- Structure-activity relationship of a series of diaminoalkyl substituted benzimidazole as neuropeptide Y Y1 receptor antagonists
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A series of benzimidazoles (4) was synthesized and evaluated in vitro as potent and selective NPY Y1 receptor antagonists. Substitution of the piperidine nitrogen of 4 with appropriate R groups resulted in compounds with more than 80-fold higher affinity
- Zarrinmayeh, Hamideh,Zimmerman, Dennis M.,Cantrell, Buddy E.,Schober, Douglas A.,Bruns, Robert F.,Gackenheimer, Susan L.,Ornstein, Paul L.,Hipskind, Philip A.,Britton, Thomas C.,Gehlert, Donald R.
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- Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)
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Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.
- Matsuoka, Keitaro,Komami, Narumi,Kojima, Masahiro,Mita, Tsuyoshi,Suzuki, Kimichi,Maeda, Satoshi,Yoshino, Tatsuhiko,Matsunaga, Shigeki
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supporting information
p. 103 - 108
(2021/01/13)
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- Iodinated Choline Transport-Targeted Tracers
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We present a novel series of radioiodinated tracers and potential theranostics for diseases accompanied by pathological function of proteins involved in choline transport. Unlike choline analogues labeled with 11C or 18F that are currently used in the clinic, the iodinated compounds described herein are applicable in positron emission tomography, single-photon emission computed tomography, and potentially in therapy, depending on the iodine isotope selection. Moreover, favorable half-lives of iodine isotopes result in much less challenging synthesis by isotope exchange reaction. Six of the described compounds were nanomolar ligands, and the best compound possessed an affinity 100-fold greater than that of choline. Biodistribution data of 125I-labeled ligands in human prostate carcinoma bearing (PC-3) mice revealed two compounds with a biodistribution profile superior to that of [18F]fluorocholine.
- ?vec, Pavel,Novy, Zbyněk,Ku?ka, Jan,Pet?ík, Milo?,Sedlá?ek, Ond?ej,Kucha?, Martin,Li?ková, Barbora,Medvedíková, Martina,Kolouchová, Kristyna,Groborz, Ond?ej,Loukotová, Lenka,Konefa?, Rafa? ?.,Hajdúch, Marián,Hruby, Martin
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p. 15960 - 15978
(2020/12/23)
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- Ortho-stabilized 18F-azido click agents and their application in PET imaging with single-stranded DNA aptamers
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Azido 18F-arenes are important and versatile building blocks for the radiolabeling of biomolecules via Huisgen cycloaddition ("click chemistry") for positron emission tomography (PET). However, routine access to such clickable agents is challenged by inefficient and/or poorly defined multistep radiochemical approaches. A high-yielding direct radiofluorination for azido 18F-arenes was achieved through the development of an ortho-oxygen-stabilized iodonium derivative (OID). This OID strategy addresses an unmet need for a reliable azido 18F-arene clickable agent for bioconjugation reactions. A ssDNA aptamer was radiolabeled with this agent and visualized in a xenograft mouse model of human colon cancer by PET, which demonstrates that this OID approach is a convenient and highly efficient way of labeling and tracking biomolecules. Markedly apt: A high-yielding direct radiofluorination strategy via ortho-oxygen-substituted iodonium derivatives is described. A ssDNA aptamer (sgc8), labelled with the resulting 18F azido agent through click chemistry, was used for PET imaging and provides the first example for the noninvasive in vivo PET imaging of protein tyrosine kinase 7 (PTK-7).
- Wang, Lu,Jacobson, Orit,Avdic, Din,Rotstein, Benjamin H.,Weiss, Ido D.,Collier, Lee,Chen, Xiaoyuan,Vasdev, Neil,Liang, Steven H.
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supporting information
p. 12777 - 12781
(2015/10/28)
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- Support curvature and conformational freedom control chemical reactivity of immobilized species
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We show that bimolecular reactions between species confined to the surfaces of nanoparticles can be manipulated by the nature of the linker, as well as by the curvature of the underlying particles.
- Zdobinsky, Tino,Sankar Maiti, Pradipta,Klajn, Rafal
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supporting information
p. 2711 - 2714
(2014/03/21)
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- Electric-field-responsive handle for large-area orientation of discotic liquid-crystalline molecules in millimeter-thick films
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Current events: An electric-field-responsive handle (see picture) was developed that enables large-area and millimeter-thick unidirectional orientation of columnarly assembled π-conjugated liquid-crystalline molecules. The handles in the columns are hydrogen-bonded and align along the direction of an applied electric field.
- Miyajima, Daigo,Araoka, Fumito,Takezoe, Hideo,Kim, Jungeun,Kato, Kenichi,Takata, Masaki,Aida, Takuzo
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supporting information; experimental part
p. 7865 - 7869
(2011/10/08)
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- INHIBITORS OF HISTONE DEACETYLASE
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This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I); wherein Y, L, Z, W, X, Q, R1, R2 and R3 are as defined in the specification.
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Page/Page column 121
(2010/11/24)
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- 3-(4-PIPERIDINE-1YLMETHYL-PHENYL)-PROPION ACID-PHENYLAMIDE-DERIVATIVES AND RELATED COMPOUNDS USED IN THE FORM OF MCH ANTAGONISTS (MELANINE CONCENTRATING HORMONE) FOR TREATING EATING DISORDERS
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The invention relates to amid compounds of general formula (I), wherein groups and residuals A, B, b, W, X, Y, Z, R1, R2 and R3 have significances given in a claim 1. In addition, said invention relates to drugs containing at least one type of inventive amid. Because of the antagonist activity of an MCH-receptor, the inventive drugs are suitable for treating metabolic disturbances and/or eating disorders, in particular adiposity, bulimia, anorexia, hyperphagia and diabetes.
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Page/Page column 134
(2008/06/13)
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- Synthesis, receptor potency, and selectivity of halogenated diphenylpiperidines as serotonin 5-HT2a ligands for PET or SPECT brain imaging
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A series of 4′-substituted phenyl-4-piperidinylmethanol and benzoyl-4-piperidine derivatives was synthesized as potential novel serotonin 5-HT2A receptor ligands that can be radiolabeled for in vivo brain imaging. Compounds were prepared by alk
- Fu, Xing,Tan, Ping-Zhong,Kula, Nora S.,Baldessarini, Ross,Tamagnan, Gilles,Innis, Robert B.,Baldwin, Ronald M.
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p. 2319 - 2324
(2007/10/03)
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- Oligonucleotide-directed assembly of materials: Defined oligomers
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A nano-architectural system that has high variability while maintaining component specificity is described. Tetraphenylcyclobutadiene(cyclopentadienyl)cobalt complexes and phenyleneethynylene trimers were synthesized and subsequently modified with oligonu
- Waybright,Singleton,Wachter,Murphy,Bunz
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p. 1828 - 1833
(2007/10/03)
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- 6-phenyl-pyridin-2-ylamine derivatives
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The present invention relates to certain 6-phenyl-pyridin-2-ylamine derivatives that exhibit activity as nitric oxide synthase (NOS) inhibitors, to pharmaceutical compositions containing them and to their use in the treatment and prevention of central nervous system disorders.
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- Supramolecular Phosphoryl Transfer Reactions Mediated by Amidinium Phosphate Ion-Pair Complexes
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In order to build up simplified synthetic models of staphylococcal nuclease two derivatives of 8-phenylnaphthalene-1-carboxamidine equipped with nucleophilic side chains have been prepared (1, 2).After protonation these amidinium alcohols bind phosphodiester anions via hydrogen bonds and react within the ion-pair complexes to give zwitterionic products 27 and 28.The rate accelerations (DMF, 30 deg C) compared to the phosphorylation of noncharged alcohols are 2700-fold (2) and 930-fold (1). - Key Words: Artificial phosphodiesterase / Naphthalene, 1,8-disubstituted / Molecular Recognition / Staphylococcal nuclease, model of / Enzymes / Amidinium phosphate / Ion-Pair Complexes / Guanidine
- Mueller, Gilbert,Duerner, Gerd,Bats, Jan W.,Goebel, Michael W.
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p. 1075 - 1092
(2007/10/02)
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- Electron Transfer Mechanism for Periodic Acid Oxidation of Aromatic Substrates
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Evidence for the involvement of cation radicals during the periodic acid oxidation of aromatic substrates like hydrocarbons, phenolic ethers, phenols etc. has been presented.
- Bhatt, M. V.,Hosur, B. M.
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p. 1004 - 1005
(2007/10/02)
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- Iodo-aryl carbonates for use in methods in radiography
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A method for using iodo-aryl carbonates, such as for example, p-iodo-benzyl carbonates, p-iodo-sec-phenethyl carbonates, p-iodo-phenethyl carbonates, p-iodo-phenyl carbonates, 3-(p-iodophenyl)propyl carbonates, 3-(p-iodophenyl)butyl carbonates, 2-(p-iodobenzyl)butyl carbonates and 2-(p-iodobenzyl)-n-hexyl carbonates, to provide radiopaques for various radiography purposes in connection with such techniques as X-ray applications including myelography, salpingography, lymphography and bronchography. The method first comprises selecting a compound generally categorized as a carbonate and having the general formula STR1 wherein R represents an alkyl group having from 1 to 10 carbon atoms and R' represents an iodinated phenyl linked directly to the ester oxygen or through an alkyl chain consisting of 1 to 3 carbon atoms. An effective amount of a pharmaceutically acceptable carbonate, as defined herein, is then placed into the subject body cavity and the particular X-ray or other study performed of this area.
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- Iodine containing organic carbonates for use as radiographic agents
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Iodo-aryl carbonates, such as for example, p-iodo-benzyl carbonates, p-iodo-sec-phenethyl carbonates, p-iodo-phenethyl carbonates, p-iodo-phenyl carbonates, 3-(p-iodophenyl)propyl carbonates, 3-(p-iodophenyl)butyl carbonates, 2-(p-iodobenzyl)butyl carbonates and 2-(p-iodobenzyl)-n-hexyl carbonates, for use as radiographic media in connection with such techniques as x-ray applications including myelography, salpingography, lymphography and bronchography. An effective quantity of iodinated organic carbonate provides x-ray contrast, and the compounds of the invention may be characterized generally as carbonates having the general formula STR1 wherein R represents an alkyl group having from 4 to 10 carbon atoms and R' represents an iodinated phenyl linked to the ester oxygen through an alkyl chain consisting of 1 to 3 carbon atoms.
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