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SML2144

Sigma-Aldrich

TB5

≥98% (HPLC)

Synonym(s):

(2E)-1-(5-bromothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

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About This Item

Empirical Formula (Hill Notation):
C15H14BrNOS
CAS Number:
948841-07-4
Molecular Weight:
336.25
MDL number:
MFCD30718167
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN(C)C(C=C1)=CC=C1/C=C/C(C2=CC=C(Br)S2)=O

InChI

1S/C15H14BrNOS/c1-17(2)12-6-3-11(4-7-12)5-8-13(18)14-9-10-15(16)19-14/h3-10H,1-2H3/b8-5+

InChI key

PTLDLBSWTKNYCY-VMPITWQZSA-N

Biochem/physiol Actions

TB5 is a potent and selective reversible inhibitor of monoamine oxidase B (MAOB) with a Ki value of 110 nM. A reversible inhibitor should have an advantage over irreversible inhibitors such as selegiline in limiting side effects. Parallel artificial membrane permeation (PAMPA) assays indicated TB5 should be able to cross the blood–brain barrier. TB5 was found nontoxic to cells.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Bijo Mathew et al.
ChemMedChem, 11(11), 1161-1171 (2016-05-10)
A series of (2E)-1-(5-bromothiophen-2-yl)-3-(para-substituted phenyl)prop-2-en-1-ones (TB1-TB11) was synthesized and tested for inhibitory activity toward human monoamine oxidase (hMAO). All compounds were found to be competitive, selective, and reversible toward hMAO-B except (2E)-1-(5-bromothiophen-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one (TB7) and (2E)-1-(5-bromothiophen-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one (TB8), which were selective inhibitors
Bijo Mathew et al.
The journal of physical chemistry. B, 121(6), 1186-1203 (2017-01-14)
Selective monoamine oxidase-B (MAO-B) inhibitors are imperative in the treatment of various neurodegenerative disorders. Herein, we describe the pharmacophore generation and atom-based three-dimensional quantitative structure-activity relationship (3D-QSAR) analyses of previously reported thiophene-based hMAO-B inhibitors by our research group. The aim

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