- A general and efficient method to form self-assembled cucurbit[n]uril monolayers on gold surfaces
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A general protocol based on spontaneous adsorption of cucurbit[n]uril (CB[n]) molecules through a strong multivalence interaction between CB[n] and gold is described, by which the formation of self-assembled CB[n] monolayers on gold surfaces can be efficiently achieved. The Royal Society of Chemistry.
- An, Qi,Li, Guangtao,Tao, Chengan,Li, Yan,Wu, Yiguang,Zhang, Weixia
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Read Online
- Fluorescence response of anthracene modified D-π-A heterocyclic chromophores containing nitrogen atom to mechanical force and acid vapor
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Three new 9-vinyl anthracene derivatives functionalized naphthalene (ANNP), quinoline (ANQL) and quinoxaline (ANQX) have been synthesized, and they exhibit excellent solid state luminescence. Optical properties and quantum chemical calculations indicate the absence of D-π-A structure in ANNP, and the presence of typical D-π-A structures in ANQL and ANQX. Though the differences between the three molecules are marginal, their stimuli-responsive behaviors are contrasting. Non-heteroatom-assisted ANNP has no clear chromic property. In contrast, heteroatom-assisted ANQL and ANQX show a clear response to external stimuli such as mechanical force (mechanofluorochromism) and protons (acidofluorochromism). On one hand, both of them exhibit contrasting MFC effects. Upon grinding, emission wavelength shifts are 16 nm and 28 nm, respectively. ANQX shows a large spectral change, which might be originated from nitrogen atom induced ICT process and twisted molecular conformation. On the other hand, two molecules show difference acidofluorochromic response. The presence of nitrogen atom leads to the formation of a stable complex between target molecule and TFA. The solution and film of ANQX achieve a fast response to TFA with high sensitivity and low detection limit. The present results suggest that the anthracene modified D-π-A heterocyclic chromophores containing nitrogen atom can achieve fluorescence response to mechanical forces and acid vapor.
- Zhan, Yong
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Read Online
- Mechanochemical Nucleophilic Substitution of Alcohols via Isouronium Intermediates**
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An expansion of the solvent-free synthetic toolbox is essential for advances in the sustainable chemical industry. Mechanochemical reactions offer a superior safety profile and reduced amount of waste compared to conventional solvent-based synthesis. Here
- Dalidovich, Tatsiana,Nallaparaju, Jagadeesh Varma,Shalima, Tatsiana,Aav, Riina,Kananovich, Dzmitry G.
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- METHOD FOR MANUFACTURING AROMATIC NITRILE COMPOUND
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The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.
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Paragraph 0289-0293
(2021/03/19)
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- Bioisosteric Modification of To042: Synthesis and Evaluation of Promising Use-Dependent Inhibitors of Voltage-Gated Sodium Channels
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Three analogues of To042, a tocainide-related lead compound recently reported for the treatment of myotonia, were synthesized and evaluated in vitro as skeletal muscle sodium channel blockers possibly endowed with enhanced use-dependent behavior. Patch-clamp experiments on hNav1.4 expressed in HEK293 cells showed that N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine, the aryloxyalkyl bioisostere of To042, exerted a higher use-dependent block than To042 thus being able to preferentially block the channels in over-excited membranes while preserving healthy tissue function. It also showed the lowest active transport across BBB according to the results of P-glycoprotein (P-gp) interacting activity evaluation and the highest cytoprotective effect on HeLa cells. Quantum mechanical calculations and dockings gave insights on the most probable conformation of the aryloxyalkyl bioisostere of To042 in solution and the target residues involved in the binding, respectively. Both approaches indicated the conformations that might be adopted in both the unbound and bound state of the ligand. Overall, N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine exhibits an interesting toxico-pharmacological profile and deserves further investigation.
- Milani, Gualtiero,Cavalluzzi, Maria Maddalena,Altamura, Concetta,Santoro, Antonella,Perrone, Mariagrazia,Muraglia, Marilena,Colabufo, Nicola Antonio,Corbo, Filomena,Casalino, Elisabetta,Franchini, Carlo,Pisano, Isabella,Desaphy, Jean-Fran?ois,Carrieri, Antonio,Carocci, Alessia,Lentini, Giovanni
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p. 3588 - 3599
(2021/10/07)
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- Investigating the influence of a CrO42?/Cr2O72? template in the formation of a series of silver-chalcogenide clusters
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Three new silver-chalcogenide clusters protected by naphthyl ligands are described in this work, namely [Ag14(SCH2C10H7)6(CF3COO)8(DMAc)6] (1), [Ag30(SCH2C10H7)18(CrO4)2(DMAc)2 (CF3COO)8] (DMAc = dimethylacetamide) (2) and {Ag12(SCH2C10H7)6(CF3COO)4(CH3CN)6(Cr2O7)}n (3). Their crystal structures were studied by X-ray crystallography, and they show hollow-core-shell (1), template-core-shell (2) and 1D infinite (3) structures, respectively. The luminescence properties of cluster 1 were investigated, which showed interesting thermochromic variation from red to bright yellow. Moreover, the chromate ions were proven to act as templates in forming the silver clusters through a series of experiments to prepare compounds 2 and 3, which could be considered as derivatives of cluster 1.
- Li, Yan-Ling,Xu, Qing-Qing,Li, Si,Huang, Ren-Wu,Liu, Xiao-Fei,Wei, Yong-Li,Zang, Shuang-Quan
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supporting information
p. 115 - 120
(2019/01/04)
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- Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes
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The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular charge transfer from the donor to acceptor, thereby enhancing a pathway to produce, within the solvent cage, the desired diarylethane products. These in-cage naphthylarylethanes are produced in good yields, in a single photochemical step, with the use of cyclohexane as a solvent providing optimal yields.
- Hilborn, James W.,Moya-Barrios, Reinaldo,Thompson, Alison
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p. 11992 - 11999
(2019/10/02)
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- Promotion of Appel-type reactions by N-heterocyclic carbenes
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N-Heterocyclic carbenes (NHCs) have been extensively used as a versatile class of catalysts and ligands in organocatalytic and organometallic chemistry. However, there are only a small number of synthetic applications where they act as reagents. Here we demonstrate that NHCs can be used as stoichiometric redox reagents for Appel-type halogenation reactions of alcohols. This new reactivity reveals a fresh and interesting aspect and enriches the chemistry of NHCs in an underexplored area. The potential of performing this chemical transformation at the catalytic level using an NHC-oxide derivative is also investigated.
- Hussein, Mohanad A.,Nguyen, Thanh Vinh
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supporting information
p. 7962 - 7965
(2019/07/12)
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- PH clock instructed transient supramolecular peptide amphiphile and its vesicular assembly
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A new strategy to construct a transient supramolecular peptide amphiphile (SPA) and its vesicular aggregates is displayed. The construction of the amphiphile is assisted by the ternary complexation of cucurbit[8]uril and pH responsive imine bond formation. The transient assembly follows a pH clock set by urea/urease and hydrolysis of glucono delta-lactone (GdL). The transient assembly can be repeated for several cycles through feeding the system with the fuel (urea).
- Dowari, Payel,Das, Saurav,Pramanik, Bapan,Das, Debapratim
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supporting information
p. 14119 - 14122
(2019/12/02)
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- Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.
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The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).
- Ni, Shengjun,El Remaily, Mahmoud Abd El Aleem Ali Ali,Franzén, Johan
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supporting information
p. 4197 - 4204
(2018/09/25)
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- Halogenation through Deoxygenation of Alcohols and Aldehydes
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An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.
- Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang
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supporting information
p. 3061 - 3064
(2018/05/28)
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- Synthesis of pentacyclic compounds via intramolecular [3 + 2] photocycloaddition of cycloalkene linked naphthalenes
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Intramolecular photocycloaddition reactions of cycloalkene linked naphthalenes lead to formation of pentacyclic compounds in a high yielding and stereoselective manner. Intramolecular [2 + 2] cycloadducts are formed initially in photoreactions of cycloalkene linked 1-cyanonaphthalenes. The initially formed intramolecular [2 + 2] cycloadducts absorb light at wavelengths used to promote the photochemical reactions and, as a result, they undergo efficient photocycloreversion to regenerate the starting substrates. In a less efficient competing process, the cycloalkene linked 1-cyanonaphthalenes react to form [3 + 2] intramolecular photoadducts, which do not absorb incident light under the conditions used. Consequently, these photoadducts become the major products in these processes. The relative configuration of the major diastereomers of the pentacyclic products formed from photoreactions of cyclopentene linked naphthalenes (cis-cis) differ from those (cis-trans) arising from the cyclooctene linked substrates. The results of theoretical calculations, which show that steric factors govern the preferred facial mode of intramolecular addition, are in good agreement with the stereochemical course of these photoreactions.
- Maeda, Hajime,Uesugi, Tomoya,Fujimoto, Yasufumi,Mukae, Hirofumi,Mizuno, Kazuhiko
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p. 198 - 206
(2017/02/10)
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- CATALYST COMPRISING A METALLOCENE COMPLEX AND A CO-CATALYST
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The invention relates to a metallocene complex according to formula I or II wherein M is a metal selected from lanthanides or transition metals from group 3, 4, 5 or 6 of the Periodic System of the Elements, Q is an anionic ligand to M, k is the number of Q groups and equals the valence of M minus 2, R is a divalent bridging group, R1, R2, R3 and R4 are each independently chosen from the group consisting of hydrogen (H); a halogen atom; a silyl, alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl group; and R5, R6, R7 and R8 are each independently chosen from the group consisting of hydrogen (H); a halogen atom; a silyl, alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl group; or two adjacent radicals R5 and R6, R6 and R7, and R7 and R8 are connected with each other in a hydrocarbon ring system. The invention also relates to a catalyst comprising the metallocene complex, to a process for making polyolefins and to the use of the polyolefins for making articles.
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Page/Page column 18; 19
(2017/08/01)
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- Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation part 1: Evidence for naphthalene as a DNA intercalator
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N-Acyloxy-N-alkoxyamides are direct-acting mutagens in S. typhimurium TA100 with a linear dependence upon log P that maximises at log P0 = 6.4. Eight N-acyloxy-N-alkoxyamides (2-9) bearing a naphthalene group on any of the three side-chains and with log P0 6.4 have been demonstrated to be significantly and uniformly more mutagenic towards S. typhimurium TA100 than 50 mutagens without naphthalene. The activity enhancement of 2-9 is likely due to intercalative binding of naphthalene to bacterial DNA as a number are also active in TA98, a frame-shift strain of S. typhimurium, which is modified by intercalators. DNA damage profiles for naphthalene-bearing mutagens confirm enhanced reactivity with DNA when naphthalene is incorporated and a different binding mode when compared to mutagens without naphthalene. The effect is independent of whether the naphthalene is attached to an electron-donating alkyl or electron-withdrawing acyl group, alkyl tether length or, in the case of 6 and 7, the point of attachment to naphthalene. A new quantitative structure activity relationship has been constructed for all 58 congeners incorporating log P and an indicator variable, I, for the presence (I = 1) or absence (I = 0) of naphthalene and from which the activity enhancing effect of a naphthalene has been quantified at between three and four log P units. Contrary to conventional views, simple naphthalene groups could target molecules to DNA through intercalation.
- Banks, Tony M.,Clay, Samuel F.,Glover, Stephen A.,Schumacher, Rhiannon R.
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supporting information
p. 3699 - 3714
(2016/05/09)
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- Synthesis and Photophysical Properties of Aza[n]helicenes
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Synthesis and study of aza[7]helicene and aza[9]helicene is presented in this paper. Photo-dehydrocyclization of the 3,6-bis-styryl derivative of carbazole leading to sterically less demanding aza[7]helicene resulted in smooth reaction, and only the desired angular-angular product was detected. However, in the case of aza[9]helicene, along with the expected angular-angular cyclization, three other products involving linear mode of cyclization were also isolated and characterized. In this case, the helical compound aza[9]helicene was predominantly formed at lower concentration while the other isomers were obtained at higher concentration. All of the compounds formed by angular-angular, angular-linear, and linear-linear modes of cyclization were fully characterized, and their photophysical properties were investigated.
- Upadhyay, Gourav M.,Talele, Harish R.,Bedekar, Ashutosh V.
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supporting information
p. 7751 - 7759
(2016/09/09)
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- Discovery and structural optimization of 4-(4-(benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-ones as RORc inverse agonists
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Aim: Retinoic acid receptor-related orphan nuclear receptors (RORs) are orphan nuclear receptors that show constitutive activity in the absence of ligands. Among 3 subtypes of RORs, RORc is a promising therapeutic target for the treatment of Th17-mediated autoimmune diseases. Here, we report novel RORc inverse agonists discovered through structure-based drug design. Methods: Based on the structure of compound 8, a previously described agonist of RORa, a series of 4-(4-(benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-one derivatives were designed and synthesized. The interaction between the compounds and RORc was detected at molecular level using AlphaScreen assay. The compounds were further examined in 293T cells transfected with RORc and luciferase reporter gene. Thermal stability shift assay was used to evaluate the effects of the compounds on protein stability. Results: A total of 27 derivatives were designed and synthesized. Among them, the compound 22b was identified as the most potent RORc inverse agonist. Its IC50 values were 2.39 μmol/L in AlphaScreen assay, and 0.82 μmol/L in inhibition of the cell-based luciferase reporter activity. Furthermore, the compound 22b displayed a 120-fold selectivity for RORc over other nuclear receptors. Moreover, a molecular docking study showed that the structure-activity relationship was consistent with the binding mode of compound 22b in RORc. Conclusion: 4-(4-(Benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-one derivatives are promising candidates for the treatment of Th17-mediated autoimmune diseases, such as rheumatoid arthritis, psoriasis, and multiple sclerosis.
- Wu, Xi-Shan,Wang, Rui,Xing, Yan-Li,Xue, Xiao-Qian,Zhang, Yan,Lu, Yong-Zhi,Song, Yu,Luo, Xiao-Yu,Wu, Chun,Zhou, Yu-Lai,Jiang, Jian-Qin,Xu, Yong
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p. 1516 - 1524
(2016/11/11)
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- Synthesis of novel dihydronaphthothiazine S,S-dioxides by intramolecular sulfonylamidomethylation of 2-naphthylmethanesulfonamides using Amberlyst XN-1010
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We describe herein an efficient synthetic method for novel dihydronaphthothiazines S,S-dioxides by aromatic intramolecular sulfonylamidomethylation of 2-naphthylmethanesulfonamides with s-trioxane using Amberlyst XN-1010 as acid heterogeneous catalyst. Cyclization of the formed sulfonyliminium ion occurred with high regioselectivity and in excellent yields.
- Sasiambarrena, Leandro D.,Cánepa, Alicia S.,Bravo, Rodolfo D.
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supporting information
p. 7184 - 7189
(2015/12/12)
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- N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and compounds I for use to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 000537
(2015/05/19)
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- One-pot transformation of methylarenes into aromatic aldehydes under metal-free conditions
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On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N-methylmorpholine N-oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A) or with NBS in CCl4 under irradiation with a tungsten lamp at 30 °C (Method B), followed by treatment with N-methylmorpholine N-oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one-pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals. Copyright
- Tabata, Masayuki,Moriyama, Katsuhiko,Togo, Hideo
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p. 3402 - 3410
(2014/06/09)
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- Direct oxidative conversion of methylarenes into aromatic nitriles
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A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.
- Tsuchiya, Daisuke,Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
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supporting information
p. 4194 - 4197
(2013/09/12)
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- Identification of pheromone-like compounds in male reproductive organs of the oriental locust Locusta migratoria
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Despite the great economical interest of locusts in agriculture, knowledge on their chemoreception systems is still poor. Phenylacetonitrile is recognised as a pheromone of the desert locust Schistocerca gregaria, triggering gregarization, promoting aggregation and inhibiting courtship. However, in the other major locust species, Locusta migratoria, pheromones have not been reported. We have identified the two isomers of naphthylpropionitrile from the male reproductive organs of L. migratoria. Chemical synthesis has confirmed the identity of the two compounds. Both isomers show significant affinity to CSP91, a protein reported in the testis, but not to three other proteins of the same family (CSP180, CSP540 and CSP884) expressed in female accessory glands. The striking similarity of these compounds with phenylacetonitrile and the unusual nature of such chemicals strongly suggest that naphthylpropionitrile could be pheromones for L. migratoria, while their site of expression and binding activity indicate a role in communication between sexes.
- Ban, Liping,Napolitano, Elio,Serra, Andrea,Zhou, Xianhong,Iovinella, Immacolata,Pelosi, Paolo
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p. 620 - 624
(2013/09/02)
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- Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process
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A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.
- Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Gettongsong, Tanita
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supporting information
p. 1463 - 1467
(2013/05/08)
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- Scalable synthesis of a new enantiomerically pure π-extended rigid amino indanol
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A convenient route to a benzo-fused amino indanol chiral controller is disclosed. The synthesis is based on a newly optimized entry to 3H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give the target synthon in >98% ee. The resolution features (S)-naproxen as an inexpensive and highly crystalline resolving agent. Conversion of the amino alcohol to its bis(oxazolinyl)-propane is also reported. A solid state structure of the CuCl2-box complex shows preservation of the distorted square planar geometry found in the parent CuCl2(indanyl-box) despite greater steric crowding by the blocking groups.
- Rendina, Victor L.,Goetz, Samantha A.,Neitzel, Angelika E.,Kaplan, Hilan Z.,Kingsbury, Jason S.
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supporting information; experimental part
p. 15 - 18
(2012/01/06)
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- CURABLE COMPOSITION FOR IMPRINTS AND PRODUCING METHOD OF POLYMERIZABLE MONOMER FOR IMPRINTS
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Provided is a curable composition for imprints excellent in pattern transferability. Disclosed is a curable composition for imprints comprising a polymerizable monomer (A) and a polymerization initiator (B), which is substantially free from a polymer which contains at least one species of the polymerizable monomer (A) as a repeating unit.
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- Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes
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An improved procedure has been developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number of phenanthrenes and helicenes. ARKAT-USA, Inc.
- Talele, Harish R.,Chaudhary, Anju R.,Patel, Parthiv R.,Bedekar, Ashutosh V.
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scheme or table
p. 15 - 37
(2011/06/19)
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- Photo-ritter reaction of arylmethyl bromides in acetonitrile
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The photo-Ritter reaction of five arylmethyl bromides can occur in acetonitrile to give acetamides. The intermediates, carbocations, which are formed from subsequent electron transfer between the radical pairs generated from initial homolytic cleavage of the C-Br bond, are trapped by acetonitrile, and subsequent hydrolysis generates the corresponding acetamides. Taylor & Francis Group, LLC.
- Bi, Nai-Min,Ren, Ming-Guang,Song, Qin-Hua
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experimental part
p. 2617 - 2623
(2010/10/03)
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- TREATMENT OR PROPHYLAXIS OF PROLIFERATIVE CONDITIONS
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The invention relates to novel compounds for use in the treatment or prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express cytochrome P450 1B1 (CYP1B1) and allelic variants thereof. The invention also provides pharmaceutical compositions comprising one or more such compounds for use in medical therapy, for example in the treatment of prophylaxis of cancers or other proliferative conditions, as well as methods for treating cancers or other conditions in human or non-human animal patients. The invention also provides methods for identifying novel compounds for use in the treatment of prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express CYP1 B1 and allelic variants thereof. The invention also provides a method for determining the efficacy of a compound of the invention in treating cancer.
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Page/Page column 54-55
(2010/11/17)
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- Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination
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N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) [PBPS] can be used for bromination of benzylic positions in solvent.
- Ghorbani-Vaghei, Ramin,Chegini, Mohammad,Veisi, Hojat,Karimi-Tabar, Mehdi
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scheme or table
p. 1861 - 1865
(2009/07/19)
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- Benzylic brominations with N-bromosuccinimide in (Trifluoromethyl)benzene
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A variety of benzylic brominations were performed by using N-bromosuccinimide in (trifluoromethyl)benzene with photochemical activation in the presence of 2,2′-azobisisobutyronitrile, 1,1′- azobis(cyclohexanecarbonitrile), or benzoyl peroxide as the radical initiator. This system provides clean, rapid, and high-yielding reactions with replacement of conventional solvents, such as tetrachloromethane, by less-toxic (trifluoromethyl)benzene. Georg Thieme Verlag Stuttgart.
- Suarez, Diana,Laval, Gilles,Tu, Shang-Min,Jiang, Dong,Robinson, Claire L.,Scott, Richard,Golding, Bernard T.
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experimental part
p. 1807 - 1810
(2010/02/28)
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- LEWIS ACID CATALYZED HALOGENATION OF ACTIVATED CARBON ATOMS
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A practical and efficient method for halogenation of activated carbon atoms using readily available /V-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.
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Page/Page column 28-29
(2008/06/13)
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- An efficient synthesis of benzyl bromides from aromatic aldehydes using polymethylhydrosiloxane and (bromodimethyl)sulfonium bromide or N-bromosuccinimide
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Polymethylhydrosiloxane (PMHS) in combination with (bromodimethyl)sulfonium bromide or NBS has been utilized for the first time for reductive bromination of aromatic aldehydes at room temperature to afford the corresponding benzyl bromides in excellent yields.
- Das, Biswanath,Srinivas, Yallamalla,Holla, Harish,Laxminarayana, Keetha,Narender, Ravirala
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p. 6681 - 6683
(2008/03/12)
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- Contrasting chemoselectivities in the ultrasound and microwave assisted bromination reactions of substituted alkylaromatics with N-bromosuccinimide
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Ultrasound and microwave assisted bromination reactions of various alkylaryls with N-bromosuccinimide, either neat or in water, shows diverse chemoselectivity. Thus, ring substitution occurs in water with ultrasound, whereas with microwaves both side-chain α-bromination and ring substitution occur. With neat reactants, side-chain α-bromination predominates for microwave assisted reactions. In the presence of water the chemoselectivity with microwave-promoted bromination is similar to that observed using classical methods.
- Heropoulos, Georgios A.,Cravotto, Giancarlo,Screttas, Constantinos G.,Steele, Barry R.
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p. 3247 - 3250
(2008/02/02)
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- High temperature bromination. Part 22: Bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene
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The high-temperature bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene and its carboethoxy derivative was studied. Reaction of the title compound with 1 mol of bromine in refluxing carbon tetrachloride resulted in the formation of ring-opening products. In the case of the carboethoxy derivative, bromination took place both regio- and stereospecifically at the benzylic positions, the cyclopropane ring did not undergo bond cleavage. A mechanism for the formation of the products and their dehydrobromination reactions is discussed.
- Demirci-Gültekin, Demet,Günba?, Duygu D.,Ta?kesenligil, Yavuz,Balci, Metin
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p. 8151 - 8156
(2008/02/05)
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- Lewis acid catalyzed highly selective halogenation of aromatic compounds
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A simple and efficient procedure for the halogenation of aromatic compounds with NCS, NBS, NIS and NFSI in the presence of catalytic amount of ZrCl 4 is described. Chlorination, bromination, iodination and fluorination of various aromatic compounds are performed with high selectivity under mild reaction conditions. Georg Thieme Verlag Stuttgart.
- Zhang, Yanhua,Shibatomi, Kazutaka,Yamamoto, Hisashi
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p. 2837 - 2842
(2007/10/03)
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- Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety
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By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4-methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G2/M arrest of the cell cycle in human cancer cells.
- Maya, Ana B. S.,Pérez-Melero, Concepción,Mateo, Carmen,Alonso, Dulce,Fernández, José Luis,Gajate, Consuelo,Mollinedo, Faustino,Peláez, Rafael,Caballero, Esther,Medarde, Manuel
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p. 556 - 568
(2007/10/03)
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- Cryptophycin compounds
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The present invention provides cryptophycin compounds of Formula I that are useful in the treatment of neoplasms.
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Page/Page column 150
(2010/02/05)
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- Arylmethyl radicals from arylmethoxybromodiazirines
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(Chemical Equation Presented) Photolytic decompositions of 3-arylmethoxy-3-bromodiazirines afford arylmethyl radicals by homolyses of the diazirines' excited states.
- Moss, Robert A.,Fu, Xiaolin
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p. 3353 - 3356
(2007/10/03)
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- Photochemical Reactions of α-Bromoacetylarenes Studied by Product Analysis and Laser Flash Photolysis
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The hydrogen abstraction reaction and rearrangement reaction of aroylmethyl radicals were studied by product analyses and transient absorption spectroscopies. The α-bromoacetylarenes examined in this study gave aroylmethyl radicals by C-Br bond cleavage u
- Suzuki, Toshiaki,Kaneko, Yuji,Ikegami, Masashi,Arai, Tatsuo
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p. 801 - 806
(2007/10/03)
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- Environmentally-friendly Wohl-Ziegler bromination: Ionic-liquid reaction and solvent-free reaction
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Environmentally-friendly Wohl-Ziegler bromination of benzylic methyl groups was successfully camed out in ionic-liquid and solvent-free systems, to produce the corresponding benzylic bromides in good to moderate yields.
- Togo, Hideo,Hirai, Takeshi
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p. 702 - 704
(2007/10/03)
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- PROTEASOME INHIBITORS
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The present invention relates to proteasome inhibitors as the active ingredient carboxylic acid derivatives represented by general formula (I) or pharmaceutically acceptable salts thereof: wherein m and n are the same or different and represent an integer of 0 to 10; p is 0 or 1; R1 represents a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted alicyclic alkyl, or the like; and R2 represents a hydrogen atom, COR13, or CH2OR3a, or R1 and R2 together represent the formula: X1 represents a bond, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, or the like; X2 represents an oxygen atom, a sulfur atom, or NR17; R3 is has the same significance as the above R3a; R4 represents hydroxy, mercapto, substituted or unsubstituted alkoxy, or the like, or R1 and R2 together represent a bond; R5 represents a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, or the like.
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- Mass spectrometric investigation of tautomers of N-substituted 4-iminopentan-2-ones in the gas phase
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Mass fragmentation of 4-iminopentan-2-one N-substituted with organosilicon group suggests that in the gas phase upon electron ionization (EI) conditions only 4-imino-2-keto tautomer occurs. The simultaneous occurrence of 4-aminopent-3-en-2-keto tautomeric form was ruled out on the basis of mass fragmentation of some alkylaromatic derivatives of 4-aminopent-3-en-2-one.
- Urbaniak,Franski,Gierczyk
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p. 429 - 441
(2007/10/03)
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- Potential antidepressants displayed combined α2-adrenoceptor antagonist and monoamine uptake inhibitor properties
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Classical antidepressants are thought to act by raising monoamine (serotonin and noradrenaline) levels in the brain. This action is generally accomplished either by inhibition of monoamine metabolism (MAO inhibitors) or by blockade of monoamine uptake (tricyclic antidepressants and selective serotonin or noradrenaline reuptake inhibitors). However, all such agents suffer from a time lag (3-6 weeks) before robust clinical efficacy can be demonstrated. This delay may reflect inhibitory actions of noradrenaline at presynaptic α2A-adrenergic auto- or heteroreceptors which gradually down-regulate upon prolonged exposure. Blockade of presynaptic α2A-adrenoceptors by an antagonist endowed with monoamine uptake inhibition properties could lead to new antidepressants with greater efficacy and a shorter time lag. In the literature, only two molecules-have been described with such a pharmacological profile. Of these, napamezole (2) was chosen as a point of departure for the design of 4(5)-[(3,4-dihydro-2-naphthalenyl)methyl]-4,5-dihydroimidazole (4a), which displayed the desired profile: α2A-adrenoceptor antagonist properties and serotonin/noradrenaline uptake inhibition. From this original molecule, a series of derivatives was designed and synthesized, encompassing substituted as well as rigid analogues. Structure-activity relationships permitted the selection of 14c (4(5)-[(5-fluoroindan-2-yl)methyl]-4,5-dihydroimidazole) as a development candidate.
- Cordi,Berque-Bestel,Persigand,Lacoste,Newman-Tancredi,Audinot,Millan
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p. 787 - 805
(2007/10/03)
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- Design, synthesis and cytotoxic activities of naphthyl analogues of combretastatin A-4
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The 3,4,5-trimethoxyphenyl and 3-hydroxy-4-methoxyphenyl rings of combretastatin A-4 are deemed optimal for its activity as antimitotic agent. The replacement of either one by a naphthalene ring results in compounds with a potency comparable to that of the parent compound. These results show that the naphthalene ring is a good surrogate for the 3,4,5-trimethoxyphenyl or the 3-hydroxy-4-methoxyphenyl rings of combretastatin A-4 and that neither of them is essential for the antitumor activity. (C) 2000 Elsevier Science Ltd.
- Maya, Ana B. S.,Del Rey, Benedicto,Lamamie de Clairac, Rafael Pelaez,Caballero, Esther,Barasoain, Isabel,Andreu, Jose Manuel,Medarde, Manuel
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p. 2549 - 2551
(2007/10/03)
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- Piperidine derivatives having renin inhibiting activity
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Novel piperidine derivatives, their manufacture and use as medicaments, are disclosed. The invention is concerned with the novel piperidine derivatives of general formula I wherein R1, R2, R3, R4, Q, X, Z, m and n are as described herein.
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- Benzocondensed derivatives as rigid analogues of the μ-opioid agonist 3(8)-cinnamyl-8(3)-propionyl-3,8-diazabicyclo[3,2,1]octanes: Synthesis, modeling, and affinity
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A new series of rigid analogues (1a-g, 2a-g) of the previously reported analgesic 3-cinnamyl-8-propionyl-3,8-diazabicyclo[3.2.1]octane (I) and its reverted isomer 3-propionyl-8-cinnamyl (II) were synthesized, in which the cinnamyl substituent is incorporated in benzocondensed bicyclic systems. Binding assays for the affinity towards μ receptors indicated that, while in the reverted series 2 the β-naphthylmethyl (2d) and the benzocycloheptenylmethyl derivative (2g) favorably compared with II, all compounds 1 displayed a μ-affinity lower than that of the parent I. Modeling studies suggest that the flexibility of the cinnamyl side chain plays an important role for activity.
- Cignarella,Barlocco,Vianello,Villa,Pinna,Fadda,Fratta,Toma,Gessi
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p. 667 - 674
(2007/10/03)
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- Esterification of carboxylic acid salts
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Mono- or polycarboxylic acid esters are prepared by reacting a salt of such carboxylic acid with an organic halocompound, e.g., a (cyclo)alkyl, (cyclo)alkenyl, aryl or aralkyl halide, in an aqueous reaction medium, in the presence of a catalytically effective amount of a phase transfer catalyst, for example an onium salt.
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- Selective benzylic bromination of 2-methylnaphthalene
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A practical synthesis of 2-(bromomethyl)naphthalene (1) by selective benzylic bromination of 2-methylnaphthalene (2) with bromine in heptane in the presence of lanthanum acetate hydrate is described.
- Waykole, Liladhar,Prashad, Mahavir,Palermo, Stephen,Repic, Oljan,Blacklock, Thomas J.
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p. 2159 - 2163
(2007/10/03)
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- Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A.
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To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxe tanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.
- Hashizume,Ito,Yamada,Nagashima,Kanao,Tomoda,Sunazuka,Kumagai,Omura
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p. 512 - 520
(2007/10/02)
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- Enzymes in organic synthesis 51. Probing the dimensions of the large hydrophobic pocket of the active site of pig liver esterase
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The dimensions of the large hydrophobic pocket (H(L)) of the active site model of pig liver esterase (PLE) were probed using a series of aliphatic and phenylic malonates. Results from the hydrolyses of these new unnatural substrates permitted the extension of the H(L) pocket to give the new dimensions of 6.2 x 2.3 x 3.9 A for a total volume of ~56 A3.
- Provencher,Wynn,Jones,Krawczyk
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p. 2025 - 2026
(2007/10/02)
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- Halogenative Allylation and Reduction of Aromatic Acetals by Double Substitution of Alkoxyl Groups in Acetal
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In the presence of excessive amount of acetyl halide along with a catalytic amount of tin(II) halide, aromatic acetals react with allyltrimethylsilane or triethylsilane to give α-allylbenzyl halides or benzyl halides, respectively, in good to excellent yields.
- Oriyama, Takeshi,Iwanami, Katsuyuki,Tsukamoto, Kazuhisa,Ichimura, Yuichi,Koga, Gen
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p. 1410 - 1412
(2007/10/02)
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