Absolute Configuration of Staurosporine By X-Ray Analysis

Funato, Nobuyuki; Takayanagi, Hiroaki; Konda, Yaeko; Toda, Yumiko; Harigaya, Yoshihiro; Iwai, Yuzuru; Ōmura, Satoshi

doi:10.1016/0040-4039(94)88036-0

Cited by 97 publications

(64 citation statements)

References 13 publications

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“…555 Continuing, sugar C-2′-deoxygenation and C-3′-epimerization presents the methylated α-L-digitoxose 68b of RK-286C 556,557 while corresponding sugar C-3′oxidation contributes to a staurosporine analog bearing the C-3′-keto sugar, 3′-keto-2′,3′,6′-trideoxy-α-L-glucose ( 150 ). 558 Subsequent C-3′ sugar transamination and C-3′ sugar amino modification provides a range of analogs including the flagship 3′- N -methyl-4′- O -methyl-α-L-ristosamine ( 45b , staurosporine, 547,559–561 TAN-999, 562 UCNs, 563,564 and RK-1409 565 ) as well as N , N -dimethyl, 566 N -desmethyl, 567 and N -amide derivatives 568 in staurosporines; N -formyl and the corresponding C-3′/C-4′-cyclic carboxamide 45c of ZHD-0501; 569 and N -oxidation to afford the hydroxyl-amino analog ( 226 , associated with two N -hydroxystaurosporine derivatives and 4′-demethyl- N -formyl- N -hydroxystaurosporine) and hydroxylimino analog ( 148 ) of the TAN-1030A series (Fig. 30).…”

Section: Indoles and Indolocarbazolesmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.

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Section: Indoles and Indolocarbazolesmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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“…It exerts antimicrobial, hypotensive, and cytotoxic activity [57]. Staurosporine ( 31 ) is also a potent GSK-3 β inhibitor with a reported IC 50 value of 15 nM (Table 5) [58].…”

Section: Small-molecule Inhibitors Of Glycogen Synthase Kinasementioning

confidence: 99%

Small-Molecule Inhibitors of GSK-3: Structural Insights and Their Application to Alzheimer's Disease Models

Krämer

Schmidt

Monte

2012

International Journal of Alzheimer's Disease

104

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The world health organization (WHO) estimated that 18 million people are struck by Alzheimer's disease (AD). The USA, France, Germany, and other countries launched major programmes targeting the identification of risk factors, the improvement of caretaking, and fundamental research aiming to postpone the onset of AD. The glycogen synthase kinase 3 (GSK-3) is implicated in multiple cellular processes and has been linked to the pathogenesis of several diseases including diabetes mellitus, cancer, and AD. Inhibition of GSK-3 leads to neuroprotective effects, decreased β-amyloid production, and a reduction in tau hyperphosphorylation, which are all associated with AD. Various classes of small molecule GSK-3 inhibitors have been published in patents and original publications. Herein, we present a comprehensive summary of small molecules reported to interact with GSK-3. We illustrate the interactions of the inhibitors with the active site. Furthermore, we refer to the biological characterisation in terms of activity and selectivity for GSK-3, elucidate in vivo studies and pre-/clinical trials.

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“…malvinus RK-1409 [38][39][40]. Poor protein kinase inhibitory activity shown by 49-demethylamino derivatives RK-1409B (13), RK-286C (14), RK-286D (15) [35,36], and MLR-52 (16) [41] clearly stated the importance of methylamino group on the glycon part of staurosporine. Poor protein kinase inhibitory activity shown by 49-demethylamino derivatives RK-1409B (13), RK-286C (14), RK-286D (15) [35,36], and MLR-52 (16) [41] clearly stated the importance of methylamino group on the glycon part of staurosporine.…”

Section: )mentioning

confidence: 99%