2446-62-0Relevant academic research and scientific papers
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.
Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C
García-Ramírez, Jazmín,Miranda, Luis D.
, p. 1471 - 1477 (2021)
An efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N -3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.
Solid-phase synthesis of fused [2,1-b]quinazolinone alkaloids
Kamal, Ahmed,Shankaraiah,Devaiah,Reddy, K. Laxma
, p. 9025 - 9028 (2006)
Solid-phase synthesis of fused [2,1-b]quinazolinone alkaloids has been developed for the preparation of vasicinone and deoxyvasicinone by two approaches. The derivative of polymer-supported p-nitrophenyl carbonate was attached to anthranilic acid and then coupled with various bromo-lactams. This resin-linked bromo intermediate upon acetylation, hydrolysis and resin cleavage gave the cyclized [2,1-b]quinazolinones (vasicinone). Alternatively, resin-linked azido-benzoic acids were coupled with bromo-substituted lactams followed by cyclization in an aza-Wittig reductive cyclization process giving the bromo-substituted quinazolinone intermediates, with subsequent acetylation, hydrolysis and resin cleavage affording the fused [2,1-b]quinazolinones.
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.
Acetylcholinesterase inhibition by fused dihydroquinazoline compounds
Jaen, Juan C.,Gregor, Vlad E.,Lee, Chet,Davis, Robert,Emmerling, Mark
, p. 737 - 742 (1996)
A new type of dihydroquinazoline-based inibitor of acetylcholinesterase (AChE) is described. These compounds were designed to interact with the catalytic site of AChE in a manner similar to the known inhibitor tacrine. In a manner analogous to the potency enhancement obtained by addition of chlorine atoms to the tacrine molecule, a 3-chloro derivative of the parent hexahydroazepino[2,1-b]quinazoline structure was found to be about 8 times more potent as an AChE inhibitor than the unsubstituted compound.
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.
The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale
Mohammadi Metkazini, Fatemeh,Khorsandi, Zahra,Heydari, Akbar
, (2021/04/12)
Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.
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.]
Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis
, p. 9347 - 9360 (2020/08/14)
A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.
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.
