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Langtian Yuan, Jin-Soo Seo,
Nam Sook Kang,
Shahar Keinan,
Sarah E Steele,
Gregory A Michelotti,
William C Wetsel,
David N Beratan,
Young-Dae Gong,
Tong H Lee,
Jiyong Hong
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ABSTRACT: From a screen of small molecule libraries to identify potential therapeutics for psychostimulant abuse, 3-hydroxy-2-(3-hydroxyphenyl)-4H-1-benzopyran-4-ones were shown to be isoform-selective PKC-zeta inhibitors.
Molecular BioSystems 10/2009; 5(9):927-30. · 3.53 Impact Factor
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Jin-soo; Seo,
Yang-Hee; Joo,
Jung Bum; Yi,
Eun Ju; Lee Lee,
Yong-Balk; Cho,
Wie Jong; Kwak,
Jong Yeon; Hwang,
Yong Seog; Jeon,
Hyun Suk; Jeon,
Sung-eun; Yoo,
Cheol Min; Yoon,
Mi-Sook; Dong,
Young-Dae Gong
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ABSTRACT: 2,2-Dimethyl-3,4-dialkoxy-substituted 6-aminobenzopyrans were identified as prolyl 4-hydroxylase inhibitors via a screening process using HSC-T6 and LI 90 cells that express an immortalized rat hepatic stellate cell line and as part of a test of the type I collagen contents employing the ELISA method. A subsequent lead optimization effort based on solid-phase parallel synthesis led to the identification of 2,2-dimethyl-3,4-dialkoxy-substituted 6-aminobenzopyrans as potent inhibitors of prolyl 4-hydroxylase.
Bulletin of the Korean Chemical Society. 01/2006; 27(6):909-917.
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ABSTRACT: [reaction: see text] A library containing 1200 analogues of 2,6-difunctionalized 2-methyl-2H-1-benzopyran was constructed by using a solid-phase synthesis protocol. Polymer-bound 6-amido-, 6-sulfonamido-, and 6-uredo-functionalized 2-hydroxymethyl-2-methylbenzopyrans 10 were prepared as part of a first-generation diversification step by employing reactions of respective acid halides, sulfonyl chlorides, and isocyanates with the amine precursor 7. Transformations of the resin-bound intermediates 10 by reactions with alkyl and acid halides were then used to produce a diverse series of 2,6-difunctionalized 2-methyl-2H-1-benzopyran analogues 12 and 14.
The Journal of Organic Chemistry 12/2005; 70(24):10151-4. · 4.45 Impact Factor
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Bulletin of the Korean Chemical Society. 01/2002; 23(11):1658-1660.
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03/1999;
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ABSTRACT: A new vinyl ether type of linker based on 4-hydroxy phenethyl alcohol is developed for the solid-phase synthesis as demonstrated in the Suzuki type of aryl±aryl coupling reaction for the preparation of various biphenyl tetrazole derivatives. # 2000 Elsevier Science Ltd. All rights reserved. There is an enormous interest in the development of solid-phase synthetic approaches to small molecules, particularly those which embrace biphenyl moiety target molecules. 1 In connection with our research program on the development of angiotensin II receptor antagonist, 2 we needed to prepare all possible regioisomers of biphenyl derivatives and we have an interest in developing synthetic strategies and chemistries applicable to a combinatorial approach to the molecules. 3 We previously reported the solid-phase Suzuki reaction for the synthesis of biphenyltetrazole derivatives using a dehydropyran type linker for various functionalities such as alcohols, imidazoles, and tetrazoles. 4 However, diculties in the preparation of the dihydropyran linker and commercial unavailability prompted us to examine a dierent vinyl ether type linker for the same purposes. A vinyl ether moiety has been used as a protecting group for alcohols, imidazoles, and tetrazole functionality. 5 Herein we would like to report a preliminary result on the design of a new vinyl ether type of a linker 1 and the subsequent solid-phase synthesis, as demonstrated in the Suzuki reaction, 6 for the synthesis of biphenyl derivatives.
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ABSTRACT: A general method developed for the parallel solid-phase synthesis of sn-1,2- and sn-2,3-diacyglycerol derivatives. The technique relies on the use of carboxylic acid-promoted epoxide ring-opening reactions of the glycidyl-bound resin 3. The polymer-bound monoacylglycerol 5, formed in this manner, is transformed to the respective polymer-bound diacylglycerols 7 and 9 by reaction of the free alcohol moiety with a second carboxylic acid under conditions that lead to retention or inversion of C-2 stereochemistry. The sequence is completed by BCl3-promoted cleavage of 7 and 9 to form the sn-1,2- and sn-2,3-diacylglycerols, respectively.
Journal of Combinatorial Chemistry 9(3):366-9. · 3.41 Impact Factor
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ABSTRACT: A 2000-member library of benzopyran analogues was prepared by using a solid-phase synthesis protocol. Polymer-bound 6-alkylaminobenzopyrans 7 were synthesized as part of a first generation diversification step by employing reactions of a variety of alkyl halides with the amine 6. Transformations of the resin-bound intermediates 8 formed in this manner by reactions with acid halides, sulfonyl chlorides, and isocyanates leads to introduction of the second level of diversification found in the series of 6-alkylamino-2-(functionalized-aminomethyl)-2-methyl-2H-1-benzopyran analogues 11 and 12.
Journal of Combinatorial Chemistry 8(6):897-906. · 3.41 Impact Factor
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ABSTRACT: We report the solid-phase library construction of 2000 analogues of 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran. The polymer-bound hydroxyalkoxychromanes 5, produced by nucleophilic reactions with various alcohols on epoxides generated in situ, served as key intermediates for subsequent diversification. Further reactions on these hydroxyalkoxychromanes 5 with various electrophiles, such as alkyl halides and acid halides, produced the desired 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran analogues 9, 10, and 11. The progress of reactions could be monitored as solid-bound intermediates by ATR-FTIR or HR-MAS-NMR spectroscopy. The final compounds, obtained in good yields and high purity upon cleavage from the resins, were characterized by LC/MS, HRMS, (1)H NMR, and (13)C NMR spectroscopy.
Journal of Combinatorial Chemistry 5(5):577-89. · 3.41 Impact Factor
