Synthesis and Evaluation of 7.alpha.-Iodo-5.alpha.-dihydrotestosterone as a Potential Radioligand for Androgen Receptor

Hoyte, Robert M.; Borderon, K.; Bryson, Karlene; Allen, Richard B.; Hochberg, Richard B.; Brown, Theodore J.

doi:10.1021/jm00034a022

Cited by 18 publications

(14 citation statements)

References 3 publications

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“…High selectivity was found towards the formation of steroidal enones even when free hydroxyl groups, at different positions, were present. Steroids with a free hydroxyl group at the 3-position (entry 21-23, 29-30, Table 2) were oxidized successfully into the corresponding a,b-enones (17,(23)(24)(25) in good yields (68-70%). Interestingly, oxidation of dehydroepiandrosterone (DHEA, 2, entry 22) could be performed in a 1 : 1 mixture of water and 70% TBHP as a reaction medium and, after almost quantitative conversion, the 7-oxo compound was obtained exclusively without the formation of the 3-oxo compound.…”

Section: Resultsmentioning

confidence: 99%

An economical and green approach for the oxidation of olefins to enones

Marwah

Lardy

2004

Green Chem.

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Section: Resultsmentioning

confidence: 99%

An economical and green approach for the oxidation of olefins to enones

Marwah

Lardy

2004

Green Chem.

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“…This mostly represented an extension of studies conducted during the late 1980's in which radiohalogens 1-125 or F-18 were incorporated at the 7a, 16a, or 17a-positions (Fig. 8) [30][31][32][33]. These early results were generally disappointing in that the radiochemicals exhibited either little specific binding or metabolic lability, or both.…”

Section: Androgen Receptor Ligandsmentioning

confidence: 88%

A Structure Based, Solid Phase Synthesis Approach to the Development of Novel Selective Estrogen Receptor Modulatory Steroids

Hanson¹

2001

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Public reporting burden for this collection of information is estimated to average 1 hour per response, including the lime for reviewing instructions, searching existing data sources, gathering and maintaining ' the data needed, and completing and reviewing this collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden to Washington Headquarters Services, Directorate for Information Operations and Reports, 1215 Jefferson Davis Highway, Suite 1204, Arlington, VA 22202-4302, and to the Office of Management and Budget, Paperwork Reduction Project (0704-0188), Washington, DC 20503 REPORT DOCUMENTATION PAGE REPORT TYPE AND DATES COVEREDAnnual (1 Jun 99 -31 May 00) TITLE AND SUBTITLEA Structure Based, Solid Phase Synthesis Approach to the Development of Novel Selective Estrogen Receptor Modulatory Steroids AUTHOR(S)Robert Hanson, Ph.D. PERFORMING ORGANIZATION NAME(S) AND ADDRESS(ES)Northeastern University Boston, Massachusetts 02115 E-MAIL:r.hanson@nunet.neu. edu The objective of this project is the development of new chemotherapeutic agents for the treatment of hormone responsive breast cancer using a structure-based, solid-phase synthesis approach. We have successfully linked an activated derivative of estradiol to a solid support and converted it to two different series of estrogen receptor ligands. SPONSORING / MONITORING AGENCY NAME(S) AND ADDRESS(ES)UWe have begun the biological evaluation of these compounds and initail results suggest that significant receptor affinity is retained.Conformational studies using NMR and computational methods have provided results that can be used in directing the synthesis of newer estrogen receptor binding agents. Where copyrighted material is quoted, permission has been tained to use such material. SUBJECT TERMSWhere material from documents designated for limited distribution is quoted, permission has been obtained to use the material.Citations of commercial organizations and trade names in this report do not constitute an official Department of Army endorsement or approval of the products or services of these organizations.N/A In conducting research using animals, the investigator(s) adhered to the "Guide for the Care and Use of Laboratory S.Introduction:The overall objective of this project is the development of new chemotherapeutic agents for the treatment of hormone responsive breast cancer. Based upon our previous synthetic work and molecular modeling studies we selected the 17a-(substituted phenyl)vinyl estradiols as the lead compounds for our drug development program. We chose a solid-phase synthesis approach to more rapidly generate target compounds for subsequent bioevaluation studies. The review of the results and comparison with molecular conformations, determined by both computational and analytical methods, would provide insight into the interactions of the compounds with the target estrogen receptors. Our approach involved developing the solid phas...

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“…This mostly represented an extension of studies conducted during the late 1980's in which radiohalogens I-125 or F-18 were incorporated at the 7α, 16α, or 17α-positions (Fig. 8) [30][31][32][33]. These early results were generally disappointing in that the radiochemicals exhibited either little specific binding or metabolic lability, or both.…”

Section: B Progesterone Receptor Ligandsmentioning

confidence: 90%

Synthesis of Auger Electron-Emitting Radiopharmaceuticals

Hanson

2000

CPD

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Targeted radiotherapy using Auger electron-emitting pharmaceuticals offers both advantages and challenges compared to alternative alpha - or beta -emitting agents. The low energy Auger electrons deposit their energy within the target cell thereby minimizing collateral damage. To achieve this effect, however, the radiopharmaceutical must incorporate the appropriate radionuclide, be efficiently synthesized, and once administered, be distributed selectively to its biological target. This review covers the synthesis of agents which have prepared over the past decade either as Auger electron-emitting radiopharmaceuticals or which have the potential as such. While not an exhaustive review, the major classes of agents, such as hormone receptor ligands, nucleoside analogs and intercalating agents are described.

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Synthesis and Evaluation of 7.alpha.-Iodo-5.alpha.-dihydrotestosterone as a Potential Radioligand for Androgen Receptor

Cited by 18 publications

References 3 publications

An economical and green approach for the oxidation of olefins to enones

An economical and green approach for the oxidation of olefins to enones

A Structure Based, Solid Phase Synthesis Approach to the Development of Novel Selective Estrogen Receptor Modulatory Steroids

Synthesis of Auger Electron-Emitting Radiopharmaceuticals

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