81307-24-6

Basic information

• Product Name: (11aS)-7-Methoxy-8-hydroxy-2,3,5,11aβ-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one
• Synonyms: (11aS)-7-Methoxy-8-hydroxy-2,3,5,11aβ-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one;(11aS)-8-Hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one;(11aS)-8-Hydroxy-7-methoxy-1,2,3,11aβ-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one;DC-81
• CAS NO: 81307-24-6
• Molecular Formula: C₁₃H₁₄N₂O₃
• Molecular Weight: 246.265
• Mol File: 81307-24-6.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 520.5°Cat760mmHg
• Flash Point: 268.6°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 1.88E-11mmHg at 25°C
• Refractive Index: 1.675
• CAS DataBase Reference: (11aS)-7-Methoxy-8-hydroxy-2,3,5,11aβ-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (11aS)-7-Methoxy-8-hydroxy-2,3,5,11aβ-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one(81307-24-6)
• EPA Substance Registry System: (11aS)-7-Methoxy-8-hydroxy-2,3,5,11aβ-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one(81307-24-6)

Safety Data

• Hazardous Substances Data: 81307-24-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14N2O3/c1-18-12-5-9-10(6-11(12)16)14-7-8-3-2-4-15(8)13(9)17/h5-8,16H,2-4H2,1H3

Upstream product

• 175409-52-6 (11aS)-8-hydroxy-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5-one 
• 2426-84-8 4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde 
• 121-33-5 vanillin 
• 127810-77-9 (2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl dithioacetal 
• 127810-78-0 (2S)-N-(2-amino-4-benzyloxy-5-methoxybenzoyl)pyrrolidine-2-carbaldehyde diethyl dithioacetal 
• 105089-88-1 (2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-pyrrole 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 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 
• 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 
• 175409-49-1 methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate 

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, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole-pyrrolo[2,1-c][1,4]benzodiazepine conjugates

A series of benzothiazole and benzoxazole linked pyrrolobenzodiazepine conjugates attached through different alkane or alkylamide spacers was prepared. Their anticancer activity, DNA thermal denaturation studies, restriction endonuclease digestion assay and flow cytometric analysis in human melanoma cell line (A375) were investigated. One of the compounds of the series 17d showed significant anticancer activity with promising DNA-binding ability and apoptosis caused G0/G1 phase arrest at sub-micromolar concentrations. To ascertain the binding mode and understand the structural requirement of DNA binding interaction, molecular docking studies using gold program and more rigorous 2 ns molecular dynamic simulations using Molecular Mechanics-Poisson-Boltzman Surface Area (MM-PBSA) approach including the explicit solvent were carried out. Further, the compound 17d was evaluated for in vivo efficacy studies in human colon cancer HT29 xenograft mice.

Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81

An efficient method for the reduction of aromatic azides in both solution and solid-phase has been developed by employing BF3·OEt2/EtSH. This report also describes resin cleavage employing this reagent system. Further, this protocol has been utilized for the solution as well as the solid-phase synthesis of pyrrolo[2,1-c][1,4]benzodiazepines, including the naturally occurring antibiotic DC-81 and fused [2,1-b]quinazolinones.