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

Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo-and dipyridodiazepinones

KD Hargrave, JR Proudfoot, KG Grozinger…

Index: Hargrave, Karl D.; Proudfoot, John R.; Grozinger, Karl G.; Cullen, Ernest; Kapadia, Suresh R.; et al. Journal of Medicinal Chemistry, 1991 , vol. 34, # 7 p. 2231 - 2241

Full Text: HTML

Citation Number: 215

Abstract

Novel pyrido [2, 3-b][1, 4] benzodiazepinones (I), pyrido [2, 3-b][1, 5] benzodiazepinones (II), and dipyrido [3, 2-b: 2', 3'-e][1, 4] diazepinones (111) were found to inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase in vitro at concentrations as low as 35 nM. In all three series, small substituents (eg, methyl, ethyl, acetyl) are preferred at the lactam nitrogen, whereas slightly larger alkyl moieties (eg, ethyl, cyclopropyl) are favored ...

2-Chloronicotinic acid Structure

2-Chloronicotin...

2,3-diaminotoluene Structure

2,3-diaminotoluene

~50%

7-methyl-6,11-dihydropyrido[3,2-c][1,5]benzodiazepin-5-one Structure

7-methyl-6,11-d...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

6-methyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-methyl-11H-py...

o-Phenylenediamine Structure

o-Phenylenediamine

~%

6-methyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-methyl-11H-py...

6,11-DIHYDRO-5H-BENZO[B]PYRIDO[2,3-E][1,4]DIAZEPIN-5-ONE Structure

6,11-DIHYDRO-5H...

methyl iodide Structure

~%

6-methyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-methyl-11H-py...

2-Chloronicotinic acid Structure

2-Chloronicotin...

Ethyl iodide Structure

4-Chlorobenzene-1,2-diamine Structure

4-Chlorobenzene...

methyl iodide Structure

~%

Detail

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

6-ethyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-ethyl-11H-pyr...

o-Phenylenediamine Structure

o-Phenylenediamine

~%

6-ethyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-ethyl-11H-pyr...

Ethyl iodide Structure

6,11-DIHYDRO-5H-BENZO[B]PYRIDO[2,3-E][1,4]DIAZEPIN-5-ONE Structure

6,11-DIHYDRO-5H...

~%

6-ethyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-ethyl-11H-pyr...

2,6-Dichloropyridin-3-amine Structure

2,6-Dichloropyr...

~%

N-(2,6-dichloropyridin-3-yl)-2-(ethylamino)pyridine-3-carboxamide Structure

N-(2,6-dichloro...

2-Chloronicotinyl chloride Structure

2-Chloronicotin...

~%

N-(2,6-dichloropyridin-3-yl)-2-(ethylamino)pyridine-3-carboxamide Structure

N-(2,6-dichloro...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

11-ethyl-8-hydroxy-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Structure

11-ethyl-8-hydr...

3,4-Diamino anisole Structure

3,4-Diamino anisole

~%

11-ethyl-8-hydroxy-6-methylpyrido[3,2-c][1,5]benzodiazepin-5-one Structure

11-ethyl-8-hydr...

6,11-DIHYDRO-5H-BENZO[B]PYRIDO[2,3-E][1,4]DIAZEPIN-5-ONE Structure

6,11-DIHYDRO-5H...

~%

6-prop-2-enyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-prop-2-enyl-1...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

6-prop-2-enyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-prop-2-enyl-1...

o-Phenylenediamine Structure

o-Phenylenediamine

~%

6-prop-2-enyl-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one Structure

6-prop-2-enyl-1...

3-Amino-2-chloro-6-picoline Structure

3-Amino-2-chlor...

~%

11-ethyl-2,5-dimethyldipyrido[2,3-b:2',3'-f][1,4]diazepin-6-one Structure

11-ethyl-2,5-di...

2-Chloronicotinyl chloride Structure

2-Chloronicotin...

~%

11-ethyl-2,5-dimethyldipyrido[2,3-b:2',3'-f][1,4]diazepin-6-one Structure

11-ethyl-2,5-di...

2-chloro-N-(2-chloro-6-methylpyridin-3-yl)nicotinamide Structure

2-chloro-N-(2-c...

~%

11-ethyl-2,5-dimethyldipyrido[2,3-b:2',3'-f][1,4]diazepin-6-one Structure

11-ethyl-2,5-di...

11-ethyl-2-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one Structure

11-ethyl-2-meth...

~%

11-ethyl-2,5-dimethyldipyrido[2,3-b:2',3'-f][1,4]diazepin-6-one Structure

11-ethyl-2,5-di...

2-Chlorpyridin-3-amin Structure

2-Chlorpyridin-...

~%

11-ethyl-5H-dipyrido[2,3-b:2',3'-f][1,4]diazepin-6-one Structure

11-ethyl-5H-dip...

2-Chloronicotinyl chloride Structure

2-Chloronicotin...

~%

11-ethyl-5H-dipyrido[2,3-b:2',3'-f][1,4]diazepin-6-one Structure

11-ethyl-5H-dip...