2446-62-0Relevant articles and documents
OCCURRENCE IN HIGHER PLANTS OF 1-(3-AMINOPROPYL)-PYRROLINIUM AND PYRROLINE: PRODUCTS OF POLYAMINE OXIDATION
Smith, Terence A.,Croker, Stephen J.,Loeffler, R. S. Thomas
, p. 683 - 690 (1986)
The presence of 1-(3-aminopropyl)pyrrolinium (App) has been established in the leaves of oats, maize, barley and wheat seedlings.In oat leaves, concentrations of 1,3-diaminopropane (Dap), putrescine (Put) and App were greatest in the youngest plants.Changes in Dap and App could not be correlated with changes in polyamine oxidase activity.Concentrations of the amines were smaller in maize than in oats, and smallest in barley and wheat.Pyrroline, an oxidation product of Put in pea seedlings and of spermidine in oat and maize seedlings, has been demonstrated in extracts of these plants, and also in spinach leaves and in radish shoots, following distillation, derivatization with 2-aminobenzaldehyde, oxidation of the adduct and GC-MS.Piperideine was also identified in pea seedlings.Key Word Index- Gramineae; Leguminosae; 1-(3-aminopropyl)-2-pyrrolinium; 1-pyrroline; 1-piperideine; 2-aminobenzaldehyde adduct; 2,3-trimethylene-4-quinazolone; spermine; diaminopropane; amine oxidases.
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Kametani et al.
, p. 2306,2308 (1977)
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Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation
Liu, Ji-Feng,Ye, Ping,Sprague, Kevin,Sargent, Katie,Yohannes, Daniel,Baldino, Carmen M.,Wilson, Christopher J.,Ng, Shi-Chung
, p. 3363 - 3366 (2005)
(Chemical Equation Presented) Total syntheses of deoxyvasicinone (1), mackinazolinone (2), and 8-hydroxydeoxyvasicinone (3) via novel microwave-assisted domino reactions, as well as a novel three-component one-pot total synthesis of isaindigotone (5) promoted by microwave irradiation, are reported. The efficient reaction process enabled us to rapidly access related natural product derivatives and to identify a new class of cytotoxic agents.
Synthesis of 3,4-dihydroquinazolin-4-one: Selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide
Nishiyama, Yutaka,Hirose, Masaharu,Kitagaito, Wataru,Sonoda, Noboru
, p. 1855 - 1858 (2002)
A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields.
Deacylation-aided C–H alkylative annulation through C–C cleavage of unstrained ketones
Dong, Guangbin,Xu, Yan,Zhou, Xukai
, p. 703 - 710 (2021/08/09)
Arene- and heteroarene-fused rings are pervasive in biologically active molecules. Direct annulation between a C–H bond on the aromatic core and a tethered alkyl moiety provides a straightforward approach to access these scaffolds; however, such a strategy is often hampered by the need of special reactive groups and/or less compatible cyclization conditions. It would be synthetically appealing if a common native functional group can be used as a handle to enable a general C–H annulation with diverse aromatic rings. Here, we show a deacylative annulation strategy for preparing a large variety of aromatic-fused rings from linear simple ketone precursors. The reaction starts with homolytic cleavage of the ketone α C–C bond via a pre-aromatic intermediate, followed by a radical-mediated dehydrogenative cyclization. Using widely available ketones as the robust radical precursors, this deconstructive approach allows streamlined assembly of complex polycyclic structures with broad functional group tolerance. [Figure not available: see fulltext.]
Novel PDE5 inhibitors derived from rutaecarpine for the treatment of Alzheimer's disease
Dong, Yan-Hua,Huang, Xian-Feng,Ke, Heng-Ming,Song, Guo-Qiang,Wang, Jin-Hui,Xu, De-Feng
supporting information, (2020/03/23)
A series of novel rutaecarpine derivatives were synthesized and subjected to pharmacological evaluation as PDE5 inhibitors. The structure–activity relationships were discussed and their binding conformation and simultaneous interaction mode were further clarified by the molecular docking studies. Among the 25 analogues, compound 8i exhibited most potent PDE5 inhibition with IC50 values about 0.086 μM. Moreover, it also produced good effects against scopolamine-induced cognitive impairment in vivo. These results might bring significant instruction for further development of potential PDE5 inhibitors derived from rutaecarpine as a good candidate drug for the treatment of Alzheimer's disease.
