41306-64-3

Basic information

• Product Name: 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione
• Synonyms: 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione;2-(5-bromo-4-oxopentyl)isoindoline-1,3-dione
• CAS NO: 41306-64-3
• Molecular Formula: C₁₃H₁₂BrNO₃
• Molecular Weight: 310.146
• Mol File: 41306-64-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 125-127°
• Boiling Point: 443.2±25.0 °C(Predicted)
• Appearance: /
• Density: 1.550±0.06 g/cm3(Predicted)
• PKA: -2.18±0.20(Predicted)
• CAS DataBase Reference: 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione(41306-64-3)
• EPA Substance Registry System: 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione(41306-64-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 41306-64-3(Hazardous Substances Data)

Usage

General Description

2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione is a chemical compound with the molecular formula C11H10BrNO3. It is a derivative of isoindole-1,3(2H)-dione, a heterocyclic compound with a bicyclic structure. 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione contains a bromine atom and an oxopentyl group attached to the isoindole moiety. It is commonly used in pharmaceutical and research applications, with potential uses in drug discovery and development due to its unique structure and potential biological activities. 2-(5-Bromo-4-oxopentyl)-1H-isoindole-1,3(2H)-dione may also have potential applications in organic synthesis and materials science due to its unique properties and reactivity.

Upstream product

• 3783-77-5 N-(3-oxobutyl)phthalimide 
• 3197-25-9 2-(4-oxopentyl)isoindole-1,3-dione 
• 186581-53-3 diazomethane 
• 3130-75-4 4-phthalimidobutyric acid 
• 5891-21-4 5-chloro-2-pentanone 
• 1074-82-4 potassium phtalimide 
• 7504-49-6 2-(4-diazo-3-oxobutyl)isoindoline-1,3-dione 
• 39739-03-2 4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-butyric acid methyl ester 
• 85-44-9 phthalic anhydride 
• 136918-14-4 phthalimide 
• 10314-06-4 4-phthalimidobutyryl chloride 
• 84461-00-7 1-diazo-5-phthalimido-2-pentanone 

Downstream Products

• 102442-31-9 2-(4-dimethylamino-phenylimino)-3-oxo-6-phthalimido-hexanenitrile 
• 1252573-64-0 5-phthalimido-2-oxopentaldehyde bis[4-(4-chlorophenyl)-3-thiosemicarbazide] 
• 1252573-63-9 5-phthalimido-2-oxopentaldehyde bis(4-phenyl-3-thiosemicarbazide) 
• 1298017-13-6 C₂₀H₁₈N₄O₂S 
• 521268-88-2 2-[3-(2-phenyl-1H-imidazol-4-yl)-propyl]-isoindole-1,3-dione 
• 112357-43-4 Homohistamine dipicrate 
• 40546-33-6 3-[imidazol-4⁽⁵⁾-yl]propylamine 
• 106467-13-4 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-{3-[2-(tetrahydro-pyrimidin-2-ylideneamino)-thiazol-4-yl]-propyl}-guanidine 
• 106467-33-8 1-Benzoyl-2-phenyl-3-{3-[2-(tetrahydro-pyrimidin-2-ylideneamino)-thiazol-4-yl]-propyl}-isourea 
• 95914-09-3 2-[2-(2-amino-1,3-thiazol-4-yl)ethyl]-1H-isoindole-1,3(2H)-dione hydrobromide 

Relevant articles and documents

Synthesis of New Methanofullerenes with Phthalimide Fragment

Abstract: Bromo- and chloromethyl ketones based on N-phthalyl-substituted amino acids have been synthesized via the Arndt–Eistert reaction. The products [2+1] cycloaddition to the fullerene scaffold has afforded the monoadducts of fullerene C60.

Synthesis and functional characterization of imbutamine analogs as histamine H3 and H4 receptor ligands

Imbutamine (4-(1H-imidazol-4-yl)butanamine) is a potent histamine H 3 (H3R) and H4 receptor (H4R) agonist (EC50 values: 3 and 66 nM, respectively). Aiming at improved selectivity for the H4R, the imidazole ring in imbutamine was methyl-substituted or replaced by various differently substituted heterocycles (1,2,3-triazoles, 1,2,4-triazoles, pyridines, pyrimidines) as potential bioisosteres. Investigations in [35S]GTPγS binding assays using membranes of Sf9 insect cells expressing the respective human histamine receptor subtype revealed only very weak activity of most of the synthesized hetarylalkylamines at both receptors. By contrast, the introduction of substituents at the 4-imidazolyl ring was most effective regarding H 4R selectivity. This holds for methyl substitution in position 2 and, especially, in position 5. 5-Methylimbutamine (H4R: EC50 = 59 nM, α = 0.8) was equipotent with imbutamine at the hH4R, but revealed about 16-fold selectivity for the hH4R compared to the hH3R (EC50 980 nM, α = 0.36), whereas imbutamine preferred the hH3R. The functional activities were in agreement with radioligand binding data. The results support the hypothesis that, by analogy with histamine, methyl substitution in histamine homologs offers a way to shift the selectivity in favor of the H4R. According to a bioisosteric approach, the imidazole ring in the dual histamine H3/H4 receptor agonist imbutamine (n = 4) was replaced by various five- and six-membered N-heterocycles. Whereas these structural modifications resulted in a reduction or loss of activity at both receptors, 5-methyl substitution at the imidazol-4-yl ring in imbutamine changed the receptor subtype selectivity in favor of the H4R.

Synthesis and antiviral activity of phthiobuzone analogues

A series of phthiobuzone analogs, prepared from potassium phthalimide or phthalandione, have been evaluated for their antiviral activities. Among the candidates, compounds 5j and 5k, which contain the substituted 4-halogenated phenyl ring at N-4′,4″ position, show more potent antiviral activity than phthiobuzone against herpes simplex virus 1 (IC50=8.56 and 2.85 μ/ml, respectively) and herpes simplex virus 2 (IC50=1.75 and 4.11μg/ ml, respectively). Compounds 9c and 9d with a propylene linker between the phthalimide and bisthiosemicarbazone moieties display similar antiviral potency against herpes simplex virus 1 (IC50=2.85 and 4.11 μg/ml, respectively).