ChemInform Abstract: Synthesis and Anti-HIV-1 Activity of 4,5,6,7-Tetrahydro-5- methylimidazo(4,5,1-jk)(1,4)benzodiazepin-2(1H)-one (TIBO) Derivatives.
Abstract
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ChemInform Abstract
Methyl 2-bromo-3-nitrobenzoate (III), prepared from the acid (I), is coupled with the diamine (IV) to give the substitution product (V). Cyclization followed by reduction of the lactam moiety yields the benzodiazepine (VI) which is treated with the chloroformate (VII), producing the imidazobenzodiazepine (VIII) after debenzylation. This reacts with forty alkyl halides such as (IX) to form the substitution products (X) mentioned in the title. The derivative (Xb) shows the best antiviral activity in this series. Most active is the S- enantiomer of (Xb) which is synthesized independently by common methods starting with the amino acid ester (S)-(XI).
