Combretastatin A-4 Analogues
cytotoxic agents. Bioorg Med
arresters and cell migration inhibitors. Eur J Med
Chem;63:501–510.
totic
and
Chem;14:4627–4638.
3
4
5
. Wienecke A., Bacher G. (2009) Indibulin, a novel micro-
tubule inhibitor, discriminates between mature neuronal
and nonneuronal tubulin. Cancer Res;69:171–177.
. Lu Y., Chen J., Xiao M., Li W., Miller D.D. (2012) An
overview of tubulin inhibitors that interact with the col-
chicine binding site. Pharm Res;29:2943–2971.
. Pettit G.R., Singh S.B., Niven M.L., Hamel E., Schmidt
J.M. (1987) Isolation, structure, and synthesis of com-
bretastatins A-1 and B-1, potent new inhibitors of
microtubule assembly, derived from Combretum caf-
frum. J Nat Prod;50:119–131.
. Dorr R.T., Dvorakova K., Snead K., Alberts D.S., Sal-
mon S.E., Pettit G.R. (1996) Antitumor activity of com-
bretastatin-A4 phosphate, a natural product tubulin
inhibitor. Invest New Drugs;14:131–137.
. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts
D.S., Garcia-Kendall D. (1989) Isolation and structure
of the strong cell growth and tubulin inhibitor combre-
tastatin A-4. Experientia;45:209–211.
16. van Loon A.A., Holton M.K., Downey C.R., White T.M.,
Rolph C.E., Bruening S.R., Li G., Delaney K.M., Pelkey
S.J., Pelkey E.T. (2014) Preparation of dibenzo[e, g]
isoindol-1-ones via Scholl-type oxidative cyclization
reactions. J Org Chem;79:8049–8058.
17. Hong D., Zhu Y., Li Y., Lin X., Lu P., Wang Y. (2011)
Three-component synthesis of polysubstituted pyrroles
from a-diazoketones, nitroalkenes, and amines. Org
Lett;13:4668–4671.
18. Qiao F., Zuo D., Shen X., Qi H., Wang H., Zhang W.,
Wu Y. (2012) DAT-230, a novel microtubule inhibitor,
exhibits potent anti-tumor activity by inducing G2/M
phase arrest, apoptosis in vitro and perfusion decrease
in vivo to HT-1080. Cancer Chemother Pharma-
col;70:259–270.
19. Ravelli R.B., Gigant B., Curmi P.A., Jourdain I., Lach-
kar S., Sobel A., Knossow M. (2004) Insight into tubu-
lin regulation from a complex with colchicine and a
stathmin-like domain. Nature;428:198–202.
6
7
8
9
. Chaudari A., Pandeya S.N., Kumar P., Sharma P.P.,
Gupta S., Soni N., Verma K.K., Bhardwaj G. (2007)
Combretastatin a-4 analogs as anticancer agents. Mini
Rev Med Chem;12:1186–1205.
. Hsieh H.P., Liou J.P., Mahindroo N. (2005) Pharma-
ceutical design of antimitotic agents based on combre-
tastatins. Curr Pharm Des;11:1655–1677.
20. Genna D.T., Posner G.H. (2011) Cyanocuprates con-
vert carboxylic acids directly into ketones. Org
Lett;13:5358–5361.
21. Li X., Liu N., Zhang H., Knudson S.E., Li H.J., Lai C.T.,
Simmerling C., Slayden R.A., Tonge P.J. (2011) CoA
adducts of 4-oxo-4-phenylbut-2-enoates: inhibitors of
MenB from the M. tuberculosis menaquinone biosyn-
thesis pathway. ACS Med Chem Lett;2:818–823.
22. Kameo K., Ogawa K., Takeshita K., Nakaike S., Tomi-
sawa K., Sota K. (1988) Studies on antirheumatic
agents: 3-benzoylpropionic acid derivatives. Chem
Pharm Bull;36:2050–2060.
23. Nishio T. (1998) Sulfur-containing heterocycles derived
by reaction of x-Keto amides with Lawesson’s
reagent. Helv Chim Acta;81:1207–1214.
24. Jia Y., Bois-Choussy M., Zhu J. (2007) Synthesis of
DEFG ring of complestatin and chloropeptin I:
highly atropdiastereoselective macrocyclization by
intramolecular Suzuki-Miyaura reaction. Org Lett;9:
2401–2404.
25. Raposo M.M.M., Sousa A.M.R.C., Fonseca A.M.C.,
Kirsch G. (2006) Synthesis of formyl-thienylpyrroles:
versatile building blocks for NLO materials. Tetrahe-
dron;62:3493–3501.
26. Guan Q., Yang F., Guo D., Xu J., Jiang M., Liu C.,
Bao K., Wu Y., Zhang W. (2014) Synthesis and biologi-
cal evaluation of novel 3,4-diaryl-1,2,5-selenadiazol
analogues of combretastatin A-4. Eur J Med Chem;87:
1–9.
1
1
1
0. LeBlanc R., Dickson J., Brown T., Stewart M., Pati
H.N., VanDerveer D., Arman H., Harris J., Pennington
W., Holt H.L. Jr., Lee M. (2005) Synthesis and cytotox-
icity of epoxide and pyrazole analogs of the combre-
tastatins. Bioorg Med Chem;13:6025–6034.
1. Johnson M., Younglove B., Lee L., LeBlanc R., Holt H.
Jr., Hills P., Mackay H., Brown T., Mooberry S.L., Lee
M. (2007) Design, synthesis, and biological testing of
pyrazoline derivatives of combretastatin-A4. Bioorg
Med Chem Lett;17:5897–5901.
2. Ruprich J., Prout A., Dickson J., Younglove B., Nolan
L., Baxi K., LeBlanc R., Forrest L., Hills P., Holt H. Jr.,
Mackay H., Brown T., Mooberry S.L., Lee M. (2007)
Design, synthesis and biological testing of cyclo-
hexenone derivatives of combretastatin-A4. Lett Drug
Des Discov;4:144–148.
1
3. Lee L., Robb L.M., Lee M., Davis R., Mackay H.,
Chavda S., Babu B., O’Brien E.L., Risinger A.L.,
Mooberry S.L., Lee M. (2010) Design, synthesis, and
biological evaluations of 2,5-diaryl-2,3-dihydro-1,3,4-
oxadiazoline analogs of combretastatin-A4. J Med
Chem;53:325–334.
1
4. Tron G.C., Pirali T., Sorba G., Pagliai F., Busacca S.,
Genazzani A.A. (2006) Medicinal chemistry of combre-
tastatin A4: present and future directions. J Med
Chem;49:3033–3044.
Supporting Information
Additional Supporting Information may be found in the
online version of this article:
1
5. Banwell M.G., Hamel E., Hockless D.C., Verdier-Pi-
nard P., Willis A.C., Wong D.J. (2006) 4,5-Diaryl-1H-
pyrrole-2-carboxylates as combretastatin A-4/lamel-
larin T hybrids: synthesis and evaluation as antimi-
Appendix S1. Supplementary information.
Chem Biol Drug Des 2015; 86: 1541–1547
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