368
Med Chem Res (2011) 20:364–369
Fig. 3 Leishmania tarantole
control (a) and treated (b) with
12.1 lM of 5f for 72 h (940)
paclitaxel has antiangiogenic activity. Clin Cancer Res 2:
1843–1849
Carmichael J, Degraff WG, Gazdar AF, Minna JD, Mitchell JB
(1987) Evaluation of a tetrazolium-based semiautomated color-
imetric assay: assessment of radiosensitivity. Cancer Res
47:943–946
De Souza W (2002) From the cell biology to the development of new
chemotherapeutic approaches against trypanosomatids: dreams
and reality. Kinetoplastid Biol Dis 1:1–21
Dickson J, Flores L, Stewart M, Holt HL Jr, LeBlanc R, Lee M (2006)
Synthesis and cytotoxic properties of chalcones: an interactive
and investigative undergraduate laboratory project at the inter-
face of chemistry and biology. J Chem Edu 83:934–936
Dominguez JN, Charris JE, Lobo G, Gamboa de Dominguez N,
Moreno MM, Riggione F, Sanchez E, Olsone J, Rosenthal PJ
(2001) Synthesis of quinolinyl chalcones and evaluation of their
antimalarial activity. Eur J Med Chem 36:555–560
Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence NJ, McGown
AT, Rennison D (1998) Potent antimitotic and cell growth
inhibitory properties of substituted chalcones. Bioorg Med Chem
Lett 8:1051–1056
Fadda AA, Badria FA, El-Attar KM (2009) Synthesis and evaluation
Faubert G (2000) Immune response to Giardia duodenalis. Clin
Microbiol Rev 13:35–54
(d, J = 4 Hz, 1H), 5.13 (d, J = 4 Hz, 1H), 3.86 (s, 6H),
3.82 (2, 3H), 3.76 (s, 3H); EI: M? 386 (100%).
6e Off white solid, 52% yield; m.p. 150–152°C; TLC
(5% MeOH/CHCl3) Rf 0.10; IR (KBr) 3180, 2945, 2831,
1673, 1590, 1556, 1494, 1442, 1328, 1276, 1224, 1120,
1
1037, 816, 730; H-NMR: CDCl3: 8.45 (br s, 1H), 6.89 (s,
3H), 6.59 (s, 2H), 6.50 (br s, 1H), 4.95 (d, J = 8 Hz, 1H),
4.80 (d, J = 8 Hz, 1H), 3.88 (s, 6H), 3.86 (s, 3H), 3.85 (s,
3H), 3.77 (s, 3H); EI: M? 416 (100%); HRMS: obsd:
416.1409 calcd: 416.1406.
7a Off white solid, 96% yield; m.p. 198–200°C; TLC
(5% MeOH/CHCl3) Rf 0.27; IR (KBr) 3190, 2900, 2850,
1663, 1601, 1552, 1452, 1248, 1179, 1131, 1017, 799; 1H-
NMR: CDCl3 7.66 (br s, 1H), 7.36 (d, J = 8 Hz, 2H), 6.92
(d, J = 8 Hz, 2H), 6.87 (d, J = 8 Hz, 2H), 6.85 (s, 1H),
5.23 (d, J = 2.8 Hz, 1H), 5.09 (d, J = 2.8 Hz, 1H), 3.89 (s,
3H), 3.88 (s, 3H), 3.83 (s, 3H); EI: M? 356 (100%).
7b Off white solid, quantitative yield; m.p. 180–182°C;
TLC (5% MeOH/CHCl3) Rf 0.37; IR (KBr) 3208, 2994,
2942, 2838, 1670, 1601, 1552, 1511, 1463, 1324, 1297,
1
1181, 1151, 1120, 1031, 947, 817, 752; H-NMR: CDCl3
Galbraith S, Maxwel R, Lodge M, Tozer G, Wilson J, Taylor N,
Stirling J, Sena L, Padhani A, Rustin G (2003) Combretastatin
A4 phosphate has tumor antivascular activity in rat and man as
demonstrated by dynamic magnetic resonance imaging. J Clin
Oncol 21:2831–2842
7.45 (br s, 1H), 7.35 (d, J = 8 Hz, 2H), 6.80 (d, J = 8 Hz,
2H), 6.25 (br s, 1H), 6.13 (s, 2H), 5.65 (d, J = 8 Hz, 1H),
4.90 (d, J = 8 Hz, 1H), 3.82 (s, 3H), 3.81 (s, 3H), 3.80 (s,
6H); EI: M? 386 (100%).
Gardner TB, Hill DR (2001) Treatment of giardiasis. Clin Microbiol
Rev 14:114–128
Gaukoger K, Hadfield JA, Hepworth LA, Lawrence NJ, McGown AT
(2001) Novel syntheses of cis and trans isomers of combretast-
atin A-4. J Org Chem 66:8135–8138
Acknowledgments The authors are grateful for the support
received from the Howard Hughes Medical Institute, Conjura Phar-
maceuticals, LLC, and Hope College.
Go M-L, Liu M, Wilairat P, Rosenthal PJ (2004) Antiplasmodial
chalcones inhibit sorbitol-induced hemolysis of Plasmodium
falciparum-infected erythrocytes. Antimicrob Agents Chemother
48:3241–3245
References
Hsieh HP, Liou JP, Lin YT, Mahindroo N, Chang JY, Yang YN,
Chern SS, Tan UK, Chang CW, Chen TW, Lin CH, Chang YY,
Wang CC (2003) Structure activity and crystallographic analysis
of benzophenone derivatives the potential anticancer agents.
Bioorg Med Chem Lett 13:101–105
Johnson M, Younglove B, Lee L, LeBlanc R, Holt H Jr, Hills P,
Mackay H, Brown T, Mooberry SL, Lee M (2007) Design,
synthesis, and biological testing of pyrazoline derivatives of
combretastatin-A4. Bioorg Med Chem Lett 17:5897–5901
Al-Hajjar FH, Al-Farkh YA, Hamoud HS (1979) Synthesis and
spectroscopic studies of the pyrimidine-2(1)thione derivatives.
Can J Chem 57:2734–2742
Awasthi SK, Mishra N, Kumar B, Sharma M, Bhattacharya A, Mishra
LC, Bhasin VK (2009) Potent antimalarial activity of newly
synthesized substituted chalcone analogs in vitro. Med Chem
Res 18:407–420
Belotti D, Vergani V, Drudis T, Borsotti P, Pitelli MR, Viale G,
Giavazzi R, Taraboletti G (1996) The microtubule-affecting drug
123