- Isocoumarin derivative as well as preparation method and medical application thereof
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The invention belongs to the technical field of chemical medicines, and relates to an isocoumarin compound of general formula (I) and a preparation method and medical application, of the isocoumarin compound in preparation of medicines for treating and mo
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Paragraph 0249-0253; 0262-0265
(2020/03/17)
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- Discovery, synthesis, biological evaluation and molecular docking study of (R)-5-methylmellein and its analogs as selective monoamine oxidase A inhibitors
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(R)-5-Methylmellein (5-MM), the major ingredient in the fermented mycelia of the medicinal fungus Xylaria nigripes (called Wuling Shen in Chinese)? was found to be a selective inhibitor against monoamine oxidase A (MAO-A) and might play an important role in the clinical usage of this edible fungus as an anti-depressive traditional Chinese medicine (TCM). Based on the discovery and hypothesis, a variety of (R)-5-MM analogs were synthesized and evaluated in vitro against two monoamine oxidase isoforms (MAO-A and MAO-B). Most synthetic analogs showed selective inhibition of MAO-A with IC50 values ranging from 0.06 to 29 μM, and compound 13aR is the most potent analog with high selectivity (IC50, MAO-A: 0.06 μM; MAO-B: >50 μM). Interestingly, the enzyme kinetics study of 13aR indicated that this ligand seemed to bind in the MAO-A active site according to so-called “tight-binding inhibition” mode. The molecular docking study of 13aR was thereafter performed in order to rationalize the obtained biological results.
- Huang, Chao,Xiong, Juan,Guan, Hui-Da,Wang, Chang-Hong,Lei, Xinsheng,Hu, Jin-Feng
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p. 2027 - 2040
(2019/04/10)
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- Ruthenium-NHC-Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins
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A novel and practical chiral ruthenium-NHC-diamine system is disclosed for the enantioselective hydrogenation of isocoumarins, which provides a new concept to apply (chiral) NHC ligands in asymmetric catalysis. A variety of optically active 3-substituted 3,4-dihydroisocoumarins were obtained in excellent enantioselectivities (up to 99% ee). Moreover, this methodology was utilized in the synthesis of O-methylmellein, mellein, and ochratoxin A.
- Li, Wei,Wiesenfeldt, Mario P.,Glorius, Frank
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supporting information
p. 2585 - 2588
(2017/03/08)
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- Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst
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An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO2 and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp3 C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.
- Zhang, Zhiguang,Gao, Yuan,Liu, Yuan,Li, Jianjun,Xie, Hexin,Li, Hao,Wang, Wei
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supporting information
p. 5492 - 5495
(2015/11/18)
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- Synthesis of (R)-mellein by a partially reducing iterative polyketide synthase
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Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (PR-PKS) as a pentaketide product. Remarkably, despite the head-to-tail homology shared with several fungal and bacterial PR-PKSs, the mellein synthase exhibits a distinct keto reduction pattern in the synthesis of the pentaketide. We present evidence to show that the ketoreductase (KR) domain alone is able to recognize and differentiate the polyketide intermediates, which provides a mechanistic explanation for the programmed keto reduction in these PR-PKSs.
- Sun, Huihua,Ho, Chun Loong,Ding, Feiqing,Soehano, Ishin,Liu, Xue-Wei,Liang, Zhao-Xun
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supporting information; experimental part
p. 11924 - 11927
(2012/09/08)
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- Synthesis of pseudodeflectusin and ustusorane C: Structural revision of aspergione A and B
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The syntheses of racemic and optically active pseudodeflectusin and ustusorane C are described. The 1H-and 13C-NMR data for our synthetic pseudodeflectusin and ustusorane C were identical to those of the corresponding natural product
- Kuramochi, Kouji,Saito, Fumiyo,Nakazaki, Atsuo,Takeuchi, Toshifumi,Tsubaki, Kazunori,Sugawara, Fumio,Kobayashi, Susumu
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experimental part
p. 1635 - 1640
(2011/05/30)
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- Synthesis of (-)-mellein, (+)-ramulosin, and related natural products
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(-)-Mellein, (+)-ramulosin, (-)-O-methylmellein, (-)-6-hydroxymellein, (-)-6-methoxymellein, and (+)-6-hydroxyramulosin were synthesized as optically active forms using one-pot esterification-Michael addition-aldol reaction of δ-hydroxy-α,β-unsaturated aldehyde and diketene as a key step.
- Islam, Md. Sadequl,Ishigami, Ken,Watanabe, Hidenori
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p. 1074 - 1079
(2007/10/03)
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- Synthesis and absolute configuration of (+)-pseudodeflectusin: Structural revision of aspergione B
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We report herein the total synthesis and determination of the absolute configuration of (+)-pseudodeflectusin. The total synthesis of (+)-pseudodeflectusin starting from o-anisic aid was achieved in 11 total steps with an overall yield of 2.0%. The 1
- Saito, Fumiyo,Kuramochi, Kouji,Nakazaki, Atsuo,Mizushina, Yoshiyuki,Sugawara, Fumio,Kobayashi, Susumu
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p. 4796 - 4799
(2007/10/03)
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- COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA
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There is described compounds for use in therapy, said compounds being defined by Formula (1): There is also described an anti-proliferative composition comprising one or more compounds according to Formula (1), and a method of treatment of neoplasia comprising the administration of such a compound or composition.
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Page/Page column 49; 66
(2008/06/13)
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- Addition of lithiated tertiary aromatic amides to epoxides and aziridines: Asymmetric synthesis of (S)-(+)-mellein
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Addition of ortholithiated or laterally lithiated amides to epoxides or aziridines provides, in some cases stereoselectively, products which may cyclise to yield benzopyranones in good enantiomeric excess. Georg Thieme Verlag Stuttgart.
- Clayden, Jonathan,Stimson, Christopher C.,Helliwell, Madeleine,Keenan, Martine
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p. 873 - 876
(2007/10/03)
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- The first stereospecific approach to both enantiomers of mellein
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(R)-(-)-Mellein 1 and its (S)-(+)-antipode 2 are prepared in six steps and ca. 30% overall yield from (R)- and (S)-propylene oxide, 3 and ent-3, respectively.
- Dimitriadis, Christian,Gill, Melvyn,Harte, Michael F.
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p. 2153 - 2158
(2007/10/03)
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- SYNTHESES OF (+)- AND (-)-MELLEIN UTILIZING AN ANNELATION REACTION OF ISOXAZOLES WITH DIMETHYL 3-OXOGLUTARATE
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Naturally occurring dihydroisocoumarins, (+)- and (-)-mellein (2 and 3), metabolites of fungals, Cercospora sp. and Aspergillus sp., etc., were synthesized from the isoxazoles (32) and (33) by the annelation reactions with dimethyl 3-oxoglutarate.
- Takeuchi, Naoki,Goto, Kaori,Sasaki, Yuki,Fujita, Takashi,Okazaki, Kohsuke,et al.
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p. 357 - 374
(2007/10/02)
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- Lithiation of benzene derivatives promoted by β-functionalized alkyl groups. (R)-(-)mellein from (R)-(+)-propylene oxide
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A β-oxyalkyl group and a 3-methoxymethoxy group cooperatively promote the lithiation of the benzene ring at the position 2
- Napolitano, Elio
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p. 455 - 456
(2007/10/02)
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- CHIRAL SYNTHESIS OF (R)-(-)-MELLEIN AND (3R,4aS)-(+)-RAMULOSIN
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By employing an intramolecular Diels-Alder reaction as the key-step, (R)-(-)-mellein 1a (a metabolite of Aspergillus melleus) and (3R,4aS)-(+)-ramulosin 2 (a metabolite of Pestalotia ramulosa) were synthesised from ethyl(R)-3-hydroxybutanoate 3a.
- Mori, Kenji,Gupta, Ashok K.
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p. 5295 - 5300
(2007/10/02)
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