103515-22-6

Basic information

• Product Name: dibenzobarallene
• Synonyms: dibenzobarallene
• CAS NO: 103515-22-6
• Molecular Weight: 276.291
• Mol File: 103515-22-6.mol

Chemical Properties

• CAS DataBase Reference: dibenzobarallene(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzobarallene(103515-22-6)
• EPA Substance Registry System: dibenzobarallene(103515-22-6)

Safety Data

• Hazardous Substances Data: 103515-22-6(Hazardous Substances Data)

Upstream product

• 108-31-6 maleic anhydride 
• 119858-92-3 cyanoacrylate benzyl ester-anthracene adduct 
• 1442690-35-8 4-nitrobenzyl cyanoacrylate anthracene adduct 
• 1442690-41-6 propargylcyanoacrylate anthracene adduct 
• 120-12-7 anthracene 

Downstream Products

• 108-31-6 maleic anhydride 
• 120-12-7 anthracene 
• 83742-19-2 trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester 

Relevant articles and documents

Stereospecificity and concertedness of Retro-Diels-Alder fragmentation in some diester systems upon chemical ionization

Retro-Diels-Alder (RDA) fragmentation of cis- and trans-2,3-diethoxycarbonyl-5,6,7,8-dibenzobicyclo[2.2.2] octanes under isobutane and methane chemical ionization conditions is highly stereospecific, giving rise to protonated diethyl maleate and fumarate, respectively. This behaviour indicates a single-step concerted mechanism, analogous to the ground-state RDA process that occurs in neutral molecules in the condensed phase. The analogous dissociation is partially stereospecific in stereoisomeric endo-, exo- and trans-2,3-diethoxycarbonylbicyclo [2.2.1]heptanes and non-stereospecific in endo-, exo- and trans-2,3-diethoxycarbonyl-5,6-benzobicyclo [2.2.2]octanes, indicating the involvement of a stepwise mechanism in the latter two systems. The different behaviour of the above systems is explained in terms of the energy of the RDA fragmentation. The differentiation and quantitative estimates of protonated diethyl maleate and fumarate were obtained from collision-induced dissociation measurements.

Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly(ADP-ribose) polymerase-1 inhibitors

A series of novel fused isoquinolinones with isoindoloisoquinolinone, pyroloisoquinolinone, and benzoquinalizinone skeletons were synthesized from corresponding phenethylimides. The isoquinolinone derivatives were evaluated for their protective effect on chicken erythrocytes subjected to oxidative damage. The effect of isoquinolinone derivatives were analysed by estimation of cell viability, antioxidant enzyme activities, DNA damage (comet assay), PARP-1 inhibition assay and molecular docking of the compounds with PARP-1 active site. The compounds CRR-271, CRR-288 and CRR-224+225 showed significant protective effect at 100 μM concentration. The PARP-1 inhibition assay revealed the IC50 values of CRR-271, CRR-288 and CRR-224+225 as 200 nM, further molecular docking studies shows higher binding energies with PARP-1 active site. Interesting findings in this study suggest that the novel isoquinolinone derivatives inhibit PARP-1 activity and protect cells against oxidative DNA damage, which could be implemented in the treatment of inflammatory diseases.

Discovery of novel small molecule inhibitors of S100P with in vitro anti-metastatic effects on pancreatic cancer cells

S100P, a calcium-binding protein, is known to advance tumor progression and metastasis in pancreatic and several other cancers. Herein is described the in silico identification of a putative binding pocket of S100P to identify, synthesize and evaluate novel small molecules with the potential to selectively bind S100P and inhibit its activation of cell survival and metastatic pathways. The virtual screening of a drug-like database against the S100P model led to the identification of over 100 clusters of diverse scaffolds. A representative test set identified a number of structurally unrelated hits that inhibit S100P-RAGE interaction, measured by ELISA, and reduce in vitro cell invasion selectively in S100P-expressing pancreatic cancer cells at 10 μM. This study establishes a proof of concept in the potential for rational design of small molecule S100P inhibitors for drug candidate development.

Decorating the Edges of a 2D Polymer with a Fluorescence Label

This work proves the existence and chemical addressability of defined edge groups of a 2D polymer. Pseudohexagonally prismatic single crystals consisting of layered stacks of a 2D polymer are used. They should expose anthracene-based edge groups at the six (100) but not at the two pseudohexagonal (001) and (001) faces. The crystals are reacted with the isotopically enriched dienophiles maleic anhydride and a C18-alkyl chain-modified maleimide. In both cases the corresponding Diels-Alder adducts between these reagents and the edge groups are formed as confirmed by solid state NMR spectroscopy. The same applies to a maleimide derivative carrying a BODIPY dye which was chosen for its fluorescence to be out of the range of the self-fluorescence of the 2D polymer crystals stemming from contained template molecules. If the crystals are excited at λ = 633 nm, their (100) faces and thus their rims fluoresce brightly, while the pseudohexagonal faces remain silent. This is visible when the crystals lie on a pseudohexagonal face. Lambda-mode laser scanning microscopy confirms this fluorescence to originate from the BODIPY dye. Micromechanical exfoliation of the dye-modified crystals results in thinner sheet packages which still exhibit BODIPY fluorescence right at the rim of these packages. This work establishes the chemical nature of the edge groups of a 2D polymer and is also the first implementation of an edge group modification similar to end group modifications of linear polymers.

Reactions of polycyclic arene systems stabilized and activated by cyclopentadienylruthenium cations

One vinylidene group of [(CpRu)(η6-dibenzo-p-quinodimethane)]+PF 6- (1) (Cp = η5-cyclopentadienyl), in which highly reactive dibenzo-p-quinodimethane is stabilized by coordination to ruthenium, underwent Diels-Alder cycloaddition from the exo face with 2,3-dimethyl-1,3-butadiene to give a novel spiro derivative of dibenzo-p-quinodimethane (2). X-ray analysis of 2 (C27H27F6PRu) confirmed its structure and showed it to crystallize in the monoclinic space group P21/n with a = 16.079(5) A?, b = 11.682(3) A?, c = 13.508(4) A?, β = 91.03(3)°, and Z = 4. The Cp* (Cp* = η5-pentamethylcyclopentadienyl) analogue of 1 did not react with 2,3-dimethyl-1,3-butadiene. The η6-localization effect of cyclopentadienylruthenium cations can also be used to activate polycyclic aromatic hydrocarbons toward Diels-Alder and catalytic hydrogenation reactions. [(Cp*Ru)(η6-anthracene)]+TfO- (3) underwent quantitative Diels-Alder reaction from the exo face with maleic anhydride under mild conditions (83°C) to give [trans-(endo-Cp*Ru)(η 6-9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride)]+TfO- (4) selectively. Reaction of anthracene under identical conditions gave only 19% conversion. Reaction of maleic anhydride with [CpRu(η6-naphthalene)]+PF6- (6) was not successful. However, hydrogenation of 6 in methanol (1 atm, 24°C, 6 h) took place smoothly in the presence of a heterogeneous Pd/C catalyst to give [CpRu(η6-1,2,3,4-tetrahydronaphthalene)]+PF 6- (7) in high yield. The Cp* analogue of 6 gave similar results. Noncomplexed naphthalene remained largely unreacted under identical conditions (61% remaining), and a substantial proportion remained (32%) after 24 h. The Cp*Ru and CpRu groups in 4 and 7 can be removed by photolysis in acetonitrile to cleanly give 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride (5) and 1,2,3,4-tetrahydronaphthalene (8), respectively, as well as generating Cp- and Cp*-ruthenium tris(acetonitrile) salts, which can be used to make more complexed arene.

Rational design of novel TLR4 ligands by in silico screening and their functional and structural characterization in vitro

The purpose of this study was to identify new small molecules that possess activity on human toll-like receptor 4 associated with the myeloid differentiation protein 2 (hTLR4/MD2). Following current rational drug design principles, we firstly performed a ligand and structure based virtual screening of more than 130 000 compounds to discover until now unknown class of hTLR4/MD2 modulators that could be used as novel type of immunologic adjuvants. The core of the in silico study was molecular docking of flexible ligands in a partially flexible hTLR4/MD2 receptor model using a peta-flops-scale supercomputer. The most promising substances resulting from this study, related to anthracene-succimide hybrids, were synthesized and tested. The best prepared candidate exhibited 80% of Monophosphoryl Lipid A in vitro agonistic activity in cell lines expressing hTLR4/MD2.

Experimental survey of the kinetics of acene Diels-Alder reactions

The rate profiles for pseudo-first-order reactions between tetracene and selected dienophiles. The reactivity ranged roughly two orders of magnitude, from the slowest reacting dienophile (2,3-dichloromaleic anhydride, light blue) to the fastest dienophile (N-methylmaleimide, orange). Other utilized dienophiles included, in order of reactivity, maleic anhydride (navy), tetrafluoro-1,4-benzoquinone (purple), and p-benzoquinone (green).

Structure correlation study of some DielsAlder cycloadducts of anthracene

Crystal structures of some DielsAlder cycloadducts of anthracene and a variety of dienophiles reveal structural effects consistent with the manifestation of the early stages of the retro DielsAlder reaction in the ground state structure. The symmetrical cycloadducts 3 and 4 reveal a qualitative relationship between structure and reactivity, whereas the cycloadducts of 9-methoxyanthracene show structural effects suggestive of the early stages of an asynchronous retro DielsAlder reaction. CSIRO 2009.

Lipase catalyzed desymmetrization of roof shape cis-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene

Biocatalyzed desymmetrization of roof shape meso cis-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene has been achieved. The absolute configuration of the product is established by single crystal X-ray analysis of its diastereomer prepared with R-chloropropionic acid. Single crystal analysis of the chiral roof shape monoacetate shows a P-helical motif due to the extended intramolecular hydrogen bonding while the racemic sample exhibits intermolecular double hydrogen bonding holding two molecules together as a dimmer.

Design and synthesis of c3-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

We have developed an efficient synthetic strategy to assemble C3-symmetric molecules containing propellane moieties as end groups and a benzene ring as a central core. The synthesis of these C3-symmetric molecules involves simple starting materials. Our approach to C3-symmetric compounds relies on a Diels–Alder reaction, cyclotrimerization and ring-closing metathesis as key steps.