79950-85-9Relevant articles and documents
Synthesis of sorbicillinoid analogues with anti-inflammation activities
Ding, Wenjuan,Li, Xiaosan,Tang, Jinshan,Tian, Danmei,Wang, Fangfang,Xu, Zhipeng,Zhang, Meng,Zhang, Youwei
, (2022/01/06)
Recently, we demonstrated potential anti-inflammatory effects of sorbicillinoids isolated from marine fungi. Here, we report the synthesis of a series of new sorbicillinoid analogues and assessed their anti-inflammatory activities. Our results reveal that side chain substitution with (E)-2-butenoyl, (E)-3-(4-fluorophenyl)-2-propenoyl, and (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl significantly enhanced the inhibitory effects of the derivatives on nitric oxide (NO) production and inducible NO synthesis (iNOS) expression stimulated by lipopolysaccharides (LPS) in mouse macrophage. Further chemical derivatization shows that the monomethylresorcinol skeleton worked better than the dimethylresorcinol skeleton in inhibiting LPS-induced inflammatory response in cultured cells. Among the 29 synthesized sorbicillinoid analogues, compounds 4b and 12b exhibited the strongest anti-inflammatory activities, holding the promise of being developed into lead compounds that can be explored as potent anti-inflammation agents.
Bypassing Biocatalytic Substrate Limitations in Oxidative Dearomatization Reactions by Transient Substrate Mimicking
Milzarek, Tobias M.,Einsiedler, Manuel,Aldemir, Hülya,D'Agostino, Paul M.,Evers, Julia K.,Hertrampf, Gesa,Lamm, Katharina,Malay, Mert,Matura, Anke,Müller, Jonas I.,Gulder, Tobias A. M.
supporting information, p. 4520 - 4524 (2019/06/27)
Enzymatic oxidative dearomatization is an efficient way to generate chiral molecules from simple arenes. One example is the flavin-dependent monooxygenase SorbC involved in sorbicillinoid biosynthesis. However, SorbC requires a long-chain keto substituent at its phenolic substrate, thus preventing its application beyond the synthesis of natural sorbicillinoids or close structural analogues. This work describes an approach to broaden the accessible product spectrum of SorbC by employing an ester functionality mimicking the natural substrate structure during enzymatic oxidation.
Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization
Sib, Anna,Gulder, Tobias A. M.
supporting information, p. 12888 - 12891 (2017/09/14)
Natural products are a virtually inexhaustible source of small molecules with spectacular molecular architectures and biomedical potential. Their structural complexity generates formidable challenges to total synthesis but often also precludes time- and resource-efficient, stereoselective synthetic access. Biosynthetically, nature frequently uses dimerization and oligomerization reactions to produce highly challenging frameworks from simple starting materials. Impressive examples are the bisorbicillinoids, a family of fungal natural products thought to originate from the polyketide precursor sorbicillin. Utilizing the recombinant oxidoreductase SorbC from the sorbicillin biosynthetic gene cluster, a robust, fully stereoselective synthesis of bisorbicillinoid natural products and unnatural side-chain analogues was developed.
Biomimetic Total Synthesis of Bisorbicillinol, Bisorbibutenolide, Trichodimerol, and Designed Analogues of the Bisorbicillinoids
Nicolaou,Vassilikogiannakis, Georgios,Simonsen, Klaus B.,Baran, Phil S.,Zhong, Yong-Li,Vidali, Veroniki P.,Pitsinos, Emmanuel N.,Couladouros, Elias A.
, p. 3071 - 3079 (2007/10/03)
The bisorbicillinoids are a growing class of novel natural products endowed with unique biological activity and are associated with fascinating hypotheses for their biosynthesis. A full account of our biomimetic explorations toward the bisorbicillinoids including the total syntheses of bisorbicillinol (1), bisorbibutenolide (2), and trichodimerol (4) from sorbicillin (3) is disclosed. Utilizing the novel dimerization reactions discovered and fine-tuned en route to 1 and 4, several analogues of these natural products have been synthesized. Furthermore, studies on the scope of these novel cycloaddition reactions and the isolation of a number of unexpected products along with proposed mechanisms for their formation are reported. These findings add to our knowledge of the largely unexplored chemistry of o-quinols and related aromatic systems.
Biomimetic explorations towards the bisorbicillinoids: Total synthesis of bisorbicillinol, bisorbibutenolide, and trichodimerol
Nicolaou,Simonsen, Klaus B.,Vassilikogiannakis, Georgios,Baran, Phil S.,Vidali, Veroniki P.,Pitsinos, Emmanuel N.,Couladouros, Elias A.
, p. 3555 - 3559 (2007/10/03)
Strikingly simple cascade dimerization sequences can be used to assemble the complex frameworks of bisorbicillinoids such as bisorbicillinol (1), bisorbibutenolide (2), and trichodimerol (3). The mechanistic facets of the biomimetic total syntheses of these bioactive natural products were also explored. Inspection of the unique molecular architecture of these compounds reveals that they are likely to be assembled in nature by a dimerization of two oxidized forms of sorbicillin.
UNUSUAL FRIEDEL-CRAFTS REACTIONS, IX. ONE-STEP ORTHO-ACYLATION OF PHENOLS WITH α,β-UNSATURATED ACYL CHLORIDES. SYNTHESIS OF 2'-HYDROXYCHALCONES AND SORBICILLIN ANALOGUES
Bigi, Franca,Casiraghi, Giovanni,Casnati, Giuseppe,Marchesi, Stefania,Sartori, Giovanni,Vignali, Carlo
, p. 4081 - 4084 (2007/10/02)
The reaction of bromomagnesium phenolates 1 in toluene with α,β-unsaturated acyl chlorides 2 at room temperature provides a straightforward highly selective synthesis of α,β-unsaturated 2-hydroxyarylketones 3. 2'-Hydroxychalcones, ortho-sorbylphenols including sorbicillin 3g, and ortho-propiolylphenols were usefully synthesized by this way.This reaction provides a further example of the synthetic versatility of the chelation-controlled approach in the elaboration of phenol derivatives.
