Synthesis of novel zerumbone derivatives via regioselective palladium catalyzed decarboxylative coupling reaction: a new class of α-glucosidase inhibitors

Ajish, K.R.; Dhanya, B. P.; Joseph, Nayana; Rani, Mubeen; Raghu, K.; Vineetha, Vadavanath Prabhakaran; Radhakrishnan, K. V.

doi:10.1016/j.tetlet.2013.11.110

Cited by 18 publications

(6 citation statements)

References 48 publications

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“…The structures of the known compounds were identified by comparing their spectroscopic data with those reported in the literature (Ajish et al 2014;Santosh Kumar et al 2013).…”

Section: Resultsmentioning

confidence: 99%

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

Bao

Wang

Han

et al. 2015

Natural Product Research

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We report the isolation of a new sesquiterpene, named as syripinol (1), and two known compounds from the volatile oil of the stems of Syringa pinnatifolia, for the first time. The structures of the isolated compounds were elucidated on the basis of spectroscopic methods including UV, IR, ESI-MS, 1D and 2D NMR techniques. The antibacterial activities of the compounds were also evaluated against various bacteria which showed good results.

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“…The structures of the known compounds were identified by comparing their spectroscopic data with those reported in the literature (Ajish et al 2014;Santosh Kumar et al 2013).…”

Section: Resultsmentioning

confidence: 99%

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

Bao

Wang

Han

et al. 2015

Natural Product Research

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“…As described above, many compoundsh ave been provent ob ep otent AGIs in vitro or in vivo. [42,43,45] Though many other compounds have been shown to exert higher inhibitorya ctivity against yeast a-glucosidase, further in vivo investigationsa re neededt op rove their superiority as antidiabetes agents.…”

Section: Discussionmentioning

confidence: 99%

“…Regioselective palladium-catalyzed decarboxylative coupling reaction. [43] Table 8. a-Glucosidase inhibitory activities of macrocyclic compounds.…”

Section: Discussionmentioning

confidence: 99%

“…In 2014, as eries of novel zerumbone derivatives were synthesized as potent AGIs in yields up to 90 %b yu sing regioselective palladium as the catalyst for the decarboxylative coupling reaction ( Figure 6). [43] Amongt he derivatives, compound 79 showst he highest inhibitory activity against baker's yeast a- Table 7. a-Glucosidase inhibitory activities of chromonederivatives.…”

Section: Macrocyclic Compoundsmentioning

confidence: 99%

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Recent Advances in Synthetic α‐Glucosidase Inhibitors

Liu

2017

ChemMedChem

116

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Over the past few years, the number of people diagnosed with type 2 diabetes has increased owing to an unhealthy diet, a limited amount of exercise, and obesity. The search for novel and efficient antidiabetes agents has become an urgent task for scientists. Among the antidiabetes drugs, α-glucosidase inhibitor drugs have been proven to have many advantages over other drugs, and therefore, a large number of new compounds as α-glucosidase inhibitors has recently been reported. In this review, we summarize these newly found α-glucosidase inhibitors and their structure-activity relationships in antidiabetic studies and provide better structures for α-glucosidase inhibitors or even preclinical candidates. Beyond that, some enlightening strategies for the synthesis of relevant compounds are highlighted.

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“…Our next attempt in 1,4‐conjugate addition reaction at C6 of zerumbone involved palladium catalyzed decarboxylative cross‐coupling with functionalized benzoic acids (Scheme 5), [61] inspired by the methodology developed by Myers et al [62] . In our first attempt, zerumbone was treated with 2,4‐dimethoxybenzoic acid in the presence of Pd(O 2 CCF 3 ) 2 as a catalyst, interestingly, an unexpected conjugate addition took place with repositioning of the endocyclic double bond to exocyclic double bond to afford compound 7 .…”

Section: Transition‐metal Catalyzed Transformations Of Functionalized Zerumbone By 14‐conjugate Additionmentioning

confidence: 99%

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

Biji

Prabha

Lankalapalli

et al. 2021

The Chemical Record

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Zerumbone is a naturally occurring humulene type sesquiterpene, isolated from the rhizomes of Zingiber zerumbet (L.) Smith with excellent therapeutic potential and is recognized as a valuable synthon for the construction of diverse array of natural product motifs. In this review, we intended to highlight our achievements in utilizing abundant natural product zerumbone and its derivatives for the development of pharmacologically relevant molecular scaffolds. We provided an account of the transition‐metal catalyzed 1,4‐conjugate addition reactions of zerumbone and its derivatives along with palladium‐catalyzed cross‐couplings, transition metal‐based Lewis acid promoted interrupted Nazarov cyclisation reaction with substituted indoles and transannular cyclizations, photo‐induced transformations of zerumbone and its epoxide.

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Synthesis of novel zerumbone derivatives via regioselective palladium catalyzed decarboxylative coupling reaction: a new class of α-glucosidase inhibitors

Cited by 18 publications

References 48 publications

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

Recent Advances in Synthetic α‐Glucosidase Inhibitors

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

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