.
    F. Bohlmann, R. Zeisberg, Chem. Ber. 108, 1043 (1975)CrossRefGoogle Scholar
  9. 9.
    A. Ueno, K. Morinaga, S. Fukushima, S. Okuda, Chem. Pharm. Bull. 26, 1832 (1978)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013

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