24427-33-6

Basic information

• Product Name: Isoamarine
• Synonyms: Isoamarine
• CAS NO: 24427-33-6
• Molecular Formula: C₂₁H₁₈N₂
• Molecular Weight: 0
• Mol File: 24427-33-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isoamarine(CAS DataBase Reference)
• NIST Chemistry Reference: Isoamarine(24427-33-6)
• EPA Substance Registry System: Isoamarine(24427-33-6)

Safety Data

• Hazardous Substances Data: 24427-33-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 92-29-5 (E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene 
• 92-29-5 hydrobenzamide 
• 54874-97-4 N-(erythro-α'-amino-bibenzyl-α-yl)-benzamide 
• 951-87-1 meso-1,2-diphenyl-1,2-diaminoethane 
• 65-85-0 benzoic acid 
• 57-13-6 urea 

Downstream Products

• 58821-34-4 2r,3t,5,6-tetraphenyl-(6ξH)-7-oxa-1,4-diaza-bicyclo[4.1.0]hept-4-ene 
• 33722-46-2 isoamarine 
• 484-47-9 lophine 
• 3190-22-5 erythro-N-benzoyl-N'-phenylmethylidene-1,2-diamino-1,2-diphenylethane 
• 911306-52-0 (-)-(4S,5S)-1-[(R)-α-acetoxyphenylacetyl]-4,5-dihydro-2,4,5-triphenyl-1H-imidazole 
• 911306-54-2 (+)-(1S,2S)-N-[(R)-α-acetoxyphenylacetyl]-N'-benzoyl-1,2-diamino-1,2-diphenylethane 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 40102-64-5 racem.-1,2-diphenyl-ethane-1,2-diamine; dihydrochloride 
• 91840-93-6 (1S,2S)-N,N'-diethyl-1,2-diphenyl-1,2-ethanediamine 
• 216861-21-1 (1S,2S)-N,N'-(1,2-diphenylethane-1,2-diyl)diacetamide 
• 33722-47-3 DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole 

Relevant articles and documents

Convenient one-step synthesis of cis-2,4,5-triarylimidazolines from aromatic aldehydes with urea

A simple and efficient method has been developed for the synthesis of cis-2,4,5-triarylimidazolines based on a one-step procedure of aldehydes and urea in the presence of cesium carbonate. Taylor & Francis Group, LLC.

Nuclear factor-κB mediated inhibition of cytokine production by imidazoline scaffolds

The mammalian nuclear transcription factor NF-κB is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-α) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-κB has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-κB mediated gene transcription in cell culture as well as inhibitors of TNF-α and IL-6 production in interleukin 1 beta (IL-1β) stimulated human blood.

Cycloaddition reactions of 1,3-diazabuta-1,3-dienes with alkynyl ketenes

The cycloaddition reactions of 'all-carbon' 1,3-diazabuta-1,3-dienes with a few conjugated and unconjugated alkynyl ketenes are described. The reactions provide some interesting azetidinones and dihydropyrimidinones bearing an alkynyl moiety. The regiochemistry of cycloadduct is related with the degree of conjugation of the alkynyl ketene. Moreover, two alternative approaches to 'all-carbon' 1,3-diazabuta-1,3-dienes are reported.

A convenient preparation of enantiomerically pure (+)-(1R,2R)- and (-)-(1S,2S)-1,2-diamino-1,2-diphenylethanes

A gram-scale preparation of (1S,2S)- and (1R,2R)-1,2-diamino-1,2- diphenylethanes, (1S,2S)-1 and (1R,2R)-1, is reported via (±)-iso-amarine 4. Strategically, the activation of (±)-iso-amarine 4 for hydrolysis to the required diamines and enantiomeric resolution is achieved simultaneously by formation of two separable diastereoisomeric N-acylamidines 5 and 6 derived from direct DCC-mediated coupling of (±)-iso-amarine 4 with (R)-acetylmandelic acid. iso-Amarine 4 is conveniently obtained from amarine 3, and a one-pot synthesis of the latter is reported from benzaldehyde and hexamethyldisilazane as catalysed by benzoic acid.

Synthesis and SAR of novel 4,5-diarylimidazolines as potent P2X7 receptor antagonists

The synthesis and SAR of a series of potent P2X7 receptor antagonists is described. The synthesis featured high-throughput solution- and solid-phase techniques including a microwave induced imidazoline formation. A series of 4,5-diarylimidazoline libraries were prepared using high-throughput solid-phase and microwave techniques. The compounds were evaluated as P2X 7 antagonists and their SAR is described.

Alumina-ammonium acetate as an efficient reagent for the one-pot synthesis of cis-2,4,5-triarylimidazolines from aromatic aldehydes

A simple, efficient, and new method has been developed for the synthesis of 2,4,5-triarylimidazolines from aldehydes through a one-pot reaction of aldehydes in the presence of alumina-ammonium acetate under solvent-free conditions using microwave irradiation. This method is easy, rapid, one-pot and good to high-yielding reaction for the synthesis of 2,4,5-triarylimidazolines.

Synthesis of N,N-di(arylmethylidene)arylmethanediamines by flash vacuum pyrolysis of arylmethylazides

Flash vacuum pyrolysis of arylmethylazides 7a-d gave 2,4-diazapentadienes 5a-d in high yield (76-92%). The thermal cyclization of 5a-d gave cis-imidazolines 1a-d, further heating or Swern oxidation of 1a-d gave dehydrogenated products, imidazoles 2a-d.

Studies on the synthesis of 1-aminoalkylphosphonates from aldehydes using silica-supported ammonium hydrogen carbonate

Studies on the use of silica-supported ammonium hydrogen carbonate as an efficient reagent for the synthesis of 1-amino-phosphonates under microwave irradiation in solvent-free conditions is reported. Investigations showed that this reaction proceeds by the formation of methanediamine as an intermediate. The reaction in the absence of diethyl phosphite gave cis-imidazolines as the major products.

Regioselective synthesis of cis- and trans-2,4,5-triarylimidazolines and 2,4,5-triarylimidazoles from available reagents

Novel data were obtained concerning the reaction of aromatic aldehydes with ammonia. A preparative method for the synthesis of new substituted 1,3,5-triaryl-2,4-diazapenta-1,4-dienes was developed. These products are the starting reactants for syntheses of cis- and trans-2,4,5-triaryl-2-imidazolines and 2,4,5-triarylimidazoles.

Microwave-assisted rapid and selective synthesis of cis- and trans-2,4,5-triarylimidazolines from aromatic aldehydes

Microwave irradiation of a mixture of aromatic aldehydes and hexamethyldisilazane in the presence of a solid catalyst such as alumina afforded methanediamines which were efficiently converted to either cis- or trans-2,4,5-triarylimidazolines depending on the base used. A one-pot selective synthesis of cis- and transimidazolines from aromatic aldehydes was achieved under microwave irradiation.