18877-34-4

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

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

Downstream Products

• 104769-66-6 Pyrrolidine-2-carboxylic acid (2-hydroxymethyl-phenyl)-methoxymethyl-amide 
• 1233669-19-6 (S)-10-(2-nitrobenzoyl)-2,3-dihydro-1H-benzopyrrolo[1,2][1,4]diazepine-5,11(10H,11aH)-dione 
• 214277-12-0 (+)-(11aS)-1,2,3,10,11,11a-hexahydro-10-(benzyloxycarbonyl)-11-hydroxy-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one 
• 125299-54-9 (+)-(11S,11aS)-1,2,3,10,11,11a-hexahydro-10-(benzyloxycarbonyl)-11-(3'-indolyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one 
• 86116-84-9 (R)-2-benzylpyrrolidine-2-carboxylic acid 
• 125299-58-3 (+)-(11aS)-1,2,3,10,11,11a-hexahydro-10-(benzyloxycarbonyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione 
• 98442-30-9 (5aR,9aS,11aS)-5a-benzyl-1,2,3,8,9,9a,10,11,11a-nonahydro-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5,11-dione 
• 1388843-38-6 C₂₂H₁₈N₄O₃ 

Relevant academic research and scientific papers

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,

Development of selective ligands for benzodiazepine receptor subtypes by manipulating the substituents at positions 3- and 7- of optically active BzR ligands

Two series of analogs of the optically active α5 subtype selective imidazobenzodiazepine 20 have been prepared. The framework constrained analogs were synthesized by variation of the C (3) ethyl ester function 20 to either t-butyl 7 or 2, 2, 2-trifluoroet

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.

Palladium catalyzed synthesis of quinazolino [1,4] benzodiazepine alkaloids and analogous

A concise synthesis of enantiopure quinazolino [1,4] benzodiazepine was accomplished by palladium-catalyzed N-arylation of amidines with o-bromobenzoates followed by intra molecular cyclization. The strategy was successfully applied to the total synthesis of pyrrolo quinazolino [1,4] benzodiazepine alkaloids such as circumdatin H, J and other analogues.

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.

Identification of an Orally Bioavailable, Brain-Penetrant Compound with Selectivity for the Cannabinoid Type 2 Receptor

Modulation of the endocannabinoid system (ECS) is of great interest for its therapeutic relevance in several pathophysiological processes. The CB2 subtype is largely localized to immune effectors, including microglia within the central nervous system, where it promotes anti-inflammation. Recently, a rational drug design toward precise modulation of the CB2 active site revealed the novelty of Pyrrolo[2,1-c][1,4]benzodiazepines tricyclic chemotype with a high conformational similarity in comparison to the existing leads. These compounds are structurally unique, confirming their chemo-type novelty. In our continuing search for new chemotypes as selective CB2 regulatory molecules, following SAR approaches, a total of 17 selected (S,E)-11-[2-(arylmethylene)hydrazono]-PBD analogs were synthesized and tested for their ability to bind to the CB1 and CB2 receptor orthosteric sites. A competitive [3H]CP-55,940 binding screen revealed five compounds that exhibited >60% displace-ment at 10 μM concentration. Further concentration-response analysis revealed two compounds, 4k and 4q, as potent and selective CB2 ligands with sub-micromolar activities (Ki = 146 nM and 137 nM, respectively). In order to support the potential efficacy and safety of the analogs, the oral and intravenous pharmacokinetic properties of compound 4k were sought. Compound 4k was orally bioavailable, reaching maximum brain concentrations of 602 ± 162 ng/g (p.o.) with an elimination half-life of 22.9 ± 3.73 h. Whether administered via the oral or intravenous route, the elimination half-lives ranged between 9.3 and 16.7 h in the liver and kidneys. These compounds represent novel chemotypes, which can be further optimized for improved affinity and selectivity toward the CB2 receptor.

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

Low-valent titanium-mediated enantioselective synthesis of quinazolinone alkaloids circumdatins F, H, and analogs

We report the concise and protecting-group-free enantioselective total syntheses of circumdatins F and H. In view of the extreme importance of analogs of quinazolinone alkaloids in drug research and discovery, four analogs of bioactive quinazolinobenzodiazepine alkaloids, including demethoxycircumdatin H (12) and N-demethylbenzomalvin A (13), have been synthesized. The method is based on the low-valent titanium-promoted intramolecular reductive coupling of imides with o-nitrobenzimides, which yielded quinazolino[3,2-a][1,4]benzodiazepines under mild conditions. In addition, heptacyclic dehydraasperlicin E (16) has been synthesized from asperlicin C by a NCS-mediated dehydra-cyclization reaction.

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.

Synthesis and cytotoxicity testing of new amido-substituted triazolopyrrolo[2,1-c][1,4]benzodiazepine (PBDT) derivatives

A series of amido-substituted triazolopyrrolo[2,1-c][1,4]benzodiazepine (PBDT) derivatives was synthesized from isatoic anhydride, and their cytotoxicity against the MRC-5 and Mahlavu cell lines was evaluated. The results suggest that compound PBDT-7i with the meta-trifluoromethylbenzoyl substituent can selectively inhibit the growth of Mahlavu cells and has low toxicity towards MRC-5 cells.