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[Study on the structure of epimerides of cycloclausenamide]
1Institute of Material Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100050, China.
Aim:
To study the structures of the epimerides of cycloclausenamide.
Methods:
The structures of compound I, extracted from Clausena lansium (Lour.) Skeels, and synthesized compound III were determined by single crystal X-ray diffraction analysis. The stereo-structures of compound II and IV were also built up through Tripos force field based on crystal structures of compound I and III.
Results:
The molecular formula and molecular weight were found to be C18H17O2N and 279.34 respectively. Compound I crystallized in monoclinic system, space group P2(1) with a = 0.5928(1), b = 1.5014(1), c = 1.6190(1) nm, V = 1.4410(3) nm3, Z = 4, Dx = 1.288 g.cm-3, Rf = 0.075, Rw = 0.073(w = 1/sigma 2|F|), S = 3.983; compound III crystallized in triclinic system, space group P1 with a = 0.5667(1), b = 1.2934(1), c = 2.1119 (1) nm, alpha = 102.17(1), beta = 90.25(1), gamma = 102.65(2) degrees, V = 1.4770(5) nm3, Z = 4, Dx = 1.224 g.cm-3, Rf = 0.047, Rw = 0.051(w = 1/sigma 2|F|), S = 0.467.
Conclusion:
These results showed that compound I and III both are cycloclausenamide except that the directions of the phenyl group on C6 are different. Cycloclausenamide can form 4 pairs of epimerides but the directions of the phenyl group does not affect their energy in free state.