505-18-0Relevant academic research and scientific papers
Condensation of 2-alkylcyclohexane-1,3-diones with cyclic azomethines
Rubinova,Rubinova
, p. 1187 - 1189 (2004)
Reaction of 2-acylcyclohexane-1,3-diones with 5- and 6-membered cyclic azomethines (3,4-dihydro-2H-pyrrole and 2,3,4,5-tetrahydropyridine) furnished derivatives of 2,3,3a;,4,8,9-hexahydropyrrolo[1,2-a]quinoline-5,6(1H,5aH)-dione and 3,4,4a,5,9,10-hexahydro-1H-pyrido[1,2-a]quinoline-6,7(2H,8H)-dione respectively. In reaction with 7-membered 3,4,5,6-tetrahydro-2H-azepine we failed to isolate polycyclic nitrogen-containing products.
Oxidation of di- and polyamines: In vitro effect of amino aldehydes on the vitality of Leishmania promastigotes
Massa, Silvia,Spano, Delia,Pintus, Francesca,Medda, Rosaria,Floris, Giovanni
, p. 77 - 83 (2010)
The aminoaldehydes 4-aminobutanal and 5-aminopentanal, derived from the oxidation of the diamines putrescine and cadaverine, and 1-(3-aminopropyl)-4- aminobutanal and aminodialdehyde, derived from the oxidation of the polyamines spermidine and spermine, were produced utilizing a copper amine oxidase (CAO) from Euphorbia characias latex and tested with in vitro cultivation of Leishmania infantum promastigotes. Whereas the aminoaldehydes derived from the oxidation of the diamines were stimulating factors for growth of Leishmania infantum promastigotes, the aldehydes derived from polyamines oxidation had a drastic inhibitory effect on the vitality and growth of these parasites. Thus, a double scenario arises, showing the use of aldehydes from diamines to obtain a large number of organisms of Leishmania infantum promastigotes to use in serological studies, whereas the aldehydes derived from polyamines could be used as a new strategy for therapeutic treatment against these parasites.
Generation and trapping of non-aromatic cycloimines via diazotization/dediazotization of N-amino cyclic amines: theoretical and experimental results
Ojha, Minita,Bansal, Raj K.
, p. 2179 - 2187 (2020)
A theoretical investigation of the model diazotization/dediazotization of N-aminopiperidine and N-aminomorpholine at the DFT (B3LYP/6-31+G(d)) level indicated that the corresponding cycloimines can be generated transiently, which can be trapped with dimethyl acetylenedicarboxylate (DMAD) to form a 1,4-dipole followed by cycloaddition of the latter with a second molecule of DMAD to give the corresponding pyrido-annelated products. All steps have low activation free energy barriers and are thermodynamically favoured. Based on the theoretical results, we carried out successfully diazotization of N-amino cyclic amines, namely N-aminopiperidine, 4-aminomorpholine and 1-amino-4-methylpiperazine with tert.-butyl nitrite followed by dediazotization to generate transiently the corresponding cycloimines, which could be trapped with dimethyl acetylenedicarboxylate. to afford new annelated pyridine derivatives, namely tetramethyl 9H-5,6,7,8-tetrahydroquinolizine-1,2,3,4-tetracarboxylate, tetramethyl 5,6,8,9-tetrahydropyrido[2,1-c][1,4]oxazine-1,2,3,4-tetracarboxylate and tetramethyl 9H-5,6,7,8-tetrahydro-7-methylpyrido[1,2-a]pyrazine-1,2,3,4-tetracarboxylate which were duly characterized.
Molecular cloning and characterization of copper amine oxidase from Huperzia serrata
Sun, Jieyin,Morita, Hiroyuki,Abe, Ikuro,Noguchi, Hiroshi,Chen, Guoshen
, p. 5784 - 5790,7 (2012)
A cDNA encoding a novel copper amine oxidase (CAO) was cloned and sequenced from the Chinese club moss Huperzia serrata (Huperziaceae), which produces the Lycopodium alkaloid huperzine A. A 2043-bp open reading frame encoded an Mr 76,854 protein with 681 amino acids. The deduced amino acid sequence shared 44-56% identity with the known CAOs of plant origin, and contained the active site consensus sequence of Asn-Tyr-Asp/Glu. The phylogenetic tree analysis revealed that HsCAO from the primitive vascular plant H. serrata is closely related to Physcomitrella patens subsp CAO. The recombinant enzyme, heterologously expressed in Escherichia coli, catalyzed the oxidative deamination of aliphatic and aromatic amines. Among them, the enzyme accepted cadaverine as the best substrate to catalyze the oxidative deamination to Δ1-piperideine, which is the precursor of the Lycopodium alkaloids. Furthermore, a homology modeling and site-directed mutagenesis studies predicted the active site architecture, which suggested the crucial active site residues for the observed substrate preference. This is the first report of the cloning and characterization of a CAO enzyme from the primitive Lycopodium plant.
Green remediation of textile dyes containing wastewater by Ipomoea hederifolia L.
Rane, Niraj R.,Chandanshive, Vishal V.,Khandare, Rahul V.,Gholave, Avinash R.,Yadav, Shrirang R.,Govindwar, Sanjay P.
, p. 36623 - 36632 (2014)
Wild plant and tissue cultures of Ipomoea hederifolia decolorize Scarlet RR (SRR) dye at a concentration of 50 mg L-1 up to 96% and 90% within 60 and 96 h, respectively. Significant induction in the enzyme activities of Lignin peroxidase, laccase, 2,6-dichlorophenol indophenol reductase, superoxide dismutase, catalase and tyrosinase was found in the plant roots and shoots during decolorization. I. hederifolia was also able to treat a dye mixture and a real textile effluent efficiently with a reduction in the American Dye Manufacturers Institute (ADMI) value (color removal) up to 85% and 88%, BOD up to 65% and 63% and COD up to 62% and 68%, respectively. Detailed anatomical studies of the stem and root cells of I. hederifolia during uptake and degradation were carried out, showing a stepwise and mechanistic degradation of the model dye SRR. Products formed after dye degradation were analyzed by UV-Vis spectroscopy, FTIR, HPLC and HPTLC, which confirmed the phytotransformation of SRR, dye mixture and textile effluent. A possible pathway for the phytotransformation of SRR was proposed based on GC-MS analysis, which confirmed the formation of different metabolites with lower molecular weights. The phytotoxicity study revealed the non-toxic nature of the formed products. the Partner Organisations 2014.
Diversification of Unprotected Alicyclic Amines by C?H Bond Functionalization: Decarboxylative Alkylation of Transient Imines
Paul, Anirudra,Kim, Jae Hyun,Daniel, Scott D.,Seidel, Daniel
supporting information, p. 1625 - 1628 (2020/11/30)
Despite extensive efforts by many practitioners in the field, methods for the direct α-C?H bond functionalization of unprotected alicyclic amines remain rare. A new advance in this area utilizes N-lithiated alicyclic amines. These readily accessible intermediates are converted to transient imines through the action of a simple ketone oxidant, followed by alkylation with a β-ketoacid under mild conditions to provide valuable β-amino ketones with unprecedented ease. Regioselective α′-alkylation is achieved for substrates with existing α-substituents. The method is further applicable to the convenient one-pot synthesis of polycyclic dihydroquinolones through the incorporation of a SNAr step.
α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines
Kim, Jae Hyun,Paul, Anirudra,Ghiviriga, Ion,Seidel, Daniel
supporting information, p. 797 - 801 (2021/02/06)
Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF3 etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding β-lactams.
α-C-H/N-H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams
Chen, Weijie,Seidel, Daniel
supporting information, p. 3729 - 3734 (2021/05/31)
Polycyclic lactams are prepared in a single operation from o-toluamides and cyclic amines in a process that involves transient cyclic imines, species that are conveniently obtained in situ from the corresponding lithium amides and simple ketone oxidants. Imines thus generated, such as 1-pyrroline and 1-piperideine, engage lithiated o-toluamides in a facile annulation process. Undesired side reactions such as imine deprotonation and o-toluamide dimerization are suppressed through the judicious choice of reaction conditions.
α,α′-C-H Bond Difunctionalization of Unprotected Alicyclic Amines
Valles, Daniel A.,Dutta, Subhradeep,Paul, Anirudra,Abboud, Khalil A.,Ghiviriga, Ion,Seidel, Daniel
supporting information, p. 6367 - 6371 (2021/08/18)
A simple one-pot procedure enables the sequential, regioselective, and diastereoselective introduction of the same or two different substituents to the α- and α′-positions of unprotected azacycles. Aryl, alkyl, and alkenyl substituents are introduced via their corresponding organolithium compounds. The scope of this transformation includes pyrrolidines, piperidines, azepanes, and piperazines.
Total synthesis of novel skeleton flavan-alkaloids
Simon, James E.,Wu, Qingli,Zhen, Jing
, (2020/10/18)
The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated fromthe African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, through which the piperidine moiety couples to the flavan moiety. The identities of synthesized kinkeloids were further confirmed through a comparison with the ones in the plant leaves extract using LC/MS.
