Ultrasound-promoted synthesis and immunosuppressive activity of novel quinazoline derivatives

Mol Divers. 2012 Aug;16(3):579-90. doi: 10.1007/s11030-012-9390-1. Epub 2012 Aug 14.

Abstract

An environmentally friendly and mild Bischler cyclization was developed to access quinazolines with diverse substitution. Based on this method, a library of 53 quinazoline derivatives was prepared and tested in vitro for cytotoxicity and inhibition on T-cell and B-cell proliferation. Compounds 6b, 7b, 17b, 33, and 35 showed higher inhibitory activity on both T-cell and B-cell proliferations, with IC(50) values of 6.16, 6.30, 5.43, 2.54, and 9.80 μM on T-cell, respectively. All the tested compounds showed no obvious cytotoxicity at 10 μM concentration. The preliminary structure-activity relationship was concluded revealing that 4-position is the key modification site for potent quinazoline immunosuppressive agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • B-Lymphocytes / cytology
  • B-Lymphocytes / drug effects
  • Cell Proliferation / drug effects
  • Chemistry Techniques, Synthetic
  • Female
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology*
  • Immunosuppressive Agents / toxicity
  • Male
  • Mice
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • Quinazolines / toxicity
  • Structure-Activity Relationship
  • T-Lymphocytes / cytology
  • T-Lymphocytes / drug effects
  • Ultrasonics*

Substances

  • Immunosuppressive Agents
  • Quinazolines