65273-47-4

Basic information

• Product Name: 4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE
• Synonyms: 4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE;4-Phthalimidobutyl triphenlphosphonium bromide
• CAS NO: 65273-47-4
• Molecular Formula: Br*C₃₀H₂₇NO₂P
• Molecular Weight: 544.42
• Mol File: 65273-47-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 200-202°C
• Appearance: /
• Sensitive: Hygroscopic
• CAS DataBase Reference: 4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE(65273-47-4)
• EPA Substance Registry System: 4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE(65273-47-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 65273-47-4(Hazardous Substances Data)

Usage

General Description

4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE is a chemical compound that belongs to the family of phosphonium salts. It is commonly used in organic synthesis as a phase-transfer catalyst, which facilitates the transfer of reactants between immiscible phases, such as aqueous and organic solvents. 4-PHTHALIMIDOBUTYL TRIPHENYLPHOSPHONIUM BROMIDE has a quaternary phosphonium cation, which provides it with high stability and reactivity. Its bromide anion also contributes to its solubility in organic solvents and its ability to form complexes with various organic substrates. The 4-phthalimidobutyl group attached to the phosphonium center further modifies its reactivity and selectivity. Overall, this compound serves as a versatile and efficient catalyst in various chemical reactions.

InChI:InChI=1/C30H27NO2P/c32-29-27-20-10-11-21-28(27)30(33)31(29)22-12-13-23-34(24-14-4-1-5-15-24,25-16-6-2-7-17-25)26-18-8-3-9-19-26/h1-11,14-21H,12-13,22-23H2/q+1

Upstream product

• 136918-14-4 phthalimide 
• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 603-35-0 triphenylphosphine 

Downstream Products

• 214283-55-3 2-[5-(1-trityl-1H-imidazol-4-yl)pent-4-enyl]isoindole-1,3-dione 

Relevant articles and documents

Probing the Existence of a Metastable Binding Site at the β2-Adrenergic Receptor with Homobivalent Bitopic Ligands

Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous molecular dynamics studies on ligand binding to the β2-adrenergic receptor (β2AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacological characterization revealed ligands with similar potency and affinity, slightly increased β2/β1AR-selectivity, and/or substantially slower β2AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β2AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacological profiles of ligands.

Phosphonium lipocations as antiparasitic agents

Phosphonium lipocations were synthesized and evaluated for inhibition of the development of Plasmodium falciparum and Trypanosoma cruzi, etiological agents of malaria and Chagas disease, respectively. Optimal phthalimides and 1,4-naphthoquinone-based lipocations were active in vitro at mid-high nM concentrations against P. falciparum and low μM concentrations against T. cruzi.

3,6-Bicyclolides

The present invention discloses compounds of formula (I) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.