Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide
Publication type: Journal Article
Publication date: 1981-12-01
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
7310817
Drug Discovery
Molecular Medicine
Abstract
Hydrogenolysis of 3-(benzyloxy)cyclophosphamide (10) using Pd/C catalyst and ethyl acetate as solvent leads to the formation of 3-hydroxycyclophosphamide (3, approximately 20%) and cyclophosphamide (1, approximately 10%), accompanied by regioselective hydrogen-exchange reactions at the C-4 and C-5 positions in 3 and 1. A variety of oxidizing reagents and liver microsomal incubation failed to provide evidence (31P NMR) for conversion of 1 into 3, whereas identical incubation of 3 led to its reduction to 1. Compound 3 is stable at pH 6.5-8.2, 37 degrees C, and exhibits anticancer activity comparable to 1 when tested against L1210 leukemia in mice. Data are discussed with regard to a previously reported suggestion that metabolism of 1 may involved oxidation to give 3 followed by rearrangement of 3 to 2.
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Brandt J. A. et al. Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide // Journal of Medicinal Chemistry. 1981. Vol. 24. No. 12. pp. 1404-1408.
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Brandt J. A., Ludeman S. M., Zon G., EGAN W., Todhunter J. A., Dickerson R. Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide // Journal of Medicinal Chemistry. 1981. Vol. 24. No. 12. pp. 1404-1408.
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RIS
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TY - JOUR
DO - 10.1021/jm00144a007
UR - https://doi.org/10.1021/jm00144a007
TI - Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide
T2 - Journal of Medicinal Chemistry
AU - Brandt, Joan A
AU - Ludeman, Susan Marie
AU - Zon, Gerald
AU - EGAN, WILLIAM
AU - Todhunter, John A
AU - Dickerson, Ruth
PY - 1981
DA - 1981/12/01
PB - American Chemical Society (ACS)
SP - 1404-1408
IS - 12
VL - 24
PMID - 7310817
SN - 0022-2623
SN - 1520-4804
ER -
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BibTex (up to 50 authors)
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@article{1981_Brandt,
author = {Joan A Brandt and Susan Marie Ludeman and Gerald Zon and WILLIAM EGAN and John A Todhunter and Ruth Dickerson},
title = {Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide},
journal = {Journal of Medicinal Chemistry},
year = {1981},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jm00144a007},
number = {12},
pages = {1404--1408},
doi = {10.1021/jm00144a007}
}
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MLA
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Brandt, Joan A., et al. “Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide.” Journal of Medicinal Chemistry, vol. 24, no. 12, Dec. 1981, pp. 1404-1408. https://doi.org/10.1021/jm00144a007.