Development of a photoaffinity label for respiratory syncytial virus inhibitors

✍ Scribed by Douglas D. Dischino; Christopher W. Cianci; Rita Civiello; Mark Krystal; Nicholas A. Meanwell; Hiromi Morimoto; Philip G. Williams; Kuo-Long Yu

• Book ID: 102374093
• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: French
• Weight: 127 KB
• Volume: 46
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.743

✦ Synopsis

Abstract

The syntheses of tritiated and radio‐iodinated respiratory syncytial virus inhibitor photoaffinity labels are reported. ^3^H‐1‐Isopropyl‐3‐(1‐[2‐(3‐methyl‐3H‐diazirin‐3‐yl)‐ethyl]‐1H‐benzoimidazol‐2‐yl)methyl)‐1,3‐dihydrobenzoimid‐azol‐2‐one (1), was prepared in two steps by the initial tritiation of N‐isopropenyl‐2‐benzimidazolone followed by coupling to 2‐chloromethyl‐1‐[2‐(3‐methyl‐3H‐diazirin‐3‐yl)ethyl]‐1H‐benzoimidazole. The mono and diiodo‐radio‐iodinated derivatives of 1‐(4‐hydroxybenzyl)‐3‐(1‐[2‐(3‐methyl‐3H‐diazirin‐3‐yl)‐ethyl]‐2,3‐dihydro‐1H‐benzo‐imidazol‐2‐ylmethyl)‐1,3‐dihydro‐benzoimidazol‐2‐one (2, 3), were prepared by the radio‐iodination of the corresponding phenol with Na^125^I and iodogen. Copyright © 2003 John Wiley & Sons, Ltd.