Quinazolinethiones and quinazolinediones, novel inhibitors of inosine monophosphate dehydrogenase: synthesis and initial structure–activity relationships

https://doi.org/10.1016/j.bmcl.2004.11.015Get rights and content

Abstract

The development of a series of novel quinazolinethiones and quinazolinediones as inhibitors of inosine monophosphate dehydrogenase (IMPDH) is described. The synthesis, in vitro inhibitory values for IMPDH II and in vitro inhibitory value for PBMC proliferation are discussed.

Graphical abstract

Novel quinazolinethiones and quinazolinediones are reported which exhibit IMPDH II inhibitory activity.

  1. Download : Download full-size image

References and notes (15)

  • F.R. Collart et al.

    J. Biol. Chem.

    (1988)
  • Y. Natsumeda et al.

    J. Biol. Chem.

    (1990)
  • G. Jones et al.

    J. Mol. Biol.

    (1995)
  • R.C. Jackson et al.

    Nature

    (1975)
  • H.N. Jayaram et al.

    Curr. Med. Chem.

    (1999)
There are more references available in the full text version of this article.

Cited by (55)

  • Surfactant based nanoreactor micellar assembly: An innovative route for synthesis of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones

    2022, Journal of Molecular Liquids
    Citation Excerpt :

    In addition, 2-thioxo-2,3-digydroquinazolin-4(1H)-ones find prime role as suitable intermediates for synthesis of valuable bioactive compounds [29]. Owing to their diverse applications in distinct fields, many methodologies have been reported for synthesis of thioxoquinazolinone [31-38]. Sayahi et al. synthesized 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives by multi component reaction of methyl 2-bromobenzoate, phenyl isothiocyanate and sodium azide in the presence of copper bromide, L-proline and DMSO as catalyst, ligand and solvent, respectively [39] (Fig. 2A).

  • Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines

    2013, European Journal of Medicinal Chemistry
    Citation Excerpt :

    The (5-oxazolyl) phenyl compounds containing amide (e.g., 8 and 9) [26] and diamide (e.g., 10) [27] linkers have been synthesized as inhibitors of IMPDH, and compound 9 is a dual inhibitor of IMPDH and histone deacetylases (HDACs) [28,29]. The analogues of oxazolyl-indole [30], oxazolyl-quinolone [31,32], oxazolyl-quinazolinone and quinazolinethione [33,34] based linkers, compounds 11, 12, 13 and 14 yield good IMPDH inhibitors. As mentioned above, many kinds of inhibitors of IMPDH have been reported.

View all citing articles on Scopus

Present address: Argenta Discovery Ltd, 8/9 Spire Green Centre, Flex Meadow, Harlow, CM19 5TR, UK.

View full text