Gossypol is a polyphenolic secondary metabolite produced by cotton plants, which is toxic to many organisms. Gossypol's aldehyde groups are especially reactive, forming Schiff bases with amino acids of proteins and cross-linking them, inhibiting enzyme activities and contributing to toxicit...
Plant based natural products cover a major sector of the medicinal field, as such focus on plant research has been increased all over the world. As an attempt to aid that research, we have performed structural and spectroscopic analysis of a natural product, an alkaloid: canadine. Both ab initio...
BackgroundBerberine acts primarily as an important active ingredient in Coptis chinensis and has been traditionally applied in clinical treatment. Nevertheless, little information has been released about C. chinensis, as far as functional genes and biosynthetic pathway of berberine are concerned...
(S)-(−)-Tetrahydropalmatine 2 and (S)-(−)-canadine 4 were synthesized in three steps from (S)-6, in 33% and 34% overall yield, respectively. Thus, condensation of the (S)-(E)-sulfinylimines 10 and 11 with the carbanion derived from (S)-6 gave the tetrahydroisoquinolines 12 and 13, respectively, ...
Noscapine biosynthesis in opium poppy is thought to occur via N-methylcanadine, which would be produced through 9-O-methylation of (S)-scoulerine, methylenedioxy bridge formation on (S)-tetrahydrocolumbamine, and N-methylation of (S)-canadine. Only scoulerine 9-O-methyltransferase has been funct...
The cytotoxic effects of four alkaloids, berberine, canadine, anonaine, and antioquine were evaluated using three different cell cultures, a primary culture (rat hepatocytes) and two cell lines (HepG2 and HeLa). Our results indicate that berberine, anonaine, and antioquine possess a significant ...
A set of quinolizidinyl and quinolizidinylalkyl derivatives of 4-amino-7-chloroquinoline and of 9-amino-6-chloro-2-methoxyacridine were prepared and tested in vitro against CQ-sensitive (D-10) and CQ-resistant (W-2) strains of Plasmodium falciparum. All compounds but one exerted significant anti...
t-BuOK-catalyzed cyclization of 2-chloroquinoline-3-carbonitriles with guanidine hydrochloride provided simple and rapid synthesis of 2-amino-3H-pyrimido[4,5-b]quinolin-4-ones in very short reaction time with good yield. Other 1,3-binucleophiles are found to react at the same rate. This methodol...
In the present communication, newly synthesized 8-quinolinamines (25–27) related to previously reported 2-tert-butylprimaquine (2) were evaluated for their in vitro antimalarial activity against chloroquine sensitive and resistant Plasmodium falciparum strains, in vivo antimalarial activity aga...
Synthesis and antimalarial activities of N8-(4-amino-1-methylbutyl)-5-alkoxy-4-ethyl-6-methoxy-8-quinolinamines (5) and their pro prodrug analogues (6–7) prepared by covalently linking 5 to the redox-sensitive (8) and esterase-sensitive (9) linkers through the amide linkage are reported. The mo...
Resistance to benznidazole in certain strains of Trypanosoma cruzi may be caused by the increased production of enzymes that act on the oxidative metabolism, such as mitochondrial tryparedoxin peroxidase which catalyses the reduction of peroxides. This work presents cytotoxicity assays performed...
A combination of sulfanyl radical addition–cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiopheno...
Aryl acylamidase (aryl-acylamine amidohydrolase, E.C.3.5.1.13) isolated from lettuce (Lactuca sativa L.) leaf and stem tissue was assayed using propanil [N-(3,4-dichlorophenyl)propanamide] as substrate. EPTC (S-ethyl dipropyl carbamothioate) inhibited aryl acylamidase activity 20 to 65% at conce...
Radical addition–cyclization–elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radi...
We have developed a novel synthetic route to nitrogen-containing heterocycles via radical addition–ionic cyclization reaction. Treatment of oxime ethers carrying the tosyloxy group with Et3B and alkyl iodide in the presence of Lewis acid gave the substituted pyrrolidines and piperidines. The re...
Two different series of N-substituted imidazolium oximes and their monoquaternary salts were synthesized and biologically tested with respect to their ability to inhibit growth a diverse panel of antibiotic susceptible Gram-positive and antibiotic resistant Gram-negative bacteria as well fungal ...
Two series of bicyclic oxime ethers viz, 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one O-benzyloximes 13–24 and 2,4,6,8-tetraaryl-3,7-diazabicyclo[3.3.1]nonan-9-one O-benzyloximes 31–36 were synthesized and stereochemistry was established by their spectral (1D and 2D NMR) and crystal studies. Synt...
Thermolysis of N-arylnicotinamide oximes 1a–c (R = H, CH3 and Cl) under nitrogen gives rise to benzimidazoles 3a–c as the major products (60–62%), in addition to nicotinonitrile 4, arylamines 5a–c, nicotinic acid 6, phenols 7a–c and 8a–c, nicotinanilides 9a–c, 2-(pyridin-3-yl) benzoxazol...
The synthesis of N-benzyl-2-chloroindole-3-carboxylic acids related to indomethacin is reported. These compounds were tested on in vitro human neutrophil activation. Some of them, more soluble in water, were tested to define the influence on prostaglandin biosynthesis via inhibition of cyclooxyg...
The CNS neurotoxic effects of lead (Pb) are well documented; however, the molecular toxicity targets have not been clearly delineated. Astroglial cells, which are the most abundant cells in the brain and provide critical support to the neurons, are known to accumulate Pb. Although NO generated b...
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