Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues

Eissler S, Bogner T, Nahrwold M, Sewald N (2009)
CHEMISTRY-A EUROPEAN JOURNAL 15(42): 11273-11287.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Cryptophycins are a family of highly cytotoxic, cyclic depsipeptides. They display antitumour activity that is largely maintained for multidrug-resistant tumour cells. Cryptophycins are composed of four building blocks (units A-D) that correspond to the respective amino and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres in a short, efficient and reliable synthesis and contributes to an easier and faster synthesis of cryptophycins. The first two stereogenic centres are introduced by a catalytic asymmetric dihydroxylation, whereas the remaining two stereogenic centres are introduced with substrate control of diastercoselectivity. The stereogenic diol function also serves as the epoxide precursor. The approach was used to synthesise the native unit A building block as well as three para-alkoxymethyl analogues from which cryptophycin-52 and three analogous cryptophycins were prepared. Macrocyclisation of the seco-depsipeptides was based on ring-closing metathesis.
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Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
15
Ausgabe
42
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11273-11287
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eISSN
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Eissler S, Bogner T, Nahrwold M, Sewald N. Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL. 2009;15(42):11273-11287.
Eissler, S., Bogner, T., Nahrwold, M., & Sewald, N. (2009). Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL, 15(42), 11273-11287. doi:10.1002/chem.200901750
Eissler, S., Bogner, T., Nahrwold, M., and Sewald, N. (2009). Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL 15, 11273-11287.
Eissler, S., et al., 2009. Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL, 15(42), p 11273-11287.
S. Eissler, et al., “Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 15, 2009, pp. 11273-11287.
Eissler, S., Bogner, T., Nahrwold, M., Sewald, N.: Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL. 15, 11273-11287 (2009).
Eissler, Stefan, Bogner, Tobias, Nahrwold, Markus, and Sewald, Norbert. “Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues”. CHEMISTRY-A EUROPEAN JOURNAL 15.42 (2009): 11273-11287.

6 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

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Cazzamalli S, Figueras E, Pethő L, Borbély A, Steinkühler C, Neri D, Sewald N., ACS Omega 3(11), 2018
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Total synthesis and biological evaluation of fluorinated cryptophycins.
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Drugs that target dynamic microtubules: a new molecular perspective.
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56 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0

Schwartz, J. Ind. Microbiol. 5(), 1990

Trimurtulu, J. Am. Chem. Soc. 116(), 1994

Golakoti, J. Am. Chem. Soc. 117(), 1995
Three new cryptophycins from Nostoc sp. GSV 224.
Subbaraju GV, Golakoti T, Patterson GM, Moore RE., J. Nat. Prod. 60(3), 1997
PMID: 9090872
Isolation and structure determination of cryptophycins 38, 326, and 327 from the terrestrial cyanobacterium Nostoc sp. GSV 224.
Chaganty S, Golakoti T, Heltzel C, Moore RE, Yoshida WY., J. Nat. Prod. 67(8), 2004
PMID: 15332864

AUTHOR UNKNOWN, 0

Kobayashi, Chem. Pharm. Bull. 42(), 1994

Kobayashi, Tetrahedron Lett. 35(), 1994

AUTHOR UNKNOWN, 0

Eissler, Synthesis (), 2006
The cryptophycins: their synthesis and anticancer activity.
Eggen M, Georg GI., Med Res Rev 22(2), 2002
PMID: 11857635

Hamel, Curr. Med. Chem. 9(), 2002

Tius, Tetrahedron 58(), 2002

Nahrwold, Chim. Oggi 23(), 2008

AUTHOR UNKNOWN, 0
Phase I trial of the cryptophycin analogue LY355703 administered as an intravenous infusion on a day 1 and 8 schedule every 21 days.
Stevenson JP, Sun W, Gallagher M, Johnson R, Vaughn D, Schuchter L, Algazy K, Hahn S, Enas N, Ellis D, Thornton D, O'Dwyer PJ., Clin. Cancer Res. 8(8), 2002
PMID: 12171879
Phase I and pharmacological studies of the cryptophycin analogue LY355703 administered on a single intermittent or weekly schedule.
Sessa C, Weigang-Kohler K, Pagani O, Greim G, Mora O, De Pas T, Burgess M, Weimer I, Johnson R., Eur. J. Cancer 38(18), 2002
PMID: 12460783
A multicenter phase II study of the cryptophycin analog LY355703 in patients with platinum-resistant ovarian cancer.
D'Agostino G, del Campo J, Mellado B, Izquierdo MA, Minarik T, Cirri L, Marini L, Perez-Gracia JL, Scambia G., Int. J. Gynecol. Cancer 16(1), 2006
PMID: 16445613
Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain.
Ravelli RB, Gigant B, Curmi PA, Jourdain I, Lachkar S, Sobel A, Knossow M., Nature 428(6979), 2004
PMID: 15014504

AUTHOR UNKNOWN, 0
Cryptophycins-309, 249 and other cryptophycin analogs: preclinical efficacy studies with mouse and human tumors.
Liang J, Moore RE, Moher ED, Munroe JE, Al-awar RS, Hay DA, Varie DL, Zhang TY, Aikins JA, Martinelli MJ, Shih C, Ray JE, Gibson LL, Vasudevan V, Polin L, White K, Kushner J, Simpson C, Pugh S, Corbett TH., Invest New Drugs 23(3), 2005
PMID: 15868377
Biological evaluation of cryptophycin 52 fragment A analogues: effect of the multidrug resistance ATP binding cassette transporters on antitumor activity.
Al-Awar RS, Corbett TH, Ray JE, Polin L, Kennedy JH, Wagner MM, Williams DC., Mol. Cancer Ther. 3(9), 2004
PMID: 15367700
A convergent approach to cryptophycin 52 analogues: synthesis and biological evaluation of a novel series of fragment a epoxides and chlorohydrins.
Al-Awar RS, Ray JE, Schultz RM, Andis SL, Kennedy JH, Moore RE, Liang J, Golakoti T, Subbaraju GV, Corbett TH., J. Med. Chem. 46(14), 2003
PMID: 12825938

Kobayashi, Chem. Pharm. Bull. 42(), 1994

AUTHOR UNKNOWN, 0
Total synthesis of cryptophycin analogues via a scaffold approach.
McCubbin JA, Maddess ML, Lautens M., Org. Lett. 8(14), 2006
PMID: 16805535

Tripathy, Tetrahedron Lett. 45(), 2004
Biosynthetic characterization and chemoenzymatic assembly of the cryptophycins. Potent anticancer agents from cyanobionts.
Magarvey NA, Beck ZQ, Golakoti T, Ding Y, Huber U, Hemscheidt TK, Abelson D, Moore RE, Sherman DH., ACS Chem. Biol. 1(12), 2006
PMID: 17240975

AUTHOR UNKNOWN, 0

Mast, Chem. Eur. J. 11(), 2005
Stereospecific synthesis of cryptophycin 1.
Li LH, Tius MA., Org. Lett. 4(10), 2002
PMID: 12000261

Pousset, Tetrahedron 57(), 2001

AUTHOR UNKNOWN, 0

Kolb, Tetrahedron 48(), 1992

Kotoku, Tetrahedron Lett. 48(), 2007

Eissler, Synlett (), 2008
Short and efficient synthesis of cryptophycin unit A.
Eissler S, Nahrwold M, Neumann B, Stammler HG, Sewald N., Org. Lett. 9(5), 2007
PMID: 17284043

Wang, J. Org. Chem. 62(), 1997

Maryanoff, J. Am. Chem. Soc. 107(), 1985

Cheskis, Russ. Chem. Bull. 102(), 1993

Ragoussis, J. Chem. Soc. Perkin Trans. 1 (), 1998

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Wang, Tetrahedron Lett. 33(), 1992

Harcken, Synlett (), 2001

Larcheveque, Tetrahedron 40(), 1984
3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors.
Weide T, Arve L, Prinz H, Waldmann H, Kessler H., Bioorg. Med. Chem. Lett. 16(1), 2005
PMID: 16236508

Ducry, Helv. Chim. Acta 82(), 1999

Inanaga, Bull. Chem. Soc. Jpn. 52(), 1979
Isolation of human mdr DNA sequences amplified in multidrug-resistant KB carcinoma cells.
Roninson IB, Chin JE, Choi KG, Gros P, Housman DE, Fojo A, Shen DW, Gottesman MM, Pastan I., Proc. Natl. Acad. Sci. U.S.A. 83(12), 1986
PMID: 3459187
Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity.
O'Brien J, Wilson I, Orton T, Pognan F., Eur. J. Biochem. 267(17), 2000
PMID: 10951200

AUTHOR UNKNOWN, 0

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