Carbapenem and penem antibiotics. VI. Synthesis and antibacterial activity of 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl 1-methylcarbapenems

The synthesis and antibacterial activity of the 1-methylcarbapenems, 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl derivatives having a 6-[(R)-1-hydroxyethyl] side chain, are described. The introduction of a methyl substituent at the C-1 position was accomplished by a newly developed procedure using crotyl halides and zinc dust. The 2-hydroxymethyl carbapenems as key intermediates allowed an easy entry into the preparation of title carbapenems.     

Carbapenem and penem antibiotics. V. Synthesis and antibacterial activity of 2-functionalized-methyl 1-methylcarbapenems related to asparenomycins

The synthesis of 1 alpha- and/or 1 beta-methylcarbapenems, 2-unsubstituted and 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl derivatives having a 1-(hydroxy)methylethylidene or cyclic carbonate side chain at the C-6 position, is described. The in vitro antibacterial activities of these compounds and their corresponding 1-unsubstituted carbapenems are compared.     

Rapid and highly sensitive method for determination of methamphetamine and amphetamine in urine by electron-capture gas chromatography

A rapid and sensitive method for determination of methamphetamine and amphetamine in urine was developed by using electron-capture gas chromatography. The extraction procedure, the experimental conditions for pentafluorobenzoyl derivative formation and the percentage recovery of the drugs from urine are described. The pentafluorobenzoyl derivative of methamphetamine showed a higher electron-capture sensitivity and was detected in at least 23-fold lower concentration than the heptafluorobutyryl derivative which is commonly used as a derivatizing agent for the amine. The detection limit of pentafluorobenzoyl derivatives of methamphetamine and amphetamine was ca. 10 pg. A concentration as low as 10 ng/ml of methamphetamine and amphetamine in urine was easily detected by this method.     

Enhancement of electroluminescence intensity in poly(3-alkylthiophene) with different alkyl side-chain length by doping of fluorescent dye

Electroluminescent diodes utilizing poly(3-alkylthiophene) (PAT) containing fluorescent dyes have been fabricated and their unique enhancement of emission characteristics have been studied. Remarkable enhancement of the electroluminescence efficiency has been observed for diodes with PAT doped with oxadiazole derivative (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole; PBD) and perylene derivative (N,N′ - Bis(2,5 - di - tert - butylphenyl) - 3,4,9,10 - perylenedi- carboximide; BPPC). The mechanism of emission enhancement by doping of PBD into PAT has been discussed with different alkyl side-chain lengths. © 1997 John Wiley & Sons, Ltd.     

Solid‐Phase Combinatorial Synthesis and Biological Evaluation of Destruxin E Analogues

The solid‐phase combinatorial synthesis of cyclodepsipeptide destruxin E has been demonstrated. The combinatorial synthesis of cyclization precursors 8 was achieved by using a split and pool method on SynPhase Lanterns. The products were successfully macrolactonized in parallel in the solution phase by using 2‐methyl‐6‐nitrobenzoic anhydride and 4‐(dimethylamino)pyridine N‐oxide to afford macrolactones 9 , and the subsequent formation of an epoxide in the side chain gave 18 member destruxin E analogues 6 . Biological evaluation of analogues 6 indicated that the N‐MeAla residue was crucial to the induction of morphological changes in osteoclast‐like multinuclear cells (OCLs). Based on structure–activity relationships, azido‐containing analogues 15 were then designed for use as a molecular probe. The synthesis and biological evaluation of analogues 15 revealed that 15 b , in which the Ile residue was replaced with a Lys(N₃) residue, induced morphological changes in OCLs at a sufficient concentration, and modification around the Ile residue would be tolerated for attachment of a chemical tag toward the target identification of destruxin E ( 1 ).     

The nature of sulfur bonding in thiopyrylium cation

Comparison of the PMR spectrum ofthiopyrylium cation with those of the oxygen (pyrylium cation) and nitrogen (pyridinium cation) analogs has suggested the unique electronic structure of the thiopyrylium cation. To investigate this structure the extended Hückel MO calculations have been carried out using two basis sets, one with and another without sulfur 3d orbitals. The electronic structure of thiopyrylium cation can be rationalized by the 3d orbital involvement of the S atom in the basis set. The primary effect of the involvement of 3d orbitals on the S atom is shown to be the electron transfer from the ring carbon fragment, in particular from the β ring carbons, to the S atom, with an accompanying increase in sulfur-α-carbon bond order.     

New functional microspheres with active succinimide groups

Radiation-induced polymerization of monomers, for example N-methacryl-oxysuccinimide (MASu) and diethylene glycol dimethacrylate (2G), in ethyl propionate, was performed from +25°C to –78°C. The copoly (MASu/2G) microspheres were obtained in MASu monomer compositions of 30 wt % or below. The average particle diameter of copoly(MASu/2G, 20/80 wt %) microspheres obtained at irradiation temperatures of 25°, 0°, and –43 °C were 0.81±0.29, 0.63±0.26, and 0.90±0.43 m, respectively. No microspheres were formed when irradiated at –78 °C. The reactivity of the succinimide groups on the surface of copoly(MASu/2G, 20/80 wt%) microspheres was checked by reacting with ethylene diamine. The maximal amount of reacting succinimide groups was 9.4±0.5 nol/g, which corresponds to about 1 % of the total number of succinimide groups in the microsphere.