- Ethyl 2-formamido-2-(4-iodobenzyl)-3-(4-iodophenyl)propionate and ethyl 2-(3-bromobenzyl)-3-(3-bromophenyl)-2-formamidopropionate
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The title compounds, C19H19I2NO3 and C19H19Br2NO3, are derivatives of α-aminoisobutyric acid with halogen substituents at the para and meta positions, respectively. The ethoxycarbonyl and formamide side chains attached to the Cαatom of the molecule adopt extended and folded conformations, respectively. The crystal structures are stabilized by N -H...O, C - H...O, C - Br...O and C - I...O interactions.
- Damodharan, Lakshminarasimhan,Pattabhi, Vasantha,Behera, Manoranjan,Kotha, Sambasivarao
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Read Online
- Design and synthesis of substituted (1-(benzyl)-1: H -1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: Study on their apoptosis inducing ability and tubulin polymerization inhibition
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A library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives were designed, synthesized and screened for their in vitro cytotoxic activity against BT-474, HeLa, MCF-7, NCI-H460 and HaCaT cells by employing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized analogues, compound 10ec displayed the highest cytotoxicity with the IC50 value of 0.99 ± 0.01 μM towards BT-474 cancer cell line. The target compound (10ec) was also evaluated for its tubulin polymerization inhibition study. Detailed biological studies such as acridine orange/ethidium bromide (AO/EB), DAPI and annexin V-FITC/propidium iodide staining assay suggested that compound 10ec induced the apoptosis of BT-474 cells. The clonogenic assay revealed that the inhibition of colony formation in BT-474 cells by 10ec in concentration-dependent manner. Moreover, the flow cytometric analysis revealed that 10ec induced apoptosis via cell cycle arrest at the sub-G1 and G2/M phase. In silico studies of sulfonyl piperazine-integrated triazole conjugates unveil that they possess drug-like properties. According to the molecular modelling studies, compound 10ec binds to the colchicine binding site of the tubulin.
- Alvala, Mallika,Babu, Bathini Nagendra,Devi, Ganthala Parimala,Godugu, Chandraiah,Manasa, Kesari Lakshmi,Nagesh, Narayana,Sigalapalli, Dilep Kumar,Thatikonda, Sowjanya,Vuppaladadium, Sowmya
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supporting information
p. 1295 - 1302
(2020/12/01)
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- Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN2 Pincer Ligand Complex
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An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp3-carbon fragments. The method, which relies on the application of nickel complexed with an NN2-type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.
- Andersen, Thomas L.,Donslund, Aske S.,Neumann, Karoline T.,Skrydstrup, Troels
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supporting information
p. 800 - 804
(2017/12/26)
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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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- A General Strategy to Enhance the Performance of Dye-Sensitized Solar Cells by Incorporating a Light-Harvesting Dye with a Hydrophobic Polydiacetylene Electrolyte-Blocking Layer
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A unique strategy to suppress charge recombination effectively and enhance light harvesting in dye-sensitized solar cells (DSSCs) is demonstrated by the design of a new dipolar organic dye functionalized with a diacetylene unit, which is capable of underg
- Desta, Mekonnen Abebayehu,Liao, Chia-Wei,Sun, Shih-Sheng
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p. 690 - 697
(2017/03/22)
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- Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
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A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
- Das, Riki,Kapur, Manmohan
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p. 1114 - 1126
(2018/06/18)
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- Investigation of pyrolysis temperature in the one-step synthesis of L10 FePt nanoparticles from a FePt-containing metallopolymer
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Ferromagnetic (L10 phase) FePt alloy nanoparticles (NPs) with extremely high magnetocrystalline anisotropy are considered to be very promising candidates for the next generation of ultrahigh-density data storage systems. The question of how to generate L10 FePt NPs with high coercivity, controllable size, and a narrow size distribution is a challenge. We report here a single-step fabrication of L10 FePt NPs by employing one of the two new polyferroplatinyne bimetallic polymers as precursors. The influence of the pyrolysis temperature on the size and magnetic properties of the resulting FePt alloy NPs has been investigated in detail.
- Dong, Qingchen,Li, Guijun,Wang, Hua,Wing-Tat Pong, Philip,Leung, Chi-Wah,Manners, Ian,Ho, Cheuk-Lam,Li, Hua,Wong, Wai-Yeung
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p. 734 - 741
(2015/07/27)
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- P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters
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A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.
- Wang, Sunewang Rixin,Radosevich, Alexander T.
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supporting information
p. 3810 - 3813
(2015/08/18)
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- A scalable procedure for light-induced benzylic brominations in continuous flow
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A continuous-flow protocol for the bromination of benzylic compounds with N-bromosuccinimide (NBS) is presented. The radical reactions were activated with a readily available household compact fluorescent lamp (CFL) using a simple flow reactor design based on transparent fluorinated ethylene polymer (FEP) tubing. All of the reactions were carried out using acetonitrile as the solvent, thus avoiding hazardous chlorinated solvents such as CCl4. For each substrate, only 1.05 equiv of NBS was necessary to fully transform the benzylic starting material into the corresponding bromide. The general character of the procedure was demonstrated by brominating a diverse set of 19 substrates containing different functional groups. Good to excellent isolated yields were obtained in all cases. The novel flow protocol can be readily scaled to multigram quantities by operating the reactor for longer time periods (throughput 30 mmol h-1), which is not easily possible in batch photochemical reactors. The bromination protocol can also be performed with equal efficiency in a larger flow reactor utilizing a more powerful lamp. For the bromination of phenylacetone as a model, a productivity of 180 mmol h -1 for the desired bromide was achieved.
- Cantillo, David,De Frutos, Oscar,Rincon, Juan A.,Mateos, Carlos,Oliver Kappe
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supporting information
p. 223 - 229
(2014/01/17)
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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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- Electrogenerated conductive polymers from triphenylamine end-capped dendrimers
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Electroactive end-capped dendritic macromolecules were designed and synthesized. Their structures contain triphenylamine moieties as part of the core or dendrons. The electrogenerated films produced with these monomers behaved as conductive dendritic poly
- Mangione, Maria I.,Spanevello, Rolando A.,Rumbero, Angel,Heredia, Daniel,Marzari, Gabriela,Fernandez, Luciana,Otero, Luis,Fungo, Fernando
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p. 4754 - 4763
(2013/07/26)
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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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- Water-soluble red-emitting distyryl-borondipyrromethene (BODIPY) dyes for biolabeling
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A series of water-soluble red-emitting distyryl-borondipyrromethene (BODIPY) dyes were designed and synthesized by using three complementary approaches aimed at introducing water-solubilizing groups on opposite faces of the fluorescent core to reduce or c
- Niu, Song-Lin,Massif, Cedrik,Ulrich, Gilles,Renard, Pierre-Yves,Romieu, Anthony,Ziessel, Raymond
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scheme or table
p. 7229 - 7242
(2012/07/03)
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- The application of a monolithic triphenylphosphine reagent for conducting Appel reactions in flow microreactors
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Herein we describe the application of a monolithic triphenylphosphine reagent to the Appel reaction in flow-chemistry processi to generate various brominated products with high purity and in excellent yields, and with no requirement for further off-line pu fication.
- Roper, Kimberley A.,Lange, Heiko,Polyzos, Anastasios,Berry, Malcolm B.,Baxendale, Ian R.,Ley, Steven V.
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supporting information; experimental part
p. 1648 - 1655
(2012/02/04)
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- Synthesis of organometallic poly(dendrimer)s by macromonomer polymerization: effect of dendrimer size and structural rigidity on the polymerization efficiency
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Two series of first to third generation (G1-G3) oligoether dendrimers, one hearing a shorter spacer chain (C-O) and the other having a longer spacer branch (C-C-C-O) were prepared. Both series of compounds, containing two reactive C≡CH moieties on the dendrimer surface, were used as macromonomers and copolymerized with trans-[Pt(PEt3)2Cl2] to form organometallic poly(dendrimer)s by an outer-sphere-outer-sphere connection strategy. It was found that concentration of monomer used in the polymerization, the dendrimer generation, and, most strikingly, the length of the spacer were key factors that determined the polymerization efficiency. Hence, the structurally more rigid and compact C-O linked dendrimers formed poly(dendrimer)s with a higher degree of polymerization than the structurally less rigid and more bulky C-C-C-O dendrimers. This result was due to the higher tendency to form cyclic oligomers in the latter series of compounds. In addition, the differences in the polymerization efficiency among the three generations of dendrimers could be explained by the gradual decrease of reactive functional group density on the dendrimer surface.
- Cheung, Siu-Yin,Chow, Hak-Fun,Ngai, To,Wei, Xiaoling
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supporting information; experimental part
p. 2278 - 2288
(2009/10/23)
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- A synthetic method for diversification of the P1′ substituent in phosphinic dipeptides as a tool for exploration of the specificity of the S1′ binding pockets of leucine aminopeptidases
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A novel, general, and versatile method of diversification of the P1′ position in phosphinic pseudodipeptides, presumable inhibitors of proteolytic enzymes, was elaborated. The procedure was based on parallel derivatization of the amino group in the suitably protected phosphinate building blocks with appropriate alkyl and aryl halides. This synthetic strategy represents an original approach to phosphinic dipeptide chemistry. Its usefulness was confirmed by obtaining a series of P1′ modified phosphinic dipeptides, inhibitors of cytosolic leucine aminopeptidase, through computer-aided design basing on the structure of homophenylalanyl-phenylalanine analogue (hPheP[CH2]Phe) bound in the enzyme active site as a lead structure. In this approach novel interactions between inhibitor P1′ fragment and the S1′ region of the enzyme, particularly hydrogen bonding involving Asn330 and Asp332 enzyme residues, were predicted. The details of the design, synthesis, and activity evaluation toward cytosolic leucine aminopeptidase and aminopeptidase N are discussed. Although the potency of the lead compound has not been improved, marked selectivity of the synthesized inhibitors toward both studied enzymes was observed.
- Vassiliou, Stamatia,Xeilari, Metaxia,Yiotakis, Athanasios,Grembecka, Jolanta,Pawelczak, Malgorzata,Kafarski, Pawel,Mucha, Artur
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p. 3187 - 3200
(2008/02/07)
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- NOVEL HETEROARYL DERIVATIVE
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A heteroaryl derivative of the formula (1): (wherein Ring Z is an optionally substituted heteroaryl, R1 is a carboxyl group or an alkoxycarbonyl group, etc., W1 and W2 are an optionally substituted lower alkylene, Ar1 is an optionally substituted arylene or an optionally substituted heteroarylene, W3 is a single bond, a lower alkylene, a lower alkenylene, etc., W4 is a single bond, -NR10-, etc., Ar2 is an optionally substituted aryl or an optionally substituted heteroaryl), or a prodrug thereof, or a pharmaceutically acceptable salt thereof.
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Page/Page column 54
(2008/06/13)
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- Synthesis and structure-activity relationship effects on the tumor avidity of radioiodinated phospholipid ether analogues
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Radioiodinated phospholipid ether analogues have shown a remarkable ability to selectively accumulate in a variety of human and animal tumors in xenograft and spontaneous tumor rodent models. It is believed that this tumor avidity arises as a consequence of metabolic differences between tumor and corresponding normal tissues. The results of this study indicate that one factor in the tumor retention of these compounds in tumors is the length of the alkyl chain that determines their hydrophobic properties. Decreasing the chain length from C12 to C7 resulted in little or no tumor accumulation and rapid clearance of the compound in tumor-bearing rats within 24 h of administration. Increasing the chain length had the opposite effect, with the C15 and C18 analogues displaying delayed plasma clearance and enhanced tumor uptake and retention in tumor-bearing rats. Tumor uptake displayed by propanediol analogues NM-412 and NM-413 was accompanied by high levels of liver and abdominal radioactivity 24 h postinjection to tumor-bearing rats. Addition of a 2-O-methyl moiety to the propanediol backbone also retarded tumor uptake significantly. A direct comparison between NM-404 and its predecessor, NM-324, in human PC-3 tumor bearing immune-compromised mice revealed a dramatic enhancement in both tumor uptake and total body elimination of NM-404 relative to NM-324. On the basis of imaging and tissue distribution studies in several rodent tumor models, the C18 analogue, NM-404, was chosen for follow-up evaluation in human lung cancer patients. Preliminary results have been extremely promising in that selective uptake and retention of the agent in tumors is accompanied by rapid clearance of background radioactivity from normal tissues, especially those in the abdomen. These results strongly suggest that extension of the human trials to include other cancers is warranted, especially when NM-404 is radiolabeled with iodine-124, a new commercially available positron-emitting isotope. The relatively long physical half-life of 4 days afforded by this isotope appears well-suited to the pharmacodynamic profile of NM-404.
- Pinchuk, Anatoly N.,Rampy, Mark A.,Longino, Marc A.,Skinner, R. W. Scott,Gross, Milton D.,Weichert, Jamey P.,Counsell, Raymond E.
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p. 2155 - 2165
(2007/10/03)
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- Radioactive iodine-labeled compound
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A radioactive iodine-labeled compound represented by the following formula wherein X represents a radioactive iodine atom which may substitute at an arbitrary position on the benzene ring (preferably 123I, 125I and the like.), n repr
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Page/Page column 4
(2008/06/13)
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- Double elimination protocol for convenient synthesis of dihalodiphenylacetylenes: Versatile building blocks for tailor-made phenylene-ethynylenes
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Dihalodiphenylacetylenes are conveniently synthesized by a double elimination reaction of β-substituted sulfones which are readily obtained from halogen-substituted benzyl sulfone and benzaldehyde derivatives. Halogens can be incorporated at any desired positions in the diphenylacetylene skeleton simply by choosing the substitution position of the halogen on the aromatic rings of the starting compounds. The diphenylacetylenes with different halogen substituents thus obtained undergo sequential carbon-carbon bond formations due to the different reactivities of the halogens. Thus, various moieties can be incorporated on the diphenylacetylene skeleton at whichever positions so that a variety of tailor-made phenylene-ethynylenes with regulated structure and composition could be designed.
- Orita, Akihiro,Miyamoto, Kazuhiko,Nakashima, Mikio,Ye, Fangguo,Otera, Junzo
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p. 767 - 776
(2007/10/03)
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- π-extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge-transfer complexes
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The conjugate (E)- and (Z)-(4′-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4′-pyridylethenyl-4-phenyl-β-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4′-pyridylethenyl)-4-phenyl]-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono- and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD.
- Rodríguez, J. Gonzalo,Martín-Villamil, Rosa,Lafuente, Antonio
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p. 1021 - 1032
(2007/10/03)
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- Polyfluorenes with polyphenylene dendron side chains: Toward non-aggregating, light-emitting polymers
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A polyfluorene 12 has been prepared in which bulky polyphenylene dendrimer substituents suppress formation of long wavelength emitting aggregates, thus giving a polymer with pure blue emission. Absorption-and emission spectra and molecular modeling confirm that the bulky dendrimer side chains do not cause extra torsion between the fluorene units. New polyfluorenes with 9,9-diaryl substituents have been prepared to determine the minimum size of substituent necessary for aggregation suppression. An LED using 12 has been demonstrated to produce blue emission with onset voltages below 4 V.
- Setayesh,Grimsdale,Weil,Enkelmann,Muellen,Meghdadi,List,Leising
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p. 946 - 953
(2007/10/03)
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- Process for producing N-biphenylmethylthiadiazoline derivative or salt thereof and intermediate for producing the same
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Described is a process for producing an N-biphenyl-methylthiadiazoline derivative (7) in accordance with the reaction formula described below. According to the process of the present invention, it is possible to produce a compound (7) advantageously from the industrial viewpoint. STR1
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- TETRAHYDROPYRIDINE DERIVATIVES AS DOPAMINE RECEPTOR SUBTYPE LIGANDS
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A class of substituted 1,2,3,6-tetrahydropyridine derivatives are disclosed that are ligands for dopamine receptor subtypes within the body. These compounds are therefore useful in the treatment and/or prevention of disorders of the dopamine system, in particular schizophrenia or depression.
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- Solid-Phase Synthesis of Biaryls via the Stille Reaction
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The solid-phase synthesis of biphenyls by heterogenous cross-coupling of trialkylphenylstannanes with aryl electrophiles is described.Tributylphenyltin attached by an amide bond to the Rink amide resin undergoes palladium-catalyzed coupling with aryl triflates and aryl iodides to produce after acid cleavage 4-biphenylacetamide in 3-15percent yield. 4-Iodophenylacetic acid attached to the Rink amide resin by an amide bond also undergoes heterogeneous palladium-catalyzed coupling with trialkylphenyltins to give after acid cleavage of the support 4-biphenylacetamide in 21-33percent yield. 4-Iodobenzylbromide was then attached to the photocleavable (+/-)-2-methoxy-5--1-oxopropyl>phenylacetamide (NpSSMpact) resin through the formation of a thioether bond.Both substituted and unsubstituted trimethylphenyltins were shown to undergo palladium-catalyzed Stille coupling with the resin bound aryl iodide to give after photolytic cleavage biphenyls containing no residual amide, carboxylic acid, or alcohol appendages.
- Forman, Frank W.,Sucholeiki, Irving
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p. 523 - 528
(2007/10/02)
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- Solid-Phase Synthetic Methods in Combinatorial Chemistry
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The gel-phase carbon NMR spectra of various polymer supports are evaluated as to their suitability in the production of non-peptide combinatorial libraries. The solid-phase synthesis of biphenyls as scaffolds for the production of combinatorial libraries is also described. Both substituted and unsubstituted trialkylphenyltins were shown to undergo heterogenous palladium-catalyzed Stille coupling with aryl electrophiles to give after photolytic cleavage using the NpSSMpact linker biphenyls containing no residual amide, carboxylic acid, or alcohol appendages.
- Sucholeiki, Irving
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p. 618 - 630
(2007/10/03)
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- Synthesis of an unnatural product - 4,4′ biaryl formation as a macrocyclisation step
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A novel macrocycle featuring a crown ether ring, amide functionality and a rigid biaryl unit has been prepared as a potential receptor for small peptidic guests. The synthesis of the macrocycle includes a palladium catalysed biaryl formation as the ring-closing step.
- Patel, Hitesh K.,Kilburn, Jeremy D.,John Langley,Edwards, Peter D.,Mitchell, Tim,Southgate, Robert
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p. 481 - 484
(2007/10/02)
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- ORGANIC PHOSPHORUS COMPOUNDS 91. SYNTHESIS AND PROPERTIES OF 1-AMINO-2-ARYLETHYLPHOSPHONIC AND -PHOSPHINIC ACIDS AS WELL AS -PHOSPHINE OXIDES
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The preparation, physical and spectroscopic properties of 1-amino-2-arylethylphosphonic, and -phosphinic acids as well as -phosphine oxides, the phosphorus analogues of phenylalanine are described, and the reactions of 1-amino-2-(4-fluorophenyl)ethylphosphonates with acetals, isocyanides, esters, acid anhydrides, activated aromatic nitro- and halogen compounds, and with N-protected alanine are reported.It is shown that several of the 1-amino-2-arylethylphosphonic acids are strong inhibitors of PAL and anthocyanin synthesis and also are quite active botryticides.Among the active compounds were 1-amino-2-(4-fluorophenyl)ethylphosphonic acid, 3f, and the methyl-substituted compounds 3k, 3l, and 3m.The fluoroderivative 3f was also effective as a seed-dressing agent in barley showing a 100percent protection against the fungus Fusarium nivale at 600 ppm.
- Maier, Ludwig
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- Synthesis and biological evaluation of [125I]- and [123I]-4-iododexetimide, a potent muscarinic cholinergic receptor antagonist
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A series of halogenated racemic analogues of dexetimide (1) was synthesized and their affinity for the muscarinic cholinergic receptor measured. One analogue, 4-iododexetimide (21), was efficiently labeled with 125I and 123I at high
- Wilson,Dannals,Ravert,Frost,Wagner Jr.
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p. 1057 - 1062
(2007/10/02)
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