1373346-87-2Relevant academic research and scientific papers
Polycyclic aromatics with flanking thiophenes: Tuning energy level and band gap of conjugated polymers for bulk heterojunction photovoltaics
Price, Samuel C.,Stuart, Andrew C.,You, Wei
, p. 797 - 804 (2010)
In the pursuit of donor-acceptor low band gap polymers for photovoltaic applications, finding an optimal donor monomer which maximizes the photovoltaic efficiency is a complex synthetic optimization problem. We synthesized three different bithiophenes flanking a center aromatic ring (pyrrole, benzene, or pyridine) as the donor monomers (DTPr, DTBn, and DTPn) with decreasing electron-donating ability. An array of six electrochemically and optically unique polymers were prepared by copolymerizing these three monomers with 2,1,3-benzothiadiazole and with thiophene. The optical, electronic, and photovoltaic properties of these polymers were investigated. Among this series, we found that the HOMO energy level of the polymer is dominated by the most electron-rich ring in the polymer backbone. The optical band gap, conversely, involves the entire polymeric system. Among the three donor monomers investigated, we identified that DTBn-based polymers exhibited the most potential in photovoltaic applications due to their moderately low band gaps and low HOMO energy levels.
Lead optimization studies on FimH antagonists: Discovery of potent and orally bioavailable ortho-substituted biphenyl mannosides
Han, Zhenfu,Pinkner, Jerome S.,Ford, Bradley,Chorell, Erik,Crowley, Jan M.,Cusumano, Corinne K.,Campbell, Scott,Henderson, Jeffrey P.,Hultgren, Scott J.,Janetka, James W.
experimental part, p. 3945 - 3959 (2012/07/16)
Herein, we describe the X-ray structure-based design and optimization of biaryl mannoside FimH inhibitors. Diverse modifications to the biaryl ring to improve druglike physical and pharmacokinetic properties of mannosides were assessed for FimH binding affinity based on their effects on hemagglutination and biofilm formation along with direct FimH binding assays. Substitution on the mannoside phenyl ring ortho to the glycosidic bond results in large potency enhancements several-fold higher than those of corresponding unsubstituted matched pairs and can be rationalized from increased hydrophobic interactions with the FimH hydrophobic ridge (Ile13) or "tyrosine gate" (Tyr137 and Tyr48) also lined by Ile52. The lead mannosides have increased metabolic stability and oral bioavailability as determined from in vitro PAMPA predictive model of cellular permeability and in vivo pharmacokinetic studies in mice, thereby representing advanced preclinical candidates with promising potential as novel therapeutics for the clinical treatment and prevention of recurring urinary tract infections.
