cas 1527-12-4, 2-(phenylthio)benzoic acid | Articles data

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Synthesis and characterization of ortho-thio-functionalized triarylmethyl palladium complexes
A series of triarylmethyl palladium complexes with ortho coordination sites were synthesized. Thereby, the palladium atom exhibits various inter- and intramolecular binding modes towards the organic ligand. Further, the first crystallographically proven, exclusively σ-coordinated triarylmethyl palladium complexes, stabilized by ortho-thio-substituents, were discovered. The NMR spectra of the palladium complexes indicate temperature-dependent dynamic behavior.
Sch?ler, Stephan,Merz, Klaus,Puls, Arik,Winter, Manuela,Dyker, Gerald
p. 53 - 57
(2015)
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Design and synthesis of novel 4-thiazolidinone derivatives with promising anti-breast cancer activity: Synthesis, characterization, in vitro and in vivo results
Novel lead compounds as anticancer agents with the ability to circumvent emerging drug resistance have recently gained a great deal of interest. Thiazolidinones are among such compounds with well-established biological activity in the field of oncology. Here, we designed, synthesized and characterized a series of thiazolidinone structures (8a-8k). The results of anti-proliferative assay led to the discovery of compound 8j with a high potent cytotoxic effect using colon, liver and breast cancer cells. Furthermore, MDA-MB-231 and 4T1 cell lines were used to represent triple negative breast cancer (TNBC). Next, a number of in vitro and in vivo evaluations were carried out to demonstrate the potential activity against TNBC and also elucidate the possible mechanism of cell death induction. Our in vitro outcomes exhibited an impressive anticancer activity for compound 8j toward MDA-MB-231 cells through inducing apoptosis and a remarkable anti-metastatic feature via suppressing MMP-9 expression as well. Consistently, the in vivo and immunohistopathologic evaluations demonstrated that this compound significantly inhibited the 4T1 induced tumor growth and its metastasis to the lung. Altogether, among numerous thiazolidinone derivatives, compound 8j might represent a promising anticancer agent for TNBC, which is a major concern in the developed and developing countries.
Almasirad, Ali,Bayat, Peyman,Dehghani, Soudeh,Khaleghi, Sepideh,Kooshafar, Zahra,Salimi, Mona,Tahmasvand, Raheleh,Vahdaniparast, Seyyed Mahmood
(2020)
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COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
The present invention provides a novel compound that can improve the luminous efficiency, stability and life span of the element, an organic electronic element using the same, and an electronic device thereof.
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(2021/05/21)

COMPOSITION AND METHOD FOR MANUFACTURING DEVICE USING SAME
An onium salt and a composition having high sensitivity and excellent pattern characteristics such as LWR, which is preferably used for a resist composition for a lithography process using two active energy rays of a first active energy ray such as an electron beam or an extreme ultraviolet and a second active energy ray such as UV.
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(2020/02/27)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
The present invention provides a compound represented by chemical formula 1, an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric device. By including the compound represented by chemical formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered, luminous efficiency and lifespan can be improved, and in particular, the lifespan can be improved.COPYRIGHT KIPO 2021
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(2020/10/31)

Positive resist composition, resist pattern forming process, and photomask blank
A positive resist composition comprising a polymer adapted to be decomposed under the action of acid to increase its solubility in alkaline developer and a sulfonium compound of specific structure has a high resolution. When the resist composition is processed by lithography, a pattern with minimal LER can be formed.
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(2019/10/01)

Cerium catalyst promoted C-S cross-coupling: Synthesis of thioethers, dapsone and RN-18 precursors
In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C-S cross-coupling reaction with the assistance of [Ce(l-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The catalyst [Ce(l-Pro)2]2Ox was recovered and it was shown to be effective for five more reaction cycles.
Tavares Junior, José M. Da C.,Da Silva, Caren D. G.,Dos Santos, Beatriz F.,Souza, Nicole S.,De Oliveira, Aline R.,Kupfer, Vicente L.,Rinaldi, Andrelson W.,Domingues, Nelson L. C.
supporting information
p. 10103 - 10108
(2019/12/23)

Cobalt-Catalyzed Direct C-H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine
A direct C(sp2)-H thiolation of aromatic amides with disulfides was developed. The coupling reaction proceeds between the thioether radical and cobaltacycle intermediate. This method exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that the cobalt(IV) intermediate is probably formed during the course of the reaction. The thiolation product can be transformed to Quetiapine, which is an atypical antipsychotic agent approved for the treatment of schizophrenia and bipolar disorder.
Li, Mingliang,Wang, Jun Joelle
p. 6490 - 6493
(2018/10/20)

Negative resist composition and resist pattern forming process
A negative resist composition comprising (A) a sulfonium compound of betaine type and (B) a polymer is provided. The resist composition is effective for controlling acid diffusion during the exposure step, exhibits a very high resolution during pattern formation, and forms a pattern with minimal LER.
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(2018/11/24)

Synthesis and Crystal Structures of Diaryl Thioethers and Aryl Benzyl Thioethers Derived from Thiosalicylic Acid
Abstract: Reaction of thiosalicylic acid and iodobenzene or 1-fluoro-2-nitrobenzene in the presence of two equiv. of K2CO3 in acetone–water afforded the according diaryl thioethers 1 and 2 bearing carboxyl groups. Treatment of thiosalicylic acid with benzyl bromide-type compounds under similar reaction conditions gave aryl benzyl thioethers 3–8 in excellent yields. Moreover, reactions of thiosalicylic acid and benzyl bromide in the presence of excess K2CO3 led to isolation of compound 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013) through further esterification of the carboxyl group. Crystal structures of 2, 5–7 and 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013), along with their spectroscopic properties are reported. Weak hydrogen-bonding interactions exist in compound 2 and isomers 5–7. Compounds 2 and 7 crystallize in the monoclinic space group P21/n and C2/c, respectively, with a = 12.04(3), b = 7.311(19), C=14.22(4) ?, β = 93.94(3)°, and Z = 4 for 2, and a = 14.934(13), b = 5.116(5), C=33.76(3) ?, β = 91.523(12)°, and Z = 8 for 7. The unit cell of 5 has triclinic P-1 symmetry with the cell parameters a = 5.4334(14), b = 7.7787(19), C=16.488(4) ?, α = 76.601(3)°, β = 86.078(3)°, γ = 70.772(3)°, and Z = 2 for 5. Compound 6 crystallizes in the orthorhombic space group Pbca with a = 15.1881(12), b = 7.3288(6), C=23.7366(19) ?, and Z = 8. Graphical Abstract: Reactions of thiosalicylic acid and a series of aryl- or benzyl halides in the presence of K2CO3 in acetone–water resulted in the formation of according diaryl thioethers and aryl benzyl thioethers in excellent yields.
Liu, Dan,Chen, Min,Fang, Duowen,Jia, Ai-Quan,Zhang, Qian-Feng
p. 1 - 11
(2018/04/26)

Tuning the Diiron Core Geometry in Carboxylate-Bridged Macrocyclic Model Complexes Affects Their Redox Properties and Supports Oxidation Chemistry
We introduce a novel platform to mimic the coordination environment of carboxylate-bridged diiron proteins by tethering a small, dangling internal carboxylate, (CH2)nCOOH, to phenol-imine macrocyclic ligands (H3PIMICn). In the presence of an external bulky carboxylic acid (RCO2H), the ligands react with [Fe2(Mes)4] (Mes = 2,4,6-trimethylphenyl) to afford dinuclear [Fe2(PIMICn)(RCO2)(MeCN)] (n = 4-6) complexes. X-ray diffraction studies revealed structural similarities between these complexes and the reduced diiron active sites of proteins such as Class I ribonucleotide reductase (RNR) R2 and soluble methane monooxygenase hydroxylase. The number of CH2 units of the internal carboxylate arm controls the diiron core geometry, affecting in turn the anodic peak potential of the complexes. As functional synthetic models, these complexes facilitate the oxidation of C-H bonds in the presence of peroxides and oxo transfer from O2 to an internal phosphine moiety.
Wang, Fang,Becker, Sabine,Minier, Mikael A.,Loas, Andrei,Jackson, Megan N.,Lippard, Stephen J.
supporting information
p. 11050 - 11058
(2017/09/26)

Discovery and Optimization of Thiazolidinyl and Pyrrolidinyl Derivatives as Inhaled PDE4 Inhibitors for Respiratory Diseases
Phosphodiesterase 4 (PDE4) is a key cAMP-metabolizing enzyme involved in the pathogenesis of inflammatory disease, and its pharmacological inhibition has been shown to exert therapeutic efficacy in chronic obstructive pulmonary disease (COPD). Herein, we describe a drug discovery program aiming at the identification of novel classes of potent PDE4 inhibitors suitable for pulmonary administration. Starting from a previous series of benzoic acid esters, we explored the chemical space in the solvent-exposed region of the enzyme catalytic binding pocket. Extensive structural modifications led to the discovery of a number of heterocycloalkyl esters as potent in vitro PDE4 inhibitors. (S?,S??)-18e and (S?,S??)-22e, in particular, exhibited optimal in vitro ADME and pharmacokinetics properties and dose-dependently counteracted acute lung eosinophilia in an experimental animal model. The optimal biological profile as well as the excellent solid-state properties suggest that both compounds have the potential to be effective topical agents for treating respiratory inflammatory diseases.
Carzaniga, Laura,Amari, Gabriele,Rizzi, Andrea,Capaldi, Carmelida,De Fanti, Renato,Ghidini, Eleonora,Villetti, Gino,Carnini, Chiara,Moretto, Nadia,Facchinetti, Fabrizio,Caruso, Paola,Marchini, Gessica,Battipaglia, Loredana,Patacchini, Riccardo,Cenacchi, Valentina,Volta, Roberta,Amadei, Francesco,Pappani, Alice,Capacchi, Silvia,Bagnacani, Valentina,Delcanale, Maurizio,Puccini, Paola,Catinella, Silvia,Civelli, Maurizio,Armani, Elisabetta
p. 10026 - 10046
(2018/01/10)

Development of Potent Type i Protein Arginine Methyltransferase (PRMT) Inhibitors of Leukemia Cell Proliferation
Protein Arginine Methyltransferases (PRMTs) are crucial players in diverse biological processes, and dysregulation of PRMTs has been linked to various human diseases, especially cancer. Therefore, small molecules targeting PRMTs have profound impact for both academic functional studies and clinical disease treatment. Here, we report the discovery of N1-(2-((2-chlorophenyl)thio)benzyl)-N1-methylethane-1,2-diamine (28d, DCPR049-12), a highly potent inhibitor of type I PRMTs that has good selectivity against a panel of other methyltransferases. Compound 28d effectively inhibits cell proliferation in several leukemia cell lines and reduces the cellular asymmetric arginine dimethylation levels. Serving as an effective inhibitor, 28d demonstrates the mechanism of cell killing in both cell cycle arrest and apoptotic effect as well as downregulation of the pivotal mixed lineage leukemia (MLL) fusion target genes such as HOXA9 and MEIS1, which reflects the critical roles of type I PRMTs in MLL leukemia. These studies present 28d as a valuable inhibitor to investigate the role of type I PRMTs in cancer and other diseases.
Wang, Chen,Jiang, Hao,Jin, Jia,Xie, Yiqian,Chen, Zhifeng,Zhang, Hao,Lian, Fulin,Liu, Yu-Chih,Zhang, Chenhua,Ding, Hong,Chen, Shijie,Zhang, Naixia,Zhang, Yuanyuan,Jiang, Hualiang,Chen, Kaixian,Ye, Fei,Yao, Zhiyi,Luo, Cheng
p. 8888 - 8905
(2017/11/14)

NOVEL SULPHONIUM COMPOUND AND METHOD FOR PRODUCING THE SAME, RESIST COMPOSITION, AND PATTERN FORMING METHOD
PROBLEM TO BE SOLVED: To provide a resist composition that gives a resist film excellent in resolution, LWR, MEF and CDU, in far-ultraviolet lithography and EUV lithography, and provide a sulphonium compound for use therein, and provide a pattern forming method using the resist composition. SOLUTION: The present invention provides a sulphonium compound represented by the following formula (1) (where R1, R2 and R3 independently represent a C1-20 linear, branched or cyclic monovalent hydrocarbon group, which may contain a hetero atom. p and q independently represent an integer of 0-5. r is an integer of 0-4). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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(2017/12/01)

Quetiapine synthesizing method
The invention discloses a quetiapine synthesizing method. O-chlorobenzoic acid with the low price is adopted as a starting material to react with thiophenol, and then ring closure is performed to obtain thioxanthone. Hydroxyl amination and Beckmann rearrangement are performed to obtain a key intermediate dibenzo[b,f][1,4]thiazepines-11-(10H)one, chlorination is performed, then, a reaction is performed on 1-(2-hydroxyethoxy)ethylpiperazine with the existence of acid-binding agent to obtain quetiapine, and the quetiapine and fumaric acid form a salt in an absolute ethyl alcohol system to obtain a product. According to the quetiapine synthesizing method, raw materials are low in price and easy to obtain, the steps are simple, operation is easy, and the cost can be effectively lowered. According to the method, the high-purity quetiapine can be obtained, the liquid phase purity of the obtained semi-fumaric acid quetiapine obtained through salt forming is 99% or above, and the quetiapine synthesizing method can be applied to the field of medicine.
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(2017/06/27)

Synthetic method of 2-thiophenylbenzoic acid
The invention discloses a synthetic method of 2-thiophenylbenzoic acid. The synthetic method is characterized by including the steps of: 1) dissolving raw materials, comprising phenylboric acid represented as the formula I and thiosalicylic acid represented as the formula II, in an alkaline solution and adding anhydrous ethylenediamine; 2) in the presence of a metal salt catalyst and a ligand, carrying out a heating reaction at higher than 100 DEG C for more than 16 h with TLC tracing detection, and when then reactant, thiosalicylic acid, disappears, the reaction is determined to be finished; 3) naturally cooling the mixture to room temperature to obtain a mother liquid, extracting the mother liquid with ethyl acetate, drying an organic layer with anhydrous magnesium sulfate, and performing reduced-pressure rotary evaporation to remove the solvent and obtain a solid; and 4) purifying the solid crude product through a silica gel column, collecting an eluent, and performing rotary evaporation to dry the eluent to obtain the 2-thiophenylbenzoic acid represented as the formula III. The method is simple in reaction conditions and high in yield, is easy to enlarge in large scale, and is environment-friendly and low-pollution.
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(2017/01/02)

Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.
Hossian, Asik,Jana, Ranjan
supporting information
p. 9768 - 9779
(2016/10/31)

COMPOUNDS AND METHODS FOR USE IN TREATING NEOPLASIA AND CANCER
The present invention relates to a novel method for the treatment of neoplasia, including cancer and other diseases and conditions in humans and mammals. More particularly, in preferred aspects, the present invention provides a method for the use of novel compounds for the treatment of neoplasia, hyperproliferative cell growth including psoriasis, restenosis following cardiovascular surgery, hyperplasia, including renal hyperplasia, chronic inflammatory diseases including rheumatoid and osteoarthritis, among others.
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(2013/03/26)

Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions
CuI nanoparticles efficiently catalyzed the C-S cross coupling of aryl and alkyl thiols with aryl halides in the absence of ligands on water under mild conditions. A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized in good to excellent yields utilizing this protocol. This procedure is particularly noteworthy given its mild conditions, avoiding the undesired formation of disulfides through oxidation of thiols. The recovery and successful reutilization of the catalyst is described. Furthermore, the directed synthesis of bisarylated product is presented. The Royal Society of Chemistry 2012.
Xu, Hua-Jian,Liang, Yu-Feng,Zhou, Xin-Feng,Feng, Yi-Si
supporting information; experimental part
p. 2562 - 2568
(2012/04/23)

Heterogeneous magnetic catalyst for S-arylation reactions
A convenient method for the synthesis of monodisperse, superparamagnetic copper ferrite (CuFe2O4) nanoparticles with high surface area has been described. The synthesized material was characterized by various techniques. XRD showed the nanocrystalline nature of CuFe2O 4 with a crystallite size of 6 nm. TEM analysis showed that uniform spherical CuFe2O4 particles are formed with a size of 55 ± 5 nm. N2 adsorption/desorption measurements confirmed the mesoporous nature of the sample with surface area >216 m2 g -1. The field dependent magnetization, illustrated by VSM and saturation magnetization was found to be 44 emu g-1. The catalytic applications of the synthesized CuFe2O4 nanoparticles were explored for the cross-coupling of thiols with diverse range of aryl halides. Aryl iodides and bromides result in biarylsulfides in good to excellent yields (62-98%) whereas aryl chlorides gave significant amount of diaryldisulfide. Scope of this catalytic protocol further extended to one-pot synthesis of biologically important tricyclic dibenzothiazepines. The superparamagnetic nature of CuFe2O4 nanoparticles was found to be advantageous for their easy, quick and quantitative separation from the reaction mixture. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign.
Panda, Niranjan,Jena, Ashis Kumar,Mohapatra, Sasmita
experimental part
p. 258 - 264
(2012/08/28)

Chan-lam-type s-arylation of thiols with boronic acids at room temperature
In this work, an efficient CuSO4-catalyzed S-arylation of thiols with aryl and heteroaryl boronic acids at room temperature is established. This catalytic system can tolerate a wide variety of thiols and arylboronic acids in the presence of only 5 mol % of CuSO4 as the catalyst and inexpensive 1,10-phen?H2O as the ligand. Moreover, this catalytic system used environment-friendly solvent (EtOH) and oxidant (oxygen).
Xu, Hua-Jian,Zhao, Yong-Qiang,Feng, Teng,Feng, Yi-Si
experimental part
p. 2878 - 2884
(2012/05/04)

Amide-modified prenylcysteine based Icmt inhibitors: Structure-activity relationships, kinetic analysis and cellular characterization
Human protein isoprenylcysteine carboxyl methyltransferase (hIcmt) is the enzyme responsible for the α-carboxyl methylation of the C-terminal isoprenylated cysteine of CaaX proteins, including Ras proteins. This specific posttranslational methylation event has been shown to be important for cellular transformation by oncogenic Ras isoforms. This finding led to interest in hIcmt inhibitors as potential anti-cancer agents. Previous analog studies based on N-acetyl-S-farnesylcysteine identified two prenylcysteine-based low micromolar inhibitors (1a and 1b) of hIcmt, each bearing a phenoxyphenyl amide modification. In this study, a focused library of analogs of 1a and 1b was synthesized and screened versus hIcmt, delineating structural features important for inhibition. Kinetic characterization of the most potent analogs 1a and 1b established that both inhibitors exhibited mixed-mode inhibition and that the competitive component predominated. Using the Cheng-Prusoff method, the K i values were determined from the IC50 values. Analog 1a has a KIC of 1.4 ± 0.2 μM and a KIU of 4.8 ± 0.5 μM while 1b has a KIC of 0.5 ± 0.07 μM and a KIU of 1.9 ± 0.2 μM. Cellular evaluation of 1b revealed that it alters the subcellular localization of GFP-KRas, and also inhibits both Ras activation and Erk phosphorylation in Jurkat cells.
Majmudar, Jaimeen D.,Hodges-Loaiza, Heather B.,Hahne, Kalub,Donelson, James L.,Song, Jiao,Shrestha, Liza,Harrison, Marietta L.,Hrycyna, Christine A.,Gibbs, Richard A.
experimental part
p. 283 - 295
(2012/02/17)

Diazaphospholane as an efficient ligand for copper-catalyzed cross-coupling of thiols with aryl iodides
Copper-catalyzed cross-coupling of thiols with aryl iodides performed well using an air-stable diazaphospholane ligand in presence of NaOH in DMF at 110 °C and a variety of diaryl sulfides are synthesized in good yields.
Yang, Minghua,Pei, Ji,Yan, Guobing,Zheng, Yunfa
experimental part
p. 587 - 591
(2012/05/31)

An efficient copper-catalyzed carbon-sulfur bond formation protocol in water
An efficient protocol of copper-catalyzed C-S bond formation between aryl halides and potassium thiocyanate leading to diaryl sulfides is reported. A variety of diaryl sulfides can be synthesized in good to excellent yields up to 94%.
Ke, Fang,Qu, Yanyang,Jiang, Zhaoqiong,Li, Zhengkai,Wu, Di,Zhou, Xiangge
supporting information; experimental part
p. 454 - 457
(2011/04/15)

Design, synthesis, enzyme inhibition, and tumor cell growth inhibition of 2-anilinobenzamide derivatives as SIRT1 inhibitors
A series of 2-anilinobenzamide derivatives were designed, synthesized and evaluated for their SIRT1-inhibitory activity. Among these, compounds 3 and 5 inhibited SIRT1 activity in enzyme assays and suppressed the growth of Daudi and HCT116 cells.
Suzuki, Takayoshi,Imai, Keiko,Imai, Erika,Iida, Shinsuke,Ueda, Ryuzo,Tsumoto, Hiroki,Nakagawa, Hidehiko,Miyata, Naoki
experimental part
p. 5900 - 5905
(2009/12/24)

Iron-catalyzed S-arylation of thiols with aryl iodides
(Chemical Equation Presented) Strike while the iron is hot: An efficient iron-catalyzed protocol for the S-arylation of aromatic and heteroaromatic thiol derivatives has been developed, which involves an inexpensive catalyst system formed by combining FeCl3 and N,N′-dimethylethylenediamine at 135°C. This method avoids the use of expensive and/or air-sensitive ligands and provides in most cases the desired sulfide in high yields.
Correa, Arkaitz,Carril, Monica,Bolm, Carsten
p. 2880 - 2883
(2008/12/23)

Regioselective copper-catalyzed C-N and C-S bond formation using amines, thiols and halobenzoic acids
A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu2O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81-99% yield. Georg Thieme Verlag Stuttgart.
Liu, Shuanglong,Pestano, John Paul C.,Wolf, Christian
p. 3519 - 3527
(2008/09/19)

PHARMACOLOGICAL MODULATORS OF VOLTAGE-GATED POTASSIUM ION CHANNELS
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(2008/06/13)

Trypanothione reductase inhibition/trypanocidal activity relationships in a 1,4-bis(3-aminopropyl)piperazine series
A series of symmetrically substituted 1,4-bis(3-aminopropyl)piperazines was synthesized and tested towards trypanothione reductase and for its in vitro trypanocidal potency. The most trypanocidal amongst them was found to be totally inactive towards the enzyme and thus constitutes a lead structure for the identification of new potential Trypanosoma cruzi target(s). (C) 2000 Elsevier Science Ltd.
Bonnet, B.Eatrice,Soullez, David,Girault, Sophie,Maes, Louis,Landry, Valerie,Davioud-Charvet, Elisabeth,Sergheraert, Christian
p. 95 - 103
(2007/10/03)

Aromatic pyrrolidine amide prolyl endopeptidase inhibitors
A series of aromatic pyrrolidine derivatives and suitable pharmaceutically acceptable salts thereof are disclosed. These compounds are useful as PEP inhibitors in the treatment of Alzheimer's disease, amnesia, dementia, anxiety ischemia, or stroke.
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(2008/06/13)

TRICYCLIC NEUROLEPTICS: SYNTHESIS OF METABOLITES OF ISOFLOXYTHEPIN AND SOME RELATED COMPOUNDS
The isofloxythepin(I) metabolite IV was synthesized via the acids IX and XI and the esters X and XII.The enamine VIII was prepared from 3-fluoro-8-(2-propyl)dibenzothiepin-10(11H)-one by two methods and was reduced to I.Cloflumide (II) was obtained by reaction of 2,10-dichloro-7-fluoro-10,11-dihydrodibenzothiepin with 3-(1-piperazinyl)propionamide and was oxidized to the sulfoxide XVI.The unsaturated analogue XVII of clopithepin (III) was prepared from 2-chlorodibenzothiepin-10(11H)-one by reaction with 2-bromoethanol in the presence of 4-toluenesulfonic acid in boiling benzene and by the following substitution reaction with 2-(1-piperazinyl)ethanol.An improved synthesis of 6-methyldibenzothiepin-10(11H)-one (XIX) was elaborated.The acid XXVII was synthesized and cyclized with polyphosphate ester.A mixture of compounds was formed from which the ketone XXXVI was isolated and processed by reaction with formamide and formic acid at 200 deg C.One of the products was characterized as the formamide XXXIII and was reduced with lithium aluminium hydride to a basic product supposed to be XXXIV.A series of by-products was isolated and characterized.The enamine VIII (VUFB-17156) was found to be a strong neuroleptic agent, similar to isofloxythepin (I).The enol ether XVII (VUFB-17733) was characterized as a mild, practically noncataleptic neuroleptic agent.
Sindelar, Karel,Jilek, Jiri,Pomykacek, Josef,Valenta, Vladimir,Hrubantova, Marta,et al.
p. 2282 - 2303
(2007/10/02)

Studies on hypolipidemic agents. IV. 3-[4-(phenylthio)benzoyl]propionic acid derivatives
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Kameo,Asami,Ogawa,Matsunaga,Saito,Tomisawa,Sota
p. 1260 - 1267
(2007/10/02)

REACTIONS OF BENZYNE WITH SULFIDES HAVING A CARBOXYL GROUP. A NOVEL SYNTHESIS OF ESTER AND LACTONE
Reactions of benzyne with o- and p-(alkylthio)benzoic acids afford alkyl o- and p-(phenylthio)benzoates in varied yields, while reaction with o-(phenylthio)methylbenzoic acid gives phtalide and diphenyl sulfide in good yields.
Nakayama, Juzo,Fujita, Toko,Hoshino, Masamatsu
p. 1777 - 1780
(2007/10/02)

ORTHO-LITHIATION OF PHENYLTHIOETHERS- AND SOME APPLICATIONS
A preparative procedure for the ortho-lithiation of phenylthioethers C6H5SR 1 is described.The preparations of 2-alkylthio-substituted benzoic acids 3, benzophenones 5 and phenylphosphines 6 were carried out in isolated yields of 38-73percent, depending on reaction and substituent.The procedure provides a simple route to dithiocatechol and trithiopyrogallol derivatives 7 and 8.The ring-lithiation step gives the best results for R=t-C4H9 (80-90percent) and R=i-C3H7 (70-80percent).R=C2H5 gave lower yields (ca.45percent), while R=CH3 gave principally lithiation at alkyl carbon.
Horner, L.,Lawson, A. J.,Simons, G.
p. 353 - 356
(2007/10/02)

Studies in Rearrangement of 2-(Arylthio)benzohydroxamic Acids to the Corresponding 2-(Arylsulphinyl)benzamides
2-(2'-Methoxyphenylthio)-(III)-, 2-(4'-methoxyphenylthio)-(IV)-, 2-(2'-methylphenylthio)-(V)- and 2-(4'-methylphenylthio)-(VI)-benzohydroxamic acids on treatment with polyphosphoric acid yield 2-(2'-methoxyphenylsulphinyl)-(VII)-, 2-(4'-methoxyphenylsulphinyl)-(VIII)-, 2-(2'-methylphenylsulphinyl)-(IX)- and 2-(4'-methylphenylsulphinyl)-(X)-benzamides respectively, illustrating the generality of rearrangement reported earlier .The rearrangement can also be effected with other reagents like xylene-P2O5, perchloric acid- gl. acetic acid and trifluoracetic acid. 2-Methylthiobenzohydroxamic acid (XI) and 4-(phenylthio)benzohydroxamic acid (XII) when treated with PPA yield benzothiazolone (XIII) and 4-aminodiphenyl sulphide (XIV).Experimental evidence has been presented which points to a concerted mechanism for the intramolecular oxygen transfer.
Dhareshwar, G. P.,Chhaya, P. N.,Hosangadi, B. D.
p. 831 - 835
(2007/10/02)