BIS(4-AMINOPHENYL)DISELENIDE - CAS 35507-35-8

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Category
Main Product
Product Name
BIS(4-AMINOPHENYL)DISELENIDE
Catalog Number
35507-35-8
Synonyms
BIS(4-AMINOPHENYL)DISELENIDE; 4,4'-Diselenobisaniline; Bis(4-aminophenyl) perselenide
CAS Number
35507-35-8
Molecular Weight
342.15708
Molecular Formula
C12H12N2Se2
COA
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MSDS
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Canonical SMILES
C1=CC(=CC=C1N)[Se][Se]C2=CC=C(C=C2)N
InChI
InChI=1S/C12H12N2Se2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H,13-14H2
InChIKey
YKWRUFUXIJXQGC-UHFFFAOYSA-N
Structure
CAS 35507-35-8 BIS(4-AMINOPHENYL)DISELENIDE
Specification
Purity
95%
Boiling Point
501.8ºC at 760 mmHg
Reference Reading
1.Selenocyanates and diselenides: a new class of potent antileishmanial agents.
Plano D1, Baquedano Y, Moreno-Mateos D, Font M, Jiménez-Ruiz A, Palop JA, Sanmartín C. Eur J Med Chem. 2011 Aug;46(8):3315-23. doi: 10.1016/j.ejmech.2011.04.054. Epub 2011 Apr 28.
Thirty five selenocyanate and diselenide compounds were subjected to in vitro screening against Leishmania infantum promastigotes and the most active ones were also tested in an axenic amastigote model. In order to establish the selectivity indexes (SI) the cytotoxic effect of each compound was also assayed against Jurkat and THP-1 cell lines. Thirteen derivatives exhibit better IC(50) values than miltefosine and edelfosine. Bis(4-aminophenyl)diselenide exhibits the best activity when assayed in infected macrophages and one of the lowest cytotoxic activities against the human cell lines tested, with SI values of 32 and 24 against Jurkat and THP-1 cells, respectively. This compound thus represents a new lead for further studies aimed at establishing its mechanism of action.
2.Molecular descriptors calculation as a tool in the analysis of the antileishmanial activity achieved by two series of diselenide derivatives. An insight into its potential action mechanism.
Font M1, Baquedano Y2, Plano D2, Moreno E2, Espuelas S3, Sanmartín C2, Palop JA2. J Mol Graph Model. 2015 Jul;60:63-78. doi: 10.1016/j.jmgm.2015.06.002. Epub 2015 Jun 18.
A molecular modeling study has been carried out on two previously reported series of symmetric diselenide derivatives that show remarkable antileishmanial in vitro activity against Leishmania infantum intracellular amastigotes and in infected macrophages (THP-1 cells), in addition to showing favorable selectivity indices. Series 1 consists of compounds that can be considered as central scaffold constructed with a diaryl/dialkylaryl diselenide central nucleus, decorated with different substituents located on the aryl rings. Series 2 consists of compounds constructed over a diaryl diselenide central nucleus, decorated in 4 and 4' positions with an aryl or heteroaryl sulfonamide fragment, thus forming the diselenosulfonamide derivatives. With regard to the diselenosulfonamide derivatives (2 series), the activity can be related, as a first approximation, with (a) the ability to release bis(4-aminophenyl) diselenide, the common fragment which can be ultimately responsible for the activity of the compounds.
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