Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors

Wu, Yangjie; Yang, Jinghua; Dai, Gui-Fu; Liu, Cong-Jun; Tian, Guangjin; Ma, Wei; Tao, Jing‐Chao

doi:10.1016/j.bmc.2009.01.017

Cited by 44 publications

(17 citation statements)

References 29 publications

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“…Isosteviol 1 was obtained from commercially available natural stevioside by acid-catalysed hydrolysis and rearrangement [30]. Diol 2 was synthesised in a stereoselective manner with good yield in a one-pot Aldol-Cannizzaro process in two steps according to literature methods [31,32]. Esterifi-cation of 2 was carried out with diazomethane in Et 2 O resulting in methyl ester 3 [31].…”

Section: Synthesis Of Isosteviol-based 13-aminoalcoholsmentioning

confidence: 99%

“…Diol 2 was synthesised in a stereoselective manner with good yield in a one-pot Aldol-Cannizzaro process in two steps according to literature methods [31,32]. Esterifi-cation of 2 was carried out with diazomethane in Et 2 O resulting in methyl ester 3 [31]. The TBAB-catalysed oxidisation of 3 with TEMPO and NCS gave regioselectively 4 in excellent yield.…”

Section: Synthesis Of Isosteviol-based 13-aminoalcoholsmentioning

confidence: 99%

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Synthesis and Biological Application of Isosteviol-Based 1,3-Aminoalcohols

Nagy

Zupkó

Szakonyi

2021

IJMS

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Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were stereoselectively synthesised. The acid-catalysed hydrolysis and rearrangement of natural stevioside gave isosteviol, which was transformed to the key intermediate methyl ester. In the next step, Mannich condensation of diterpenoid ketone, paraformaldehyde, and secondary amines resulted in the formation of 1,3-aminoketones with different stereoselectivities. During the Mannich condensation with dibenzylamine, an interesting N-benzyl → N-methyl substituent exchange was observed. Reduction of 1,3-aminoketones produced diastereoisomeric 1,3-aminoalcohols. Alternatively, aminoalcohols were obtained via stereoselective hydroxy-formylation, followed by oxime preparation, reduction, and finally, reductive alkylation of the obtained primary aminoalcohols. An alternative 1,3-aminoalcohol library was prepared by reductive amination of the intermediate 3-hydroxyaldehyde obtained from isosteviol in two-step synthesis. Cytotoxic activity of compounds against human tumour cell lines (A2780, SiHa, HeLa, MCF-7 and MDA-MB-231) was investigated. In our preliminary study, the 1,3-aminoalcohol function and N-benzyl substitution seemed to be essential for the reliable antiproliferative activity. To extend their application, a diterpenoid condensed with 2-phenylimino-1,3-thiazine and -1,3-oxazine was also attempted to prepare, but only formation of thioether intermediate was observed.

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Section: Synthesis Of Isosteviol-based 13-aminoalcoholsmentioning

confidence: 99%

Section: Synthesis Of Isosteviol-based 13-aminoalcoholsmentioning

confidence: 99%

Synthesis and Biological Application of Isosteviol-Based 1,3-Aminoalcohols

Nagy

Zupkó

Szakonyi

2021

IJMS

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“…Another expanded series of compounds containing hydroxyl, a hydroxymethyl group and heteroatom-containing frameworks fused with the isosteviol structure were synthesized and was found to inhibit α-glucosidase with moderate to good activity. The next lead compound that was further investigated was the indole derivative (Figure 3C) with the highest activity [174].…”

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent isosteviol derivatives. It has potential biological applications and improves the field of medicinal chemistry by designing novel drugs with the ability to cope against resistance developing diseases. The outstanding advancement in the design and synthesis of isosteviol and its derivative has proved its effectiveness and importance in the field of medicinal chemical research. The present review is an effort to integrate recently developed novel drugs syntheses from isosteviol and potentially active pharmacological importance of the isosteviol derivatives covering the recent advances.

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“…Based on our previous research [33,34], the special features of isosleviol have been invoked our interest: hydrophobic polycyclic skeleton and chiral concave structure consist of the cis-junction of the 19-carboxyl group and D cyclopentane rings (Fig. 1).…”

Section: Synthesis Of Catalystsmentioning

confidence: 99%

Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media

Wang

et al. 2011

Catal Lett

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Chiral amphiphilic conjugate catalysts were designed and synthesized by covalently connecting L-proline with an inexpensive natural product, isosteviol. These catalysts demonstrated remarkable efficiency in the asymmetric a-aminoxylation of aldehydes and ketones using nitrosobenzene in phosphate buffer solution, resulting in good to high yields and excellent enantioselectivities without using any additives. At pH 9.1, the amphiphilic catalysts showed a pH responsive ability in phosphate buffer solution, which facilitated the excellent O-selectivity reactions, illustrating a viable approach for the development of asymmetric supra-molecular catalysts.

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Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors

Cited by 44 publications

References 29 publications

Synthesis and Biological Application of Isosteviol-Based 1,3-Aminoalcohols

Synthesis and Biological Application of Isosteviol-Based 1,3-Aminoalcohols

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media

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