123355-42-0

Basic information

• Product Name: (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
• CAS NO: 123355-42-0
• Molecular Weight: 246.266
• Mol File: 123355-42-0.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one(123355-42-0)
• EPA Substance Registry System: (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one(123355-42-0)

Safety Data

• Hazardous Substances Data: 123355-42-0(Hazardous Substances Data)

Upstream product

• 166451-19-0 (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde 
• 140647-01-4 4-hydroxy-5-methoxy-2-nitrobenzoic acid 
• 175409-49-1 methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate 
• 140850-28-8 (2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde dimethyl acetal 
• 140647-00-3 (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde dimethyl acetal 
• 140646-99-7 (S)-methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylate 
• 140693-22-7 (S)-1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carbaldehyde 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 140647-02-5 (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 132391-70-9 (11aS)-8-hydroxy-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 
• 188115-31-3 (S)-8-Hydroxy-7-methoxy-11-thioxo-1,2,3,10,11,11a-hexahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 182277-06-1 4-Hydroxy-5-methoxy-2-nitro-benzoyl chloride 
• 182277-11-8 (S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 339291-87-1 N-(10-methoxymethyl)-8-benzyloxy-7-methoxypyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 

Downstream Products

• 1128035-57-3 7-methoxy-8-[5-(2-phenylethynyl-phenyl)-pent-4-ynyloxy]-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 1128035-55-1 7-methoxy-8-[3-(2-phenylethynyl-phenyl)-prop-2-ynyloxy]-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 1128035-67-5 7-methoxy-8-{(Z)-4-[4-(2-phenylethynyl-phenyl)-but-3-ynyloxy]-but-2-enyloxy}-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 1128035-65-3 7-methoxy-8-{(Z)-4-[3-(2-phenylethynyl-phenyl)-prop-2-ynyloxy]-but-2-enyloxy}-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 1128035-61-9 7-methoxy-8-{(E)-4-[3-(2-phenylethynyl-phenyl)-prop-2-ynyloxy]-but-2-enyloxy}-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 

Relevant articles and documents

Synthesis and biological evaluation of a novel C8-pyrrolobenzodiazepine (PBD) adenosine conjugate. A study on the role of the PBD ring in the biological activity of PBD-conjugates

Here we sought to evaluate the contribution of the PBD unit to the biological activity of PBD-conjugates and, to this end, an adenosine nucleoside was attached to the PBD A-ring C8 position. A convergent approach was successfully adopted for the synthesis of a novel C8-linked pyrrolo(2,1-c)(1,4)benzodiazepine(PBD)-adenosine(ADN) hybrid. The PBD and adenosine (ADN) moieties were synthesized separately and then linked through a pentynyl linker. To our knowledge, this is the first report of a PBD connected to a nucleoside. Surprisingly, the compound showed no cytotoxicity against murine cells and was inactive against Mycobacterium aurum and M. bovis strains and did not bind to guanine-containing DNA sequences, as shown by DNase I footprinting experiments. Molecular dynamics simulations revealed that the PBD-ADN conjugate was poorly accommodated in the DNA minor groove of two DNA sequences containing the AGA-PBD binding motif, with the adenosine moiety of the ligand preventing the covalent binding of the PBD unit to the guanine amino group of the DNA duplex. These interesting findings shed further light on the ability of the substituents attached at the C8 position of PBDs to affect and modulate the biological and biophysical properties of PBD hybrids.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines and their conjugates by azido reductive cyclization strategy as potential DNA-binding agents

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via azido reductive cyclization process employing FeCl3-NaI reagent system. This methodology has been extended for the preparation of new nicotinamido- pyrrolobenzodiazepine hybrids linked through piperazino-alkane-oxy spacers that exhibit good DNA binding affinity.

NOVEL CYTOTOXIC AGENTS FOR CONJUGATION OF DRUGS TO CELL BINDING MOLECULE

Provided are cytotoxic agents, pyrrolo[2,1-c][1,4]benzodiazepine (PBD) derivatives, their conjugates with a cell-binding agent, the preparation and the therapeutic uses in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

Chemoselective aromatic azido reduction with concomitant aliphatic azide employing Al/Gd Triflates/Nal and ESI-MS mechanistic studies

Aluminium and gadolinium inflates catalyze the chemoselective reduction of aromatic azides to the corresponding amines in combination with sodium iodide. This mild chemoselective method has been applied to the synthesis of various aryl amines, C2azido-substituted pyrrolo[2,1-c]-[1,4]benzodiazepines, and fused[2,1b]quinazolinones by an intramolecular azido reduction tandem cyclization reaction. Interestingly, this methodology selectively reduces aryl azides with enhanced yields and proceeds in shorter reaction times than previous strategies. The mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS.