259178-06-8Relevant academic research and scientific papers
Synthesis, structure, and SAR of tetrahydropyran-based LpxC inhibitors
Murphy-Benenato, Kerry E.,Olivier, Nelson,Choy, Allison,Ross, Philip L.,Miller, Matthew D.,Thresher, Jason,Gao, Ning,Hale, Michael R.
, p. A1213 - A1218 (2015/04/27)
In the search for novel Gram-negative agents, we performed a comprehensive search of the AstraZeneca collection and identified a tetrahydropyran-based matrix metalloprotease (MMP) inhibitor that demonstrated nanomolar inhibition of UDP-3-O-(acyl)-N-acetylglucosamine deacetylase (LpxC). Crystallographic studies in Aquifex aeolicus LpxC indicated the tetrahydropyran engaged in the same hydrogen bonds and van der Waals interactions as other known inhibitors. Systematic optimization of three locales on the scaffold provided compounds with improved Gram-negative activity. However, the optimization of LpxC activity was not accompanied by reduced inhibition of MMPs. Comparison of the crystal structure of the native product, UDP-3-O-(acyl)-glucosamine, in Aquifex aeolicus to the structure of a tetrahydropyran-based inhibitor indicates pathways for future optimization.
Synthesis and preliminary testing of molecular wires and devices
Tour, James M.,Rawlett, Adam M.,Kozaki, Masatoshi,Yao, Yuxing,Jagessar, Raymond C.,Dirk, Shawn M.,Price, David W.,Reed, Mark A.,Zhou, Chong-Wu,Chen, Jia,Wang, Wenyong,Campbell, Ian
, p. 5118 - 5134 (2007/10/03)
Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.
A practical route to functionalized (phenylethynyl)phenylthiol acetates for self-assembled monolayer studies
Collman,Zhong,Costanzo,Sunderland,Aukauloo,Berg,Zeng
, p. 367 - 369 (2007/10/03)
Functionalized (phenylethynyl)phenylthiol acetates, such as 4-(4′formylphenyl-ethynyl)phenylthiol acetate (8a) and 4-(4′-hydroxycarbonylphenylethynyl)phenylthiol acetate (9), were readily synthesized from commercially available 4-bromobenzenethiol (1) as
Synthesis of porphyrins bearing trans-thiols
Jagessar, Raymond C.,Tour, James M.
, p. 111 - 113 (2007/10/03)
(matrix presented) A route to porphyrins bearing frans-thiols is described using a thioacetyl-containing aldehyde or a thioacetyl-containing dipyrromethane in the presence of catalytic BF3·OEt2 followed by oxidation. Metal complexation and ammonium hydroxide induced acetyl removal provides a route to these important molecular systems for future electronics experiments in which the thiols would serve as the adhesion points to gold probes.
Synthesis of "Porphyrin-Linker-Thiol" Molecules with Diverse Linkers for Studies of Molecular-Based Information Storage
Gryko, Daniel T.,Clausen, Christian,Roth, Kristian M.,Dontha, Narasaiah,Bocian, David F.,Kuhr, Werner G.,Lindsey, Jonathan S.
, p. 7345 - 7355 (2007/10/03)
The attachment of redox-active molecules such as porphyrins to an electroactive surface provides an attractive approach for electrically addressable molecular-based information storage. Porphyrins are readily attached to a gold surface via thiol linkers. The rate of electron transfer between the electroactive surface and the porphyrin is one of the key factors that dictates suitability for molecular-based memory storage. This rate depends on the type and length of the linker connecting the thiol unit to the porphyrin. We have developed different routes for the preparation of thiol-derivatized porphyrins with eight different linkers. Two sets of linkers explore the effects of linker length and conjugation, with one set comprising phenylethyne units and one set comprising alkyl units. One electron-deficient linker has four fluorine atoms attached directly to a thiophenyl unit. To facilitate the synthesis of the porphyrins, convenient routes have been developed to a wide range of aldehydes possessing a protected S-acetylthio group. An efficient synthesis of 1-(S-acetylthio)-4-iodobenzene also has been developed. A set of porphyrins, each bearing one S-acetyl-derivatized linker at one meso position and mesityl moieties at the three remaining meso positions, has been synthesized. Altogether seven new aldehydes, eight free base porphyrins and eight zinc porphyrins have been prepared. The zinc porphyrins bearing the different linkers all form self-assembled monolayers (SAMs) on gold via in situ cleavage of the S-acetyl protecting group. The SAM of each porphyrin is electrochemically robust and exhibits two reversible oxidation waves.
