8-Amino quinoline structural

The degree of toxicity in the 8-amino quinoline structural analogues appears to be directly associated with the degree of substitution at the terminal amino function. Using the said criterion pamaquine, having a tertiary amino moiety, happens to be more toxic than primaquine, having a... 

This concept may also be extended to polynuclear helicates [38]. When 2-amino-quinoline and 4-chloroaniline were mixed with the phenanthroline dialdehyde shown in Scheme 1.10, a dynamic library of potential ligands was observed to form. The addition of copper(I) causes this library to collapse, generating only dicopper and tricopper helicates. As in the mononuclear case of Scheme 1.9, the driving force behind this selectivity appeared to be the formation of structures in which all ligand and metal valences are satisfied. The use of supramolecular (coordination) chemistry to drive the covalent reconfiguration of intraligand bonds thus... 

Chemical/Pharmaceutical/Other Class Amino-quinoline antimalarial/antirheumatic Chemical Formula C18H26CIN3 Chemical Structure ... 

Parke, Davis workers have reported on the effects of introducing distal and proximal hydrazine moieties into the structures of active acridines and 4-aminoquinolines [266, 267]. Substitution of a hydrazine moiety for the amine function at the distal position of compounds such as azacrin, quin-acrine, and chloroquine, had a deleterious effect on antimalarial activity. Several such compounds containing proximal hydrazino functions, however, showed activity greater than chloroquine 4,4 -(l,4-piperazinediyldi-imino) bis (7-chloroquinoline) (74) and 7-chloro-4-[(4-methyl-l-piperazinyl)amino] quinoline (75) had quinine coefficients of 27 and 28 respectively against P. berghei compared to chloroquine s 11, but these compounds were highly... 

In the case of the 2-dimethylamino- (or 2-amino-)methylene derivatives, the products were at first thought to be pyrimido[4,5-c]isoquinolines (267), but later work with 6-(N-substituted amino)uracils assigned the structures of the products (268) as belonging to the isomeric pyrimido[4,5-f>]quinoline system (74CB2537), in agreement with the regioselection rules above. 

The proposed structure of 97 isolated from broiled sardines was confirmed by straightforward synthesis starting from5,6-diaminoquinolines. After reaction with cyanogen bromide it afforded the 2-amino-imidazo[4,5-/]quinolines 99 (R = H, Me), which was then converted into its 3-A-methyl derivative 100 by... 

The pioneering work carried out in Germany in the 1920s showed that appropriately substituted aminoquinolines and amino-acridines afforded a series of synthetic compounds that exhibited antimalarial activity.The exigencies of the Second World War led to a massive program aimed at the same goal in this country. This work led to the development of two distinct structural classes of quinoline antimalarials the 4-amino-7-chloroquino-... 

R. Edenharder, 1. von Petersdorff, and R. Rauscher, Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo(4,5-f quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res. 287 261 (1993). 

Methoxy-3-isobutylpyrazine 176 (Structure 4.53) is found in galbanum oil obtained from Ferula galbaniflua. 2,4-disubstituted pyridines 177, N,N-dimeth-ylated amino compounds 178, alkyl pyrazines 179, quinoline 180 and methyl quinolines 181 were isolated from fig leaf absolute [64]. 

The solid-state structure of (lS)-5,8,9-trihydroxy-2,3-dihydro-l/7-pyrimido-[l,2-a]quinoline-l-carboxylic acid pentahydrate was determined by X-ray investigations [91ZN(C)933. The structure of an iron(III)-containing pseudobactin, a siderophore containing a (lS)-5-amino-8,9-dihydroxy-2,3-dihydro-l//-pyrimido[l,2-a]quinazoline-l-carboxylic acid moiety (8), was determined by X-ray diffraction investigations (81 Mil). 

The wide variety of ketomethylene and amino ketone monomers that could be synthesized, and the ability of the quinoline-forming reaction to generate high molar mass polymers under relatively mild conditions, allow the synthesis of a series of polyquinolines with a wide structural variety. Thus poly quinolines with a range of chain stiffness from a semirigid chain to rod-like macromolecules have been synthesized. Polyquinolines are most often prepared by solution polymerization of bis(o-amino aryl ketone) and bis (ketomethylene) monomers, where R = H or C.H , in w-cresol with di-/ /-cresyl phosphate at 135—140°C for a period of 24—48 h (92). 

New Synthetic Approaches. There have been a number of efforts to prepare quinolines by routes quite different from the traditional methods. In one, the cyclization of 3-amino-3-phcnyl-2-alkcnimines using alkali metals leads to modest yields of various 4-arylaminoquinolines. Because this structure is found in many natural products and few syntheses of it exist, the method merits further investigation. 

From grilled sun-dried sardines, two mutagenic fractions were obtained with high performance liquid chromatography using pBondapak Cie. Their structures were determined, by 270 MHz 1H-NMR and low- and high-resolution mass spectra, to be 2-amino-3-methylimidazo[4,5-/]quinoline (IQ) and 2-amino-3,4-dimethyl-imidazo[4,5-/]quinoline (MelQ) (12,13,14). The structures of these new compounds were confirmed by chemical synthesis. 

The H mode of the pyrimidine ring construction assuming the stepwise formation of the N(l)-C(2) and C(2)-N(3) bonds as a result of the insertion of a component serving as the source of the C(2) atom is more often used in practice. The simplest modification involves intramolecular condensation of 3-(acylamino)thienopyri-dines produced by acylation of 3-amino-2-carbamoylthieno[2,3-Z>]pyridines or their structural analogs (1995PS83). An example is the synthesis of pyrimidothienobenzo-quinoline 98 from chloroacetamide 99. 

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