256429-28-4

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 1141-88-4 2-Aminophenyl disulfide 

Downstream Products

• 1035114-09-0 [(μ-S-2-(4-FC6H4CONHC6H4))2Fe2(CO)6] 

Relevant academic research and scientific papers

Acyl Derivatives of Eudesmanolides To Boost their Bioactivity: An Explanation of Behavior in the Cell Membrane Using a Molecular Dynamics Approach

Semisynthetic analogs of natural products provide an important approach to obtain safer and more active drugs and they can also have enhanced physicochemical properties such as persistence, cross-membrane processes and bioactivity. Acyl derivatives of different natural product families, from sesquiterpene lactones to benzoxazinoids, have been synthesized and tested in our laboratories. These compounds were evaluated against tumoral and nontumoral cell lines to identify selective derivatives with a reduced negative impact upon application. The mode of action of these compounds was analyzed by anti-caspase-3 assays and molecular dynamics simulations with cell membrane re-creation were also carried out. Aryl derivatives of eudesmanolide stand out from the other compounds and are better than current anticancer drugs such as etoposide in terms of selectivity and activity. Computational studies provide evidence that lipophilicity plays a key role and the 4-fluorobenzoyl derivative can pass easily through the cell membrane.

Cooperative redox regulation of [4Fe-4S] ferredoxin model arenethiolate complexes by NH· · ·S hydrogen bonds and an aromatic C-H···S interaction

A series of the model complexes containing ortho-substituted arenethiolato ligands, ((Et4N)2[Fe4S4(S-2- RCONHC6H4)4] {R=Ph (1), 4-MeO-C6H4 (2), and4-F-C6H4 (3)} and (Et4N)2[Fe 4S4{S-2,6-(RCONH)2C6H 3}4] {R=Ph (4), 4-MeO-C6H4 (5), and 4-F-C6H4 (6)}) was synthesized and characterized by 1NMR, IR spectroscopy, and cyclic voltammetry. The solution structures of these complexes are discussed based on their 1NMR T1 data and moleculardynamics calculations. Complex 4 has a shorter distance (av. 4.3 A) between the protons of the benzoyl group and the inorganic sulfur atom of the [4Fe-4S] cluster than the corresponding ones of 1 (av. 6.2 A). These results indicate the C-H · · · S interaction between the protons of the benzoyl group and the sulfur atom of the [4Fe-4S] cluster. The [Fe4S4(SAr)4] 2-/[Fe4S4(SAr)4]3- redox potential for 1 and 4 are-0.86 and-0.65 V, respectively. The difference between 1 and 4 is Δ0.21 V. This is larger than the value Δ0.11 V between [Fe4S4(S-2-t-BuCONHC6H4)4] 2- (-0.91 V) and [Fe4S4{S-2,6-(t-BuCONH) 2C6H3}4]2- (-0.80 V), considered to be the difference between singly and doubly NH· · ·S hydrogen-bonded complexes. The redox potentials for 1-6 follow the trend of the Hammett σ mvalues, showing that the aromatic ring of the benzoyl group interacts with the [4Fe-4S] cluster directly. A cooperative effect between the C-H· · ·S interaction and the NH ·· · S hydrogen bond is thus found to regulate the redox potential of the model complexes.