- Preparation of the iodine-124 derivative of the Bolton-Hunter reagent ([124I]I-SHPP) and its use for labelling a VEGF antibody as a PET tracer
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This study describes the radioiodination of an antibody specific to the vascular endothelial growth factor (VEGF), VG76e, with [124I]iodine to obtain a novel PET tracer for measurement of angiogenesis. In vitro binding assays showed a significantly higher immunoreactive fraction with the protein labelling reagent N-succinimidyl 3-(4-hydroxy-5-[125I]iodophenyl) propionate ([125I]Bolton-Hunter reagent, [125I]I-SHPP) (34.0 ± 4.0%) as compared with N-succinimidyl 3-[125I]iodobenzoate (10.9 ± 6.4%) or direct radioiodination using [125I]iodide and IodoGen (3.1 ± 3.0%). Consequently, the cyclotron-produced positron-emitting [124I]iodine (T1/2 = 4.2 days) was employed to prepare [124I]I-SHPP. Using an improved radioiodination methodology, [124I]I-SHPP was prepared from sodium [124I] iodide with IodoGen at pH 6.5. The [124I]Bolton-Hunter reagent was isolated with 25-58% (n = 3) radiochemical yield and 88-95% (n = 3) radiochemical purity by the conventional extraction procedure. The conjugate of VG76e with [124I]I-SHPP was prepared with 17-18% (n=3) labelling efficiency and 98% radiochemical purity. The immunoreactive fraction was determined to be 33.5% (n = 2). Copyright
- Glaser, Matthias,Carroll, Veronica A.,Collingridge, David R.,Aboagye, Eric O.,Price, Pat,Bicknell, Roy,Harris, Adrian L.,Luthra, Sajinder K.,Brady, Frank
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Read Online
- Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source
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A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.
- Wu, Zhuo,Wei, Feng,Wan, Bin,Zhang, Yanghui
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supporting information
p. 4524 - 4530
(2021/05/04)
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- Preparation method 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone
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The invention provides a preparation method of 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone, which comprises the following steps of (1) taking compound II as a raw material, adding a halogenating agent and hydrogen peroxide to halogenate to obtain compound III: 3 - X - 4 - hydroxybenzoic acid. (2) The compound III was mixed with 1 - bromo -2 - chloroethane and an alkali metal hydroxide to give compound IV: 3 - X - 4 - (2 - chloroethoxy) phenylpropionic acid. (3) Compound IV was added to nitrobenzene, and an acylation reagent was added to react to give compound V: 3 - X - 4 - (2 - chloroethoxy) phenylpropionyl chloride. (4) To the reaction system, aluminum trichloride was added to react to give compound VI: 4 - X - 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone. (5) Compound VI was added to toluene, and a palladium carbon and sodium acetate aqueous solution were added to catalyze hydrogenation to give compound I: 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone.
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Paragraph 0053-0057
(2021/09/21)
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- PROCESS FOR PRODUCTION OF PHENOL DERIVATIVES SUBSTITUTED WITH IODINE AT ORTHO POSITION
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A process in which a phenol derivative is iodinated to produce a 2-iodophenol or 2,6-diiodophenol derivative substituted with iodine at an ortho position thereof is provided, which does not require any step of recovery of iodine but can produce it at low cost, in high yield and with high quality. A phenol derivative is mixed with a pyridine and hydrogen peroxide or iodic acid as an oxidizing agent, and reacted with molecular iodine. As a result, iodination can be performed very efficiently with iodine in an amount close to the theoretical amount relative to the phenol derivative, and the 2-iodophenol or 2,6-diiodophenol derivative can be obtained in high yield and with high quality.
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Page/Page column 5
(2010/07/06)
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