78133-84-3

Usage

Uses

Used in Organic Synthesis:
(2-Aminobenzyl)triphenylphosphonium bromide is used as a reactant for intramolecular Wittig reactions, which are a type of olefination reaction used to form carbon-carbon double bonds in organic molecules.
Used in Pharmaceutical Industry:
(2-Aminobenzyl)triphenylphosphonium bromide is used as a reactant for the preparation of 2,3-disubstituted indoles, which are important structural motifs found in various bioactive compounds and pharmaceuticals.
Used in Medicinal Chemistry:
(2-Aminobenzyl)triphenylphosphonium bromide is used as a reactant for the preparation of pyrrolocarbazoles, which are a class of compounds that act as poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. These inhibitors have potential applications in the treatment of various cancers by targeting DNA repair mechanisms in cancer cells.

InChI:InChI=1/C25H23NP.BrH/c26-25-19-11-10-12-21(25)20-27(22-13-4-1-5-14-22,23-15-6-2-7-16-23)24-17-8-3-9-18-24;/h1-19H,20,26H2;1H/q+1;/p-1

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 6399-81-1 triphenylphosphine hydrobromide 
• 88-72-2 1-methyl-2-nitrobenzene 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 

Downstream Products

• 123217-79-8 [2-((E)-But-2-enoylamino)-benzyl]-triphenyl-phosphonium; bromide 
• 119691-16-6 (2-(propenoylamino)benzyl)triphenylphosphonium bromide 
• 101315-55-3 2-(2-methoxycarbonylethylcarbonylamino)benzyl triphenyl phosphonium bromide 
• 115983-48-7 o,o'-<(1,2-Dioxo-1,2-ethandiyl)bisimino>bis(benzyltriphenylphosphoniumbromid) 
• 115983-50-1 o,o'-<<(E)-1,4-Dioxo-2-buten-1,4-diyl>bisimino>bis(benzyltriphenylphosphoniumbromid) 
• 3770-50-1 2-carbethoxyindole 
• 2721-59-7 3-methylcarbostyril 
• 1022-86-2 2-benzoylindole 
• 38035-81-3 3-phenyl-1H-quinolin-2-one 
• 101315-56-4 3-(4-bromophenyl)quinolin-2(1H)-one 
• 15432-24-3 2-(pyridin-3-yl)-indole 
• 1040399-65-2 C₁₇H₁₉N 
• 40015-09-6 2-(4-nitrophenyl)-1H-indole 
• 948-65-2 2-phenyl-indole 

Relevant academic research and scientific papers

A formal approach to the cyanobacterial sunscreen indole, prenostodione

The synthesis of the indole sunscreen pigment prenostodione was attempted via an LDA-initiated condensation of N-carbamate indole-2-methyl ester 22 with 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (14) and a late-stage Vilsmeier-Haack formylation. Difficulties with the ensuing oxidation required installation of a C-3 carboxylic acid necessitating the use of a recently reported protocol and thus a formal synthesis of the natural product was realized from 2-aminobenzyl alcohol (17) in nine steps.

New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile

In previous studies, the 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid was identified as pharmacophoric core for PPARγ activation. In this structure-activity relationship study the C2-alkyl chain was elongated and the 2-COOH group was changed to a carbamide/carbonitrile or shifted to the 3- or 4-position. Furthermore, the benzo[d]imidazole was exchanged by 2,3-dihydrobenzo[d]thiazole or 1H-indole. C2-propyl derivatives showed the profile of partial agonists, while elongation of the C2-chain to that of an n-heptyl group or a 4-COOH shift changed the pharmacological profile to that of a potent full agonist. This finding can be explained by binding to the LBD in different ligand conformations. Two anchoring points (Tyr473 and Arg288) exist in the LBD, which have to be contacted to achieve receptor activation. In a crystal violet chemosensitivity assay using COS-7?cells and LNCaP cells expressing PPARγ only the carbamide derivatives influenced the cell growth, independently on the presence of the PPARγ. Therefore, receptor mediated cytotoxicity can be excluded.

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Modulators of ATP-binding cassette transporters

Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

Benzocarbapenems from indoles

The 8,8a-dihydroazeto[1,2-a]indol-2(1H)-ones (benzocarbapenems) 1a, 16, 17, 22, 27, 35 and 36 have been prepared by cyclodehydration of the corresponding β-amino acids, these amino acids being obtained by reduction of the analogous 2-substituted or 2,7-disubstituted indoles. The hydroxy group of compound 36 is designed to mimic the carboxylic acid function of the carbapenems on the basis of molecular modelling. The azetidinones 1a and 27, which are unsubstituted at the methylene group of the four-membered ring, are unstable and highly susceptible to ring opening by nucleophiles but the compounds 22,35 and 36 with two methyl substituents at this position are much more stable. The carbonyl stretching frequency in the IR is close to 1770 cm-1 for all the azetidinones except the phenol 36 for which the absorption is at 1735 cm-1. An X-ray crystal structure of compound 36 is reported.

A PRACTICAL REGIOSELECTIVE SYNTHESIS OF ω-FUNCTIONALIZED, LONG-CHAIN 2,3-DIALKYLINDOLES

Several routes towards the regioselective synthesis of ω-functionalized 2,3-dialkylindoles (1 and 2) have been compared and discussed.A synthesis based on the appropriately modified indolization reaction according to Leimgruber and Batcho resulted the method of choice, being versatile and of quite general applicability for inoles of this type.

New Syntheses of 2-Acylbenzofurans, 2-Acylindoles, 2-Indolylcarboxylates, and 2-Quinolones by Intramolecular Wittig Reaction

The title compounds are obtained by intramolecular Wittiig reaction of 2-(α-ketoacyloxy)-, 2-(α-ketoacylamino)-, or 2-benzyltriphenylphosphonium salts, respectively.

UNE NOUVELLE VOIE D'ACCES AUX INDOLES PAR CONDENSATION YLURE-AMIDE

o-Acylaminobenzylidenephosphoranes lead to indoles in good yield by an intramolecular Wittig reaction with the amide carbonyl group.Mechanistic aspects are discussed.A general method is described for the synthesis of indoles from o-nitrobenzyl bromides and o-aminobenzyl alcohols.

New Synthesis of Indoles from o-Acylaminobenzyltriphenylphosphonium Salts

The action of bases on o-acylaminobenzyltriphenylphosphonium salts gives indoles in high yields.