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Anticancer activity of triazolo-thiadiazole derivatives and inhibition of akt1 and akt2 activation
The fusion of 1,2,4-triazole and 1,3,4-thiadiazole rings results in a class of heterocycles compounds with an extensive range of pharmacological properties. A series of 1,2,4-triazolo[3,4-b]-1,2,4-thiadiazoles was synthesized and tested for its enzyme inhibition potential and anticancer activity. The results show that 1,2,4-triazolo[3,4-b]-1,2,4-thiadiazoles display potent anticancer properties in vitro against a panel of cancer cells and in vivo efficacy in HT-29 human colon tumor xenograft in CB17 severe combined immunodeficient (SCID) mice. Preliminary mechanistic studies revealed that KA25 and KA39 exhibit time-and concentration-dependent inhibition of Akt Ser-473 phosphorylation. Molecular modeling experiments indicated that 1,2,4-triazolo[3,4-b]-1,2,4-thiadiazoles bind well to the ATP binding site in Akt1 and Akt2. The low acute toxicity combined with in vitro and in vivo anticancer activity render triazolo[3,4-b]thiadiazoles KA25, KA26, and KA39 promising cancer therapeutic agents.
Trafalis, Dimitrios T.,Sagredou, Sofia,Dalezis, Panayiotis,Voura, Maria,Fountoulaki, Stella,Nikoleousakos, Nikolaos,Almpanakis, Konstantinos,Deligiorgi, Maria V.,Sarli, Vasiliki
(2021/04/27)

DOPAMINE RECEPTOR D1 AGONISTS AND METHODS OF USE
Described herein are small molecule agonists of dopamine receptor D1 that inhibit YAP/TAZ, compositions, and methods of using these compounds and compositions.
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Paragraph 00212

(2021/02/05)

Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides
An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.
Coles, Simon J.,Hareram, Mishra Deepak,Harnedy, James,Morrill, Louis C.,Tizzard, Graham J.
supporting information
p. 12643 - 12646
(2021/12/07)

Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
supporting information
p. 15593 - 15598
(2021/10/12)

3,6-disubstituted 1,2,4-triazolo[3,4-b] thiadiazoles with anticancer activity targeting topoisomerase II alpha
Background: Topoisomerase IIα (topIIα) maintains the topology of DNA in order to ensure the proper functioning of numerous DNA processes. Inhibition of topIIα leads to the killing of cancer cells thus constituting such inhibitors as useful tools in cancer therapeutics. Triazolo[3,4-b]thiadiazole derivatives are known for their wide range of pharmacological activities while previous studies have documented their in vitro anticancer activity. The purpose of the current study was to investigate if these chemical compounds can act as topIIα inhibitors in cell-free and cell-based systems. Materials and Methods: The MTT assay was performed in DLD-1, HT-29, and LoVo cancer cells so as to evaluate the antiproliferative activity of KA25, KA26, and KA39 triazolo[3,4-b]thiadiazole derivatives. The KA39 compound was tested as a potential topIIα inhibitor using the plasmid-based topoisomerase II drug screening kit. The inhibitory effect of the three derivatives on topIIα phosphorylation was studied in HT-29 and LoVo cancer cells according to Human Phospho-TOP2A/Topoisomerase II Alpha Cell-Based Phosphorylation ELISA Kit. Moreover, flow cytometry was utilized in order to explore apoptotic induction and cell cycle growth arrest, upon treatment with KA39, in DLD-1 and HT-29 cells, respectively. In silico studies were also carried out for further investigation. Results: All three triazolo[3,4-b]thiadiazole derivatives showed an in vitro antiproliferative effect with the KA39 compound being the most potent one. Our results indicated that KA39 induced both early and late apoptosis as well as cell cycle growth arrest in S phase. In addition, the compound blocked the relaxation of supercoiled DNA while it also inhibited topIIα phosphorylation (upon treatment; P0.001). Conclusion: Among the three triazolo[3,4-b]thiadiazole derivatives, KA39 was shown to be the most potent anticancer agent and catalytic inhibitor of topIIα phosphorylation as well.
Almpanakis, Konstantinos,Dalezis, Panagiotis,Nikolaou, Michail,Nikoleousakos, Nikolaos,Panayiotidis, Mihalis I.,Sagredou, Sofia,Sarli, Vasiliki,Trafalis, Dimitrios T.,Voura, Maria
p. 7369 - 7386
(2020/08/05)

Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.
da Silva, Amanda F.,Afonso, Marco A. S.,Cormanich, Rodrigo A.,Jurberg, Igor D.
supporting information
p. 5648 - 5653
(2020/04/22)

1 - (2, 2 - Difluorobenzene and [d] [1, 3] dioxo heterocyclic pentene - 5 - yl) cyclopropanecarboxylic acid synthetic method and intermediate
The invention belongs to the field of chemical synthesis of drugs, particularly relates to a synthetic method of 1-(2,2-difluoro-benzo[d][1,3]) dioxole-5-yl) cyclopropanecarboxylic acid and an intermediate and aims to provide a synthesis method of a compound (1). The method comprises steps as follows: a, a compound (4) and boron tribromide react, and a compound (3) is synthesized; b, the compound (3) and difluorodibromomethane have a ring closing reaction in the presence of a phase-transfer catalyst, and a compound (2) is synthesized; c, the compound (2) is hydrolyzed, and the compound (1) is synthesized. According to the synthetic method and the intermediate, one novel compound (4) is provided, one novel preparation method of the compound (1) is obtained, with the adoption of the method, not only can the overall yield of the reaction be increased, but also expensive reaction raw materials can be avoided, and the reaction cost is reduced to the great extent; besides, according to the method, utilization of a palladium catalyst and a dangerous sodium cyanide reagent can further be avoided, the safety of pharmaceutical production is guaranteed, and the method is applicable to industrial production.
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Paragraph 0068-0070

(2018/04/02)

Synthesis of Benzo[a]carbazoles and an Indolo[2,3-a]carbazole from 3-Aryltetramic Acids
A simple and flexible approach to 3-pyrrolin-2-one fused carbazoles is disclosed. The key step involves the BF3-mediated electrophilic substitution of indoles with N-alkyl-substituted 3-aryltetramic acids, which provides access to indole-substituted 3-pyrrolin-2-ones. Scholl-type oxidative cyclizations of these materials led to the formation of the corresponding 3-pyrrolin-2-one-fused benzo[a]carbazoles and indolo[2,3-a]carbazoles. This work represents the first synthesis of the benzo[a]pyrrolo[3,4-c]carbazol-3(8H)-one ring system, while the indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one ring system is found in a number of biologically active compounds including the protein kinase C (PKC) inhibitor, staurosporine.
Truax, Nathanyal J.,Banales Mejia, Fernando,Kwansare, Deborah O.,Lafferty, Megan M.,Kean, Maeve H.,Pelkey, Erin T.
p. 6808 - 6815
(2016/08/16)

Development of a simple system for the oxidation of electron-rich diazo compounds to ketones
Mild heating of diazo compounds in DMSO furnishes ketone products in moderate to excellent yields. The reaction is particularly effective on electron-rich substrates and exhibits high chemoselectivity, allowing for the use of diazo compounds containing additional oxidation-prone functional groups. This straightforward protocol offers an alternate route to synthetically useful α-ketoesters from readily available aryl diazoacetates.
O'Connor, Nicholas R.,Bolgar, Peter,Stoltz, Brian M.
supporting information
p. 849 - 851
(2016/02/05)

Higher-order cyclopropenimine superbases: Direct neutral br?nsted base catalyzed michael reactions with α-aryl esters
The synthesis and characterization of six new classes of higher-order superbases, including five that incorporate cyclopropenimine functionality, has been achieved. We propose a nomenclature that designates these as the CG2, GC2, PC3, PC1, C3, and GP2 classes of superbases. The pKBH+ values were measured to be between 29.0 and 35.6 in acetonitrile. Linear correlations of ten superbase basicities vs that of their substituents demonstrated the insulating effect of the cyclopropenimine core. The molecular structures of several of these materials were obtained by single-crystal X-ray analysis, revealing interesting aspects of conformational bias and noncovalent organization. The types of superbasic cores and substituents were each reliably shown to affect selectivity for deprotonation over alkylation. Higher-order cyclopropenimine and guanidine superbase stability to hydrolysis was found to correlate to basicity. Finally, a GC2 base was found to catalyze conjugate additions of α-aryl ester pronucleophiles, representing the first report of a neutral Br?nsted base to catalyze such reactions.
Nacsa, Eric D.,Lambert, Tristan H.
supporting information
p. 10246 - 10253
(2015/09/01)

NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
The present invention relates to a novel compound inhibiting Hsp 90 and to a pharmaceutical composition including same as an active ingredient. Compounds of formula 1 and formula 2 according to the present invention inhibit the accumulation of HIF-1α protein, which is an Hsp90 client protein, by suppressing Hsp90 expression, and effectively inhibit the activity of vascular endothelial growth factor (VEGF). Furthermore, said compounds have low cytotoxicity and can thus be used as an active ingredient for the treatment of diabetic retinopathy and arthritis.
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Paragraph 0063-0064

(2015/05/26)

NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
The present invention relates to a compound inhibiting Hsp90 and a pharmaceutical composition comprising the same as an active ingredient. The compounds represented by formula 1 and formula 2 of the present invention suppress the expression of Hsp90 so that they can inhibit the accumulation of HIF-1α, the Hsp90 client protein, and also efficiently inhibit the activation of VEGF. In addition, these compounds display low cytotoxicity, so that they can be effectively used as an active ingredient of an anti-cancer agent, a diabetic retinopathy treating agent, and an anti-arthritic agent.
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Paragraph 0160-0162

(2015/07/15)

Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.
Das, Braja Gopal,Nallagonda, Rajender,Dey, Dhananjay,Ghorai, Prasanta
supporting information
p. 12601 - 12605
(2015/09/01)

Efficient microwave-assisted esterification reaction employing methanesulfonic acid supported on alumina as catalyst
A rapid and efficient protocol assisted by microwave irradiation for the synthesis of esters using methanesulfonic acid (CH3SO3H) supported on Al2O3 (AMA) as catalyst and free of solvent is described. The products were obtained in good yields and purity, with reduced reaction time, and the process is simple and environmentally benign. Copyright
Fabian, Lucas,Gomez, Matias,Kuran, Juan A. Caturelli,Moltrasio, Graciela,Moglioni, Albertina
p. 2386 - 2392
(2014/07/22)

Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1
To find novel compounds against H5N1, three series of known or novel small molecular polyphenols were synthesized and tested in vitro for anti-H5N1 activity. In addition, the preliminary structure-antiviral activity relationships were elaborated. The results showed that some small molecular polyphenols had better anti-H5N1 activity, and could serve as novel virus entry inhibitors against H 5N1, likely targeting to HA2 protein. Noticeably, compound 4a showed the strongest activity against H5N1 among these compounds, and the molecular modeling analysis also suggested that this compound might target to HA2 protein. Therefore, compound 4a is well qualified to serve as a lead compound or scaffold for the further development of H 5N1 entry inhibitor.
Yang, Jian,Yang, Jing Xiang,Zhang, Fang,Chen, Gang,Pan, Wei,Yu, Rui,Wu, Shuwen,Tien, Po
p. 2680 - 2684
(2014/06/09)

Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids
Oxa-Pictet-Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g]chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps.
Kapadia, Nirav,Harding, Wayne
p. 8914 - 8920
(2013/09/23)

Sequential C-H functionalization reactions for the enantioselective synthesis of highly functionalized 2,3-dihydrobenzofurans
The enantioselective synthesis of 2,3-dihydrobenzofurans was achieved by using two sequential C-H functionalization reactions, a rhodium-catalyzed enantioselective intermolecular C-H insertion followed by a palladium-catalyzed C-H activation/C-O cyclization. Further diversification of the 2,3-dihydrobenzofuran structures was possible by a subsequent palladium-catalyzed intermolecular Heck-type sp2 C-H functionalization.
Wang, Hengbin,Li, Gang,Engle, Keary M.,Yu, Jin-Quan,Davies, Huw M. L.
supporting information
p. 6774 - 6777
(2013/06/05)

SUBSTITUTED 6,7-DIALKOXY-3-ISOQUINOLINOL DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE10A)
The invention relates to compounds of the formula wherein R′, R1, through R7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.
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(2012/09/05)

Design, synthesis, and biological evaluation of novel deguelin-based heat shock protein 90 (HSP90) inhibitors targeting proliferation and angiogenesis
Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers. Our initial studies confirmed that deguelin disrupts ATP binding to HSP90 and consequently induces destabilization of its client proteins such as HIF-1α. Interestingly, a fluorescence probe assay revealed that deguelin and its analogues do not compete with ATP binding to the N-terminus of HSP90, unlike most HSP90 inhibitors. To determine the key parts of deguelin that contribute to its potent HSP90 inhibition, as well as its antiproliferative and antiangiogenic activities, we have established a structure-activity relationship (SAR) of deguelin. In the course of these studies, we identified a series of novel and potent HSP90 inhibitors. In particular, analogues 54 and 69, the B- and C-ring-truncated compounds, exhibited excellent antiproliferative activities with IC50 of 140 and 490 nM in the H1299 cell line, respectively, and antiangiogenic activities in zebrafish embryos in a dose dependent manner (0.25-1.25 μM).
Chang, Dong-Jo,An, Hongchan,Kim, Kyoung-Suk,Kim, Hyun Ho,Jung, Jinkyung,Lee, Jung Min,Kim, Nam-Jung,Han, Young Taek,Yun, Hwayoung,Lee, Sujin,Lee, Geumwoo,Lee, Seungbeom,Lee, Ju Sung,Cha, Jong-Ho,Park, Ji-Hyeon,Park, Ji Won,Lee, Su-Chan,Kim, Sang Geon,Kim, Jeong Hun,Lee, Ho-Young,Kim, Kyu-Won,Suh, Young-Ger
p. 10863 - 10884
(2013/03/13)

CYCLOPROPYL DERIVATIVES AND METHODS OF USE
The disclosure relates to cyclopropyl derivatives and methods of use. In some embodiments, the disclosure relates to methods of managing medical disorders with pharmaceutical compositions disclosed herein administered to subject in need thereof. In certain embodiments, the disclosure relates to methods of managing mental disorders, mood disorders, pain, and fibromyalgia and related conditions with pharmaceutical compositions disclosed herein.
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Page/Page column 31-32

(2012/11/07)

Microwave-assisted synthesis of 5-substituted 2-aminothiophenes starting from arylacetaldehydes
An easy three-step pathway for the synthesis of arylacet-aldehydes from the corresponding carboxylic acids in very high yields is described. Their use as precursors of 5-substituted-2-aminothiophenes is illustrated via a microwave-assisted Gewald reaction. This method allows obtaining the expected compounds in a shorter time and with better yields and purities than the classical procedures. Georg Thieme Verlag Stuttgart - New York.
Revelant, Germain,Dunand, Sandrine,Hesse, Stephanie,Kirsch, Gilbert
experimental part
p. 2935 - 2940
(2011/11/01)

New PDE4 inhibitors based on pharmacophoric similarity between papaverine and tofisopam
Pharmacophoric comparison between papaverine and tofisopam led to identify three new series of microto sub-micromolar inhibitors of phosphodiesterase-4, including 7,8-dialkoxy-2,3-benzodiazepin-4-one derivatives, 7,8-dialkoxy-1,4- benzodiazepin-2-one derivatives, and dialkoxybenzophenone derivatives.
Bihel, Frédéric J.J.,Justiniano, Héléne,Schmitt, Martine,Hellal, Malik,Ibrahim, Mohamed A.,Lugnier, Claire,Bourguignon, Jean-Jacques
scheme or table
p. 6567 - 6572
(2011/12/04)

Conjugate addition - Dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: Application to the total synthesis of (±)-yohimbenone
A highly efficient total synthesis of (±)-yohimbenone and a formal synthesis of (±)-emetine is described. The key element of the synthesis consists of a conjugate addition-dipolar cycloaddition of 2,3- bis(phenylsulfonyl)-l,3-butadiene with an appropriate oxime. The resulting cycloadducts are cleaved reductively to provide azapolycyclic scaffolds with strategically placed functionality for further manipulation to the target compounds.
Stearman, Chad J.,Wilson, Michael,Padwa, Albert
experimental part
p. 3491 - 3499
(2009/09/08)

Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding
The synthesis of a series of berberine, phenantridine and isoquinoline derivatives was realized to explore their Rho GTPase nucleotide inhibitory activity. The compounds were evaluated in a nucleotide binding competition assay against Rac1, Rac1b, Cdc42 and in a cellular Rac GTPase activation assay. The insertion of 19 AA in the splice variant Rac1b is shown to be sufficient to introduce a conformational difference that allows compounds 4, 21, 22, and 26 to exhibit selective inhibition of Rac 1b over Rac1.
Beausoleil, Eric,Chauvignac, Cedric,Taverne, Thierry,Lacombe, Sandrine,Pognante, Laure,Leblond, Bertrand,Pallares, Diego,Oliveira, Catherine De,Bachelot, Florence,Carton, Rachel,Peillon, Helene,Coutadeur, Severine,Picard, Virginie,Lambeng, Nathalie,Desire, Laurent,Schweighoffer, Fabien
scheme or table
p. 5594 - 5598
(2010/04/05)

Light-Emitting Biomarker
The invention concerns novel 1,2-dioxetane derivatives of general formula (I) as defined in the description, capable of emitting a detectable luminescent signal, their use in a method for detecting and/or quantizing a physical, chemical or biological, in particular enzymatic, phenomenon, as well as a kit for implementing said method.
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(2009/03/07)

Oxoammonium salt/NaClO2: An expedient, catalytic system for one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability
A facile, green, one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability has been developed by employing an expedient catalytic system consisting of 1-Me-AZADO+X-/NaClO 2. The Royal Society of Chemistry.
Shibuya, Masatoshi,Sato, Takahisa,Tomizawa, Masaki,Iwabuchi, Yoshiharu
supporting information; experimental part
p. 1739 - 1741
(2009/08/08)

Formation and ring contraction of benzo[f][1,2]thiazepine-1,1-dioxides from and to benzo[e][1,2]thiazine-1,1-dioxides
Alkoxide-promoted ring expansion of the novel ethyl 2-(6,7-dimethoxy-3-oxo- 3,4-dihydrobenzo[e][1,2]thiazine-1,1-dioxide-2-yl)acetate 3a and analogous 4,4-diethyl derivative 3b and cyclization of methyl 2-[2- (phenylaminocarbonylmethyl sulfamoyl)-4,5-dimethoxyphenyl] acetate 9 to the corresponding new 3-carboxylates and 3-carboxanilide of 7,8-dimethoxy-4-hydroxy- 2,5-dihydrobenzo[f][1,2]thiazepine-1,1-dioxide (5a,b and 10 respectively) is described. Compound 5a was deacylated upon treatment with sodium hydroxide followed by hydrochloric acid to give 7,8-dimethoxy-2,3-dihydrobenzo[f][1,2] thiazepine-1,1-dioxide-4 (5H)-one 8 and its N-ethyl derivative transferred to 6,7-dimethoxy-2-ethyl-3-oxo-3,4-dihydrobenzo[e][1,2]thiazine-1,1-dioxide 7 by the reaction with ethyl methyl ketone in the presence of pyrrolidine. Copyright Taylor & Francis Group, LLC.
Khalaj, Ali,Adibpour, Neda
p. 3662 - 3671
(2008/12/23)

Intramolecular versus intermolecular oxidative couplings of ester tethered di-aryl ethers
The oxidative cyclization of 3,4-dimethoxyphenyl 3,4-dimethoxyphenylacetate, through intramolecular biphenyl bond formation, was successful and gave the target seven-membered lactone in good yield (85-86%). All other ester substrates gave biphenyl products or their further oxidized products via intermolecular coupling of their radical cation intermediate with the neutral substrate. It appears that matching of the oxidation potentials and nucleophilicity of the two phenyl rings, the positioning of the ring substituents and the ease of E to Z isomerization about the ester C-O bond are important factors contributing to these product outcomes. Crown Copyright
Taylor, Stephen R.,Ung, Alison T.,Pyne, Stephen G.,Skelton, Brian W.,White, Allan H.
p. 11377 - 11385
(2008/03/13)

Substituted 3-cyanopyridines as protein kinase inhibitors
The present teachings provide compounds of formula I and their pharmaceutically acceptable salts, hydrates, and esters, wherein R1, R2, and X are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating autoimmune and inflammatory diseases by administering a therapeutically effective amount of a compound or compounds of formula I to a mammal including a human.
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Page/Page column 28

(2008/06/13)

Substituted Cyanopyridines as protein kinase inhibitors
The present teachings provide compounds of formula I and their pharmaceutically acceptable salts, hydrates, and esters, wherein R1, R2, and X are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating autoimmune and inflammatory diseases by administering a therapeutically effective amount of a compound or compounds of formula I to a mammal including a human.
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Page/Page column 17

(2008/06/13)

The synthesis of 2′,2′-bis-benzylisoquinolines and their cytostatic activities
The novel laudanosine dimers in which two laudanosine units are linked via a C-2′ biaryl bond have been prepared by a sequence that involves formation of the biaryl bond first and then formation of the isoquinoline rings. Two of these compounds showed higher cytostatic activity on three cancer cell lines than thalicarpine. Crown Copyright
Taylor, Stephen R.,Ung, Alison T.,Pyne, Stephen G.
p. 10896 - 10901
(2008/03/17)

2, 6 BISHETEROARYL-4-AMINOPYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
4-Aminopyrimidine derivatives of formula (I) FORMULA heteroaryl groups, including pharmaceutically acceptable salts thereof, wherein R1 and R2 are adenosine A2A receptor antagonists useful in the treatment of movement disorders such as Parkinson's disease.
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Page/Page column 133

(2010/02/12)

A highly convenient, efficient, and selective process for preparation of esters and amides from carboxylic acids using Fe3+-K-10 montmorillonite clay
In the presence of Fe3+-K-10 montmorillonite clay as a catalyst, aliphatic carboxylic acids selectively produced the corresponding esters in the presence of aromatic carboxylic acids by treatment with alcohols. Both the aliphatic and aromatic carboxylic acids formed the amides by reacting with the aliphatic amines, but only the aliphatic carboxylic acids yielded the anilides by treatment with aromatic amines. The catalyst is recoverable and recyclable.
Srinivas,Das, Biswanath
p. 1165 - 1167
(2007/10/03)

Photochromic 6-aryl substituted 3H-naphtho(2,1-b)pyrans
Described are novel photochromic 6-aryl substituted 3H-naphtho[2,1-b]pyran compounds, examples of which are naphthopyran compounds having a substituted aryl group at the number 6 carbon atom and certain substituents at the 3-position of the pyran ring. Certain substituents may also be present at the number 7, 8, 9 or 10 carbon atoms of the compounds. These compounds may be represented by the following graphic formula: Also described are polymeric organic host materials that contain one or more of such compounds or combinations of such compounds) with complementary photochromic compounds, e.g., other naphthopyrans, benzopyrans and spiro(oxazine)type compounds.
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(2008/06/13)

Amine derivatives, processes for producing them and a use of them as antiarrhythmic drugs
PCT No. PCT/JP95/01138 Sec. 371 Date May 27, 1997 Sec. 102(e) Date May 27, 1997 PCT Filed Jun. 7, 1995 PCT Pub. No. WO96/04231 PCT Pub. Date Feb. 15, 1996Novel amine derivatives of the following general formula (I): (wherein) A may denote -(CH2)-O-, -(CH2)2-O-, or -(CH2)2-NH-; B may denote -(CH2)2-; R1 may denote a hydrogen atom, a halogen atom, a nitro group, a 1-pyrrolyl group, an acetamido group, an amino group or a dimethylamino group; R2 may denote a hydrogen atom or a nitro group; R3 and R4 may denote a hydrogen atom; R8a and R8b which are the same may denote a chlorine atom or a methoxy group; R9 may denote a hydrogen atom or an amino group; R may denote a methyl group; and X may denote a methanesulfonamido group, a 1-imidazolyl group or a nitro group or a salts thereof are useful as antiarrhythmic drugs.
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(2008/06/13)

Synthesis and biological activity of KCB-328 and its analogues: Novel class III antiarrhythmic agents with little reverse frequency dependence
A series of 3,4-dimethoxyphenethylamine derivatives was prepared, and their prolongation effects on effective refractory period of contractile response (ERPc) and action potential duration (APD) in isolated guinea-pig papillary muscles at 1 Hz and 3 Hz were examined. SAR studies led to the identification of KCB-328 (51) which is a novel class III antiarrhythmic agent with little reverse frequency dependence.
Kim, Dong-Ick,Kim, Hak-Yeop,Kwon, Lae-Sung,Park, Sung-Dae,Jeon, Gee-Ho,Jung, Kyung-Yun,Min, Jae-Ki,Nam, Woong-Hyun,Lee, Kiho,Chung, You-Sup,Tanabe, Shigeru,Kozono, Toshiro
p. 85 - 90
(2007/10/03)

Regioselectivity of the Base-Induced Ring Cleavage of 1-Oxygenated Derivatives of Cyclobutabenzene
Oxy anions 3 generated from 1,2-dihydrocyclobutabenzen-1-ones 1 through addition of a charged nucleophile or from 1-hydroxy-1,2-dihydrocyclobutabenzenes 2 by deprotonation with base lead to stable products through distal and/or proximal cleavage of the strained four-membered ring via benzyl carbanion 4 and/or aryl carbanion 5. A systematic study of this process reveals the relative stability of the two isomeric carbanions 4 and 5 as a key factor in determining the course of the ring-cleavage reaction. While benzyl carbanions 4 can be trapped with carbon electrophiles, attempts at trapping aryl carbanions 5 with electrophiles other than H+ failed. In protic solvents, the magnesium salt of the tertiary alcohol 2 shows an increased rate of proximal cleavage as compared to its alkali salts. From this, we conclude that, in contrast to benzyl carbanions 4, free aryl carbanions 5 are of transient existence only. Proximal C,C-bond cleavage seems to occur either through protonation of 5 from a fast, reversible equilibrium 3?5 in which 3 strongly predominates, or in protic solvents possibly even through a rate-limiting protonation of 3 at the aromatic C-atom, bypassing free anion 5 altogether. Thus, additional factors other than just the relative stability of isomeric carbanions 4 and 5 are of importance in determining the regiochemistry of the base-induced C,C-bond cleavage in ketones 1 and in alcohols 2.
Gokhale, Abha,Schiess, Peter
p. 251 - 267
(2007/10/03)

Unexpected alkylation reaction of amines, acids and phenols by alkyl (triphenylphosphoranylidene)acetates
Reaction of methyl (triphenylphosphoranylidene)acetate in methanol with primary and secondary amines led to N-methylated derivatives. Similarly this mixture reacted with acids, phenol and phthalimide to afford methyl esters, anisole and N-methylphthalimide respectively. Treatment of ketolactam 2 by this mixture under high pressure activation gave the rearranged quinolinone 5.
Desmaele, Didier
p. 1233 - 1236
(2007/10/03)

Cephem compounds
Cephalosporin antibiotics having a 3-position substituent of the formula: STR1 are described, wherein X is --CO--, --SO2 -- or --COCH2 --; Y is --CO--, --SO2 -- or --CH2 --; Q is a benzene, pyridine or naphthalene ring, R1 and R2 are ortho with respect to each other and are independently hydroxy or of the formula O--M wherein M is a moiety and the O--M bond is cleavable in vivo and ring Q may be further substituted by a variety of atoms and groups. Processes for their preparation and use are described.
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(2008/06/13)

A common and general access to berberine and benzo [c] phenanthridine alkaloids
The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a highly-yielding and versatile access to both classes of alkaloids.
Beugelmans,Bois-Choussy
p. 8285 - 8294
(2007/10/02)

Cephalotaxine analogues: Stereospecific synthesis of spiro-fused 3-benzazepine and 1,3-benzodiazepine derivatives
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Gardiner,Bryce,Bates,Hursthouse
p. 1261 - 1266
(2007/10/02)

IRIDOID AND PHENOLIC GLYCOSIDES FROM HARPAGOPHYTUM PROCUMBENS
Key Word Index - Harpagophytum procumbens; Pedaliaceae; iridoid and phenolic glycosides; synthesis.A novel bioside, β-(3',4'-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1 -> 3)-β-D-glucopyranoside, was obtained from the secondary roots of Harpagophytum procumbens.It is accompained by the known iridoid glucosides harpagoside, procumbide, and its 6'-O-p-coumaroyl ester, and phenolic glycosides, acteoside and isoacteoside, the latter pair being obtained from H. procumbens for the first time.The structures of these metabolites were differentiated by high resolution NMR studies, while that of the bioside is additionally supported by synthesis.
Burger, Johann F. W.,Brandt, E. Vincent,Ferreira, Daneel
p. 1453 - 1458
(2007/10/02)