1994
DOI: 10.1021/cr00026a006
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Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines

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Cited by 276 publications
(167 citation statements)
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“…1) and defined by a common pyrrolo [1,4]benzodiazepine ring system (41). They are sequence-selective DNA alkylating agents with significant antitumor properties (21).…”
mentioning
confidence: 99%
“…1) and defined by a common pyrrolo [1,4]benzodiazepine ring system (41). They are sequence-selective DNA alkylating agents with significant antitumor properties (21).…”
mentioning
confidence: 99%
“…KEYWORDS Pyrrolo[2,1-c] [1,4]benzodiazepine (PBD), antitumor agents, GWL-78, DNA, minor-groove binder T he pyrrolo [2,1-c] [1,4]benzodiazepines (PBDs) are a well-known class of sequence-selective covalent-binding DNA-interactive agents [1][2][3][4] that fit perfectly in the minor groove of DNA due to their chiral C11a(S)-position, which provides a right-handed longitudinal twist isohelical with double-stranded DNA. 3 They also possess an electrophilic N10-C11 imine moiety (or the carbinolamine or carbinolamine methyl ether equivalent) that can form a covalent aminal linkage between their C11-position and the nucleophilic C2-NH 2 group of a guanine base.…”
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confidence: 99%
“…The alkene 14 (78.0 mg, 0.32 mmol) was dissolved in CHCl3 (10 mL) and heated at reflux under an inert atmosphere of nitrogen for 16 h whilst being monitored by TLC (EtOAc/Hex; 3:2). The reaction mixture was concentrated under reduced pressure and purified by silica chromatography (20 g) (EtOAc/Hex; 3:2-4:1) to yield two inseparable close-running spots on TLC which were found to be the aziridine 16 (15). To a stirring suspension of KOH (4.280 g, 76.5 mmol) in ethylene glycol (15 mL), hydrazine hydrate (0.46 mL, 471 mg, 14.7 mmol) was added under nitrogen followed by the ester protected alkene 23 (497 mg, 2.94 mmol), and the whole was heated at reflux (195 °C) for 4.5 h. The reaction mixture was cooled to ambient temperature and was diluted with Et2O (9 mL) and water H2O (9 mL).…”
Section: N-(ethoxycarbonyl)-prolinal (22)mentioning
confidence: 99%
“…PBDs with additional fused rings such as the circumdatin (4) [12], bretazenil (5) [13] and the 1,2,3-triazolo-fused system 6 [14] are attractive as potential antitumour compounds, neurological agents, and protease inhibitors, respectively. As a result of this interest, the replacement of the PBD pyrrole ring with other rings has attracted attention [5,15] and hence pyrido- [16], oxazolo- [17], thiazolo- [18] and imidazo- [19][20][21] analogues are all known. The replacement of the PBD tertiary amide with a sulfonamide leads to the pyrrolobenzothiadiazepines (PBTDs) which are synthetic analogues of the PBDs [22].…”
Section: Introductionmentioning
confidence: 99%