- Analysis of functionalization degree of single-walled carbon nanotubes having various substituents
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Introducing substituents onto SWNT sidewalls increases their solubility and tunes their properties. Controlling the degree of functionalization is important because the addition of numerous functional groups on the sidewall degrades their intrinsic useful electronic properties. We examined the synthesis and characterization of sidewall-functionalized SWNTs in this study. The functionalized SWNTs (1R-SWNTs-2R) were prepared in a one-pot reaction of SWNTs with alkyllithium (1RLi) followed by alkyl bromide (2RBr). The functionalized SWNTs were characterized by the absorption and Raman spectroscopy and thermogravimetric analysis. Not only the total number of functional groups introduced on the SWNT sidewall (formula mass: 1R = 2R) but also the ratio of 2R to 1R in the functionalized SWNTs (formula mass: 1R ≠ 2R) having two different substituents were clarified using the relation between results of Raman spectroscopy and thermogravimetric analysis. Results show that the degree of functionalization of 2R to 1R in 1R-SWNTs-2R can be well controlled by the bulkiness of the alkyl groups of 1RLi and 2RBr. Moreover, substituent effects of reductive alkylation and reductive silylation of SWNTs via Birch reduction were investigated.
- Maeda, Yutaka,Saito, Kazuma,Akamatsu, Norihisa,Chiba, Yuriko,Ohno, Seina,Okui, Yumi,Yamada, Michio,Hasegawa, Tadashi,Kako, Masahiro,Akasaka, Takeshi
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Read Online
- Synthesis of functional near infrared pyrrolopyrrole cyanine dyes for optical and photoacoustic imaging
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Fluorescence lifetime and photoacoustic imaging (PAI) provide attractive strategies for in vivo molecular imaging in the near infrared (NIR) region. Pyrrolopyrrole cyanine (PPCy) dyes are promising molecules for these applications. In this study, we synth
- Bai, Mingfeng,Achilefu, Samuel
-
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Read Online
- Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles
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The present work demonstrates the ability of carboxylic acid tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. The optimized reaction conditions involve the use of pTsOH in DCE at 90 °C. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C5 and aryl positions of CPOBD significantly hinders the ring-opening reactions leading to decreased yields of ring-opened products, although high regioselectivity for the Type 3 ring-opened products is still maintained. Herein, the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles are reported.
- Ho, Angel,Pounder, Austin,Koh, Samuel,Macleod, Matthew P.,Carlson, Emily,Tam, William
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p. 1422 - 1430
(2021/12/02)
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- Stereoselective desymmetrizations of dinitriles to synthesize lactones
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Nitriles are important organic functional groups, allowing for installation of nitrogen in organic synthesis. The Pinner reaction transforms nitriles into esters via the imidate group, but in general has previously necessitated harsh acid conditions. This
- Kelley, Amber M.,Frost, Joshua A.,Baber, Tylisha M.,Youngblood, Kala C.,Michishita, Emiri,Bain, Schuyler A.,Caleb Lykins,Petersen, Kimberly S.
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supporting information
(2021/12/17)
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- Amide compounds and uses thereof
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Provided herein are novel amide compounds of formula (I), pharmaceutical compositions comprising same, methods for preparing same, and uses thereof, wherein the definition of each symbol is as described in the description.
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Page/Page column 54
(2021/10/11)
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- Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source
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Palladium-catalyzed C(sp3)–P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp3)–P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent.
- Zhang, Mengyue,Ma, Zhichao,Du, Hongguang,Wang, Zhiqian
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supporting information
(2020/06/29)
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- In vivomonitoring of carbonic anhydrase expression during the growth of larval zebrafish: a new environment-sensitive fluorophore for responsive turn-on fluorescence
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This study monitors the dynamic progress of a newly developed background-free, target responsive strategy; 2,3-dihydroquinolin-4-imine (DQI) that can instantly respond to environmental changes with fluorescence enhancement, revealing a comprehensive platf
- Chen, Chun-Lin,Chen, Hsing-Yin,Chou, Chih-Hung,Kao, Yu-Chen,Lin, Po-Chiao,Wu, Chang-Yi,Zhou, Jun-Qing
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supporting information
p. 11307 - 11310
(2020/10/06)
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- Preparation method of diosgenin ether
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The invention discloses a preparation method of diosgenin ether and belongs to the field of organic chemistry. The preparation method comprises: S1) generating an intermediate C from diosgenin A and acompound B; S2) hydrolyzing the intermediate C to prepare the target product, diosgenin ether (I). The method is less in process steps and simple in reactions, is high in one-step conversion rate, employs low-cost and accessible raw materials, is gentle in reaction conditions, can reach more than 85% in two-step total yield, and is suitable for industrial large-scale production.
- -
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Paragraph 0019; 0037-0038
(2019/03/25)
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- Stereoselective Synthesis of Molecular Square and Granny Knots
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We report on the stereoselective synthesis of both molecular granny and square knots through the use of lanthanide-complexed overhand knots of specific handedness as three-crossing "entanglement synthons". The composite knots are assembled by combining two entanglement synthons (of the same chirality for a granny knot; of opposite handedness for a square knot) in three synthetic steps: first, a CuAAC reaction joins together one end of each overhand knot. Ring-closing olefin metathesis (RCM) then affords the closed-loop knot, locking the topology. This allows the lanthanide ions necessary for stabilizing the entangled conformation of the synthons to subsequently be removed. The composite knots were characterized by 1H and 13C NMR spectroscopy and mass spectrometry and the chirality of the knot stereoisomers compared by circular dichroism. The synthetic strategy of combining building blocks of defined stereochemistry (here overhand knots of λ- or Δ-handed entanglement) is reminiscent of the chiron approach of using minimalist chiral synthons in the stereoselective synthesis of molecules with multiple asymmetric centers.
- Leigh, David A.,Pirvu, Lucian,Schaufelberger, Fredrik
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supporting information
p. 6054 - 6059
(2019/04/26)
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- CERTAIN PLADIENOLIDE COMPOUNDS AND METHODS OF USE
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The present disclosure provides novel pladienolide compounds, pharmaceutical compositions containing such compounds, and methods for using the compounds as therapeutic agents. These compounds may be useful in the treatment of cancers, particularly cancers in which agents that target the spliceosome and mutations therein are known to be useful. Also provided herein are methods of treating cancers by administering at least one compound disclosed herein and at least one additional therapy.
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Page/Page column 221
(2019/11/04)
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- METHODS FOR ADMINISTERING STING AGONISTS
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The present invention relates to methods of treating disease states, including cancer, in a human comprising systemically administering a STING agonist, or a pharmaceutically acceptable salt thereof, to said human.
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Page/Page column 60-61
(2019/04/27)
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- MODULATORS OF STIMULATOR OF INTERFERON GENES (STING) USEFUL IN TREATING HIV
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Disclosed are compounds having the formula: (I-N) wherein q, r, s, A, B, C, RA1, RA2, RB1, RB2, RC1, RC2, R3, R4, R5, R6, R14, R15, R16, and R17, are as defined herein, or a tautomer thereof, or a salt, particularly a pharmaceutically acceptable salt, thereof, along with combinations thereof, all of which are useful in HIV therapies.
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Page/Page column 200
(2019/04/27)
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- MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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Disclosed are compounds having the formula: (I) wherein q, r, s, A, B, C, RA1, RA2, RB1, RB2, RC1, RC2, R3, R4, R5, R6, R14, R15, R16, R17, Rx, and Ry are as defined herein, or a tautomer thereof, or a salt, particularly a pharmaceutically acceptable salt, thereof.
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Page/Page column 145
(2019/04/27)
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- CATIONIC LIPID
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The present invention provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1a) or a pharmaceutically acceptable salt thereof. (In formula (1a), each of L1 and L2 independently represent an alkylene group having 3-10 carbon atoms; each of R1 and R2 independently represent an alkyl group having 4-22 carbon atoms or an alkenyl group having 4-22 carbon atoms; X1 represents a single bond or -CO-O-; and ring P represents one of formulae (P-1) to (P-5).)(In formulae (P-1) to (P-5), R3 represents an alkyl group having 1-3 carbon atoms.)
- -
-
Paragraph 0129-0131
(2019/05/10)
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- Synthesis and antitumor activity of novel pyridinium fullerene derivatives
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Purpose: We have previously reported that some cationic fullerene derivatives exhibited anticancer activity, and they are expected to be a potential lead compound for an anti-drug resistant cancer agent. However, they are bis-adducts and a mixture of multiple regioisomers, which cannot be readily separated due to the variability of substituent positions on the fullerene cage. To overcome this issue, we evaluated the antiproliferative activities of a set of mono-adduct derivatives and examined their structure-activity relationship. In addition, the in vivo antitumor activity of selected derivatives was also examined. Methods: Nineteen pyridinium fullerene derivatives were newly designed and synthesized in this study. Their antiproliferative activities were evaluated using several cancer cell lines including drug-resistant cells. Furthermore, in vivo antitumor activity of several derivatives was investigated in mouse xenograft model of human lung cancer. Results: The derivatives inhibited the proliferation of cancer cell lines, including cisplatin-resistant cells and doxorubicin-resistant cells. It was also shown that compound 10 (10 μM), 13 (10 μM) and cis-14 (10 μM) induced the intracellular oxidative stress. In addition, compound 13 (20 mg/kg) and cis-14 (15 mg/kg) significantly exhibited antitumor activity in mouse xenograft model of human lung cancer. Conclusion: We synthesized a novel set of mono-adduct fullerene derivatives functionalized with pyridinium groups and found that most of them show potent antiproliferative activities against cancer cell lines and some of them show significant antitumor activities in vivo. We propose that these fullerene derivatives serve as the lead compounds for a novel type of antitumor agents.
- Yasuno, Takumi,Ohe, Tomoyuki,Ikeda, Hitomi,Takahashi, Kyoko,Nakamura, Shigeo,Mashino, Tadahiko
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p. 6325 - 6337
(2019/08/28)
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- Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant
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Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.
- Targel, Tom,Ramesh, Palakuri,Portnoy, Moshe
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supporting information
p. 3017 - 3021
(2018/06/27)
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- Genetic control of predominantly error-free replication through an acrolein-derived minor-groove DNA adduct
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Acrolein, anα,β-unsaturated aldehyde, is generated in vivo as the end product of lipid peroxidation and from metabolic oxidation of polyamines, and it is a ubiquitous environmental pollutant. The reaction of acrolein with the N2 of guanine in DNA leads to the formation of γ-hydroxy-1-N2-propano-2′ deoxyguanosine (γ-HOPdG), which can exist inDNAin a ring-closed or a ring-opened form. Here, we identified the translesion synthesis (TLS) DNA polymerases (Pols) that conduct replication through the permanently ring-opened reduced form of γ-HOPdG ((r) γ-HOPdG) and show that replication through this adduct is mediated via Rev1/Polη-, Poli/Polκ-, and Polθ- dependent pathways, respectively. Based on biochemical and structural studies, we propose a role for Rev1 and Poli in inserting a nucleotide (nt) opposite the adduct and for Polsη and κ in extending synthesis from the inserted nt in the respective TLS pathway. Based on genetic analyses and biochemical studies with Polθ, we infer a role for Polθ at both the nt insertion and extension steps of TLS. Whereas purified Rev1 and Polθ primarily incorporate a C opposite (r)γ-HOPdG, Poli incorporates a C or a T opposite the adduct; nevertheless, TLS mediated by the Poli-dependent pathway as well as by other pathways occurs in a predominantly error-free manner in human cells. We discuss the implications of these observations for the mechanisms that could affect the efficiency and fidelity of TLS Pols.
- Yoon, Jung-Hoon,Hodge, Richard P.,Hackfeld, Linda C.,Park, Jeseong,Choudhury, Jayati Roy,Prakash, Satya,Prakash, Louise
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p. 2949 - 2958
(2018/02/28)
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- Total Synthesis of Huperzine R
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A total synthesis of huperzine R was accomplished. Intramolecular cycloaddition of a nitrile oxide and reductive cleavage of the resulting isoxazoline induced sequential cleavage of the C-C and C-O bonds to form the characteristic bicyclic lactam core with an enone moiety. Construction of the butenolide moiety from the enone afforded huperzine R.
- Nomura, Toshimune,Yokoshima, Satoshi,Fukuyama, Tohru
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supporting information
p. 119 - 121
(2018/01/17)
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- HETEROARYL-SUBSTITUTED TRIAZOLES AS APJ RECEPTOR AGONISTS
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Compounds of Formula (I) and Formula (II), pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: where the definitions of the variables are provided herein.
- -
-
Paragraph 0291
(2018/06/12)
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- HETEROCYCLIC AMIDES USEFUL AS PROTEIN MODULATORS
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Disclosed are compounds having the formula (I-N), wherein q, r, s, A, B, C, RA1, RA2, RB1, RB2, RC1, RC2, R3, R4, R5, R6, R14, R15, R16, and R17, are as defined herein, or a tautomer thereof, or a salt, particularly a pharmaceutically acceptable salt, thereof.
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Page/Page column 183; 184
(2017/11/06)
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- Containing piperazinone quinazoline ketone PARP - 1/2 inhibitor and its preparation method, pharmaceutical composition and use thereof (by machine translation)
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The invention discloses a new class of containing piperazinone quinazoline - 2, 4 (1 H, 3 H) - dione PARP - 1/2 inhibitor, and its preparation and pharmaceutical composition and use. Specifically, the invention relates to the general formula I shown containing of the piperazinone quinazoline - 2, 4 (1 H, 3 H) - dione derivatives and their pharmaceutically acceptable salt, and its preparation method, comprising one or more of the compounds of the composition, and the compounds in the preparation, the prevention and/or treatment with PARP - 1/2 of a disease associated with the use of the medicament. (by machine translation)
- -
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Paragraph 0501; 0502
(2017/09/08)
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- Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin
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A general synthetic sequence involving simply prepared starting materials provides rapid access to diverse, novel tricyclic architectures inspired by pleuromutilin. SmII-mediated radical cyclization cascades of dialdehydes, prepared using a new
- Ruscoe, Rebecca E.,Fazakerley, Neal J.,Huang, Huanming,Flitsch, Sabine,Procter, David J.
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supporting information
p. 116 - 119
(2016/01/26)
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- ARGININE METHYLTRANSFERASE INHIBITORS AND USES THEREOF
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Described herein are compounds of Formula (S-I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds described herein are useful for inhibiting arginine methyltransferase activity. Methods of using the compounds for treating arginine methyltransferase-mediated disorders are also described.
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Paragraph 00505
(2016/04/20)
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- Synthesis of Macrocyclic Lactones via Ring Transformation of 4-(ω-Hydroxyalkyl)-1,3-oxazol-5(4H)-ones
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The synthesis of α-benzamido-α-benzyl lactones 23 of various ring size was achieved either via ‘direct amide cyclization’ by treatment of 2-benzamido-2-benzyl-ω-hydroxy-N,N-dimethylalkanamides 21 in toluene at 90 – 110° with HCl gas or by ‘ring transformation’ of 4-benzyl-4-(ω-hydroxyalkyl)-2-phenyl-1,3-oxazol-5(4H)-ones under the same conditions. The precursors were obtained by C-alkylations of 4-benzyl-2-phenyl-1,3-oxazol-5(4H)-one (15) with THP- or TBDMS-protected ω-hydroxyalkyl iodides. Ring opening of the THP-protected oxazolones by treatment with Me2NH followed by deprotection of the OH group gave the diamides 21, whereas deprotection of the TBDMS series of oxazolones 25 with TBAF followed by treatment with HCl gas led to the corresponding lactones 23 in a one-pot reaction.
- Fritschi, Stephan P.,Linden, Anthony,Heimgartner, Heinz
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p. 523 - 538
(2016/07/22)
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- Light-mediated deoxygenation of alcohols with a dimeric gold catalyst
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A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.
- McCallum, Terry,Slavko, Ekaterina,Morin, Mathieu,Barriault, Louis
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supporting information
p. 81 - 85
(2015/02/18)
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- Ultralight mesoporous magnetic frameworks by interfacial assembly of prussian blue nanocubes
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A facile approach for the synthesis of ultralight iron oxide hierarchical structures with tailorable macro- and mesoporosity is reported. This method entails the growth of porous Prussian blue (PB) single crystals on the surface of a polyurethane sponge, followed by in situ thermal conversion of PB crystals into three-dimensional mesoporous iron oxide (3DMI) architectures. Compared to previously reported ultralight materials, the 3DMI architectures possess hierarchical macro- and mesoporous frameworks with multiple advantageous features, including high surface area (ca. 117 m2 g-1) and ultralow density (6-11 mg cm-3). Furthermore, they can be synthesized on a kilogram scale. More importantly, these 3DMI structures exhibit superparamagnetism and tunable hydrophilicity/hydrophobicity, thus allowing for efficient multiphase interfacial adsorption and fast multiphase catalysis.
- Kong, Biao,Tang, Jing,Wu, Zhangxiong,Wei, Jing,Wu, Hao,Wang, Yongcheng,Zheng, Gengfeng,Zhao, Dongyuan
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supporting information
p. 2988 - 2992
(2014/04/03)
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- BOTPPI, a new Wittig salt for the synthesis of 12-(S)-hydroxy- eicosatetraenoic acid [12-(S)-HETE]
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An efficient route to (Z)-(8-benzyloxy-8-oxooct-3-en-1-yl) triphenylphosphonium iodide, or BOTPPI, is disclosed, complete with full experimental details, NMR spectra, and HRMS data. BOTPPI serves as a surrogate for (Z)-(8-methoxy-8-oxooct-3-en-1-yl)triphe
- Christiansen, Michael A.,Andrus, Merritt B.
-
supporting information; scheme or table
p. 4805 - 4808
(2012/09/22)
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- Conjugated 3-(indolyl)- and 3-(azaindolyl)-4-arylmaleimide compounds and their use in tumor treatment
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The present invention relates to 3-(Indolyl)- and 3-(azaindolyl)-4-phenylmaleimide compounds of formula I wherein R1, R2 and R3 are as defined in the description, and the physiologically acceptable salts, solvates and solv
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Page/Page column 16
(2012/07/27)
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- CONJUGATED 3-(INDOLYL)- AND 3-(AZAINDOLYL)-4-ARYLMALEIMIDE COMPOUNDS AND THEIR USE IN TUMOR TREATMENT
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The present invention relates to 3-(Indolyl)- and 3-(azaindolyl)-4-phenylmaleimide compounds of formula (I) wherein R1, R2 and R3 are as defined in the description, and the physiologically acceptable salts, solvates and so
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Page/Page column 23
(2012/07/13)
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- Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles
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The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated SN2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.
- Stokes, Benjamin J.,Opra, Susanne M.,Sigman, Matthew S.
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supporting information; experimental part
p. 11408 - 11411
(2012/09/05)
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- 3-(INDOLYL)- OR 3-(AZAINDOLYL)-4-ARYLMALEIMIDE COMPOUNDS AND THEIR USE IN TUMOR TREATMENT
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The present invention relates to a compound of formula (I) wherein R, R and R are as defined in the description and the physiologically acceptable salts thereof as well as the physiologically acceptable solvates of the compounds of formula I and of the salts thereof. The compounds of formula I are suitable for treating tumors
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Page/Page column 25
(2011/07/07)
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- Design, Synthesis, and Evaluation of 5′-Diphenyl Nucleoside Analogues as Inhibitors of the Plasmodium falciparum dUTPase
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Deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase) is a potential drug target for malaria. We previously reported some 5′-tritylated deoxyuridine analogues (both cyclic and acyclic) as selective inhibitors of the Plasmodium falciparum dUTPase. Mod
- Hampton, Shahienaz E.,Baragana, Beatriz,Schipani, Alessandro,Bosch-Navarrete, Cristina,Musso-Buendia, J. Alexander,Recio, Eliseo,Kaiser, Marcel,Whittingham, Jean L.,Roberts, Shirley M.,Shevtsov, Mikhail,Brannigan, James A.,Kahnberg, Pia,Brun, Reto,Wilson, Keith S.,Gonzalez-Pacanowska, Dolores,Johansson, Nils Gunnar,Gilbert, Ian H.
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experimental part
p. 1816 - 1831
(2012/07/03)
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- UTILIZATION OF NOVEL COMPOUNDS WITH AMYLOID AFFINITY AND METHOD OF PRODUCING THE SAME
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The invention provides a reagent for detecting amyloid deposited in a biological tissue which can detect amyloid in vitro and in vivo with high sensitivity using a compound which has affinity with amyloid and is suppressed in toxicity such as mutagencity. The reagent for detecting amyloid deposited in a biological tissue comprises a compound represented by the following formula (1) or a salt thereof: wherein A1, A2, A3 and A4 independently represent carbon or nitrogen; R1 is a radioactive halogen substituent; R2 is a group selected from the group consisting of hydrogen, hydroxyl group, methoxy group, carboxyl group, amino group, N-methylamino group, N,N-dimethylamino group and cyano group; and m is an integer of 0 to 2, provided that at least one of A1, A2, and A4 represents a carbon, and R1 binds to a carbon represented by A1, A2, A3 and A4.
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- Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes
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(Figure presented) Enantioenriched allenylsilanes are used in three-component propargylatlon reactions with aldehydes and silyl ethers to form syn-homopropargylic ethers that contain an imbedded azide. These materials then undergo thermally Induced intram
- Brawn, Ryan A.,Welzel, Morgan,Lowe, Jason T.,Panek, James S.
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supporting information; experimental part
p. 336 - 339
(2010/03/25)
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- Synthesis and evaluation of bis-thiazolium salts as potential antimalarial drugs
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An innovative therapeutic approach based on the use of dicationic derivatives was previously designed to inhibit the biosynthesis of phosphatidylcholine in Plasmodium spp. Among these, bis-thiazolium salts were shown to block proliferation of the malaria
- Caldarelli, Sergio A.,Duckert, Jean-Frederic,Wein, Sharon,Calas, Michele,Perigaud, Christian,Vial, Henri,Peyrottes, Suzanne
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experimental part
p. 1102 - 1109
(2011/02/22)
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- Heteroatom-directed alkylcyanation of alkynes
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Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the γ-position are found to add across alkynes stereo-and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing β-hydride elimination to allow the alkylcyanation reaction.
- Nakao, Yoshiaki,Yada, Akira,Hiyama, Tamejiro
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supporting information; experimental part
p. 10024 - 10026
(2010/10/04)
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- Structure-activity studies on the nociceptin/orphanin FQ receptor antagonist 1-benzyl-N-{3-[spiroisobenzofuran-1(3H),4′-piperidin-1-yl]propyl} pyrrolidine-2-carboxamide
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Twelve derivatives of the nociceptin/orphanin FQ (N/OFQ) receptor (NOP) antagonist 1-benzyl-N-{3-[spiroisobenzofuran-1(3H),4′-piperidin-1-yl]propyl} pyrrolidine-2-carboxamide (Comp 24) were synthesized and tested in binding experiments performed on CHOsu
- Trapella, Claudio,Fischetti, Carmela,Pela', Michela,Lazzari, Ilaria,Guerrini, Remo,Calo', Girolamo,Rizzi, Anna,Camarda, Valeria,Lambert, David G.,McDonald, John,Regoli, Domenico,Salvadori, Severo
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experimental part
p. 5080 - 5095
(2009/12/24)
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- Total synthesis and cytoprotective properties of dykellic acid
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Small molecule inhibitors of apoptosis hold considerable promise for the treatment of a host of diseases, including neurodegeneration, myocardial infarction, and stroke. Many compounds that delay or prevent apoptotic death either reduce the amount of cellular reactive oxygen species (ROS) or are direct inhibitors of caspases. With the goal of using small molecules to identify novel antiapoptotic targets, we have investigated the cytoprotective activity of the natural product dykellic acid. Described herein is the first total synthesis of dykellic acid, the synthesis of several dykellic acid derivatives, and the evaluation of these compounds in assays related to cell death. We have found that dykellic acid protects cells from death as induced by etoposide and rotenone. Further experiments strongly suggest that dykellic acid does not scavenge ROS or directly inhibit caspase enzymes, and analysis of synthetic derivatives establishes key functional groups of the molecule that are essential for its cytoprotective activity.
- Thompson, Christina M.,Quinn, Catherine A.,Hergenrother, Paul J.
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supporting information; experimental part
p. 117 - 125
(2009/08/16)
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- NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
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The present invention provides a compound which has affinity with amyloid, shows sufficiently rapid clearance from normal tissues and is suppressed in toxicity such as mutagencity. Provided is a compound represented by the following formula (1) or a salt thereof: wherein A1, A2, A3 and A4 independently represents a carbon or nitrogen; R1 is a halogen substituent; R2 is a halogen substituent; and m is an integer of 0 to 2, provided that at least one of R1 and R2 is a radioactive halogen substituent, at least one of A1, A2, A3 and A4 represents a carbon, and R1 binds to a carbon represented by A1, A2, A3 or A4 as well as a low-toxic diagnostic agent comprising a compound represented by the preceding formula or a salt thereof.
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Page/Page column 38
(2009/02/10)
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- Structure-activity relationships of lipopolysaccharide sequestration in guanylhydrazone-bearing lipopolyamines
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The toxicity of Gram-negative bacterial endotoxin (lipopolysaccharide, LPS) resides in its structurally highly conserved glycolipid component called lipid A. Our major goal has been to develop small-molecules that would sequester LPS by binding to the lipid A moiety, so that it could be useful for the prophylaxis or adjunctive therapy of Gram-negative sepsis. We had previously identified in rapid-throughput screens several guanylhydrazones as potent LPS binders. We were desirous of examining if the presence of the guanylhydrazone (rather than an amine) functionality would afford greater LPS sequestration potency. In evaluating a congeneric set of guanylhydrazone analogues, we find that C16 alkyl substitution is optimal in the N-alkylguanylhydrazone series; a homospermine analogue with the terminal amine N-alkylated with a C16 chain with the other terminus of the molecule bearing an unsubstituted guanylhydrazone moiety is marginally more active, suggesting very slight, if any, steric effects. Neither C16 analogue is significantly more active than the N-C16-alkyl or N-C16-acyl compounds that we had characterized earlier, indicating that basicity of the phosphate-recognizing cationic group, is not a determinant of LPS sequestration activity.
- Wu, Wenyan,Sil, Diptesh,Szostak, Michal L.,Malladi, Subbalakshmi S.,Warshakoon, Hemamali J.,Kimbrell, Matthew R.,Cromer, Jens R.,David, Sunil A.
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experimental part
p. 709 - 715
(2009/07/11)
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- β-Iodoallenolates as springboards for annulation reactions
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β-Iodoallenolates II, generated from alkynones I with tetra-n-butylammonlum iodide and a Lewis acid, underwent selective single or double annulation, depending on the Lewis acid promoter. Treatment with TiCl4 gave cyclohexenyl alcohols III, whe
- Ciesielski, Jennifer,Canterbury, Daniel P.,Frontier, Alison J.
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supporting information; experimental part
p. 4374 - 4377
(2009/12/24)
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- The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide
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An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr. The Royal Society of Chemistry 2008.
- Shah, Syed Tasadaque A.,Guiry, Patrick J.
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experimental part
p. 2168 - 2172
(2009/02/01)
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- Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase
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We report the discovery of novel uracil-based acyclic compounds as inhibitors of deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase), an enzyme involved in nucleotide metabolism that has been identified as a promising target for the development of
- Nguyen, Corinne,Ruda, Gian Filippo,Schipani, Alessandro,Kasinathan, Ganasan,Leal, Isabel,Musso-Buendia, Alexander,Kaiser, Marcel,Brun, Reto,Ruiz-Pérez, Luis M.,Sahlberg, Britt-Louise,Johansson, Nils Gunnar,González-Pacanowska, Dolores,Gilbert, Ian H.
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p. 4183 - 4195
(2007/10/03)
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- 5-SUBSTITUTED-4-`(SUBSTITUTED PHENYL)!AMINO!-2-PYRIDONE DEVIATIVES FOR USE AS MEK INHIBITORS
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The present invention relates to 5-substituted-4-(substituted) phenylamino-2-pyridone derivatives of formula (I), pharmaceutical compositions and methods of use thereof as MEK inhibitors. Formula (I) wherein W is formula (II), formula (III), formula (IV),
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- Syntheses of deuterated jasmonates for mass spectrometry and metabolism studies
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Jasmonic acid and its metabolites play an essential role in the regulation of plant development and systemic defense responses. Isotopically labeled standards are required to quantify plant hormones for metabolism studies using mass spectrometry. A conven
- Galka, Patrycja W.,Ambrose, Stephen J.,Ross, Andrew R. S.,Abrams, Suzanne R.
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p. 797 - 809
(2007/10/03)
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- Tandem cyclisations involving α-ketenyl alkyl radicals. New syntheses of the natural triquinanes pentalenene and modhephene
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New synthetic approaches to the angular and propellane sesquiterpene triquinanes (±)-pentalenene 2 and (±)-modhephene 3, respectively, are described. The syntheses are based on tandem cyclisations involving α-ketene alkyl radical intermediates produced fr
- De Boeck, Benoit,Harrington-Frost, Nicole M.,Pattenden, Gerald
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p. 340 - 347
(2007/10/03)
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- Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate
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The diene system of 1α,25-dihydroxy-19-norvitamin D3 was replaced by a stable amide bond. A 3-hydroxypropoxy group, which was effective on enhancing binding affinity of 1α,25-dihydroxyvitamin D3 for vitamin D receptor (VDR), was introduced to the C2-position of the amide type analogue of 1α,25-dihydroxy-19-norvitamin D3. The amide analogue was found to be not suitable for binding to the ligand binding domain of the bovine thymus VDR, and additional modification at the C2-position did not improve the affinity. Potency in induction of HL-60 cell differentiation was evaluated for the novel amide analogues (3a-c).
- Suhara, Yoshitomo,Ono, Keiichiro,Yoshida, Akihiro,Fujishima, Toshie,Saito, Nozomi,Honzawa, Shinobu,Kishimoto, Seishi,Sugiura, Takayuki,Waku, Keizo,Takayama, Hiroaki,Kittaka, Atsushi
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p. 423 - 436
(2007/10/03)
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- Synthesis of DNA triangles with vertexes of Bis(terpyridine)iron(II) complexes
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The synthesis of the terpyridine derivative 1 tethered to a DNA oligonucleotide and its use for the preparation of two-way branched metal-organic modules capable of self-assembling into DNA triangles are described. Copyright
- Choi, Jin Seok,Kang, Chang Won,Jung, Kisung,Yang, Jung Woon,Kim, Yang-Gyun,Han, Hogyu
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p. 8606 - 8607
(2007/10/03)
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- Nitrosated and nitrosylated nonsteroidal antiinflammatory compounds, compositions and methods of use
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The present invention describes novel nitrosated and/or nitrosylated nonsteroidal antiinflammatory compounds, and novel compositions comprising at least one nitrosated and/or nitrosylated nonsteroidal antiinflammatory compound, and, optionally, at least o
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- Dendrimeric organochalcogen catalysts for the activation of hydrogen peroxide: Improved catalytic activity through statistical effects and cooperativity in successive generations
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Dendrimeric polyphenylsulfides, -selenides, and -tellurides are prepared in high yield using propyloxy spacers to connect the phenylchalcogeno groups to the dendrimeric core. The selenides and tellurides catalyze the oxidation of bromide with hydrogen peroxide to give positive bromine species that can be captured by cyclohexene in two-phase systems. The corresponding sulfides show no catalytic activity. The increase in the rate of catalysis followed statistical effects for 1, 6, and 12 phenyltelluro groups. However, the increase in the rate of catalysis exceeds statistical contributions for the first few generations with 1, 3, 6, and 12 phenylseleno groups and suggested cooperativity among phenylseleno groups. The increase in catalytic rate was lost upon replacing all but one phenylseleno group with phenoxy groups. On the basis of H2O2 consumed, the dendrimer with 12 phenylseleno groups has a turnover number of >60 000 mol of H2O2 consumed per mole of catalyst.
- Francavilla,Drake,Bright,Detty
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