18877-34-4

Basic information

• Product Name: (S)-(+)-2,3-DIHYDRO-1H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-5,11(10H,11AH)-DIONE
• Synonyms: PBD-5,11-DIONE;(S)-1,2,3,11A-TETRAHYDRO-10H-PYRROLO[2,1-C][1,4]-BENZODIAZEPINE-5,11-DIONE;(S)-(+)-2,3-DIHYDRO-1H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-5,11(10H,11AH)-DIONE;(S)-(+)-2,3-dihydro-1H-pyrrolo(2,1C)(1,4)-benzodi;(S)-(+)-2,3-DIHYDRO-1H-PYRROLO(2,1C)(1,4 )-BENZODIAZEPINE-5,11(10H,11AH)DION, 99%;(S)-(+)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-;2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione;1,2,3,11a-Tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione
• CAS NO: 18877-34-4
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Others
• Mol File: 18877-34-4.mol
• Article Data: 43

Chemical Properties

• Melting Point: 218-220 °C(lit.)
• Boiling Point: 477.4°Cat760mmHg
• Flash Point: 242.5°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 2.82E-09mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Sonicated), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: (S)-(+)-2,3-DIHYDRO-1H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-5,11(10H,11AH)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2,3-DIHYDRO-1H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-5,11(10H,11AH)-DIONE(18877-34-4)
• EPA Substance Registry System: (S)-(+)-2,3-DIHYDRO-1H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-5,11(10H,11AH)-DIONE(18877-34-4)

Safety Data

• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 18877-34-4(Hazardous Substances Data)

Usage

Uses

PBD-5,11-dione is a Bnzodiazepines which is used as antileishmanial agents.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 5165, 1983 DOI: 10.1016/S0040-4039(00)88387-2

InChI:InChI=1/C12H12N2O2/c15-11-10-6-3-7-14(10)12(16)8-4-1-2-5-9(8)13-11/h1-2,4-5,10H,3,6-7H2,(H,13,15)/t10-/m0/s1

Upstream product

• 67900-22-5 5,10,11,11a-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione 
• 118-48-9 isatoic anhydride 
• 147-85-3 L-proline 
• 105089-64-3 N-(2-nitrobenzoyl)-L-proline methyl ester 
• 552-16-9 ortho-nitrobenzoic acid 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 118-92-3 anthranilic acid 
• 1233669-19-6 (S)-10-(2-nitrobenzoyl)-2,3-dihydro-1H-benzopyrrolo[1,2][1,4]diazepine-5,11(10H,11aH)-dione 
• 142114-82-7 methyl (2S)-N-(2-azidobenzoyl)pyrrolidine-2-carboxylate 
• 201230-82-2 carbon monoxide 
• 615-36-1 2-bromoaniline 
• 609-36-9 rac-Pro-OH 

Downstream Products

• 1233669-19-6 (S)-10-(2-nitrobenzoyl)-2,3-dihydro-1H-benzopyrrolo[1,2][1,4]diazepine-5,11(10H,11aH)-dione 
• 923973-17-5 (11aS)-10-(4-nitrobenzyl)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione 
• 923973-12-0 (11aS)-10-benzyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione 
• 1388843-38-6 C₂₂H₁₈N₄O₃ 
• 1388843-33-1 C₂₇H₂₂N₂O₃ 
• 1388843-32-0 C₂₃H₂₃N₃O₃ 

Relevant articles and documents

First in class (S,E)-11-[2-(arylmethylene)hydrazono]-PBD analogs as selective CB2 modulators targeting neurodegenerative disorders

Newly designed pyrrolo[2,1-c][1,4]benzodiazepines tricyclic skeleton has shown potential clusters of cannabinoid receptors CB1/CB2 selective ligands. CB2 plays a critical role in microglial-derived neuroinflammation, where it modulates cell proliferation,

Highly enantioselective synthesis of rigid, quaternary 1,4-benzodiazepine- 2,5-diones derived from proline

(Chemical Equation Presented) Proline-derived 1,4-benzodiazepine-2,5-diones are extremely useful scaffolds in medicinal chemistry. In this paper, we describe a protocol for retentive C3 alkylation of these materials, thus accomplishing the direct synthesis of enantiopure quaternary 1,4-benzodiazepine-2,5-diones. The high enantioselectivities (up to 99.5%) are attributed to memory of chirality.

Eco-friendly synthesis of 1,4-benzodiazepine-2,5-diones in the ionic liquid [bmim]Br

The green reaction of isatoic anhydrides with α-amino acids in presence of the ionic liquid 1-butyl-3-methylimidazolium bromide afforded 1,4-benzodiazepine-2,5-diones in excellent yields in absence of a catalyst. The reaction workup is simple and the ionic liquid was easily recovered from the reaction and reused. The methodology was quite general and a range of cyclic and acyclic α-amino acids were examined to produce 1,4-benzodiazepine-2,5- diones.

The synthesis and anti-inflammatory evaluation of 1,2,3-triazole linked isoflavone benzodiazepine hybrids

Copper catalyzed azide-alkyne cycloaddition was used for the first time to access a small series of eight novel 1,2,3-triazole linked isoflavone benzodiazepine hybrids. As part of this work, a previously unreported alkyne substituted pyrrolo[1,4]benzodiaz

One-Step Preparation of Pyrrolo[1,4]benzodiazepine Dilactams: Total Synthesis of Oxoprothracarcin, Boseongazepines B and C

A one-step synthesis of pyrrolo[1,4]benzodiazepine dilactams has been developed. The high yielding method involves direct coupling of unprotected anthranilic acids with proline esters. This transformation was successfully applied in the first total syntheses of boseongazepines B and C as well as oxoprothracarcin and limazepine E.