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Synthesis of 2-[11C]methoxy-3,17β-estradiol to measure the pharmacokinetics of an antitumor drug candidate, 2-methoxy-3,17β-estradiol

✍ Scribed by Jiyoung Mun; Ronald J. Voll; Mark M. Goodman

Book ID
102367932
Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
129 KB
Volume
49
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

2‐Methoxy‐3,17β‐estradiol, an endogenous estrogen metabolite, showed cytotoxicity in various cancer cell lines and also has antiangiogenic and proapoptotic activities. Clinical I and II trials of 2‐methoxy‐3,17β‐estradiol for multiple myeloma, advanced solid tumors, metastatic breast and prostate cancer are underway. We prepared 2‐[^11^C]methoxy‐3,17β‐estradiol to measure the pharmacokinetics and organ distribution of 2‐methoxy‐3,17β‐estradiol in clinical trials. 2‐[^11^C]Methoxy‐3,17β‐estradiol was synthesized from a precursor, 2‐hydroxy‐3,17β‐O‐bis(methoxymethyl)estradiol, in two steps with over 99% radiochemical purity. The overall reaction time was 45 min and the decay‐corrected radiochemical yield was 32.9%. The distribution coefficient (logP~7.4~) of 2‐[^11^C]methoxy‐3,17β‐estradiol at pH 7.4 was measured as 2.95. Copyright © 2006 John Wiley & Sons, Ltd.

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A new approach for 11C–C bond formation:
A new approach for 11C–C bond formation: Synthesis of 17α-(3′-[11C]prop-1-yn-1-yl)-3-methoxy-3,17β-estradiol
✍ F. Wüst; J. Zessin; B. Johannsen 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 French ⚖ 200 KB

## Abstract A new approach for ^11^C–C bond formation via a Sonogashira‐like cross‐coupling reaction of terminal alkynes with [^11^C]methyl iodide was exemplified by the synthesis of 17__α__‐(3′‐[^11^C]prop‐1‐yn‐1‐yl)‐3‐methoxy‐3,17__β__‐estradiol. The LC‐purified title compound was obtained in dec