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MOM 2006 journal for pdf.pmd - University of Michigan-Flint

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As seen from the distance data above, it is possible that there is a collation between the<br />

backbone <strong>of</strong> the structure and the distance between the rings. The structures that had similar ring<br />

distances to paclitaxel were either analog 28 or 29 there<strong>for</strong>e, seems to be a preference <strong>for</strong> the 6-8-<br />

6 backbone to achieve a similar ring distance.<br />

By comparison <strong>of</strong> 28-NH-CH 2<br />

-RRR and 29-NH-CH 2<br />

-RRR from above it could be concluded<br />

that the additional methyl group on 29 makes no difference in determining the distance between<br />

the methyl groups. 28-NH-CH 2<br />

-RRR has a distance <strong>of</strong> 10.87Å and 29-NH-CH 2<br />

-RRR has a<br />

distance <strong>of</strong> 10.77Å. There<strong>for</strong>e, the additional methyl group is not necessary <strong>for</strong> the molecule to<br />

have a similar ring distance.<br />

References:<br />

[1] Eisenhauer, E.A.; Vermorken, J. B. Drugs 1998, 55, 9.<br />

[2] Kobayashi, M.; Takaori-Kondo, A.; Shindo, K.; Mizutani, C.; Ishikawa, T.; Uchiyama, T.<br />

Intern. Med. 2002, 41, 1209.<br />

[3] Georg, G.I.; Chen, T. C.; Oijma, I. ACS Symposium Series No. 583; Vyas, D.M., Ed.;<br />

American Chemical Society: Washington DC, 1995.<br />

[4] Hamel, E. Med. Res. Rev. 1996, 16, 207.<br />

[5] Snyder, J. P.; Nettles, J.H.; Cornett, B.; Downing, K.H.; Nogales, E. Proc. Natl. Acad. Sci.<br />

USA 2001, 98, 5312.<br />

[6] Geng, X.; Geney, R.; Pera, P.; Bernacki, R.J.; Oijma, I. Biorg. Med. Chem. Lett. 2004,<br />

14, 3491.<br />

[7] Holton, R.A.; Somora, C.; Kin, H.B.; Liang, F.; Biedger, R.J.; Boatman, P.D.; Shino, M.;<br />

Smith, C.C.; Kim, S.C.; Nadizadeh, H.; Suzuki, Y.; Tao, C.L.; Vu, P.; Tang, S.H.; Zhang,<br />

P.S.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1597.<br />

[8] Edwards, N. www.bris.ac.uk/Depts/Chemistry/MOTM/taxol/taxol.htm, June 20, <strong>2006</strong>.<br />

[9] Abdessamad, A.; Saha, N.; Schmidt, F.; Monneret, C.; Florent, J.C., Bioorganic & Medicinal<br />

Chemistry. <strong>2006</strong>, 5012-5019.<br />

[10] Zand, A.; Wagner, G.; Song, J.; Tischler, J, Letters in Drug Design & Discovery. 2005,<br />

2, 355-363.<br />

Meeting <strong>of</strong> Minds <strong>2006</strong> 83

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