cas 45438-73-1, THIOPHENE, 2-(BROMOMETHYL)-

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Identification of intermediates in the reaction of 2-thenyl halides with magnesium
The reaction of 2-thenyl chloride with magnesium was shown by the ESR method to proceed via the intermediate formation of radicals and radical ion pairs, whereas similar reactions of 2-thenyl bromide and iodide occur through the formation of free radicals only.
Egorov,Kuznetsova,Anisimov
p. 1544 - 1547
(2000)
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Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis
Herein we report a direct vicinal difunctionalization of thiophenes via the palladium/norbornene (Pd/NBE) cooperative catalysis. A series of mono- and disubstituted thiophenes can be difunctionalized site-selectively and regioselectively at the C4 and C5 positions in good yields, enabled by an arsine ligand and a unique amide-based NBE. The synthetic utility has been shown in derivatizations of complex bioactive compounds and an open-flask gram-scale preparation. Preliminary results have been obtained in the difunctionalization of furans and a direct C4-selective arylation of 2-substituted thiophenes.
Li, Renhe,Zhou, Yun,Xu, Xiaolong,Dong, Guangbin
p. 18958 - 18963
(2019)
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Optimization of interactions in crystal packing revealed by crystal structures [ethyl 2-(formylamino)-3-thien-2-yl-2-(thien-2-ylmethyl)propanoate and ethyl 3-(5-bromothien-2-yl)-2-[(5-bromothien-2-yl)methyl]-2-(formylamino) propanoate]
The title compounds, C15H14NO3S 2 (I) and C15H15Br2NO 3S2 (II), are derivatives of Aib (α-aminoisobutyric acid) with thiophene rings substituted at the Cα position. The Cα substitution causes the backbone to assume an extended conformation in the crystal structure. N-H and C-H donors share the thiophene ring π system for X-H?π interactions. The packings of the molecules are stabilized by intermolecular N-H?O, C-H?O, C-H?π and C-H?Br hydrogen bonds. Br?O interactions and a weak dihydrogen bond have also been observed in the crystal structure of II. The packing adopted by II has maximized the number of interactions that are possible.
Damodharan, Lakshminarasimhan,Pattabhi, Vasantha,Behera, Manoranjan,Kotha, Sambasivarao
p. 101 - 106
(2004)
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From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water
The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).
Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.
supporting information
p. 87 - 93
(2021/11/03)

Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors
(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is
Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.
supporting information
p. 9154 - 9162
(2021/11/16)

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.
Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
supporting information
p. 890 - 895
(2021/02/01)

MLKL INHIBITORS
Purine derivatives that inhibit cellular necroptosis and/or human MLKL, pharmaceutical compositions thereof, and methods of treating an MLKL-mediated disorder with an effective amount of the compound or composition. Said MLKL-mediated disorder is pathology associated necroptosis, including ischemia-reperfusion damage, neurodegeneration, and inflammatory diseases such as acute pancreatitis, multiple sclerosis, inflammatory bowel disease, and allergic colitis.
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Paragraph 0718-0719

(2018/09/26)

Aromatic heterocycle and alkyl side chain disubstituted benzenesulfonamide compound and application thereof to preparation of medicine for resisting influenza A virus
The invention discloses an aromatic heterocycle and alkyl side chain disubstituted benzenesulfonamide compound and application thereof to the preparation of a medicine for resisting influenza A virusand belongs to the technical field of medicine. The structure of the benzenesulfonamide compound is shown as a formula (I); a preparation method of the benzenesulfonamide compound comprises the following steps: generating a 3-((thiophene-2-ylmethyl)amino)propionitrile derivative with R1 and R2 substituent groups by a bromomethyl compound with the R1 substituent group and a methylamine compound with the R2 substituent group under the condition of sodium hydride and N,N-dimethylformamide; carrying out sulfonylation reaction on the 3-((thiophene-2-ylmethyl)amino)propionitrile derivative under thecondition of taking triethylamine as an acid binding agent and dichloromethane as a solvent, so as to generate the aromatic heterocycle and alkyl side chain disubstituted benzenesulfonamide compound.The benzenesulfonamide compound disclosed by the invention can be used for effectively inhibiting the replication of the influenza A virus, has small toxicity in cells and can be used for preparing the medicine for resisting the influenza A virus. (The formula (I) is shown in the description.).
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Paragraph 0037; 0038; 0039; 0040

(2018/07/07)

Synthesis and structure-activity relationship study of arylsulfonamides as novel potent H5N1 inhibitors
H5N1 virus, one subtype of highly pathogenic influenza A virus in human infection, has recently received attention due to its unpredictable and high mortality. In this study, a series of arylsulfonamide derivatives were identified as improved H5N1 inhibitors for the influenza treatment by systematic structure-activity relationship investigation. Among them, the most potent H5N1 inhibitor 3h exhibited excellent antiviral activity against H5N1 virus with EC50 value of 0.006 μM and selectivity index 33543.3. Moreover, the molecular docking of 3h with M2 proton channel protein provides practical way for understanding the inhibition of H5N1 with this kind of compounds.
Yu, Yongshi,Tang, Qi,Xu, Zhichao,Li, Siliang,Jin, Mengyu,Zhao, Zixuan,Dong, Chune,Wu, Shuwen,Zhou, Hai-Bing
p. 206 - 216
(2018/10/15)

Synthetic process of tiaprofenic acid
The invention relates to a synthetic process of tiaprofenic acid. The synthetic process comprises the following steps: adopting 2-thiotolene as a starting raw material, enabling 2-thiotolene to reactwith trimethylsilyl cyanide to synthesize 2-thiopheneacetonitrile by virtue of bromation, then enabling the 2-thiopheneacetonitrile to react with dimethyl carbonate to be methylated, hydrolyzing cyanogroups, and finally performing F-K reaction with benzoyl chloride, and preparing tiaprofenic acid. The synthetic process has the advantages that the conventional safe raw materials low in price are used for substituting the rare expensive and dangerous raw materials, so that the severe pollution problem is avoided, and the production cost is greatly decreased; and in addition, the process route adopted by the invention is simple, the reaction period is short, the reaction condition is stable, the yield is high and can reach more than 90 percent, the produce obtained after the reaction is highin purity, and the purity can reach more than 99 percent, so that the synthetic process is suitable for the industrialized production.
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Paragraph 0044; 0045

(2018/04/01)

COMPOUND HAVING ZNF143 INHIBITORY ACTIVITY AND USE THEREOF
PROBLEM TO BE SOLVED: To provide a compound having a ZNF143 inhibitory activity as well as to provide a ZNF143 inhibitory agent and pharmaceutical composition containing the same. SOLUTION: Provided is a compound represented by formula (I) or a salt thereof as well as a ZNF143 inhibitory agent containing the same and a pharmaceutical composition having the same as an active ingredient. A-B-C-D (I)[A is H, a methyl group, a naphthyl group, a phenyl group or a nitrogen-containing heterocyclic ring; B is as shown below, and C is an amide bond or a heteroaromatic ring containing N and O; D is a substituted/unsubstituted phenyl group or a monocyclic heteroaromatic ring containing N or S; and C and D are both fused heterocyclic ring or the like optionally having a substituent group.]. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0322

(2016/10/27)

Using functionalized nonlinear optical chromophores to prepare NLO-active polycarbonate films
Novel functionalized second order nonlinear optical (NLO) chromophores have been prepared with functionalized aniline as electron donor, thiophene or isophorone as a π-spacer and 1,3-diethyl-2-thiobarbituric acid as electron acceptor. The films prepared from dyes with alkylsilyl bulky groups gave better performance than the corresponding non functionalized chromophores due to the reduction of the intermolecular electrostatic interactions. The incorporation of chromophores 4 and 10 in a polycarbonate matrix allowed the preparation of good optical-quality films. Nonlinear coefficients d33 and d31 as high as 17 and 5.6 pm V-1, respectively, were obtained. Moreover, the temporal stability of these host-guest films was confirmed up to eight months (>80%).
González-Lainez,Jiménez-Ruiz,Martínez De Baroja,Garín,Orduna,Villacampa,Blesa
p. 30 - 40
(2015/04/14)

CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines
A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.
Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai
supporting information
p. 484 - 487
(2014/04/03)

SUBSTITUTED PYRIDINE DERIVATIVES AS FABI INHIBITORS
The present invention provides substituted pyridine derivatives of formula (I), which may be therapeutically useful as as anti-bacterial agents, more particulalrly FabI inhibitors. Formula(I) in which R1 to R5 and L have the meanings given in the specification, and pharmaceutically acceptable salts thereof that are useful in the treatment and prevention in diseases or disorder, in particular their use in diseases or disorder where there is an advantage anti-bacterial agents, more particularly FabI inhibitors. The present invention also provides methods for synthesizing and administering the FabI inhibitor compounds. The present invention also provides pharmaceutical formulations comprising at least one of the FabI inhibitor compounds together with a pharmaceutically acceptable carrier, diluent or excipient therefor.
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Page/Page column 37

(2013/06/27)

Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers
In the search for new ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified.
Otto, Nicola,Opatz, Till
supporting information; experimental part
p. 1105 - 1111
(2012/09/07)

COMPETITIVE INHIBITORS OF TYPE II DEHYDROQUINASE ENZYME
The present invention is directed to a compound of formula (I), its diastereoisomers, its enantiomers or its pharmaceutically acceptable salts or solvates, formula (I), to procedures of obtaining the same, to intermediates thereof, and use as competitive inhibitors of the third enzyme of the shikimic acid pathway, the type II dehydroquinase.
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Page/Page column 22-23

(2012/01/13)

Homobinuclear sulfato-bridged and mononuclear nitrato complexes of Cu(II) with thiophen-2-yl-dipicolylamine; Structure and anion-dependent absorption spectra
A new ligand, bispyridin-2-ylmethyl-thiophen-2-ylmethylamine, 2ThDPA (1), was synthesized and its complexes of Cu(II) were isolated. When Cu(NO 3)2 was used as the metal source, a mononuclear complex with the formula [Cu(1)(NO3)2], 2, was isolated featuring both nitro groups coordinated bidentate to the Cu. 2 crystallizes in the monoclinic P21/c space group with a = 14.848, b = 8.212, c = 32.752 ?, β = 102.52° and V = 3898.3 ?3. When CuSO4 was used as the metal source, a homobinuclear sulfato-bridged complex was isolated with the formula [Cu(1)SO4]2?CH 3CN, 3. 3 crystallizes in the monoclinic P21/n space group with a = 10.457, b = 17.035, c = 12.425 ?, β = 108.72° and V = 2096.17 ?3. The structures of 2 and 3 are shown to be stabilized by an extended system of π-π stacking and hydrogen-bonding interactions. Comparison of the electronic absorption spectra of the ligand and complexes shows that complexation is maintained in solution and that the ligand absorption is attenuated in the complexes, depending on the counter-anion utilized.
Zimmerman, Joshua R.,De Bettencourt-Dias, Ana
experimental part
p. 753 - 758
(2011/06/17)

Synthesis of benzyl bromides with hexabromoacetone: An alternative path to drug intermediates
A series of benzyl bromides were efficiently prepared from the corresponding alcohols with Br3CCOCBr3/PPh3 at low temperatures and under neutral conditions. The present protocol was applied to the heterocyclic analogues and to the successful synthesis of the precursor of the antiulcer drug omeprazole, thus furnishing an alternate, mild method for the preparation of these drug intermediates. A significant steric factor was observed throughout both series supporting a SN2 mechanism.
Joseph, Kara M.,Larraza-Sanchez, Isabel
experimental part
p. 13 - 16
(2011/02/25)

Synthesis and properties of novel t-type nonlinear optical polyurethane containing tricyanovinylthienyl group with enhanced thermal stability of dipole alignment
A novel T-type polyurethane 7 containing 1-(2,5-dioxyphenyl)-2-(5-(1,2,2- tricyanovinyl)-2-thienyl)ethenes as NLO chromophores, which constitute part of the polymer backbone, was prepared. Polyurethane 7 is soluble in common organic solvents such as DMF and DMSO. It shows a thermal stability up to 270 °C from TGA thermogram with Tg value obtained from DSC thermogram near 155 °C. The second harmonic generation (SHG) coefficient (d33) of poled polymer film at 1560 nm fundamental wavelength is 3.56 × 10-9 esu. Polymer 7 exhibits a thermal stability even at 5 °C higher than T g, and no significant SHG decay is observed below 160 °C, which is acceptable for nonlinear optical device applications.
Cho, You Jin,Kim, Mi Sung,Lee, Ju-Yeon
experimental part
p. 424 - 430
(2011/12/22)

Synthesis and nonlinear optical properties of novel T-type polyurethane containing tricyanovinylthiophene
A novel T-type polyurethane 7 containing 1-(2,5-dioxyphenyl)-2-{5-(1,2,2- tricyanovinyl)-2-thienyl}ethene groups as nonlinear optical (NLO) chromophores was prepared and characterized. Polyurethane 7 is soluble in common organic solvents such as DMF and DMSO. Polymer 7 shows a thermal stability up to 270°C from TGA thermogram and the Tg value obtained from DSC thermogram is around 155°C. The second harmonic generation (SHG) coefficient (d 33) of poled polymer film at 1560nm fundamental wavelength is 3.56 × 10-9esu. The dipole alignment exhibits a thermal stability even at 5°C higher than Tg, and there is no SHG decay below 160°C due to the partial main-chain character of the polymer structure, which is acceptable for nonlinear optical device applications. Copyright Taylor & Francis Group, LLC.
Cho, You Jin,Kim, Mi Sung,Lee, Ju-Yeon
scheme or table
p. 442 - 448
(2011/12/01)

Synthesis, structural characterization and catalytic activity of a palladium(II) complex bearing a new ditopic thiophene-N-heterocyclic carbene ligand
A new thiophene-functionalized benzimidazolium salt (2) has been prepared by reacting N-methylbenzimidazole with 2-bromomethylthiophene (1), which in turn was obtained by bromination of 2-thiophenemethanol with PBr3. Subsequent reaction of salt 2 with Pd(OAc)2 afforded the cis-configured bis(carbene) Pd(II) complex (cis-3), which in solution exists as an inseparable mixture of cis-anti and cis-syn-rotamers in a 3.5:1 ratio. All new compounds have been fully characterized by spectroscopic and spectrometric methods. A preliminary catalytic study shows that cis-3 is highly active in the Suzuki-Miyaura coupling of aryl bromides with phenylboronic acid in/on water as environmentally benign reaction media.
Huynh, Han Vinh,Chew, Ying Xia
experimental part
p. 1979 - 1983
(2011/01/07)

Synthesis and biological evaluation of new nanomolar competitive inhibitors of Helicobacter pylori type II dehydroquinase. Structural details of the role of the aromatic moieties with essential residues
The shikimic acid pathway is essential to many pathogens but absent in mammals. Enzymes in its pathway are therefore appropriate targets for the development of novel antibiotics. Dehydroquinase is the third enzyme of the pathway, catalyzing the reversible dehydratation of 3-dehydroquinic acid to form 3-dehydroshikimic acid. Here we present the synthesis of novel inhibitors with high affinity for Helicobacter pylori type II dehydroquinase and efficient inhibition characteristics. The structure of Helicobacter pylori type II dehydroquinase in complex with the most potent inhibitor shows that the aromatic functional group interacts with the catalytic Tyr22 by π-stacking, expelling the Arg17 side chain, which is essential for catalysis, from the active site. The structure therefore explains the favorable properties of the inhibitor and will aid in design of improved antibiotics.
Prazeres, Verónica F. V.,Tizón, Lorena,Otero, José M.,Guardado-Calvo, Pablo,Llamas-Saiz, Antonio L.,Van Raaij, Mark J.,Castedo, Luis,Lamb, Heather,Hawkins, Alastair R.,González-Bello, Concepción
experimental part
p. 191 - 200
(2010/05/19)

Electronic structural dependence of the photophysical properties of fluorescent heteroditopic ligands - Implications in designing molecular fluorescent indicators
Two fluorescent heteroditopic ligands (2a and 2b) for zinc ion were synthesized and studied. The efficiencies of two photophysical processes, intramolecular charge transfer (ICT) and photoinduced electron transfer (PET), determine the magnitudes of emission bathochromic shift and enhancement, respectively, when a heteroditopic ligand forms mono- or dizinc complexes. The electron-rich 2b is characterized by a high degree of ICT in the excited state with little propensity for PET, which is manifested in a large bathochromic shift of emission upon Zn2+ coordination without enhancement in fluorescence quantum yield. The electron-poor 2a displays the opposite photophysical consequence where Zn2+ binding results in greatly enhanced emission without significant spectral shift. The electronic structural effects on the relative efficiencies of ICT and PET in 2a and 2b as well as the impact of Zn2+-coordination are probed using experimental and computational approaches. This study reveals that the delicate balance between various photophysical pathways (e.g. ICT and PET) engineered in a heteroditopic ligand is sensitively dependent on the electronic structure of the ligand, i.e. whether the fluorophore is electron-rich or poor, whether it possesses a donor-acceptor type of structure, and where the metal binding occurs.
Younes, Ali H.,Zhang, Lu,Clark, Ronald J.,Davidson, Michael W.,Zhu, Lei
experimental part
p. 5431 - 5441
(2011/01/12)

Synthesis and nonlinear optical properties of a novel polyester containing tricyanovinylthienyl group
A novel T-type polyester (7) containing 1-(2,5-dioxyphenyl)-2-{5-(1,2,2- tricyanovinyl)-2-thienyl}ethene groups as NLO-chromophores was synthesized and characterized. Polymer 7 was soluble in common organic solvents such as DMF and DMSO. It showed thermal stability up to 300°C in TGA with Tg value obtained from DSC near 113°C. The second harmonic generation (SHG) coefficient (d33) of poled polymer film at the 1560nm fundamental wavelength was around 4.42×10-9esu. The dipole alignment exhibited a greater thermal stability even at 10C higher than Tg, and there was no SHG decay below 125°C due to the partial main-chain character of the polymer structure, which is acceptable for nonlinear optical device applications.
No, Hyo Jin,Lee, Ga-Young,Cho, You Jin,Lee, Ju-Yeon
scheme or table
p. 186 - 192
(2011/09/12)

Synthesis and nonlinear optical properties of novel T-type polyester containing thiophene with enhanced thermal stability
A novel T-type polyester 7 containing 1-(2,5-dioxyphenyl)-2-{5-(1,2,2- tricyanovinyl)-2-thienyl}ethenes as nonlinear optical (NLO) chromophores, which are part of the polymer backbone, was prepared and characterized. Polyester 7 is soluble in common organic solvents such as dimethylsulfoxide and N,N-dimethylformamide. It showed a thermal stability up to 300°oC in thermogravimetric analysis thermogram and the glass-transition temperature (Tg) obtained from differential scanning calorimetry thermogram was around 113 °C. The second harmonic generation (SHG) coefficient (d 33) of poled polymer films at 1,560 nm fundamental wavelength was around 1.85 pm/V. The dipole alignment exhibits a greater thermal stability even at 10 °C higher than Tg, and there is no SHG decay below 125 °C due to the partial mainchain character of the polymer structure, which is acceptable for nonlinear optical device applications.
No, Hyo Jin,Cho, You Jin,Lee, Ju-Yeon
experimental part
p. 429 - 434
(2010/08/19)

Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion
The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective α-glucosylation of a trichloroacetimidate donor; increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor.
Cox, Daniel J.,Fairbanks, Antony J.
experimental part
p. 773 - 780
(2009/09/30)

Design, parallel synthesis, and crystal structures of biphenyl antithrombotics as selective inhibitors of tissue factor FVIIa complex. Part 1: Exploration of S2 pocket pharmacophores
Factor VIIa (FVIIa), a serine protease enzyme, coupled with tissue factor (TF) plays an important role in a number of thrombosis-related disorders. Inhibition of TF·FVIIa occurs early in the coagulation cascade and might provide some safety advantages over other related enzymes. We report here a novel series of substituted biphenyl derivatives that are highly potent and selective TF·FVIIa inhibitors. Parallel synthesis coupled with structure-based drug design allowed us to explore the S2 pocket of the enzyme active site. A number of compounds with IC50 value of 10 nM were synthesized. The X-ray crystal structures of some of these compounds complexed with TF·FVIIa were determined and results were applied to design the next round of inhibitors. All the potent inhibitors were tested for inhibition against a panel of related enzymes and selectivity of 17,600 over thrombin, 450 over trypsin, 685 over FXa, and 76 over plasmin was achieved. Two groups, vinyl 36b and 2-furan 36ab, were identified as the optimum binding substituents on the phenyl ring in the S2 pocket. Compounds with these two substituents are the most potent compounds in this series with good selectivity over related serine proteases. These compounds will be further explored for structure-activity relationship.
Kotian, Pravin L.,Krishnan, Raman,Rowland, Scott,El-Kattan, Yahya,Saini, Surendra K.,Upshaw, Ramanda,Bantia, Shanta,Arnold, Shane,Sudhakar Babu,Chand, Pooran
experimental part
p. 3934 - 3958
(2009/10/02)

Synthesis and nonlinear optical properties of novel polyester containing tricyanovinylthiophene with enhanced thermal stability of second harmonic generation
A novel Y-type polyester (7) containing 1-(2,4-dioxyethoxy)phenyl-2-{5-(1, 2,2- tricyanovinyl)-2-thiophenyl)}ethenyl groups as NLO-chromophores was synthesized and characterized. Polymer 7 was soluble in common organic solvents such as DMF and DMSO. It showed thermal stability up to 300°C in TGA with Tg value obtained from DSC near 134°C. The second harmonic generation (SHG) coefficient (d33) of poled polymer film at the 1,560nm fundamental wavelength was around 6.74×10-9 esu. The dipole alignment exhibited high thermal stability and there was no SHG decay below Tg due to the partial main-chain character of polymer structure, which was acceptable for NLO device applications. Copyright Taylor & Francis Group, LLC.
Lee, Ga-Young,No, Hyo Jin,Lee, Ju-Yeon
scheme or table
p. 196 - 203
(2012/08/08)

Synthesis of novel Y-type nonlinear optical polyurethane containing tricyanovinylthiophene with high thermal stability of dipole alignment
A novel Y-type polyurethane 7 containing 1-(2,4-dioxyethoxy)phenyl-2-{5-(1, 2,2- tricyanovinyl)-2-thiophenyl)}ethenyl groups as nonlinear optical (NLO)- chromophores, which are components of the polymer backbones, was prepared. Polyurethane 7 is soluble in common organic solvents such as DMF and DMSO. It showed a thermal stability up to 280°C in TGA thermogram and the T g value obtained from DSC thermogram was around 163°C. The second harmonic generation (SHG) coefficient (d33) of poled polymer film at 1560nm fundamental wavelength was around 3.72×10-9 esu. The dipole alignment exhibited a thermal stability up to near Tg, and there was no SHG decay below 150°C due to the partial main-chain character of the polymer structure, which is acceptable for nonlinear optical device applications. Copyright Taylor & Francis Group, LLC.
Jang, Han-Na,No, Hyo Jin,Lee, Ju-Yeon
scheme or table
p. 204 - 211
(2012/08/08)

PIPERIDINONES USEFUL IN THE TREATMENT OF INFLAMMATION
There is provided compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, m and n have meanings given in the description, and pharmaceutically acceptable derivatives thereof, which compounds are useful in the treatment of diseases and conditions associated with inflammation.
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Page/Page column 112

(2008/12/07)

Integrase inhibitors
Tricyclic compounds, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.
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Page/Page column 32

(2008/06/13)

Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents
When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (e.g., ethoxycarbonylmethyltriphenylphosphonium bromide and n- butyltriphenylphosphonium bromide) form a ylid (when an α-carbonyl group is present) or lose a phenyl group to form alkyldiphenylphosphine oxides when treated with the base. Mechanistic investigation of the homocoupling reaction indicates that the reaction proceeds through a ylid that acts as a nucleophile on an unreacted phosphonium salt. The resulting adduct undergoes elimination to form the observed product. The EIZ ratio seems to depend on the amount of the base used and the phosphonium salt involved.
Ngwendson, Julius N.,Schultze, Cassandra M.,Bollinger, Jordan W.,Banerjee, Anamitro
p. 668 - 675
(2008/09/21)

Fluorescent dyes
Fluorescent dyes useful for detecting a target material in biological assays an electron donating moiety which is linked by a conjugated ?-electron bridge to an electron accepting moiety. The ?-electron bridge includes at least one carbocyclic ring structure or heterocyclic ring structure. The electron accepting moiety is a carboxylic acid, a salt of a carboxylic acid, or has the formula: wherein: X8 is selected from the group consisting of H, CH3, and (CH2)n6-Z2?, where Z2? is a monovalent anion; and n6 is an integer from 1 through 10; and Q3 is O or S.
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(2008/06/13)

Synthesis, structures, and optical and electrochemical characteristics of novel crown-containing polythiophene systems
The synthesis, structures, and optical and electrochemical characteristics of novel crown-containing styryl mono-and polythiophenes were described. The double bonds were constructed by the Horner-Wadsworth-Emmons method. The Suzuki and Stille cross-coupling reactions were used to create polythiophene chains. Optical measurements revealed intense absorption and fluorescence of crown-containing polythiophenes; the band positions and shapes in their absorption and emission spectra depend on the structure of the polythiophene. The electrochemical characteristics of the compounds obtained were measured.
Lukovskaya,Bobylyova,Fedorova,Fedorov,Anisimov,Didane,Brisset,Fages
p. 967 - 974
(2008/09/17)

A convenient synthesis of symmetric 1,2-diarylethenes from arylmethyl phosphonium salts
Symmetric ethenyldithiophenes are important intermediates for synthesis of photochromic materials and organic conductors. When acetonitrile is used as a solvent, 3-methylthiophenylphosphonium salts form symmetric ethenyldithiophenes in the presence of a strong base (e.g., NaH, tBuOK) in moderate to high yields. This homocoupling reaction is faster than a Wittig reaction with aromatic ketones in acetonitrile. Our study shows that the presence of polar aprotic solvents promotes the homocoupling reaction.
Ngwendson, Julius N.,Atemnkeng, Walters N.,Schultze, Cassandra M.,Banerjee, Anamitro
p. 4085 - 4088
(2007/10/03)

Direct halogenation of alcohols and their derivatives with tert-Butyl halides in the ionic liquid [pmIm]Br under sonication conditions - A novel, efficient and green methodology
A novel halogenating reagent system for direct halogenation of alcohols has been developed. tert-Butyl bromide, chloride and iodide in combination with the ionic liquid [pmIm]Br have been found to convert alcohols into the corresponding bromides, chlorides and iodides under sonication conditions (or heating) in good yields. Although a variety of primary and secondary alcohols participated in this reaction without any difficulty, tertiary alcohols remained inert. Several alcohol derivatives such as OTMS, OTBDMS, OAc, OTS and OTHP are also transformed into the corresponding halides in one-pot fashion by this procedure. A plausible rationale for this transformation is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Ranu, Brindaban C.,Jana, Ranjan
p. 755 - 758
(2007/10/03)

Stepwise unidirectional synthesis of oligo phenylene vinylenes with a series of monomers. Use in plastic solar cells
Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5- dipropoxyphenyl]vinyl}benzyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5- dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]vinyl}thiophene-2-ylmethyl) phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5- dipropoxyphenyl]vinyl}thiophene-2-ylmethyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5] thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.
Jorgensen, Mikkel,Krebs, Frederik C.
p. 6004 - 6017
(2007/10/03)

Amide substituted xanthine derivatives
The present invention is a 1,3,8 substituted xanthine derivative of formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2 and R3 are as defined in the specification. Compounds of formula I and pharmaceutically acceptable salts or prodrugs thereof show activity as modulators of gluconeogenesis.
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(2008/06/13)

4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity
The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.
De Dios, Alfonso,Prieto, Lourdes,Martín, Jose Alfredo,Rubio, Almudena,Ezquerra, Jesus,Tebbe, Mark,López De Uralde, Beatriz,Martín, Justina,Sánchez, Ana,LeTourneau, Deborah L.,McGee, James E.,Boylan, Carole,Parr Jr., Thomas R.,Smith, Michele C.
p. 4559 - 4570
(2007/10/03)

INDOLE CARBOXYLATE DERIVATIVES WHICH INHIBIT LEUKOTRIENE BIOSYNTHESIS
Compounds of the structure where A is straight or branched divalent alkylene or divalent cycloalkylene, R1 is selected from hydrogen; alkylthio; optionally substituted phenylthio; optionally substituted phenylalkylthio; optionally substituted 2-, 3-, and 4-pyridyl; optionally substituted 2-, and 3-thienylthio; and optionally substituted 2-thiazolythio, R2 is selected from -COOB; -COOalkyl; -COOalkyl(carbocyclic aryl); -CONR5R6 ; -COR6 ; and -OH, R3 is selected from phenylalkyl and heteroarylalkyl, and R4 is selected from optionally substituted alkoxy(carbocyclic aryl); optionally substituted carbocyclic aryloxy; optionally substituted heteroarylalkoxy; and optionally substituted heteroaryloxy are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states
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(2008/06/13)

A NOVEL AND EFFICIENT METHOD TO PREPARE 3-(HETERO)ARYL-1-PROPYNES AND ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF (2E,4E)-N-(2-METHYLPROPYL)-6-(2-METHYLPROPYL)-6-(2-THIENYL)-2,4-HEXADIENAMIDE, PIPEROVATINE AND (E)-N-(2-METHYLPROPYL)-6-(4-METHOXYPHENYL)-4-HEXYN-2-ENAMIDE
Chemically pure 3-(hetero)aryl-1-propynes, 13, have been prepared in high overall yields by a novel method which involves: (a) a copper(I)-mediated cross-coupling between a halomethyl(hetero)arene, 16, and trimethylsilylethylmagnesium bromide, 17, to give a trimethylsilyl-3-(hetero)aryl-1-propyne, 18; (b) removal of the trimethylsilyl group from 18 by treatment with potassium fluoride dihydrate in DMF.One of these 1-alkynes, i.e. 3-(2-thienyl)-1-propyne, 13a, has been employed in the key step of a highly stereoselective synthesis of naturally-occurring (2E,4E)-N-(2-methylpropyl)-6-(2-thienyl)-2,4-hexadienamide, 6.On the other hand, 3-(4-methoxyphenyl)-1-propyne, 13b, has been used either in two stereoselective syntheses of another natural N-(2-methylpropyl) amide, i.e. piperovatine, 7, or in the preparation of a structural analogue of 7, i.e. (E)-N-(2-methylpropyl)-6-(4-methoxyphenyl)-4-hexyn-2-enamide, 15.
Rossi, Renzo,Carpita, Adriano,Lippolis, Vito,Benetti, Massimo
p. 783 - 791
(2007/10/02)

4(3H)-quinazolinone derivatives and pharmaceutical compositions
4(3H)-Quinazolinone derivatives of formula (I) are provided. STR1 wherein R1 is a hydrogen atom, a C1 -C6 alkyl group, an aryl group, a substituted aryl group, or an aralkyl group; R2 is a C1 -C6 alkylamino group, a phenyl group, a substituted phenyl group, or a 5- or 6-membered heterocyclic group containing one or more N, O or S as a hetero atom or atoms, said heterocyclic group optionally being substituted or fused with a benzene ring; n is 1 or 2; or R2 represents a geranyl group or a dipyridylmethyl group together with the group --(CH2)n --; and X is a hydrogen atom, a C1 -C6 alkyl group or a halogen atom, and pharmaceutically acceptable acid addition salts thereof. They are useful as antiulcer agents.
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(2008/06/13)

Halogenation of benzyl- and (heteroaromatic methyl)cobaloximes: Direct competition between ring halogenation and cobalt-carbon bond cleavage
(4-Acetamidobenzyl)- and (4-(dimethylamino)benzyl)cobaloximes react rapidly with low concentrations of chlorine and bromine in acetic acid or chloroform at room temperature under nitrogen. Both ring-halogenated organometallic products and direct Co-C cleavage products are formed. However, (4-methoxybenzyl)cobaloxime forms 4-methoxy-2-halotoluene as the exclusive product. (3-Methylbenzyl)cobaloxime undergoes a substantial proportion of ring substitution by both Br2 and Cl2 in competition with the cleavage of the Co-C bond. (3-Methoxybenzyl)cobaloxime forms only the ring-substituted organometallic product. A remarkable difference in reactivity between 2- and 3-isomers of the (thienylmethyl)- and (furylmethyl)cobaloximes is observed; for example, Co-C cleavage is the primary process in furfuryl- and (2-thienylmethyl)cobaloximes whereas ring halogenation occurs much faster in the 3-isomer. The results are discussed in terms of a σ-π delocalization phenomenon by which the electronic effect of a substituent in the benzyl group is effectively transmitted to the Co-C bond reactivity. The substituent effect of the metallomethyl group -CH2Co(dmgH)2py is found to be more than that of the methoxy group. The mechanism of the Co-C cleavage is described.
Gupta,Kumar, Manoj,Roy, Sujit
p. 11 - 18
(2008/10/08)

Thermally Induced Rearrangement of Thiopheniobis(alkoxycarbonyl)methanides
Thiopheniobis(alkoxycarbonyl)methanides undergo intramolecular rearrangement when heated, to give 2H-thiopyrans as thermally unstable kinetic products.When the methanides are subjected to prolonged heating thiophene-2-malonates are produced as the major rearrangement products.A mechanism for these transformations is advanced in an attempt to rationalise the known reactivity of thiophene and its derivatives towards diazoalkanes.
Bowles, Timothy,Gillespie, Roger J.,Porter, Alexander E. A.,Rechka, Josef A.,Rzepa, Henry S.
p. 803 - 808
(2007/10/02)

HALOGENATION OF THENYL AND FURYL COBALOXIMES
The reactions of thenyl and furyl cobaloximes with halogens (bromine and chlorine) in acetic acid and chloroform indicate that, Co-C bond cleavage occurs in 2-thenyl and 2-furyl case whereas the ring substitution is faster than Co-C bond cleavage in 3-thenyl and 3-furyl cobaloximes.
Gupta, B.D.,Roy, S.
p. 3255 - 3256
(2007/10/02)