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Title 

Water soluble prodrugs of the antitumor agent 3-[(3-amino-4-methoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)cyclopent-2-ene-1-one

Authors 

N H NamY KimY J YouDong Ho HongHwan Mook KimB Z Ahn

Publisher 

Elsevier

Issue Date 

2003

Citation 

Bioorganic & Medicinal Chemistry, vol. 11, no. 6, pp. 1021-1029

Keywords 

1 4 aminobutyric amide1 4 aminomethylbenzoic amide1 4 bis(2 chloroethyl)aminophenylalanine1 6 aminohexanoic amide1 [3 [2' (dibenzyloxyphosphono)oxy 4',6' dimethylphenyl] 3,3 dimethylpropionic]amide1 [3 [2' (dihydroxyphosphono)oxy 4',6' dimethylphenyl] 3,3 dimethylpropionic]amide1 alanine1 beta alanine1 cysteine1 dextro alanine

Abstract 

Fourteen prodrugs of the antitumor agent 3-[(3-amino-4-methoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)cyclopent-2-ene-1-one (1) were prepared to improve its water solubility and potency. These prodrugs include α-amino acid (1a-1h), aliphatic amino acid (1i-1l), phosphoramidate (1m), and phosphate (1n) derivatives. All of the prodrugs showed improved water solubility. A number of the amino acid prodrugs (1a, 1b, 1d-1f, 1h, 1j, and 1k) exhibited more potent antitumor activity compared to the parent compound (1). The phosphate prodrug 1n also offered a potent antitumor activity, but the phosphoramidate 1m did not show any antitumor activity in vivo. None of the prodrugs exhibited significant toxicities in mice. These results indicate that the design and preparation of the amino acid prodrugs (1a, 1b, 1d-1f, 1h, 1j, and 1k) and phosphate prodrug (1n) are beneficial for enhancing the antitumor activity of 1. The similar approaches may be used to improve water solubility and bioactivity of other poorly soluble aromatic amines.

ISSN 

0968-0896

Link 

http://dx.doi.org/10.1016/S0968-0896(02)00514-X

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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