Lurtotecan

Lurtotecan

Names
IUPAC name (8S)-8-Ethyl-8-hydroxy-15-[(4-methyl-1-piperazinyl)methyl]-2,3-dihydro-11H-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-9,12(8H,14H)-dione
Identifiers
CAS Number	149882-10-0 N
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL305666 Y
ChemSpider	54919 Y
PubChem	60956
UNII	4J1L80T08I Y
InChI InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1 Y Key: RVFGKBWWUQOIOU-NDEPHWFRSA-N Y InChI=1/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1 Key: RVFGKBWWUQOIOU-NDEPHWFRBI
SMILES O=C2OCC=1C(=O)N6/C(=C\C=1[C@@]2(O)CC)c5nc4cc3OCCOc3cc4c(c5C6)CN7CCN(C)CC7
Properties
Chemical formula	C28H30N4O6
Molar mass	518.561 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Lurtotecan is a semi-synthetic analog of camptothecin with antineoplastic activity. Liposomal lurtotecan was in clinical trials as a treatment for topotecan-resistant ovarian cancer,^[1] but was discontinued.^[2]

Synthesis

Lurtotecan synthesis^[3]

• Heck reaction
• Mitsunobu reaction
• Potassium osmate
• Sharpless asymmetric dihydroxylation
• Swern oxidation

References

1. ↑ Seiden, MV; Muggia, F; Astrow, A; Matulonis, U; Campos, S; Roche, M; Sivret, J; Rusk, J; Barrett, E (April 2004). "A Phase II Study of Liposomal Lurtotecan (OSI-211) in Patients with Topotecan Resistant Ovarian Cancer". Gynecologic Oncology. 93 (1): 229–32. doi:10.1016/j.ygyno.2003.12.037. PMID 15047241.  |access-date= requires |url= (help)
2. ↑ "Liposomal lurtotecan (OSI 211) on AdisInsight". Adis Insight. Springer International Publishing AG. Retrieved 15 July 2016. 
3. ↑ Fang, F. G.; Bankston, D. D.; Huie, E. M.; Ross Johnson, M.; Kang, M. C.; Lehoullier, C. S.; Lewis, G. C.; Lovelace, T. C.; Lowery, M. W.; McDougald, D. L.; Meerholz, C. A.; Partridge, J. J.; Sharp, M. J.; Xie, S. (1997). "Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C". Tetrahedron. 53 (32): 10953. doi:10.1016/S0040-4020(97)00357-8.