22581-72-2Relevant academic research and scientific papers
Cesium carbonate-promoted synthesis of aryl methyl sulfides using: S -methylisothiourea sulfate under transition-metal-free conditions
Zhang, Caiyang,Zhou, You,Huang, Jintao,Tu, Canhui,Zhou, Xiaoai,Yin, Guodong
, p. 6316 - 6321 (2018/09/10)
In the presence of cesium carbonate, an efficient synthesis of aryl methyl sulfides by the reactions of aryl halides with commercially available S-methylisothiourea sulfate is developed. This odourless and highly crystalline solid can be used as the subst
Design, synthesis and structure-activity relationship study of novel naphthoindolizine and indolizinoquinoline-5,12-dione derivatives as IDO1 inhibitors
Yang, Rui,Chen, Yu,Pan, Liangkun,Yang, Yanyan,Zheng, Qiang,Hu, Yue,Wang, Yuxi,Zhang, Liangren,Sun, Yang,Li, Zhongjun,Meng, Xiangbao
, p. 4886 - 4897 (2018/09/11)
Indoleamine 2,3-dioxygenase 1 (IDO1) is regarded as a promising target for cancer immunotherapy. Many naphthoquinone derivatives have been reported as IDO1 inhibitors so far. Herein, two series of naphthoquinone derivatives, naphthoindolizine and indolizinoquinoline-5,12-dione derivatives, were synthesized and evaluated for their IDO1 inhibitory activity. Most of the target compounds showed significant inhibition potency and high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). The structure-activity relationship was also summarized. The most potent compounds 5c (IC50 23 nM, IDO1 enzyme), and 5b′ (IC50 372 nM, HeLa cell) were identified as promising lead compounds.
Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions
Glasnov, Toma N.,Kappe, C. Oliver,Holbrey, John D.,Seddon, Kenneth R.,Yan, Ting
, p. 3071 - 3076,6 (2020/09/16)
The ionic liquid, tributylmethylammonium methylcarbonate, has been employed as a catalytic base for clean N-methylation of indole with dimethylcarbonate. The reaction conditions were optimised under microwave heating to give 100% conversion and 100% selectivity to N-methylindole, and subsequently transferred to a high temperature/high pressure (285 °C/150 bar) continuous flow process using a short (3 min) residence time and 2 mol% of the catalyst to efficiently methylate a variety of different amines, phenols, thiophenols and carboxylic acid substrates. The extremely short residence times, versatility, and high selectivity have significant implications for the synthesis of a wide range of pharmaceutical intermediates, as high product throughputs can be obtained via this scalable continuous flow protocol. It has also been shown that the ionic liquid can be generated in situ from tributylamine, which has the net effect of transforming an ineffective stoichiometric base into a highly efficient catalyst for this broad class of reactions.
Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 6409 - 6416 (2011/02/24)
Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright
Synthesis of substituted pyridines by the reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under focused microwave irradiation
Cherng, Yie-Jia
, p. 4931 - 4935 (2007/10/03)
The nucleophilic substitution reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under microwave irradiation was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.
Azetidine derivatives, their preparation and pharmaceutical compositions containing them
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, (2008/06/13)
Compounds of formula: in which R represents a CR1R2, C═C(R5)SO2R6 or C═C(R7)SO2alk radical, their preparation and the pharmaceutical compositions containing them.
CONFORMATIONAL AND PHOTOELECTRON ANALYSIS OF ISOMERS OF THE METHYLCHALCOGENOPYRIDINES
Dunne, Simon J.,Summers, Lindsay A.,Nagy-Felsobuky, Ellak I. von
, p. 103 - 120 (2007/10/02)
The He I/He II photoelectron spectra of 2-, 3-, and 4-methylthio- and methylselenyl-pyridine are reported and interpreted in terms of a composite-molecule model based on ab initio calculations.Results from STO-3G* calculations at STO-3G* optimised geometries suggest that, for the 2- and 4-isomers, the planar conformer is more stable than the non-planar conformer, although bands due to the minor conformers are evident in some of the spectra.The He I/He II band ratios are shown to be useful in locating those MOs with significant S or Se p AO contributions, thereby indicating the chalcogene content in the bonding and anti-bonding X-? orbitals.Based on spectral features, He I/He II ratios and in conjunction with ab initio calculations, the preferred sequence for the four lowest ionisation energies for all isomers of the methylchalcogenopyridines is ? - nX N ca. ? X, where X represents the chalcogen atom.
Cephalosporin derivatives and bactericides containing the same
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, (2008/06/13)
Cephalosporin compounds represented by the following formula (I) and pharmaceutically acceptable salts thereof have a broad bactericidal spectrum against various pathogenic bacteria including Psuedomonas aeruginosa and are useful as bactericidal remedies for pathogenic diseases of human and animals: STR1 wherein A represents an unsubstituted or substituted pyridylthio group of a formula (I-1); STR2 or an unsubstituted or substituted pyridiniumthio group of a formula (I-2): STR3 or an unsubstituted or substituted pyridinium group of a formula (I-3); STR4 or a 5- or 6-membered heterocyclicthio or bicycloheterocyclicthio group of a formula (I-4):
Syntheses of Mercaptobenzoic Acids and Mercaptopyridines Using Elemental Sulfur in the Presence of NaOH-KOH
Kamiyama, Tsutomu,Enomoto, Saburo,Inoue, Masami
, p. 5184 - 5189 (2007/10/02)
Mercaptobenzoic acids and mercaptopyridines were synthesized by using mercaptylation of halogeno compounds with elemental sulfur in the presence of molten salts (NaOH-KOH).This procedure was also applied to the preparation of selenoaryl compounds by using elemental selenium.Based on the behavior of the molten salts and sulfur, Na2S and K2S were considered to be the active species for the mercaptylation.KEYWORDS-mercaptylation; molten salt; o-mercaptobenzoic acid; o-selenobenzoic acid; 2-mercaptopyridine
Carbapenem antibiotics
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, (2008/06/13)
Disclosed are novel carbapenem derivatives characterized by a 2-substituent of the formula STR1 in which A represents cyclopentylene, cyclohexylene or C2 -C6 alkylene optionally substituted by one or more C1 -C4 alkyl groups and STR2 represents a quaternized nitrogen-containing aromatic heterocycle. Such derivatives are useful as potent antibacterial agents. Also disclosed are processes for the preparation of such derivatives and novel intermediates utilized in these processes.
