Literature DB >> 17287126

Synthesis of DL-standishinal and its related compounds for the studies on structure-activity relationship of inhibitory activity against aromatase.

Takahiro Katoh1, Taichi Akagi, Chie Noguchi, Tetsuya Kajimoto, Manabu Node, Reiko Tanaka, Manabu Nishizawa née Iwamoto, Hironori Ohtsu, Noriyuki Suzuki, Koichi Saito.   

Abstract

DL-Standishinal (1), an aromatase inhibitor isolated from Thuja standishii, was synthesized in 15 steps from p-formylanisole via aldol reaction of 12-hydroxy-6,7-secoabieta-8,11,13-trien-6,7-dial (2). In the present study, we found that the aldol condensation of 2 proceeded in excellent yield with the protonic catalyst such as d-camphorsulfonic acid in CH(2)Cl(2). Moreover, structure-activity relationship of 1 and its related compounds was studied and it was revealed that the isomers having cis-configuration on the A/B-ring generally exhibited more potent inhibitory activities against aromatase than those with trans-configuration.

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Year:  2007        PMID: 17287126     DOI: 10.1016/j.bmc.2007.01.031

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  4 in total

Review 1.  Natural products as aromatase inhibitors.

Authors:  Marcy J Balunas; Bin Su; Robert W Brueggemeier; A Douglas Kinghorn
Journal:  Anticancer Agents Med Chem       Date:  2008-08       Impact factor: 2.505

2.  Enantioselective total syntheses of (-)-taiwaniaquinone H and (-)-taiwaniaquinol B by iridium-catalyzed borylation and palladium-catalyzed asymmetric α-arylation.

Authors:  Xuebin Liao; Levi M Stanley; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-01-26       Impact factor: 15.419

3.  Diterpenoids with anti-inflammatory activity from the wood of Cunninghamia konishii.

Authors:  Yu-Chang Chen; Yen-Cheng Li; Bang-Jau You; Wen-Te Chang; Louis Kuoping Chao; Lee-Chiang Lo; Sheng-Yang Wang; Guan-Jhong Huang; Yueh-Hsiung Kuo
Journal:  Molecules       Date:  2013-01-04       Impact factor: 4.411

4.  A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H.

Authors:  Samantha E Shockley; Jeffrey C Holder; Brian M Stoltz
Journal:  Org Lett       Date:  2014-12-09       Impact factor: 6.005

  4 in total

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