Synthesis and Evaluation of Analogues of 5'-((Z)-4-Amino-2-butenylmethylamino)-5'-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

Canio J. Marasco Jr.; Debora L. Kramer; Carl W. PorterCyrus J. BacchiDonna RattendiLouis KuceraNathan IyerRalph BernackiPaula PeraJanice R. Sufrin

首页> 外文期刊>Journal of Medicinal Chemistry >Synthesis and Evaluation of Analogues of 5'-((Z)-4-Amino-2-butenylmethylamino)-5'-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

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Synthesis and Evaluation of Analogues of 5'-((Z)-4-Amino-2-butenylmethylamino)-5'-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

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A well-defined series of 5'-((Z)-4-amino-2-butenylmethylamino)-5'-deoxyadenosine analogues was designed and synthesized in order to further ascertain the optimal structural requirements for S-adenosylmethionine decarboxylase inhibition and potentially to augment and perhaps separate their antiproliferative and antitrypanosomal activities. Most structural modifications had a deleterious affect on both the antitrypanosmal and antineoplastic activity of 5'-((Z)-4-amino-2-butenylmethylamino)-5'-deoxyadenosine. However, di-O-acetylation of the parent compound produced a potential prodrug that caused markedly pronounced inhibition of trypanosomal and neoplastic cell growth and viability. Moreover, the acetylated derivative of 5'-((Z)-4-amino-2-butenylmethylamino)-5'-deoxyadenosine did inhibit HIV-1 growth and infectivity, whereas the parent compound did not.

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《Journal of Medicinal Chemistry》 |2002年第23期|5112-5122|共11页
作者
Canio J. Marasco Jr.; Debora L. Kramer; Carl W. PorterCyrus J. BacchiDonna RattendiLouis KuceraNathan IyerRalph BernackiPaula PeraJanice R. Sufrin;
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作者单位

Department of Mathematics and Natural Sciences, D'Youville college, Buffalo, New York 14213;

Department of Pharmacology and Therapeutics, Grace Cancer Drug Center, Roswell Park Cancer Institute, Buffalo, New York 14263;

Haskins Laboratories and Department of Biology, Pace University, New York, New York 10038Wake Forest University School of Medicine, Winston-Salem, North Carolina 27157;

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Synthesis and Evaluation of Analogues of 5'-((Z)-4-Amino-2-butenylmethylamino)-5'-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

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