Synthesis and biological evaluation of (S)-4-aminoquinazoline alcohols

A simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia coli WP2uvrA tester strains at 0.01, 0.1, and 1 μg/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1 μg/plate dose.     

Memory‐efficient calculation of the isotopic mass states of a molecule

Our previous work postulated a transition concept among different isotopic mass states (i.e., isotopic species) of a molecule, and developed a hierarchical algorithm for accurately calculating their masses and abundances. A theoretical mass spectrum can be generated by convoluting a peak shape function to these discrete mass states. This approach suffers from limited memory if a level in the hierarchical structure has too many mass states. Here we present a memory efficient divide‐and‐recursively‐combine algorithm to do the calculation, which also improves the truncation method used in the previous hierarchical algorithm. Instead of treating all of the elements in a molecule as a whole, the new algorithm first ‘strips’ each element one by one. For the mass states of each element, a hierarchical structure is established and kept in the memory. This process reduces the memory usage by orders of magnitude (e.g., for bovine insulin, memory can be reduced from gigabytes to kilobytes). Next, a recursive algorithm is applied to combine mass states of elements to mass states of the whole molecule. The algorithm described above has been implemented as a computer program called Isotope Calculator, which was written in C++. It is freely available under the GNU Lesser General Public License from http://www.cs.brandeis.edu/～hong/software.html or http://people.brandeis.edu/～agar . Copyright © 2010 John Wiley & Sons, Ltd.     

An investigation of the catalytic potential of mono- and dicationic imidazolium N-heterocyclic carbenes in the benzoin condensation

The catalytic potential of imidazolium salts in the benzoin condensation was investigated. Various aromatic aldehydes were tested in the benzoin condensation under the optimised protocol to afford α-hydroxyketones using N-heterocyclic carbenes derived from mono- and dicationic imidazolium salts. The products were obtained in good yields within short reaction times. Dicationic imidazolium salts with a long aliphatic chain between the imidazole rings were found to be more effective pre-catalysts for the benzoin condensation in comparison to the corresponding monocationic salts having the same aliphatic chain length.     

A modular design of ruthenium(II) catalysts with chiral C2-symmetric phosphinite ligands for effective asymmetric transfer hydrogenation of aromatic ketones

Hydrogen-transfer reduction processes are attracting increasing interest from synthetic chemists in view of their operational simplicity. The new chiral C₂-symmetric ligands N,N′-bis-[(1S)-1-sec-butyl-2-O-(diphenylphosphinite)ethyl]ethanediamide, 1 and N,N′-bis-[(1S)-1-phenyl-2-O-(diphenylphosphinite)ethyl]ethanediamide, 2 and the corresponding ruthenium complexes 3 and 4 have been prepared and their structures have been elucidated by a combination of multi-nuclear NMR spectroscopy, IR spectroscopy, and elemental analysis. ¹H–³¹P NMR, DEPT, ¹H–¹³C HETCOR, or ¹H–¹H COSY correlation experiments were used to confirm the spectral assignments. The catalytic activity of complexes 3 and 4 in transfer hydrogenation of acetophenone derivatives by iso-PrOH has also been studied. Under optimized conditions, these chiral ruthenium complexes serve as catalyst precursors for the asymmetric transfer hydrogenation of acetophenone derivatives in iso-PrOH and act as excellent catalysts, giving the corresponding chiral alcohols in 99% yield and up to 75% ee. This transfer hydrogenation is characterized by low reversibility under these conditions.     

Continuous production of (S)-1-phenylethanol by immobilized cells of Rhodotorula glutinis with a specially designed process

A specially designed process for the continuous production of a chiral alcohol by immobilized Rhodotorula glutinis was prepared and is reported. The performance of the process with immobilized cells was also investigated. The run time of the immobilized cells, the flow rates of the substrate, and tris buffer containing 4% glucose in the process were optimized. The immobilized R. glutinis biocatalyst could be used for 15 days with maximum reaction activity. Under the optimized conditions, the continuous production process was operated for 30 days and resulted in 10.8 mL (S)-1-phenylethanol [(S)-1-PE]. The process has been demonstrated on a multigram scale in 75% overall yield with a purity of >99%.     

Dendronized polymers via Diels–Alder “click” reaction

A modular approach toward the synthesis of polymers containing dendron groups as side chains is developed using the Diels–Alder “click” reaction. For this purpose, a styrene‐based polymer appended with anthracene groups as reactive side chains was synthesized. First through third‐generation polyester dendrons containing furan‐protected maleimide groups at their focal point were synthesized. Facile, reagent‐free, thermal Diels–Alder cycloaddition between the anthracene‐containing polymer and latent‐reactive dendrons leads to quantitative functionalization of the polymer chains to afford dendronized polymers. The efficiency of this functionalization step was monitored using ¹H and ¹³C NMR spectroscopy and FTIR and UV–vis spectrometry. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 410–416, 2010     

An Interactive Approach for Choosing the Best of a Set of Alternatives

In this paper we address the problem of choosing the most preferred alternative among a large number of alternatives where each alternative is defined by multiple criteria. We assume that the decision maker has a quasiconcave utility function. We develop an exact approach that combines the ideas that have appeared in the literature regarding the use of different types of dummy alternatives in conjunction with real alternatives. Our experimental results indicate that the new approach is comparable to leading existing approaches.     

Characterisation of α-chitin extracted from a lichenised fungus species Xanthoria parietina

Lichens are symbiotic associations formed mainly by ascomycete fungi and green algae or cyanobacteria. The presence of chitin in the fungal cell wall has been revealed by previous studies. Considering the presence of fungi in the lichens, this work determines the presence of chitin in a cosmopolitan lichen species Xanthoria parietina. In this study, chitin was derived from a lichen species for the first time and its physicochemical properties were determined by Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy and elemental analysis. The dry weight chitin content of X. parietina was 4.23%, and this chitin was in the α-form. The crystalline index value of the lichen chitin was calculated as 70.1%. The chitin from X. parietina had a smooth surface.