Electron impact mass spectra of novel tetrahydroimidazo [4, 5, l-jk] [1, 4]benzodiazepin-2(1H)-one derivatives

✍ Scribed by Gary W. Caldwell; Michael J. Kukla; John A. Masucci; Henry J. Breslin; William J. Jones; Diane A. Gauthier; Cynthia L. Fedde

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 175 KB
• Volume: 26
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/oms.1210260210

✦ Synopsis

Mass spectral fragmentations of nine benzodiazepin derivatives were examined by exact mass measurement and by metastable ion analysis. Under electron impact conditions, all compounds give rise to a molecular ion and ions of m/z 160, 159, 147,131, 104, 77, 56,41, and 39. Key fragmentation pathways are discussed for these ions.

I N T R O D U C T I O N

Tetrahydroimidazo[4, 5, 1 -jk][ 1, 4lbenzodiazepin-2(1H)-one (TIBO) derivatives (1-9) are a novel class of compounds that have been synthesized in our laboratory' and tested for their inhibition against the replication of human immunodeficiency virus (HIV-l), the main aetiological agent of AIDS2 The TIBO derivatives are among the most specific and potent inhibitors of HIV-1 replication studied to date and this prompted us to study the electron impact (EI) mass spectra of these compounds. We report here an investigation of the EI fragmentation pathways of TIBO derivatives 1-9. Structures and molecular masses are shown in Scheme 1. Exact mass measurements and metastable R Molecular mass (u) 1 H ( S ) -( + ) 2 CH,C(O)CH, 3 CH,CN 4 CH,CCH 5 CH,CH,OH 6 CH,CH,CH, 7 CH,CH-CH,(S) -(+) 8 CH,CH-C(CH,),(S) -(+) 9 CH,C(CO,CH,CH,)-CH,