Tumor necrosis factor-alpha production enhancing activity of substituted 3'-methylthalidomide: Influence of substituents at the phthaloyl moiety on the activity and stereoselectivity

Hiroyuki Miyachi, Yukiko Koiso, Ryuichi Shirai, Satomi Niwayama, Jun O. Liu, Yuichi Hashimoto

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The synthesis and tumor necrosis factor (TNF)-α production enhancing activity of substituted 3'-methyl-thalidomides on human leukemia cell line HL-60 stimulated with 12-O-tetradecanoyl-phorbol 13-acetate (TPA) are described. Though the introduction of an electron-donating amino group at the phthaloyl moiety of α-methylthalidomides enhanced the activity, substituted α-methylthalidomides showed decreased stereoselectivity as compared to that of non-substituted α-methylthalidomide. The data indicates that the TNF-α production enhancing activity of thalidomide derivatives depends on both the electronic-state of substituents at the fused benzene ring and the stereochemistry of the glutarimide moiety.

Original languageEnglish
Pages (from-to)1165-1168
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume46
Issue number7
Publication statusPublished - 1998
Externally publishedYes

Fingerprint

Stereoselectivity
Thermodynamic properties
Tumor Necrosis Factor-alpha
Stereochemistry
Thalidomide
Electronic states
Tetradecanoylphorbol Acetate
Benzene
Leukemia
Cells
Electrons
Derivatives
Cell Line
3'-methylthalidomide

Keywords

  • 12-O-tetradecanoyl-phorbol 13-acetate
  • 3'-methylthalidomide
  • Human leukemia cell line
  • Tumor necrosis factor-α

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Tumor necrosis factor-alpha production enhancing activity of substituted 3'-methylthalidomide : Influence of substituents at the phthaloyl moiety on the activity and stereoselectivity. / Miyachi, Hiroyuki; Koiso, Yukiko; Shirai, Ryuichi; Niwayama, Satomi; Liu, Jun O.; Hashimoto, Yuichi.

In: Chemical and Pharmaceutical Bulletin, Vol. 46, No. 7, 1998, p. 1165-1168.

Research output: Contribution to journalArticle

Miyachi, Hiroyuki ; Koiso, Yukiko ; Shirai, Ryuichi ; Niwayama, Satomi ; Liu, Jun O. ; Hashimoto, Yuichi. / Tumor necrosis factor-alpha production enhancing activity of substituted 3'-methylthalidomide : Influence of substituents at the phthaloyl moiety on the activity and stereoselectivity. In: Chemical and Pharmaceutical Bulletin. 1998 ; Vol. 46, No. 7. pp. 1165-1168.
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AU - Shirai, Ryuichi

AU - Niwayama, Satomi

AU - Liu, Jun O.

AU - Hashimoto, Yuichi

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