- BIOSYNTHESIS OF NEPETALACTONE IN NEPETA CATARIA
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Iridodial is a key intermediate in the biosynthesis of nepetalactone.One of the steps on the pathway prior to the lactonization is a hydride shift from C-1 to C-10. 10-Hydroxycitronellol is a far more efficient precursor than the C-2/C-3 unsaturated analogue.Key Word Index -- Nepeta cataria; Labiatae; nepetalactone; iridane skeleton; monoterpene biosynthesis; hydride shift.
- Bellesia, Franco,Grandi, Romano,Pagnoni, Ugo M.,Pinetti, Adriano,Trave, Roberto
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- Activity of 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines to Tetrahymena
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A series 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines (43 compounds), some of which are epidermal growth factor tyrosine kinase inhibitors, were tested for their protozoal toxicity using an environmental Tetrahymena strain as model organism. The protozoacidal activity of the analogues was found to be highly dependent on a 4-hydroxyl group at the 6-aryl ring, and a chiral 1-phenylethanamine substituent in position 4. Further, the potency was affected by the aromatic substitution pattern of the phenylethanamine: the unsubstituted, the meta-fluoro and the para-bromo substituted derivatives had the lowest minimum protozoacidal concentrations (8-16 μg/mL). Surprisingly, both enantiomers were found to have high potency suggesting that this compound class could have several modes of action. No correlation was found between the compounds protozoacidal activity and the in vitro epidermal growth factor receptor tyrosine kinase inhibitory potency. This suggests that the observed antimicrobial effects are related to other targets. Testing towards a panel of kinases indicated several alternative modes of action.
- Kaspersen, Svein Jacob,Hoff, Bard Helge,Sundby, Eirik,Charnock, Colin
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p. 35 - 41,7
(2020/07/30)
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- A sustainable byproduct catalyzed domino strategy: Facile synthesis of α-formyloxy and acetoxy ketones via iodination/nucleophilic substitution/hydrolyzation/oxidation sequences
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The sustainable byproduct catalyzed domino strategy has been performed for the facile synthesis of α-formyloxy and acetoxy ketones via iodination/nucleophilic substitution/hydrolyzation/oxidation sequences from simple and readily available aromatic ketone
- Zhu, Yan-Ping,Gao, Qing-He,Lian, Mi,Yuan, Jing-Jing,Liu, Mei-Cai,Zhao, Qin,Yang, Yan,Wu, An-Xin
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supporting information; experimental part
p. 12700 - 12702
(2012/01/03)
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- One-pot synthesis of α-formyloxy ketones from enolizable ketones
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One-pot synthesis of α-formyloxy tones as well as α-acetoxy ketones from enolizable ketones and [hydroxy(tosyloxy) iodo] benzene (HTIB)/polymer supported [hydroxy(tosyloxy) iodo] benzene (PSHTIB) in N,N-dimethylformamide (DMF)/N, N-dimethylacetamide (DMA)
- Kumar, Sunil,Kumar, Ashok,Gupta, Rakesh K.,Kumar, Devinder
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p. 338 - 345
(2008/04/01)
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- TRIS(3,6-DIOXAHEPTYL)AMINE AS A PHASE-TRANSFER CATALYST IN PHENACYL ESTER SYNTHESIS
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Tris(3,6-dioxaheptyl)amine (TDA-1) may be substituted for toxic crown ethers in the phase-transfer catalyzed synthesis of phenacyl esters from weakly nucleophilic potassium carboxylates and α,p-dibromoacetophenone in acetonitrile.
- Bartsch, Richard A.,Phillips, John B.
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p. 1777 - 1780
(2007/10/02)
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