676-35-7Relevant academic research and scientific papers
Tuning packing and solubility of donor (D)-acceptor (A) polymers by cis - Trans isomerization within alkenyl side chains
Hinkel, Felix,Marszalek, Tomasz,Zajaczkowski, Wojciech,Puniredd, Sreenivasa Reddy,Baumgarten, Martin,Pisula, Wojciech,Müllen, Klaus
, p. 4844 - 4848 (2014)
The impact of alkenyl substituents on the behavior of cyclopentadithiophene-benzothiadiazole (CDT-BTZ) donor (D)-acceptor (A) polymers in organic field-effect transistors (OFETs) and on the supramolecular organization was investigated. Linear cis- and trans-alkenes were attached to the donor unit of CDT-BTZ polymers to demonstrate the dependence of supramolecular ordering and solubility in organic solvents on chemical conformation. The layer interdigitation of the substituents differed due to shape disparities between cis- and trans-alkenes. While trans-alkenes exhibit zigzag structures that are beneficial for close packing, cis-alkenes are curved and thus possess a less regular shape that is disadvantageous to thin film ordering. This was proven by grazing incidence wide-angle X-ray scattering (GIWAXS) studies, which revealed shorter intermolecular distances for the polymer with trans-alkene substituents even in comparison to analogous polymers with saturated alkyl substituents. Furthermore, the isomerization of the cis-substituents toward their trans-conformers allowed improvement of the polymer crystallinity in thin films and was investigated in transistor devices and solubility studies.
Synthesis and biological activity of alkynoic acids derivatives against mycobacteria
Vilchze, Catherine,Leung, Lawrence W.,Bittman, Robert,Jacobs, William R.
, p. 125 - 138 (2016/01/25)
2-Alkynoic acids have bactericidal activity against Mycobacterium smegmatis but their activity fall sharply as the length of the carbon chain increased. In this study, derivatives of 2-alkynoic acids were synthesized and tested against fast- and slow-growing mycobacteria. Their activity was first evaluated in M. smegmatis against their parental 2-alkynoic acids, as well as isoniazid, a first-line antituberculosis drug. The introduction of additional unsaturation or heteroatoms into the carbon chain enhanced the antimycobacterial activity of longer chain alkynoic acids (more than 19 carbons long). In contrast, although the modification of the carboxylic group did not improve the antimycobacterial activity, it significantly reduced the toxicity of the compounds against eukaryotic cells. Importantly, 4-(alkylthio)but-2-ynoic acids, had better bactericidal activity than the parental 2-alkynoic acids and on a par with isoniazid against the slow-grower Mycobacterium bovis BCG. These compounds had also low toxicity against eukaryotic cells, suggesting that they could be potential therapeutic agents against other types of topical mycobacterial infections causing skin diseases including Mycobacterium abscessus, Mycobacterium ulcerans, and Mycobacterium leprae. Moreover, they provide a possible scaffold for future drug development.
Probing structure/affinity relationships for the Plasmodium falciparum hexose transporter with glucose derivatives
Fayolle, Martine,Ionita, Marina,Krishna, Sanjeev,Morin, Christophe,Patel, Asha Parbhu
, p. 1267 - 1271 (2008/12/20)
A series of 3-O-substituted glucose derivatives was prepared with alkyl, alkenyl, aromatic and ferrocenic substituents; to vary lipophilicity and hydrogen bonding ethylenedioxy and perfluorinated fragments were also introduced. Apparent affinities for the Plasmodium falciparum hexose transporter (PfHT) were determined after heterologous expression in Xenopus oocytes, with highest affinities for compounds with C8-C13 lipophilic chains. As no derivatives show significant affinity for the mammalian glucose transporter (GLUT1), these structure/affinity assays contribute to design of potent PfHT inhibitors and eventual development of antimalarials.
