- Silver-catalyzed intermolecular amination of fluoroarenes
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A novel highly selective Ag-catalyzed intermolecular amination of fluoroarenes has been developed. This transformation starts from readily available 4-carbonyl fluorobenzene and NaN3 or other nitrogen-source, via amination followed by C-F bond cleavage, thus affording the desired 4-carbonyl arylamine products under mild conditions. The reaction is accelerated using a small amount of water. This pathway is distinct from a previously reported radical amination reaction.
- Wang, Yu,Wei, Chenlong,Tang, Ruyun,Zhan, Haosheng,Lin, Jing,Liu, Zhenhua,Tao, Weihua,Fang, Zhongxue
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supporting information
p. 6191 - 6194
(2018/09/10)
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- Direct preparation of new organozinc reagents, aminophenylzinc iodides, and their applications
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New organozinc reagents, 4-aminophenyl zinc iodide (A) and 3-aminophenyl zinc iodide (B), have been generated easily and effectively by the direct insertion of active zinc to iodoanilines which possess acidic protons. The subsequent coupling reactions of the organozincs with various acid chlorides turned out to be an efficient tool for the preparation of aminophenyl ketones.
- Jung, Hye-Soo,Kim, Seung-Hoi
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p. 1004 - 1006
(2015/02/19)
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- SULFONAMIDE DERIVATIVE AND MEDICINAL USE THEREOF
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Provided are sulfonamide derivatives of a specific chemical structure in which a sulfonamide group having, as a substituent, a phenyl group or a heterocyclic group having a hetero atom(s) as a constituent element(s) is present at its terminal, and pharmaceutically acceptable salts thereof. These compounds are novel compounds having excellent α4 integrin-inhibitory action.
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Paragraph 0858-0859
(2015/02/25)
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- Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides
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A number of structural analogues of the known toxicant para- aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 ± 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity.
- Rennison, David,Conole, Daniel,Tingle, Malcolm D.,Yang, Junpeng,Eason, Charles T.,Brimble, Margaret A.
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supporting information
p. 6629 - 6635
(2014/01/06)
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- Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyelooctylpyranones
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Recently, cyclooctylpyranone derivatives with m-carboxamide substituents (e.g. 2c) were identified as potent, nonpeptidic HIV protease inhibitors, but these compounds lacked significant antiviral activity in cell culture. Substitution of a sulfonamide group at the meta position, however, produces compounds with excellent HIV protease binding affinity and antiviral activity. Guided by an iterative structure-based drug design process, we have prepared and evaluated a number of these derivatives, which are readily available via a seven-step synthesis. A few of the most potent compounds were further evaluated for such characteristics as pharmacokinetics and toxicity in rats and dogs. From this work, the p-cyanophenyl sulfonamide derivative 35k emerged as a promising inhibitor, was selected for further development, and entered phase I clinical trials.
- Skulnick, Harvey I.,Johnson, Paul D.,Aristoff, Paul A.,Morris, Jeanette K.,Lovasz, Kristine D.,Howe, W. Jeffrey,Watenpaugh, Keith D.,Janakiraman, Musiri N.,Anderson, David J.,Reischer, Robert J.,Schwartz, Theresa M.,Banitt, Lee S.,Tomich, Paul K.,Lynn, Janet C.,Horng, Miao-Miao,Chong, Kong-Teck,Hinshaw, Roger R.,Dolak, Lester A.,Seest, Eric P.,Schwende, Francis J.,Rush, Bob D.,Howard, Gina M.,Toth, Lisa N.,Wilkinson, Karen R.,Kakuk, Thomas J.,Johnson, Carol W.,Cole, Serena L.,Zaya, Renee M.,Zipp, Gail L.,Possert, Peggy L.,Dalga, Robert J.,Zhong, Wei-Zhu,Williams, Marta G.,Romines, Karen R.
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p. 1149 - 1164
(2007/10/03)
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- Rapid and efficient synthesis of high-purity fluorine-18 labeled haloperidol and spiperone via the nitro precursor in combination with a new HPLC separation method
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We have completed a convenient synthesis of fluorine-18 labeled butyrophenone neuroleptics from their nitro precursors. Thus, we have developed an efficient single-columm HPLC system using a C18-bonded vinyl alcohol copolymer gel (octadecyl polymer, ODP) column and strongly alkaline solvent systems for purifying of the 18F-labeled butyrophenone neuroleptics obtained by a single-stp 18F-for-nitro exchange reaction. The method has been applied to the synthesis of two typical butyrophenone neuroleptics ([18F]haloperidol and [18F]spiperone) with high purity in high yield. With information concerning the optimized conditions for the 18F-for-nitro exchange reaction, the synthetic method would be useful for synthesizing various 18F-labeled compounds.
- Hashizume, Kazunari,Hashimoto, Naoto,Miyake, Yoshihiro
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p. 681 - 687
(2007/10/03)
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