e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and anti-HIV activity of 1, 3, 4, 5-tetrahydro-2H-1, 4-benzodiazepin-2-one (TBO) derivatives. truncated 4, 5, 6, 7-tetrahydro-5-methylimidazo [4, 5, 1-jk][1, 4] …

…, H Cullis, F De Knaep, R Pauwels, K Andries…

Index: Breslin, Henry J.; Kukla, Michael J.; Kromis, Teresa; Cullis, Heather; De Knaep, Fons; Pauwels, Rudi; Andries, Koen; De Clercq, Erik; Janssen, Marcel A.C.; Janssen, Paul A.J. Bioorganic and Medicinal Chemistry, 1999 , vol. 7, # 11 p. 2427 - 2436

Full Text: HTML

Citation Number: 33

Abstract

4, 5, 6, 7-Tetrahydro-5-methylimidazo [4, 5, 1-jk][1, 4] benzodiazepin-2 (1H)-ones (TIBO), 1, have been shown to significantly inhibit HIV-1 replication, as reported in detail in our prior publications. Since our earlier reports, we have modified the TIBO structures 1 by removing the 5-membered ring of 1, generating 1, 3, 4, 5-tetrahydro-2H-1, 4-benzodiazepin-2-ones (TBO), 4, a bicyclic series of compounds. Although compounds 4 possess modest activity ...

3,3-Dimethylallyl bromide Structure

3,3-Dimethylall...

3-methyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

3-methyl-1,3,4,...

~42%

3-methyl-4-(3-methylbut-2-enyl)-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

3-methyl-4-(3-m...

5-CHLORO-2-NITROBENZYLAMINE Structure

5-CHLORO-2-NITR...

~%

7-chloro-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-1,3,4,...

ethyl N-[(5-chloro-2-nitrophenyl)methyl]glycine Structure

ethyl N-[(5-chl...

~%

7-chloro-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-1,3,4,...

ethyl N-[(2-amino-5-chlorophenyl)methyl]glycine Structure

ethyl N-[(2-ami...

~19%

7-chloro-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-1,3,4,...

(+/-)-methyl 2-[[(2-amino-5-chlorophenyl)methyl]amino]-3-methylbutanoate Structure

(+/-)-methyl 2-...

~63%

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

5-Chloro-2-nitrobenzyl alcohol Structure

5-Chloro-2-nitr...

~%

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

DL-Valine Methyl Ester Hydrochloride Structure

DL-Valine Methy...

~%

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

5-chloro-2-nitrobenzyl methanesulfonate Structure

5-chloro-2-nitr...

~%

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

N/A Structure

~%

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

3,3-Dimethylallyl bromide Structure

3,3-Dimethylall...

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

~75%

7-chloro-4-(3-methylbut-2-enyl)-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-4-(3-m...

5-Chloro-2-nitrobenzyl alcohol Structure

5-Chloro-2-nitr...

~%

7-chloro-4-(3-methylbut-2-enyl)-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-4-(3-m...

DL-Valine Methyl Ester Hydrochloride Structure

DL-Valine Methy...

~%

7-chloro-4-(3-methylbut-2-enyl)-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-4-(3-m...

5-chloro-2-nitrobenzyl methanesulfonate Structure

5-chloro-2-nitr...

~%

7-chloro-4-(3-methylbut-2-enyl)-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-4-(3-m...

N/A Structure

~%

7-chloro-4-(3-methylbut-2-enyl)-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-4-(3-m...

(+/-)-methyl 2-[[(2-amino-5-chlorophenyl)methyl]amino]-3-methylbutanoate Structure

(+/-)-methyl 2-...

~%

7-chloro-4-(3-methylbut-2-enyl)-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-4-(3-m...

(+/-)-α-[[(2-amino-5-chlorophenyl)methyl]amino]benzeneacetic acid methyl ester Structure

(+/-)-α-[[(2-am...

~41%

7-chloro-3-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-phen...

5-Chloro-2-nitrobenzyl alcohol Structure

5-Chloro-2-nitr...

~%

7-chloro-3-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-phen...

methyl 2-amino-2-phenylacetate hydrochloride Structure

methyl 2-amino-...

~%

7-chloro-3-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-phen...

5-chloro-2-nitrobenzyl methanesulfonate Structure

5-chloro-2-nitr...

~%

7-chloro-3-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-phen...

(+/-)-α-[[(5-chloro-2-nitrophenyl)methyl]amino]benzeneacetic acid methyl ester Structure

(+/-)-α-[[(5-ch...

~%

7-chloro-3-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-phen...

5-Chloro-2-nitrobenzyl alcohol Structure

5-Chloro-2-nitr...

~%

tert-butyl 7-chloro-2-oxo-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepine-4-carboxylate Structure

tert-butyl 7-ch...

DL-Valine Methyl Ester Hydrochloride Structure

DL-Valine Methy...

~%

tert-butyl 7-chloro-2-oxo-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepine-4-carboxylate Structure

tert-butyl 7-ch...

5-chloro-2-nitrobenzyl methanesulfonate Structure

5-chloro-2-nitr...

~%

tert-butyl 7-chloro-2-oxo-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepine-4-carboxylate Structure

tert-butyl 7-ch...

N/A Structure

~%

tert-butyl 7-chloro-2-oxo-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepine-4-carboxylate Structure

tert-butyl 7-ch...

Di-tert-butyl dicarbonate Structure

Di-tert-butyl d...

7-chloro-3-propan-2-yl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-prop...

~93%

tert-butyl 7-chloro-2-oxo-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepine-4-carboxylate Structure

tert-butyl 7-ch...

(+/-)-methyl 2-[[(2-amino-5-chlorophenyl)methyl]amino]-3-methylbutanoate Structure

(+/-)-methyl 2-...

~%

tert-butyl 7-chloro-2-oxo-3-propan-2-yl-3,5-dihydro-1H-1,4-benzodiazepine-4-carboxylate Structure

tert-butyl 7-ch...

7-chloro-3-methyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Structure

7-chloro-3-meth...

3,3-Dimethylallyl bromide Structure

3,3-Dimethylall...

~48%

7-chloro-3-methyl-4-(3-methylbut-2-enyl)-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-3-meth...

N/A Structure

~%

7-chloro-3-methyl-4-(3-methylbut-2-enyl)-3,5-dihydro-1H-1,4-benzodiazepin-2-one Structure

7-chloro-3-meth...