Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents

Jiang, Juan; Sun, Bin; Wang, Yanyan; Cui, Min; Zhang, Li; Cui, Changzhi; Wang, Yanfeng; Liu, Xigong; Lou, Hongxiang

doi:10.1016/j.bmc.2012.02.004

Cited by 22 publications

(18 citation statements)

References 32 publications

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“…Dr Iwai et al have reported the docking research of marchantin E with influenza PA endonuclease, which provided a very good precedent for the molecular modeling research of marchantins [20]. In a previous study, the macrocyclic bisbibenzyl compound was found to be a colchicine site binder on tubulin [35]. We anticipate that marchantin C should also target the colchicine-binding site in tubulin, due to its bisbibenzyl skeleton and microtubuledepolymerizing activity.…”

Section: Design Of Marchantin C Analoguesmentioning

confidence: 99%

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Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors

Sun

et al. 2016

European Journal of Medicinal Chemistry

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Section: Design Of Marchantin C Analoguesmentioning

confidence: 99%

“…This compound was prepared from 44 by following the procedure reported in the literature [35], for 84 h were detected by the xCELLigence system from Roche according to the manufacturer's protocol. The cells were incubated in RPMI-1640 medium containing 2% FBS at 37 ℃ and 5% CO 2 throughout.…”

Section: Macrocyclic Derivative (88)mentioning

confidence: 99%

Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors

Sun

et al. 2016

European Journal of Medicinal Chemistry

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“…Besides their characteristic odour and pungency, these compounds and their derivatives impart characteristic properties viz. allergic dermatitis, antimicrobial, anti-feedant, insecticidal, nematocidal, piscicidal, anti-radical, anti-thrombin, cytotoxic, neuro-nephro-cardioprotective properties and also possess inhibitory activities against 5lipoxygenase, calmodulin, hyaluronidase, cyclooxygenase, DNA polymerase β, α-glucosidase, calcium and tubulin polymerization [15][16][17][18][19][20][21][22][23][24]. Some bryophytes also function as inhibitor of plant growth and mimicked structural moiety of sex pheromones [25,26].…”

Section: Introductionmentioning

confidence: 99%

Bibenzyls and bisbybenzyls of bryophytic origin as promising source of novel therapeutics: pharmacology, synthesis and structure-activity

Nandy

Dey

2020

DARU J Pharm Sci

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Background The amphibian, non-vascular, gametophyte-dominant, bio-indicator class, bryophytes; with their wide ranges of habitat have attained importance due to their promising medicinal attributions and therapeutic role; mostly aided by presence of aromatic bibenzyl and bisbybenzyl class of compounds. Bibenzyls are steroidal ethane derivatives, resembling the structural moiety of bioactive dihydro-stilbenoids or iso-quinoline alkaloids. These stress triggered secondary metabolites are the byproducts of the flavonoid biosynthetic pathway. Different classes of bryophytes (Bryophyta, Marchantiophyta and Anthocerotophyta) possess different subtypes of bibenzyls and dimeric bisbibenzyls. Among the liverwort, hornwort and mosses, former one is mostly enriched with bibenzyl type constituents as per the extensive study conducted for phytochemical deposit. Considering macrocyclic and acyclic group of bibenzyls and bisbybenzyls, generally marchantin type compounds are reported vividly for significant biological activity that includes neuro-nephro-cardio-protection besides anti-allergic, anti-microbial, anti-apoptotic and cytotoxic activities studied on in-vitro and in-vivo models or on cell lines. Result The critical analysis of reported chemical and pharmaceutical attributions of bibenzyls and bis-bibenzyls yielded detailed report on this compound class along with their application, mode of action, natural source, techniques of synthesis, extraction procedure, isolation and characterization. Further, the structure activity relationship studies and bioactivity of bibenzyls derived from non-bryophytic origin were also summarized. Conclusion This review encompasses prospective biological application of botanical reservoir of this primarily ignored, primeval land plant group where recent technical advances has paved the way for qualitative and quantitative isolation and estimation of novel compounds as well as marker components to study their impact on environment, as bio-control agents and as key leads in future drug designing.

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“…Recently, Jiang et al prepared plagiochin E using an intramolecular McMurry reaction at position a for the macrocyclization (Scheme 1). 19 …”

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Total synthesis of plagiochin G and derivatives as potential cancer chemopreventive agents

Zhou

Tokuda

et al. 2014

Tetrahedron Letters

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A new and efficient total synthesis has been developed to obtain plagiochin G (22), a macrocyclic bisbibenzyl, and four derivatives. The key 16-membered ring containing biphenyl ether and biaryl units was closed via an intramolecular SNAr reaction. All synthesized macrocyclic bisbibenzyls inhibited Epstein-Barr virus early antigen (EBVEA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells and, thus, are potential cancer chemopreventive agents.

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Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents

Cited by 22 publications

References 32 publications

Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors

Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors

Bibenzyls and bisbybenzyls of bryophytic origin as promising source of novel therapeutics: pharmacology, synthesis and structure-activity

Total synthesis of plagiochin G and derivatives as potential cancer chemopreventive agents

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