Abstract
A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 876-883 |
| Number of pages | 8 |
| Journal | Journal of Natural Products |
| Volume | 72 |
| Issue number | 5 |
| DOIs | |
| State | Published - May 22 2009 |
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ASJC Scopus subject areas
- Complementary and alternative medicine
- Molecular Medicine
- Organic Chemistry
- Analytical Chemistry
- Pharmaceutical Science
- Pharmacology
- Drug Discovery
Cite this
Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2. / Pettit, George; Quistorf, Peter D.; Fry, Jeremy A.; Herald, Delbert L.; Hamel, Ernest; Chapuis, Jean.
In: Journal of Natural Products, Vol. 72, No. 5, 22.05.2009, p. 876-883.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2
AU - Pettit, George
AU - Quistorf, Peter D.
AU - Fry, Jeremy A.
AU - Herald, Delbert L.
AU - Hamel, Ernest
AU - Chapuis, Jean
PY - 2009/5/22
Y1 - 2009/5/22
N2 - A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.
AB - A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.
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UR - http://www.scopus.com/inward/citedby.url?scp=66449124775&partnerID=8YFLogxK
U2 - 10.1021/np800635h
DO - 10.1021/np800635h
M3 - Article
VL - 72
SP - 876
EP - 883
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 5
ER -