Indolyl-3-acetoxy derivatives of brassinosteroids: synthesis and growth-regulating activity

Litvinovskaya, R. P.; Minin, P. S.; Raiman, M. E.; Zhilitskaya, G. A.; Kurtikova, A. L.; Kozharnovich, K. G.; Derevyanchuk, Michael; Kravets, V. S.; Хрипач, В. А.

doi:10.1007/s10600-013-0643-8

Cited by 14 publications

(3 citation statements)

References 7 publications

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“…Chemically, the equatorial α ‐HO–C(2) is the sterically most accessible among the four secondary OH functions present in brassinolide and castasterone ( Fig. ) . Accordingly, we prepared a number of new C(2) O‐acylated 24‐epicastasterone analogs with the aim to enhance H 2 O solubility and transport compared to the rather insoluble and lipophilic parent steroid, while at the same time protecting the HO–C(2) and possibly also the HO–C(3) group against undesired glycosidation ( Fig.…”

Section: Relative Biological Potency Of Brassinosteroid Derivativesmentioning

confidence: 99%

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Biological Activity of Brassinosteroids – Direct Comparison of Known and New Analogs in planta

Wendeborn

Lachia

Jung

et al. 2017

Helvetica Chimica Acta

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A systematic investigation of structural modifications of brassinosteroids is presented. We describe in detail their synthetic preparation, which includes significant improvements of previously reported protocols as well as access to new analogs with functional modifications of the steroid skeleton and of the C(17)‐attached side chain. We report the biological potency of the prepared brassinosteroid analogs as plant hormones, which were carefully established in the French bean second internode elongation assay and discuss our observations in light of the recently reported structural data detailing the molecular interactions between brassinolide in the trimeric complex with the protein receptors kinases BRASSINOSTEROID INSENSITIVE 1 (BRI1) and SOMATIC EMBRYOGENESIS RECEPTOR KINASE 1 (SERK1). In a further part of this work we describe the preparation of H2O‐soluble pro‐forms of 24‐epicastasterone and we discuss their physical properties, hydrolytic stabilities and biological activity.

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Section: Relative Biological Potency Of Brassinosteroid Derivativesmentioning

confidence: 99%

“…Pro‐forms of 24‐epicastasterone were prepared through chemo‐selective esterification of its equatorial HO–C(2) group, the sterically most accessible among the four OH groups present in this molecule . Thus, we were able to introduce basic, acidic and zwitterionic esters into this position.…”

Section: Synthesis Of Brassinosteroids and Their Analogsmentioning

confidence: 99%

Biological Activity of Brassinosteroids – Direct Comparison of Known and New Analogs in planta

Wendeborn

Lachia

Jung

et al. 2017

Helvetica Chimica Acta

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show abstract

“…Structure-activity relationship studies showed that O-methylation at C-3, C-22, and C-23 did not significantly affect the biological activity in the rice leaf lamina inclination bioassay, whereas C-2 methylated analogs were nearly inactive suggesting an important role of the hydroxyl group at C-2 for bioactivity. This was an incentive for the preparation of indolylacetic acid diester (279) [124]. The acetonide functionalization of both diol groups in brassinolide (which is the most potent agonist of BRI1) resulted in compounds that inhibited the lamina inclination caused by brassinolide.…”

Section: Bs Analogsmentioning

confidence: 99%