cas 42772-85-0, 2-(4-methylphenyl)sulfonyloxyethanol

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Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate
The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.
Ming, Xiao-Xia,Wu, Shuai,Tian, Ze-Yu,Song, Jia-Wei,Zhang, Cheng-Pan
supporting information
p. 6795 - 6800
(2021/09/08)

Discovery of a new class of PROTAC BRD4 degraders based on a dihydroquinazolinone derivative and lenalidomide/pomalidomide
BRD4 has emerged as an attractive target for anticancer therapy. However, BRD4 inhibitors treatment leads to BRD4 protein accumulation, together with the reversible nature of inhibitors binding to BRD4, which may limit the efficacy of BRD4 inhibitors. To address these problems, a protein degradation strategy based on the proteolysis targeting chimera (PROTAC) technology has been developed to target BRD4 recently. Herein, we present our design, synthesis and biological evaluation of a new class of PROTAC BRD4 degraders, which were based on a potent dihydroquinazolinone-based BRD4 inhibitor compound 6 and lenalidomide/pomalidomide as ligand for E3 ligase cereblon. Gratifyingly, several compounds showed excellent inhibitory activity against BRD4, and high anti-proliferative potency against human monocyte lymphoma cell line THP-1. Especially, compound 21 (BRD4 BD1, IC50 = 41.8 nM) achieved a submicromolar IC50 value of 0.81 μM in inhibiting the growth of THP-1 cell line, and was 4 times more potent than compound 6. Moreover, the mechanism study established that 21 could effectively induce the degradation of BRD4 protein and suppression of c-Myc. All of these results suggested that 21 was an efficacious BRD4 degrader for further investigation.
Zhang, Fangqing,Wu, Zhenwei,Chen, Pan,Zhang, Jian,Wang, Tao,Zhou, Jinpei,Zhang, Huibin
(2019/12/24)

NOVEL COMPOUND For Organic light emitting diode AND COATING COMPOSITION FOR ORGANIC LAYER COMPRISING THE SAME
Provided are a compound represented by chemical formula (1) and a coating liquid composition comprising the same. The above formula (1) is as described in the description of the invention.
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Paragraph 0137; 0138; 0139; 0140

(2020/12/29)

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study
A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.
Dong, Hai,Liu, Yu,Lv, Jian,Zhu, Jia-Jia
p. 3307 - 3319
(2020/03/25)

Pegylated triarylmethanes: Synthesis, antimicrobial activity, anti-proliferative behavior and in silico studies
We describe herein the synthesis, characterization and biological studies of novel PEGylated triarylmethanes. Non-symmetrical and symmetrical triarylmethanes series have been synthesized by Friedel-Crafts hydroxyalkylation or directly from bisacodyl respectively followed by a functionalization with PEG fragments in order to increase bioavailability and biological effectiveness. The antimicrobial activity was investigated against Gram-positive and Gram-negative foodborne pathogens and against Candida albicans, an opportunistic pathogenic yeast. The anti-biocidal activity was also studied using Staphylococcus aureus as a reference bacterium. Almost all PEGylated molecules displayed an antifungal activity comparable with fusidic acid with MIC values ranging from 6.25 to 50 μg/mL. Compounds also revealed a promising antibiofilm activity with biofilm eradication percentages values above 80% for the best molecules (compounds 4d and 7). Compounds 7 and 8b showed a modest antiproliferative activity against human colorectal cancer cell lines HT-29. Finally, in silico molecular docking studies revealed DHFR and DNA gyrase B as potential anti-bacterial targets and in silico predictions of ADME suggested adequate drug-likeness profiles for the synthetized triarylmethanes.
Abdmouleh, Fatma,Ali, Mamdouh Ben,Arbi, Mehdi El,Ferroud, Clotilde,Goya-Jorge, Elizabeth,Guenineche, Léna,Lagarde, Nathalie,Liagre, Bertrand,Martin, Frédérique,Ricco, Christophe,Riccobono, Charlotte,Veitía, Maité Sylla-Iyarreta
supporting information

(2020/01/31)

IRAK DEGRADERS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.
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Paragraph 00920; 001496-001497

(2021/01/23)

BIVALENT ANTAGONISTS OF INHIBITORS OF APOPTOSIS PROTEINS
The present technology is directed to compounds, compositions, and methods related to treatment of cancers and viral infections mediated by IAPs, e.g., compounds of Formula I (including Formulas IA, IB, IC, ID, IE, IF, and IG), a stereoisomer thereof, or
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Paragraph 0253

(2020/10/20)

Development of small-molecule BRD4 degraders based on pyrrolopyridone derivative
Bromodomain-containing protein 4 (BRD4) plays a crucial role in the epigenetic regulation of gene transcription and some BRD4 inhibitors have been advanced to clinical trials. Nevertheless, the clinical application of BRD4 inhibitors could be limited by drug resistance. As an alternative strategy, the emerging Proteolysis Targeting Chimeras (PROTACs) technology has the potential to overcome the drug resistance of traditional small-molecule drugs. Based on PROTACs approaches, several BRD4 degraders were developed and have been proved to degrade BRD4 protein and inhibit tumor growth. Herein, we present the design, synthesis, and biological evaluation of pyrrolopyridone derivative-based BRD4 degraders. Four synthesized compounds displayed comparative potence against BRD4 BD1 with IC50 at low nanomolar concentrations. Anti-proliferative activity of 32a against BxPC3 cell line (IC50 = 0.165 μM) was improved by about 7-fold as compared to the BRD4 inhibitor ABBV-075. Furthermore, degrader 32a potently induced the degradation of BRD4 and inhibited the expression of c-Myc in BxPC3 cell line in a time-dependent manner. The exploration of intracellular antitumor mechanism showed 32a induced cell cycle arrest and apoptosis effectively. All the results demonstrated that compound 32a could be considered as a potential BRD4 degrader for further investigation.
Chen, Pan,Wang, Lixun,Wang, Tao,Xu, Changliang,Zhang, Huibin,Zhang, Jian,Zheng, Peiyuan,Zhou, Jinpei,Zhu, Peiyu
(2020/04/30)

Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors
Series of diaryl-based pyrazole and triazole derivatives were designed and synthesized in a facile synthetic approach in order to produce selective COX-2 inhibitor. These series of derivatives were synthesized by different reactions like Vilsmeier-Haack reaction and click reaction. In vitro COX-1 and COX-2 inhibition studies showed that five compounds were potent and selective inhibitors of the COX-2 isozyme with IC50 values in 0.551-0.002 μM range. In the diarylpyrazole derivatives, compound 4b showed the best inhibitory activity against COX-2 with IC50 = 0.017 μM as one of the N-aromatic rings was substituted with sulfonamide and the other aromatic ring was unsubstituted. However, when the N-aromatic ring was substituted with sulfonamide and the other aromatic ring was substituted with sulfone (compound 4d), best COX-2 selectivity was achieved (IC50 = 0.098 μM, SI = 54.847). In the diaryltriazole derivatives, compound 15a showed the best inhibitory activity in comparison to all synthesized compounds including the reference celecoxib with IC50 = 0.002 μM and SI = 162.5 as it could better fit the extra hydrophobic pocket which is present in the COX-2 enzyme. Moreover, the docking study supports the obtained SAR data and binding similarities and differences on both isozymes.
Assali, Mohyeddin,Abualhasan, Murad,Sawaftah, Hadeel,Hawash, Mohammed,Mousa, Ahmed
(2020/04/20)

Novel derivatives of anaplastic lymphoma kinase inhibitors: Synthesis, radiolabeling, and preliminary biological studies of fluoroethyl analogues of crizotinib, alectinib, and ceritinib
Anaplastic lymphoma kinase (ALK), an oncogenic receptor tyrosine kinase, is a therapeutic target in various cancers, including non-small cell lung cancer. Although several ALK inhibitors, including crizotinib, ceritinib, and alectinib, are approved for cancer treatment, their long-term benefit is often limited by the cancer's acquisition of resistance owing to secondary point mutations in ALK. Importantly, some ALK inhibitors cannot cross the blood-brain barrier (BBB) and thus have little or no efficacy against brain metastases. The introduction of a lipophilic moiety, such as a fluoroethyl group may improve the drug's BBB penetration. Herein, we report the synthesis of fluoroethyl analogues of crizotinib 1, alectinib 4, and ceritinib 9, and their radiolabeling with 18F for pharmacokinetic studies. The fluoroethyl derivatives and their radioactive analogues were obtained in good yields with high purity and good molar activity. A cytotoxicity screen in ALK-expressing H2228 lung cancer cells showed that the analogues had up to nanomolar potency and the addition of the fluorinated moiety had minimal impact overall on the potency of the original drugs. Positron emission tomography in healthy mice showed that the analogues had enhanced BBB penetration, suggesting that they have therapeutic potential against central nervous system metastases.
Radaram, Bhasker,Pisaneschi, Federica,Rao, Yi,Yang, Ping,Piwnica-Worms, David,Alauddin, Mian M.
(2019/08/20)

Pyrrolopyridone double-functional molecule compound based on Cereblon ligand induced BET degradation
The invention relates to a novel pyrrolopyridone double-functional molecule, and pharmaceutically acceptable salts, hydrates, prodrug thereof, and a pharmaceutical composition taking the novel pyrrolopyridone double-functional molecule as an active component, and applications of the above compounds and the pharmaceutical composition in treatment or prevention of tumor, inflammation, and immunity diseases. The double-functional molecule is a proteolytic targeting chimera (PROTAC); the preparation method is mature; connecting arms are adopted to connect BET protein small molecular inhibitors andCereblon protein ligand in E3 ubiquitin ligase complex so as to obtain the double-functional molecule; the obtained compound is capable of realizing selective induction of BET protein degradation; and the tumor prevention effect is obvious.
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Paragraph 0097; 0100-0102

(2019/10/01)

Pyrrolopyridone bifunctional molecular compound based on VHL ligand-induced BET degradation
The invention relates to a novel kind of pyrrolopyridone bifunctional molecule and its pharmaceutically acceptable salt, hydrate and prodrug and a pharmaceutical composition using the compounds as active ingredients, and application in the preparation of these compounds and their pharmaceutical composition and in the treatment or prevention of tumors, inflammation, diseases related immunity, etc.The bifunctional molecule involved in the invention is a proteolytic targeting chimera (PROTAC). A small molecule inhibitor of BET protein and a Von Hippel-Lindau (VHL) protein ligand in E3 ubiquitinligase complex are linked by a connecting arm to obtain the bifunctional molecule. The obtained compound can selectively induce the degradation of BET protein, and has significant anti-tumor effect.
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Paragraph 0092; 0095-0097

(2019/08/30)

Discovery of a series of selective and cell permeable beta-secretase (BACE1) inhibitors by fragment linking with the assistance of STD-NMR
Two β-secreatase (BACE1) inhibitors from natural products (cinnamic acid and flavone) were linked to furnish potent, cell permeable BACE1 inhibitors with noncompetitive mode of inhibition, with the assistance of saturated transfer difference (STD)-NMR technique. Some of these conjugates also exhibited selective BACE1 inhibition over other aspartyl proteases such as BACE-2 and renin, as well as poor cytotoxicity. Taken together, conjugates 4 represent a new series of BACE inhibitors warrants further investigation for their potential in Alzheimier's disease therapy.
Fang, Wei-Shuo,Sun, De-yang,Yang, Shuang,Cheng, Chen,Moschke, Katrin,Li, Tianqi,Sun, Shanshan,Lichtenthaler, Stefan F.,Huang, Jian,Wang, Yinghong
supporting information

(2019/09/30)

Medicine conjugate and method for prolonging half-life of medicine molecule
The invention discloses a medicine conjugate and a method for prolonging half-life of a medicine molecule. The medicine conjugate is prepared through modifying the medicine molecule with a micromolecule combined with a half antigen, wherein the half antigen is the half antigen having an endogenous antibody. The half antigen molecule is modified on the medicine molecule, and the modified medicine molecule can be specifically combined with the endogenous antibody in accordance with the half antigen, so that the in vivo half-life of the medicine molecule can be notably prolonged.
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Paragraph 0091-0092; 0097

(2019/11/19)

Cereblon ligand mediated novel BET protein degradation bifunctional molecules, preparation and application thereof
The invention relates to a preparation method of new bifunctional small molecules and pharmaceutically acceptable salts, hydrates or prodrugs thereof, and application of the compounds and pharmaceutical compositions thereof in treatment of tumors, inflammation, immunity and other diseases. The bifunctional small molecules involved in the invention are protein degradation targeting chimeras (PROTACs), and can selectively induce BET protein degradation. According to the invention, a connecting arm is employed to connect a BET protein small molecule inhibitor and a cereblon protein ligand in theE3 ubiquitin ligase complex so as to obtain the bifunctional small molecules.
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Paragraph 0097-0099

(2018/04/02)

Synthesis and evaluation of novel F-18-labeled pyrimidine derivatives: Potential FAK inhibitors and PET imaging agents for cancer detection
Based on computer-assisted drug design, a series of novel pyrimidine derivatives was successfully synthesized and characterized by 1H NMR, 13C HNMR, and MS spectra. All the new compounds were evaluated for their activity against focal adhesion kinase and showed low IC50 values in comparison with control drugs. In particular, for compound 8i, its IC50 value was 0.060 μM, suggesting its advantage as a focal adhesion kinase inhibitor. To evaluate the potentiality of these compounds as PET imaging agents in cancer detection, compounds 8a, 8c, 8h, and 8i were successively labeled with 18F. The four 18F-labeled pyrimidine derivatives showed appropriate log P values and high stability in physiological saline and mouse plasma. Noticeably, compound [18F]-8a with a 4-methoxyl group at the benzene ring exhibited good in vivo biodistribution data in mice bearing the S180 tumor, which promoted a further microPET imaging study of compound [18F]-8a. The microPET image of [18F-8a] administered into the S180 tumor-bearing mice acquired at 60 min post-injection illustrated that the uptake in S180 tumor was obvious. These results suggested that compound [18F]-8a might be a new probe for PET tumor imaging.
Wang, Dawei,Fang, Yu,Wang, Hang,Xu, Xingyu,Liu, Jianping,Zhang, Huabei
p. 22388 - 22399
(2017/07/10)

Cereblon ligand-induced BET degradation-based bifunctional molecule and preparation and application thereof
The invention relates to a novel preparation method of a bifunctional molecule and a pharmaceutically acceptable salt, hydrate or prodrug thereof and application of these compounds and a medicinal composition thereof in treatment of diseases such as tumors, inflammation and immunity. The bifunctional molecule is a protein degradation-targeted complex (PROTACs), and is capable of selectively inducing BET protein degradation. A BET protein small-molecule inhibitor is connected with a cereblon protein ligand in an E3 ubiquitin ligase complex to obtain the bifunctional molecule.
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Paragraph 0069; 0070; 0071; 0072

(2017/09/02)

OXIDIZED LIPIDS AND METHODS OF USE THEREOF
The present invention is directed to oxidized lipids and pharmaceutical compositions comprising the same. The present invention is also directed to methods of making an oxidized lipid of the invention and to methods of treating or preventing fibrosis or i
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Page/Page column 56

(2016/06/14)

ALDOSTERONE SYNTHASE INHIBITOR
PROBLEM TO BE SOLVED: To provide a novel metomidate derivative compound having increased selectivity for CYP11B2 over CYP11B1. SOLUTION: This invention provides a compound represented by a predetermined general formula or salt thereof. COPYRIGHT: (C)2015,
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Paragraph 0016; 0082; 0083

(2018/12/01)

Novel fluoroalkyl derivatives of selective kappa opioid receptor antagonist JDTic: Design, synthesis, pharmacology and molecular modeling studies
Novel N-and O-fluoroalkyl derivatives of the highly potent KOR antagonist JDTic were designed and synthesized. Their opioid receptor properties were compared in both in vitro binding assays and modeling approach. All compounds displayed nanomolar affiniti
Schmitt, Sébastien,Colloc'H, Nathalie,Perrio, Cécile
p. 742 - 750
(2015/04/14)

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges
An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N'-trimethylethane-1,2-diamine or N,N,N'- trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs. 2014 Popr et al;.
Popr, Martin,Hybelbauerova, Simona,Jindrich, Jindrich
supporting information
p. 1390 - 1396
(2014/07/22)

Synthesis of Di-, Tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization
Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl-and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.
Davis, Owen A.,Bull, James A.
supporting information
p. 14230 - 14234
(2015/02/19)

Cyclization of gold acetylides: Synthesis of vinyl sulfonates via gold vinylidene complexes
Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β-carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold-catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross-coupling reactions, for example. Gold vinylidene intermediates are generated by the cyclization of gold acetylides that carry a sulfonate leaving group. This result demonstrates for the first time that the formation of these species is not restricted to a dual activation mode. The cyclization products obtained herein contain a vinyl sulfonate moiety, which makes them useful building blocks for cross-coupling reactions.
Bucher, Janina,Wurm, Thomas,Nalivela, Kumara Swamy,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information
p. 3854 - 3858
(2014/05/06)

Novel fluoroalkyl derivatives of selective kappa opioid receptor antagonist JDTic: Design, synthesis, pharmacology and molecular modeling studies
Novel N- and O-fluoroalkyl derivatives of the highly potent KOR antagonist JDTic were designed and synthesized. Their opioid receptor properties were compared in both in vitro binding assays and modeling approach. All compounds displayed nanomolar affinit
Schmitt, Sbastien,Colloc'h, Nathalie,Perrio, Ccile
p. 742 - 750
(2015/02/19)

Effects of alkyl substitution on the physical properties and gas transport behavior in selected poly(R-phenoxyphosphazenes)
A systematic preparation of alkyl substituted phenoxyphosphazene polymers was performed and their gas transport properties determined. In this study, phosphazenes substituted with 4-methylphenol, 4-ethylphenol, and 4-isopropylphenol are reported. An additional polymer substituted with 4-tert-butylphenoxy-1-ethanol also was synthesized in this work. Data derived for these materials, including chemical, thermal and gas transport characterization, were compared to previous reports discussing poly[bis-phenoxyphosphazene] and its analog with tert-butyl substitution: poly[bis-(4-tert-butylphenoxy)phosphazene]. The tert-butyl moiety influences orderly chain packing, presumably through steric hindrance that can influence aromatic π-stacking. For the new poly[(alkylphenoxy)phosphazenes], semicrystallinity is maintained and the added steric bulk serves to decrease the polymer glass transition temperature (Tg) and increase both permeability and selectivity for the gas pairs: O2/N2 and CO 2/CH4. Removal of the tert-butyl moiety from the immediate vicinity of the backbone through a flexible spacer serves to depress the Tg as compared to poly[bis-(4-tert-butylphenoxy)phosphazene], but provides no performance enhancement for gas transport.
Ogden, Mark D.,Orme, Christopher J.,Stewart, Frederick F.
experimental part
p. 3879 - 3886
(2012/04/23)

USE OF NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID, AND PROCESS FOR PRODUCTION OF THE SAME
The invention provides a reagent for detecting amyloid in a biological tissue which can be detect amyloid in vitro and in vivo with high sensitivity using a compound which has affinity with amyloid and is suppressed in toxicity such as mutagenicity. The reagent for detecting amyloid deposited in a biological tissue comprises a compound represented by the following formula (1) or a salt thereof: wherein A1, A2, A3 and A4 independently represents a carbon or nitrogen; R1 is a halogen substituent; R2 is a halogen substituent; and m is an integer or 0 to 2, provided that at least one of R1 and R2 is a radioactive halogen substituent, at least one of A1, A2, A3 and A4 represents a carbon, and R1 binds to a carbon represented by A1, A2, A3 and A4.
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(2010/08/22)

Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans
A stereoselective method for the synthesis of substituted tetrahydrofuran derivatives employing a tandem alkylation-Michael addition sequence to vinylogous carbonates is developed. The method could be used to synthesize THFs bearing tertiary ethers. Further, the method is extended to the synthesis of adjacent bis-THFs.
Gharpure, Santosh J.,Reddy, S. Raja Bhushan
scheme or table
p. 6093 - 6097
(2011/01/04)

BENZOXAZOLE DERIVATIVES
It is intended to provide a benzoxazole derivative or a pharmaceutically acceptable salt or solvate thereof which is useful in the early diagnosis of a conformation disease; a composition or a kit containing the same for diagnosing a conformation disease; a medical composition for ttreating and/or preventing a conformation disease; and so on.
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Page/Page column 50

(2009/10/01)

NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
The present invention provides a compound which has affinity with amyloid, shows sufficiently rapid clearance from normal tissues and is suppressed in toxicity such as mutagencity. Provided is a compound represented by the following formula (1) or a salt thereof: wherein A1, A2, A3 and A4 independently represents a carbon or nitrogen; R1 is a halogen substituent; R2 is a halogen substituent; and m is an integer of 0 to 2, provided that at least one of R1 and R2 is a radioactive halogen substituent, at least one of A1, A2, A3 and A4 represents a carbon, and R1 binds to a carbon represented by A1, A2, A3 or A4 as well as a low-toxic diagnostic agent comprising a compound represented by the preceding formula or a salt thereof.
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Page/Page column 13

(2009/02/10)

Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors
Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as α-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro α-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent α-glucosidase inhibitors.
Wu, Ya,Yang, Jing-Hua,Dai, Gui-Fu,Liu, Cong-Jun,Tian, Guo-Qiang,Ma, Wen-Yan,Tao, Jing-Chao
experimental part
p. 1464 - 1473
(2009/09/05)

SULFAMOYL-CONTAINING DERIVATIVES AND USES THEREOF
Sulfamoyl-containing compounds are disclosed, having utility as inhibitors of disease-related targets, such as Heat Shock Protein 90 (HSP90), and which are useful for treating disorders, e.g., proliferative disorders, including HSP90-mediated disorders. Methods for preparing and using the disclosed compounds are also described.
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Page/Page column 20

(2008/06/13)

2-ARYLPYRAZOLO[L,5-α]PYRIMIDIN-3-YL ACETAMIDE DERIVATIVES AS LIGANDS FOR TRANSLOCATOR PROTEIN (18 KDA)
The invention provides compounds of formula (I) radiolabelled with 18F, 123I, 76Br, 124I or75Br and salts thereof, and a method of imaging translocator protein (18kDa) (TSPO) in a subject comprising a
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Page/Page column 23

(2008/06/13)

Silver(I) oxide mediated highly selective monotosylation of symmetrical diols. Application to the synthesis of polysubstituted cyclic ethers
(Matrix Presented) The reaction of symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained on the basis of the difference in acidity between the two hydroxy groups, which undergo an intramolecular hydrogen bonding.
Bouzide, Abderrahim,Sauve, Gilles
p. 2329 - 2332
(2007/10/03)

Montmorillonite clay catalyzed tosylation of alcohols and selective monotosylation of diols with p-toluenesulfonic acid: An enviro-economic route
An enviro-economic route for tosylation of alcohols and selective monotosylation of diols in good yield directly using p-toluenesulfonic acid together with metal-exchanged montmorillonite instead of p-toluenesulfonyl chloride or p-toluenesulfonic anhydrid
Choudary, Boyapati M.,Chowdari, Naidu S.,Kantam, Mannepalli L.
p. 7291 - 7298
(2007/10/03)

SYNTHESIS OF MACROCYCLIC ACETALS CONTAINING LIPOPHILIC SUBSTITUENTS
A series of new mecrocyclic acetals all containing lipophilic substituents were prepared by reacting the appropriate diols and lipophilic acetal-containing dichlorides or ditosylates.The reactions using the ditosylates gave the best yields.Several of the macrocycles contained pyridine subcyclic units.The lipophilic acetals were obtained by reacting a chain aldehyde with 2-hydroxyethyl chloride or tosylate and 3-hydroxypropyl chloride od tosylate.At least two of the new pydridino ligands complexed with metal ions as shown by the use of these materials as carriers for silver nitrate through a water-methylene chloride-water bulk liquid membrane system.
Bradshaw, Jerald S.,Krakowiak, Krzysztof E.,LindH, Gypzy C.,Izatt, Reed M.
p. 4271 - 4276
(2007/10/02)

NUCLEOPHILIC CHARACTERISTICS OF NUCLEOFUGIC ANIONS IN THE CLEAVAGE OF EPOXIDES BY PROTIC ACIDS AND NITRONIUM FLUOROBORATE
The cleavage of ethylene, propylene, and cyclohexene oxides by protic acids RCOOH (R= CH3, CF3) in the presence of sources of nucleophilic anions (the lithium or tetrabutylammonium salts of perchloric or substituted sulfonic acids) leads to the formation not only of 2-hydroxyalkyl carboxylates but also of significant amounts of 2-hydroxyalkyl perchlorates and sulfonates.In the reactions of the same oxides with nitronium fluoroborate and the above-mentioned salts in methylene chloride 2-perchloryl- and 2-sulfonyloxyalkyl nitrates are formed with high yields; these are the products from opening of the epoxide ring and subsequent combination of the perchlorate and substituted sulfonate ions.The investigated processes extend the range of reactions involving the concurrent combination of nucleofugic anions and can be used as a method for the production of β-hydroxy- and β-nitroxyalkyl perchlorates and sulfonates.
Zefirov, N. S.,Kirin, V. N.,Yur'eva, N. M.,Zhdankin, V. V.,Kozmin, A. S.
p. 1264 - 1279
(2007/10/02)

Reaction of Carboxylic Acid Esters with p-Toluenesulfonic Acid
The reaction of carboxylic acid esters with an excess of p-toluenesulfonic acid gave the corresponding p-toluenesulfonates.The mechanism of the transesterification is discussed.
Nitta, Yoshihiro,Arakawa, Yasushi
p. 1380 - 1386
(2007/10/02)

Deacylation of Pyrrole and other Aromatic Ketones
Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate (1a) reacts rapidly with ethylene glycol in refluxing benzene with p-toluenesulfonic acid or perchloric acid as a catalyst to give ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3) in high yield (96 percent).Various 2- and 3-acylpyrroles can be efficiently deacylated by using this procedure.Other ketones which undergo deacylation include phenyl(2-phenylindol-3-yl)methanone (19), 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone (20), and 2,4-dimethoxybenzophenone.Certain pyrrole ketones where the acyl group is flanked by two ring methyl groups are also cleaved under acidic conditions by using ethanedithiol.
Moon, M. W.,Wade, R. A.
p. 2663 - 2669
(2007/10/02)

Synthesis and Ligand Properties of the 2,3,11,12-Tetraphenylcrown-6 Diastereomers
The synthesis and the assignment of the complete set of diastereomers 2a-e of 2,3,11,12-tetraphenylcrown-6 are described.The trans-anti-trans isomer 2d is identified by chiral interaction of optically active 1-phenylethylammonium hydrobromides with the racemic crown ether shown by NMR spectroscopy.Complex association constants of the new crown ethers with sodium, potassium, and ammonium picrates are discussed in terms of the geometry of the diastereomers.
Merz, Andreas,Eichner, Manfred,Tomahogh, Robert
p. 1774 - 1784
(2007/10/02)