52190-28-0

Basic information

• Product Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
• Synonyms: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one;2-Bromo-3',4'-(methylenedioxy)propiophenone;1-(1,3-Benzodioxol-5-yl)-2-broMo-1-propanone;3',4'-Methylenedioxy-α-broMopropiophenone;1-(1,3-benzodioxol-5-yl)-2-bromopropan-1-one
• CAS NO: 52190-28-0
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.08066
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 52190-28-0.mol

Chemical Properties

• Boiling Point: 345.673 °C at 760 mmHg
• Flash Point: 162.857 °C
• Appearance: /
• Density: 1.585 g/cm³
• CAS DataBase Reference: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(52190-28-0)
• EPA Substance Registry System: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(52190-28-0)

Safety Data

• Hazardous Substances Data: 52190-28-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one can be used in the preparation of antifungal agents and MDMA analogs.

Upstream product

• 28281-49-4 3,4-methylenedioxypropiophenone 
• 7451-98-1 3',4'-dihydroxypropiophenone 
• 63740-97-6 1-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)butan-1-one 

Downstream Products

• 850852-86-7 4-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-2-ylamine 
• 186028-79-5 1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one 
• 161096-64-6 methyl 3-hydroxy-4-α-piperonyloylethoxy-5-methoxybenzoate 
• 161096-65-7 methyl 3-hydroxy-4-α-methyl-β-hydroxy-β-(3,4-methylenedioxyphenyl)ethoxy-5-methoxybenzoate 
• 857953-22-1 N-acetyl-sulfanilic acid-(4-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-2-ylamide) 
• 1206768-27-5 (S)-1-(3,4-(methylenedioxy)phenyl)-2-phenylpropan-1-one 
• 528-64-3 5,5'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(benzo[d][1,3]dioxole) 

Relevant articles and documents

α-PPP and its derivatives are selective partial releasers at the human norepinephrine transporter: A pharmacological characterization of interactions between pyrrolidinopropiophenones and uptake1 and uptake2 monoamine transporters

While classical cathinones, such as methcathinone, have been shown to be monoamine releasing agents at human monoamine transporters, the subgroup of α-pyrrolidinophenones has thus far solely been characterized as monoamine transporter reuptake inhibitors. Herein, we report data from previously undescribed α-pyrrolidinopropiophenone (α-PPP) derivatives and compare them with the pharmacologically well-researched α-PVP (α-pyrrolidinovalerophenone). Radiotracer-based in vitro uptake inhibition assays in HEK293 cells show that the investigated α-PPP derivatives inhibit the human high-affinity transporters of dopamine (hDAT) and norepinephrine (hNET) in the low micromolar range, with α-PVP being ten times more potent. Similar to α-PVP, no relevant pharmacological activity was found at the human serotonin transporter (hSERT). Unexpectedly, radiotracer-based in vitro release assays reveal α-PPP, MDPPP and 3Br-PPP, but not α-PVP, to be partial releasing agents at hNET (EC50 values in the low micromolar range). Furthermore, uptake inhibition assays at low-affinity monoamine transporters, i.e., the human organic cation transporters (hOCT) 1–3 and human plasma membrane monoamine transporter (hPMAT), bring to light that all compounds inhibit hOCT1 and 2 (IC50 values in the low micromolar range) while less potently interacting with hPMAT and hOCT3. In conclusion, this study describes (i) three new hybrid compounds that efficaciously block hDAT while being partial releasers at hNET, and (ii) highlights the interactions of α-PPP-derivatives with low-affinity monoamine transporters, giving impetus to further studies investigating the interaction of drugs of abuse with OCT1-3 and PMAT.

Novel benzene-based carbamates for ache/bche inhibition: Synthesis and ligand/structure-oriented sar study

A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl-and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl-compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, two compounds (23, benzyl ethyl(1-oxo-1-phenylpropan-2-yl)carbamate and 28, benzyl (1-(3-chlorophenyl)-1-oxopropan-2-yl) (methyl)carbamate) had a very high selectivity index, while the second one (28) reached the lowest inhibitory concentration IC50 value, which corresponds quite well with galanthamine. Moreover, comparative receptor-independent and receptor-dependent structure–activity studies were conducted to explain the observed variations in inhibiting the potential of the investigated carbamate series. The principal objective of the ligand-based study was to comparatively analyze the molecular surface to gain insight into the electronic and/or steric factors that govern the ability to inhibit enzyme activities. The spatial distribution of potentially important steric and electrostatic factors was determined using the probability-guided pharmacophore mapping procedure, which is based on the iterative variable elimination method. Additionally, planar and spatial maps of the host–target interactions were created for all of the active compounds and compared with the drug molecules using the docking methodology.

Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo

(–)-Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan, shows potent neurotrophic activities such as neurite-outgrowth promotion and neuroprotection. Previously, we found that (–)-(1S,2R,3S,4R)-stereoisomer 2 exhibited more significant activity than did the natural product talaumidin (1). However, the preparation of optically active (–)-2 requires a complicated synthetic route. To explore new neurotrophic compounds that can be obtained on a large scale, we established a short step synthetic route for talaumidin derivatives and synthesized fourteen analogues based on the structure of (–)-2. First, we synthesized a racemic compound of (–)-2 (2a) and assessed its neurotrophic activity. We found that the neurotrophic property of racemic 2a is similar in activity to that of (–)-2. Using the same synthetic methodology, several talaumidin derivatives were synthesized to optimize the oxy-functionality on aromatic rings. As a result, bis(methylenedioxybenzene) derivative 2b possessed the highest neurotrophic activity. Furthermore, examination of the structure-activity relationships of 2b revealed that the 2,5-diphenyl-tetrahydrofuran structure was an essential structure and that two methyl groups on THF ring could enhance neurotrophic activity. In addition, compounds 2a and 2b were found to induce mouse optic nerve regeneration in vivo.

Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation

The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total synthesis of boryquinone was also achieved in seven steps.

Pyrrole derivatives and medicinal composition

The invention relates to a pharmaceutical composition comprising a pyrrole derivative of the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate of either of them, as an active ingredient. STR1 (wherein R1 represents hydrogen or alkoxycar91 bonylamino, R2 represents alkyl, aryl which may be substituted, aromatic heterocyclyl which may be substituted, unsubstituted amino, monoalkylamino, dialkylamino, or cyclic amino which may be substituted; R3 represents cyano or carbamoyl; R4 represents hydrogen or alkyl; E represents alkylene; q is equal to 0 or 1, A represents methyl, aryl which may be substituted, or aromatic heterocyclyl which may be substituted). The pharmaceutical composition of the invention is effective for the treatment of pollakiuria or urinary incontinence.