Structure-Antinociceptive Activity Studies of Incarvillateine, a Monoterpene Alkaloid from Incarvillea sinensis

Nakamura, Motoyuki; Chi, Yu‐Ming; Yan, Wen‐Mei; Yonezawa, Akihiko; Nakasugi, Yumiko; Yoshizawa, Toyokichi; Hashimoto, Fumio; Kinjo, Junei; Nohara, Toshihiro; Sakurada, Shinobu

doi:10.1055/s-2001-11512

Cited by 56 publications

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“…The IR peak at 3392 cm -1 suggested the presence of hydroxyl groups. A secondary amide carbonyl group was deduced from the IR absorption at 1643 and 1535 cm -1 and the 13 (Table 1) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…The stereochemistry of C-2, -3, -4, and -2′ were determined to be S, S, R, and R, respectively, by comparing the 13 C NMR data and the optical rotation with those of compounds 11 and 12 (Table 3, Fig. 4) (30,31).…”

Section: Resultsmentioning

confidence: 99%

“…IR spectra were recorded on a PerkinElmer Spectrum One spectrometer. NMR spectra [ 1 H, 13 C distortionless enhancement by polarization transfer (DEPT), 1 H-1 H COSY, heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiplebond coherence (HMBC), and nuclear Overhauser effect spectroscopy (NOESY) experiments] were obtained on a Bruker Avance 500 (Bruker, Rheinstetten, Germany) at 500 MHz for 1 H NMR and at 125 MHz for 13 rel …”

Section: Methodsmentioning

confidence: 99%

“…Plants of this genus are used in Chinese folk medicine to treat rheumatism and to relieve pain (1). Previous chemical investigation of this genus led to the isolation of alkaloids with antinociceptive activity from I. sinensis and I. delavayi (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), iridoids and their glycosides (14,15) from I. olgae, and a novel monoterpene glycoside (dissectol A) from I. dissectifoliola (16,17). A bacteriostatic compound, argutone, together with ursolic acid and hentriacontane, was isolated from I. arguta, which is used to treat hepatitis and infectious diseases (18,19).…”

mentioning

confidence: 99%

“…Herein we report the isolation and structure elucidation of (2), and eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-D-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10) from the aqueous ethanolic extract of roots of I. arguta.…”

mentioning

confidence: 99%

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Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Luo

et al. 2004

Lipids

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Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxy- (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-D-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [ 1 H NMR, 13 C NMR (distortionless enhancement by polarization transfer), 1 H-1 H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Luo

et al. 2004

Lipids

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Totalsynthese und Strukturrevision der Piperarborenine: Photochemie trifft auf C‐H‐Aktivierung

Frébault

Maulide

2012

Angewandte Chemie

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Aktivieren und Wiederholen: Die Aktivierung von C(sp3)-H-Bindungen ist eine attraktive Umwandlung, da zügig molekulare Komplexität auf Kosten der einfachsten und am leichtesten zugänglichen organischen Bindung aufgebaut wird. Kürzliche Beiträge nutzten diesen Ansatz zur Kupplung an kleine Kohlenstoffringe, z. B. zur sequenziellen C-H-Aktivierung in der eleganten Totalsynthese der Piperarborenine (siehe Schema)

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Fulvenes as Effective Dipolarophiles in Copper(I)‐Catalyzed [6+3] Cycloaddition of Azomethine Ylides: Asymmetric Construction of Piperidine Derivatives

Teng

Wang

2013

Angewandte Chemie

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Catalytic asymmetric [3+2] cycloaddition of azomethine ylides is one of the best methods for constructing enantioenriched heterocyclic pyrrolidines, [1] and extensive studies have been conducted on the use of various electron-deficient alkenes as the 2p synthons over the past decade.[2] However, although there are elegant and creative azomethine-ylideinvolved cycloaddition reactions toward the construction of five-membered pyrrolidine architectures, [1,2] the direct catalytic asymmetric approach to enantioenriched six-membered heterocyclic piperidines, which are prevalent scaffolds that serve as the core structures of natural alkaloids and bioactive molecules, [3] has met with little success, [4] and we believe this represents a considerable challenge.In 2003, Hong et al. [5] reported a [6+3] cycloaddition of azomethine ylides with fulvenes [6] , in which fulvenes served as 6p components, thus leading to the synthesis of racemic sixmembered piperidine derivatives. However, there is a lack of catalytic asymmetric [6+3] cycloadditions which tolerate variations in both the azomethine ylides and fulvenes. Stimulated by the biological significance of piperidine derivatives and the challenging synthetic difficulties associated with enantio-and diastereoselectivity control, we questioned whether fulvenes containing no electron-withdrawing groups could be employed as efficient 6p dipolarophiles and provide a straightforward and asymmetric approach to enantioenriched piperidines. Very recently, one example on the asymmetric cycloaddition of unsymmetrical fulvenes and azomethine ylides has been published concurrently with the preparation of the present manuscript.[7] Herein, we report the Cu I /TF-BiphamPhos-catalyzed asymmetric synthesis of highly substituted piperidines by the [6+3] cycloaddition of azomethine ylides with various fulvenes (Scheme 1, right), and subsequent transformations which allow facile access to enantioenriched fused polycyclic piperidine derivatives without loss in diastereoselectivity and enantioselectivity.For our initial studies, the readily available fulvene 2 a [8] was chosen as the model 6p component. Initially we began our investigations by examining the ability of Cu I /TFBiphamPhos and Ag I /TF-BiphamPhos [9] complexes to probe the possibility of an asymmetric variant of this challenging [6+3] cycloaddition reaction employing the N-(4-chlorobenzylidene)glycine methyl ester 3 a as the dipole precursor (Table 1). To our delight, the reaction was completed in less than 24 hours with AgOAc/(S)-TF-BiphamPhos (1 a) as the catalyst and Et 3 N as the base in dichloromethane at room temperature, thus yielding the expected six-membered heterocyclic piperidine 4 a with excellent diastereoselectivity and 36 % ee (Table 1, entry 1). Neither [3+2] nor regioisomeric [6+3] cycloadducts were observed although the by-product [10] formed by self-cycloaddition of 3 a was isolated in 10 % yield. The cycloadduct 4 a is formed exclusively and no [1,5] Hshift [11] occurred, probably because most of the substit...

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Structure-Antinociceptive Activity Studies of Incarvillateine, a Monoterpene Alkaloid from Incarvillea sinensis

Cited by 56 publications

References 0 publications

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Totalsynthese und Strukturrevision der Piperarborenine: Photochemie trifft auf C‐H‐Aktivierung

Fulvenes as Effective Dipolarophiles in Copper(I)‐Catalyzed [6+3] Cycloaddition of Azomethine Ylides: Asymmetric Construction of Piperidine Derivatives

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