Chemistry, Pharmacology, and Clinical Efficacy of the Chinese Nootropic Agent Huperzine A

Kozikowski, Alan P.; Tückmantel, Werner

doi:10.1021/ar9800892

Cited by 147 publications

(75 citation statements)

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“…The hydration reaction, performed in aqueous ethanol at 70 °C, with 5 mol% of 1, allowed the quantitative conversion of 3 to the corresponding amide 4. (−)-Huperzine A (9) is a tricyclic alkaloid produced by the Chinese herb Hupercia serrata [26], with intense contemporary interest in clinical application for treating neurodegenerative diseases [27][28][29]. Several total syntheses of 9 have been reported [27][28][29].…”

Section: Preparation Of Complex [Pth{(pme 2 O) 2 H}(pme 2 Oh)] Firstmentioning

confidence: 99%

“…(−)-Huperzine A (9) is a tricyclic alkaloid produced by the Chinese herb Hupercia serrata [26], with intense contemporary interest in clinical application for treating neurodegenerative diseases [27][28][29]. Several total syntheses of 9 have been reported [27][28][29]. In one of the most recent and scalable (eight steps starting from (R)-4-methyl-cyclohex-2-ene-1-one (6); 35%-45% overall yield), complex 1 was employed to promote the high-yield conversion of advanced nitrile intermediate 7 into amide 8 in aqueous ethanol (Scheme 4) [30].…”

Section: Preparation Of Complex [Pth{(pme 2 O) 2 H}(pme 2 Oh)] Firstmentioning

confidence: 99%

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Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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Abstract:The air-stable hydride-platinum(II) complex [PtH{(PMe2O)2H}(PMe2OH)], reported by Parkins and co-workers in 1995, is the most versatile catalyst currently available for the hydration of C≡N bonds. It features remarkable activity under relatively mild conditions and exceptionally high functional group compatibility, facts that have allowed the implementation of this complex in the synthesis of a large number of structurally complex, biologically active molecules and natural products. In this contribution, synthetic applications of the Parkins catalyst are reviewed.

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Section: Preparation Of Complex [Pth{(pme 2 O) 2 H}(pme 2 Oh)] Firstmentioning

confidence: 99%

Section: Preparation Of Complex [Pth{(pme 2 O) 2 H}(pme 2 Oh)] Firstmentioning

confidence: 99%

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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“…Lycopodium alkaloids [1][2][3] isolated from club mosses of the genus Lycopodium (Lycopodiaceae) exhibit fascinating complex structures and have attracted the attention of synthetic organic chemists [4][5][6][7][8][9][10] as well as pharmacologists because of such potent biological activities as an inhibitory effect on acetylcholinesterase. 11) Recent extensive studies on the chemical constituents in Lycopodium plants have resulted in the isolation of a number of new alkaloids having novel and diverse structures.…”

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confidence: 99%

“…1 H-1 H correlation spectroscopy (COSY) and 1 H-detected heteronuclear multiple quantum coherence (HMQC) spectra indicated the presence of the following three fragments: -CH 2 CH 2 CH 2 -(C1-C3), -CH 2 CH 2 CH 2 -(C9-C11), and -CH 2 CHCH 2 CH(CH 3 )CH 2 -(C6-C8-C15(C16)-C14), as shown by a bold line in Fig. 1.…”

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confidence: 99%

Ten New Lycopodium Alkaloids Having the Lycopodane Skeleton Isolated from Lycopodium serratum THUNB.

et al. 2003

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(10), having lycopodine-related structures, were isolated from the club moss Lycopodium serratum THUNB. and their structures were elucidated on the basis of spectroscopic analysis and/or chemical transformation.Key words alkaloid; Lycopodium; structure elucidation; X-ray crystal structure; NMR; chemical transformation Lycoposerramine-G (2) was obtained as a colorless amorphous powder. HR-FAB-MS analysis gave m/z 280.1893 (MϩH) ϩ (D Ϫ2.0 mmu) and established the molecular formula as C 16 H 25 NO 3 , which was one oxygen atom less than 1 described above. The 1 H-and 13 C-NMR (Table 1) spectra of 2, which resembled those of 1 except for the chemical shifts of the carbons adjacent to nitrogen, indicated that 1 was an N-oxide derivative of 2. Actually, when 2 was treated with one equivalent of m-CPBA, lycoposerramine-F (1) was obtained in 63% yield, thereby establishing the structure of the new alkaloid as formula 2.Lycoposerramine-H (3) was obtained as colorless prisms (mp 227-228°C, sublimation). HR-FAB-MS analysis gave m/z 262.1809 (MϩH) ϩ (D ϩ0.2 mmu) and established the molecular formula as C 16 H 23 NO 2 , which indicated that 3 had one extra unsaturated number compared to common lycopodine-type alkaloids.1 H-and 13 C-NMR spectra (see Table 1) as well as DEPT spectra suggested the presence of one ketone, a trisubstituted olefin bearing a methyl group, one sp 3 quaternary carbon, four sp 3 methines (one of which had a hydroxyl function), and seven sp 3 methylenes. 1 H-1 H COSY and HMQC spectra revealed connectivities as shown by the bold line in Fig. 3. Further, allyl couplings between the olefinic proton (d 5.35, H-8) and methyl protons (d 1.58, H-16) and methylene protons (d 1.98, 2.70, H-14), as well as homoallyl coupling between the methyl protons (H-16) and the methine proton (d 2.52, H-7), indicated the presence of a double bond at the C-8 (d 121.6)-C-15 (d 135.9) position of the lycopodine skeleton. The location of the secondary hydroxyl group was inferred from the HMBC cross-peaks between the proton at d 3.78 (d, Jϭ2.7 Hz) and the carbonyl carbon (d 212.4, C-5) and the methine carbon at d 38.7 (C-4). The structure including the stereochemistry of the secondary hydroxyl group at C-6 was determined by X-ray analysis as formula 3 (Fig. 3). This is the first example of a lycopodine-type alkaloid that has a double bond at the C-8-C-15 position.Lycoposerramine-I (4) showed a molecular ion peak at m/z 261 and the molecular formula, C 16 H 23 NO 2 , which was established by HR-FAB-MS [m/z 262.1802 (MϩH) ϩ , D Ϫ0.5 mmu], was identical with that of 3 described above. Comparison of its1 H-and 13 C-NMR spectra (see Table 1) with those of 3 suggested that the two alkaloids were isomers at the position of the secondary hydroxyl group. The chemical shifts at C-10 (d 35.5), C-11 (d 69.2), and C-12 (d 44.6) in 4 as well as the HMBC cross-peak (Fig. 4) between the low-field proton (d 4.34) and the quaternary carbon at C-13 (d 59.7) indicated that the hydroxyl group existed at the C-11 position. The stereochemistry...

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“…[14][15][16] The success of this strategy is revealed in the total synthesis of naturally occurring anti-Alzheimer product huperzine A. 17 In this article, we…”

Section: Introductionmentioning

confidence: 99%

Domino reaction sequences leading to the formation of 2:2 adducts between acenaphthenequinone and acetophenone

Jacob¹,

Kunjachan²,

Sajitha³

et al. 2014

Arkivoc

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Chemistry, Pharmacology, and Clinical Efficacy of the Chinese Nootropic Agent Huperzine A

Cited by 147 publications

References 50 publications

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Ten New Lycopodium Alkaloids Having the Lycopodane Skeleton Isolated from Lycopodium serratum THUNB.

Domino reaction sequences leading to the formation of 2:2 adducts between acenaphthenequinone and acetophenone

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