126233-96-3

Upstream product

• 126233-79-2 4,5,6,7-tetrahydro-5-methylimidazo<4,5,1-jk><1,4>benzodiazepin-2(1H)-one 
• 870-63-3 prenyl bromide 
• 257891-58-0 4-Chloro-8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2H-2,7,9a-triaza-benzo[cd]azulen-1-one 
• 131514-77-7 methyl 3-nitro-2-<<2-<(phenylmethyl)amino>propyl>amino>benzoate 
• 126233-82-7 4,5,6,7-tetrahydro-5-methyl-6-(phenylmethyl)imidazo<4,5,1-jk><1,4>benzodiazepin-2-(1H)-one 
• 131514-79-9 2,3,4,5-tetrahydro-3-methyl-4-(phenylmethyl)-1H-1,4-benzodiazepin-9-amine 
• 5337-09-7 2-bromo-3-nitro-benzoic acid methyl ester 
• 573-54-6 2-bromo-3-nitro-benzoic acid 
• 6286-36-8 2-bromo-3-nitrobenzoic acid chloride 
• 126234-15-9 2,3,4,5-tetrahydro-3-methyl-9-nitro-4-(phenylmethyl)-1H-1,4-benzodiazepin-5-one 

Downstream Products

• 136722-80-0 4,5,6,7-tetrahydro-N,5-dimethyl-6-(3-methyl-2-butenyl)imidazo(4,5,1-jk)[1,4]benzodiazepin-2-amine 
• 136722-82-2 (+/-)-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2-butenyl)-2-(phenylthio)imidazo(4,5,1-jk)[1,4]benzodiazepine 
• 136779-93-6 (+/-)-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2-butenyl)imidazo[4,5,1-jk][1,4]-benzodiazepin-2(1H)-thione 
• 136722-81-1 Dimethyl-[8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2,7,9a-triaza-benzo[cd]azulen-1-yl]-amine 

Relevant academic research and scientific papers

Synthesis and Anti-HIV-1 Activity of 4,5,6,7-Tetrahydro-5-methylimidazobenzodiazepin-2(1H)-one (TIBO) Derivatives

A series of 6-substituted 4,5,6,7-tetrahydro-5-methylimidazobenzodiazepin-2(1H)-ones (9) have been synthesized and tested for their ability to inhibit the replication of the HIV-1 virus in MT-4 cells.Two synthetic methods are described, one of which allows the synthesis of single enantiomers of the final products.A structure-activity study was done within the series of compounds to determine the optimum group for the 6-position substitution and to determine whether the activity was enantiospecific at the 5-position, which was substituted with a methyl group.The best analogue, 9jj, inhibited HIV-1 with an IC50 of 4 μM, which is comparable to the activity level of DDI, a 2',3'-dideoxynucleoside-type structure undergoing clinical trials as an anti-AIDS therapy.

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. 2

In the first paper of this series a new structure with anti-HIV-1 activity was disclosed and analogues were synthesized to explore the structure- activity relationship of changes in the substituent (R) attached at the N-6 position of 9. This study describes the syntheses and anti-HIV-1 testing of analogues with variations of the five-membered urea ring of the 4,5,6,7- tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) structures. Although many different rings were synthesized to replace the cyclic urea of TIBO, most were found to be inactive in inhibiting the replication of the HIV-1 virus in MT-4 cells. The exceptions were replacement of the urea oxygen with sulfur or selenium to give the corresponding thio- or selenoureas. These were found to be more active than the oxygen counterparts. A small series of analogues was synthesized and tested which allowed direct comparison of urea and thiourea derivatives. Without exception, the latter were always more active than the former. The most active compound of this series (8d) was found to inhibit the HIV-1 virus with an IC50 of 0.012 μM which is comparable to that of AZT.