Molecules 2010, 15
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129.07 (2C), 129.38 (2C), 129.97 (2C), 131.19(2C), 131.98, 132.50, 135.90, 148.50, 165.05. Anal.
Calcd for C33H26N2O: C, 84.95; H, 5.62; N, 6.00. Experimental: C, 84.86; H, 5.59; N, 5.93.
1-(Chrysen-6-yl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-4-(furan-2-yl)azetidin-2-one (±)5b. Yellow crystals.
Crystallized from dichloromethane/hexane mixture; Mp: 135―137 °C; IR: 2912, 1753, 1310, 1110,
782 cm-1; 1H-NMR δ (ppm): 2.30 (s, 6H, CH3), 5.47 (d, J = 2.46, H-4), 5.65 (d, J = 2.46, H-3), 5.91 (s,
2H, pyrrole), 6.77 (m, 2H, furan), 7.35-8.59 (m, 12H, Ar-H); 13C-NMR δ (ppm): 13.45(2C), 65.63,
68.55, 107.65 (2C), 114.41, 114.77 (2C), 122.98, 123.77 (2C), 124.56, 126.86,127.00 (2C), 127.55
(2C), 127.81(2C), 128.78 (2C), 129.07 (2C), 129.38 (2C), 129.97, 135.98, 141.05, 160.14, 165.23.
Anal. Calcd for C31H24N2O2: C, 81.56; H, 5.30; N, 6.14. Experimental: C, 81.58; H, 5.29; N, 6.08.
1-(Chrysen-6-yl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-4-(thiophen-2-yl)azetidin-2-one (±)5c. Yellowish
white crystals. Crystallized from dichloromethane/hexane mixture; Mp: 231―233 °C; IR: 2914, 1755,
1306, 1105, 784 cm-1; 1H-NMR δ (ppm): 2.34 (s, 6H, CH3), 5.34 (d, J = 2.50, H-4), 5.92 (d, J = 2.50,
H-3), 5.90 (s, 2H, pyrrole), 6.85 (m, 1H, thiophene), 7.11-8.66 (m, 13H, Ar-H); 13C-NMR δ (ppm):
13.42(2C), 62.24, 69.35, 107.79 (2C), 115.42, 120.99, 122.91, 123.74, 124.37, 126.45 (2C), 127.05,
127.21 (2C), 127.51, 127.60, 127.89, 128.03 (2C), 128.79 (2C), 129.31, 130.78, 131.34 (2C), 132.33,
139.10, 148.50, 164.83. Anal. Calcd for C31H24N2OS: C, 78.78; H, 5.12; N, 5.93. Experimental: C,
78.71; H, 5.05; N, 5.90.
4. Conclusion
As part of our current research on anticancer β-lactams we have demonstrated an easy preparation
of 3-pyrrole-substituted β-lactams through molecular iodine-catalyzed reactions. This simple method
may find useful applications in drug synthesis. Furthermore, the compounds reported herein will be
tested against a number of cancer cells in vitro.
Acknowledgements
We gratefully acknowledge the funding support from the NIH-SCORE, 2506M008038-37.
References and Notes
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A new class of cannabinoid. Tetrahedron Lett. 1995, 36, 1401–1404.
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3. Gilchrist, T.L. Synthesis of aromatic heterocycles. J. Chem. Soc. Perkin Trans 1 1998, 615–628
and references cited therein.
4. Dieter, R.K.; Yu, H. A facile synthesis of polysubstituted pyrroles. Org. Lett. 2000, 2, 2283–2286.
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1486–1487.