Schinortriterpenoids: A Case Study in Synthetic Design

Li, Xin; Cheong, Paul Ha‐Yeon; Carter, Rich G.

doi:10.1002/anie.201609372

Cited by 30 publications

(19 citation statements)

References 92 publications

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“…[ 21,22 ] In lieu of the above mentioned activities, the synthesis of different furanones, their derivatives, and their applications in the area of medicine have drawn considerable attention in recent years. [ 23–28 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Husain

Bhutani

Parveen

et al. 2020

J Chinese Chemical Soc

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A series of benzimidazole‐derived–furanones (4a–l) were synthesized, characterized, and explored for their in vitro anticancer activities. The pharmacokinetic parameters assessed revealed that all the compounds followed the Lipinski's rule of five, making them potential drug candidates. Further, the results of anticancer activity revealed that (E)‐5‐(1H‐benzo[d]imidazol‐2‐yl)‐3‐(3,4,5‐trimethoxybenzylidene)furan‐2(3H)‐one (4a), was active against A549, MCF7, and DU145 with an IC50 values of 10.4 ± 0.39, 11.1 ± 0.43, and 10.7 ± 0.19 μM, respectively. While another compound (E)‐5‐(1H‐benzo[d]imidazol‐2‐yl)‐3‐([5‐phenyl]furan‐2‐yl)furan‐2(3H)‐one (4k) also exhibited good activity against A549, MCF7, and DU145 with IC50 values of 11.4 ± 0.39, 9.1 ± 0.43, and 12.7 ± 0.19 μM, respectively. Doxorubicin was used as the standard drug. Further, molecular docking studies were carried out to provide binding mode into the binding sites of vascular endothelial growth factor receptor (VEGFR). Docking scores and binding energies corroborated well with the results of experimental anticancer activity. Pharmacokinetic (ADME) parameters of the potent derivatives were also found to be in an acceptable range. The benzimidazole‐furanonone conjugates seem to be a potential source for the further development of potent cytotoxic agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Husain

Bhutani

Parveen

et al. 2020

J Chinese Chemical Soc

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“…Natural products containing complex three-dimensional structures represent challenging synthetic targets, and compounds of this type have consequently received considerable interest from research groups all over the world 1 – 3 . Notably, cage-shaped natural products have been reported to show several interesting biological activities, and numerous polycyclic terpene 4 – 7 and alkaloid 8 targets of this type have inspired synthetic chemists to develop innovative new strategies to access these compounds. Non-cage-shaped natural products that are capable of being converted to cage-shaped materials also exhibit an interesting range of biological activities, as exemplified by avenaol 9 , shagene A 10 , erythrolide A 11 and arisanlactone C 12 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of avenaol

et al. 2017

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Avenaol, isolated from the allelopathic plant black oat, was the first C20 germination stimulant related to strigolactones. Structurally, it consisted of a bicyclo[4.1.0]heptanone skeleton containing a cyclopropane ring bearing three main chains projecting in the same direction (i.e. all-cis-substituted cyclopropane). Herein, we report the total synthesis of avenaol using a robust strategy involving the formation of an all-cis-substituted cyclopropane via an alkylidenecyclopropane. The key factors in the success of this total synthesis include the Rh-catalysed intramolecular cyclopropanation of an allene, an Ir-catalysed stereoselective double-bond isomerisation, and the differentiation of two hydroxymethyl groups via the regioselective formation and oxidation of a tetrahydropyran based on the reactivity of a cyclopropyl group. This strategy effectively avoids the undesired ring opening of the cyclopropane ring and the formation of a caged structure. Furthermore, this study confirms the proposed structure of avenaol, including its unique all-cis-substituted cyclopropane moiety.

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“…attracted great attention from synthetic chemists [ 3 ] and led to the total syntheses of several members of this family.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Development of Biomimetic Synthesis of Propindilactone G^†

Wang

Chen

et al. 2020

Chin. J. Chem.

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of main observation and conclusion The natural product propindilactone G is a complex Schisandra nortriterpenoid with a unique 5/5/7/6/5 pentacyclic framework. This full paper describes the development of concise biomimetic synthesis of propindilactone G from a known steroid lactone. The key C19-OH intermediate was synthesized via Breslow and Suárez radical remote C-H functionalizations. Wagner-Meerwein rearrangement was subsequently utilized for the expansion of the B ring. To invert the configuration of the C10 tertiary alcohol, an intramolecular peroxide cyclization catalyzed by BF3•Et2O was devised. The 5/5 fused lactone system was then assembled in a biomimetic transesterification/oxa-Michael addition sequence. Our work should provide experimental support for the proposed biosynthetic pathway and facilitate investigation of the biological activities of propindilactone G.

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Schinortriterpenoids: A Case Study in Synthetic Design

Cited by 30 publications

References 92 publications

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Total synthesis of avenaol

Development of Biomimetic Synthesis of Propindilactone G^†

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Schinortriterpenoids: A Case Study in Synthetic Design

Cited by 30 publications

References 92 publications

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives

Total synthesis of avenaol

Development of Biomimetic Synthesis of Propindilactone G†

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Product

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Development of Biomimetic Synthesis of Propindilactone G^†