Abstract
Two novel taxoids were synthesized from 1-deoxybacctin VI (5) and their crystal structures were determined by X-ray crystallographic techniques. The influence of C(10) substituents of the cyclooctane ring B on molecular conformations were investigated. A larger effect on the conformation of the diterpenoid core is observed when the hydroxyl group is oxidized at the C(9) position and the hydroxyl group is acylated at the C(10) position compared to other baccatin analogs. Compounds 12a and 12c crystallize in the orthorhombic space group P212121. In the structures, the six-membered A ring exhibits a 1, 4-di-planar conformation, the eight-membered B ring adopts boat–chair conformation, and the six-membered C ring exhibits a slightly distorted half-chair conformation.
Graphic Abstract
Two novel C-10 modified taxanes from 1-deoxybaccatin VI were synthesized, in which the crystal structure of the two compounds (12a and 12c) were characterized.
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References
Wani MC, Taylor HL, Wall ME (1971) J Am Chem Soc 93:2325–2327
Xu PP, Li QF, Cui YM (2017) J Asian Nat Prod Res 19:803–822
Wheeler NC, Jech K, Masters S (1992) J Nat Prod 55:432–440
Lichtman SM (2014) J Geriatr Oncol 5:223–229
Kingston DG, Snyder JP (2014) Acc Chem Res 47:2682–2691
Kingston DGI (2001) Chem Commun 10:867–880
Guénard D, Thoret S, Dubois J, Adeline M, Wang Q, Guéritte F (2000) Bioorg Med Chem 8:145–156
Lin HX, Wang DL, Chen JM, Chen MQ (2008) Chin J Chem 26:1870–1878
Datta A, Vander VDG, Georg GI, Himes RH (1995) Tetrahedron Lett 36:1985
Ge H, Vasandani V, Huff JK (2006) Bioorg Med Chem 16:433–436
Galsky MD, Dritselis A, Kirkpatrick P, Oh WK (2010) Nat Rev Drug Discov 9:677
Mita AC, Denis LJ, Rowinsky EK, DeBono JS, Goetz AD, Ochoa L, Forouzesh B, Beeram M, Patnaik A, Molpus K, Semiond D, Besenval M, Tolcher AW (2009) Clin Cancer Res 15:723–730
Kingston DGI, Chordia MD, Jagtap PG, Liang J, Shen Y, Long BH, Fairchild CR, Johnston KA (1999) J Org Chem 64:1814–1822
Chen SH, Huang S, Gao Q, Golik J, Farina V (1994) J Org Chem 59:1475–1484
Chaudhary AG, Chordia MD, Kingston DGI (1995) J Org Chem 60:3260–3262
Lin HX, Li M, Chen JM, Chen MQ (2004) Chin J Chem 22:751–756
Hu FL, Han N, Yu J, Cui YM, Cao WG, Lin HX (2011) J Chem Crystallogr 41:1586
Sheldrick GM (2015) Acta Crystallogr Sect C 71(1):3–8
Lin HX, Han N, Chen JM (2006) J Chem Crystallogr 36(5):337–341
Mastropaolo D, Camerman A, Luo Y, Brayer GD, Camerman N (1995) Proc Natl Acad Sci 92:6920–6924
Gabetta B, de Bellis P, Pace R, Appendino G, Barboni L, Torregiani E, Gariboldi P, Viterbo D (1995) J Nat Prod 58:1508–1514
Harper JK, Dalley NK, Mulgrew AE (2001) Acta Crystallogr C 57:64–65
Li QF, Lin HX, Cui YM (2015) Eur J Med Chem 104:97–105
Ketchum REB, Tandon M, Gibson DM (1999) J Nat Prod 62:1395–1398
Lin HX, Chen JM, Chen JK (2005) J Mol Struct 738:59–65
Appendino G, Jakupovic J, Gravotto G, Varese M (1994) Tetrahedron Lett 35:6547–6550
Li L, Thomas SA, Klein LL (1994) J Med Chem 37:2655–2663
Jin DH, Cui YM, Lin HX (2012) Med Chem 8:789–798
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The authors are grateful for support from the National Natural Science Foundation of China (Project No. 21272154).
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Xie, CH., Cui, YM., Jin, DH. et al. Synthesis and Crystal Studies of Novel C(10) Modified Taxanes from 1-Deoxybaccatin VI. J Chem Crystallogr 50, 225–233 (2020). https://doi.org/10.1007/s10870-019-00804-6
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DOI: https://doi.org/10.1007/s10870-019-00804-6