9-[3-(Dimethyloxyamino)propylimino]-1-nitro-9,10-dihydroacridine monohydrate

Hempel, A.; Hull, S. E.; Bogucka-Ledóchowska, M.; Dauter, Zbigniew

doi:10.1107/s0567740879003861

Cited by 18 publications

(7 citation statements)

References 3 publications

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“…A change in the position of substitution on the chromophore can result in a drastic change in the potency of drug action. For example, 1-nitro acridine derivatives, nitracrine or leadacridine have been widely used as anti-cancer drugs [7] but the 2-nitro derivatives do not show anti-cancer property [8]. Determination of the three dimensional structure of biologically and chemically useful acridinediones should facilitate an understanding of the conformational aspects and the role of the substituent groups in determining the overall conformation of the molecules, which in turn, would correlate with physical, chemical and biological activities.…”

Section: Introductionmentioning

confidence: 99%

Crystal and Molecular Structure of an Acridinedione

Jeyakanthan¹,

Yogavel²,

Rajan³

et al. 2002

Cryst. Res. Technol.

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The title compound, 10‐(4‐hydroxybenzoylamino)‐3,4,6,7,9,10‐hexahydro‐1,8‐(2H,5H)‐acridinedione monohydrate,C20H22N2O4.H2O, consists of partially hydrogenated acridine moiety with one benzoylamino substituent on the central ring. The compound crystallizes in monoclinic system with P21/c space group and the unit cell constants are: a = 11.142(4), b = 12.266(2), c = 13.320(2) Å; β = 91.76(2)° and V = 1819.6(8) Å3.The central ring (B) adopts boat and the outer rings (A and C) adopt sofa conformations. The water molecule takes part in OW‐H...O and N‐H...OW hydrogen bond formation with acridinedione and benzoylamino group. The oxygen atom O1 interacts through O–H...O bond with the hydroxyl group and in a head‐to‐tail link up of molecules that results in the formation of an infinite “supra molecular“ chain.

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Section: Introductionmentioning

confidence: 99%

Crystal and Molecular Structure of an Acridinedione

Jeyakanthan¹,

Yogavel²,

Rajan³

et al. 2002

Cryst. Res. Technol.

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“…**Deceased, June 15, 1984. of activity of such compounds some structural studies were carried out by X-ray crystallographic techniques. The structure of ledakrin [9-(3-dimethylaminopropylimino)-1-nitro-9,10-dihydroacridine, C-283] has been determined (5,6) and shows that the close approach of the 1-nitro group to the substituted 9-amino group causes considerable distortions in the molecule. By contrast, this area in the structure of the inactive 2-nitrocompound, (II), is planar (7).…”

Section: Introductionmentioning

confidence: 99%

Intercalation Model for DNA-Cross Linking in a 1-Nitro-9-aminoacridine Derivative, an Analog of the Antitumor Agent “Ledakrin” (Nitracrine)

Stallings

Glusker²,

Carrell³

et al. 1984

Journal of Biomolecular Structure and Dynamics

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Ledakrin (nitracrine), C-283, is a 1-nitro-9-aminoacridine derivative that is used in Poland as an antitumor agent. In order to investigate the basis of the activity of this compound the structure of another analog, [9-(3-dimethyl-1-methylpropylimino)-1-nitro-9,10-dihydroacridin e], C-829, that has similar activity, was determined by X-ray crystallographic techniques and was compared with that of ledakrin, already reported in the literature. In both molecules the proximity of the 1-nitro to the substituted 9-aminoacridine group causes extensive distortions. These compounds are believed to act, after metabolic "activation", by cross-linking DNA. Such cross-linking does not occur in the absence of the 1-nitro group or if the nitro group is moved to the 2-, 3- or 4-position. Computer-assisted model-building has been used to test possible intercalative models. It has shown that functional groups on C-829 or C-283 are, when the acridine portion of the molecule is intercalated as in a proflavine dinucleoside phosphate complex, in positions suitable for DNA cross-linking by activated 1-nitro-9-aminoacridine derivatives.

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“…Acridine derivatives have similar structures to NADH (nicotinamide adenine dinucleotide) (Hempel et al, 1979); thus, this molecule group has important biological actives as antimalarial (Thull and Testa, 1994), anticancer (Grove et al, 1982), antiglaucoma (Kaya et al, 2012;Ulus et al, 2013;Yeşildag et al, 2014), antimicrobial (Kaya et al, 2015), calcium channel blocking (Di Stilo et al, 1998), and potassium cannel opening (Li et al, 1996). In addition to the properties of this molecule group, they are also known as laser dyes and intercalated agent (Lerman, 1963).…”

Section: Introductionmentioning

confidence: 99%

Rapid synthesis of novel 1,8-dioxoacridine carboxylic acid derivatives by microwave irradiation and their free radical scavenging activity

et al. 2015

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Synthesis of novel acridine carboxylic acid compounds 4-18 was performed with the reaction of 4-aminobenzoic acid 1, aromatic aldehyde 2a-n, 1,3-diketone 3a, 3b using microwave irradiation. These compounds were synthesized efficiently in one-pot procedure for 6 min without catalyst in high yields of 65-90 % using little ethanol. Radical scavenging activities of synthesized compounds 4-18 were determined by means of in vitro test using 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid radicals (ABTS Á? ). The activities of tested compounds were compared to the positive control such as butylated hydroxyanisole, butylated hydroxytoluene, and trolox. The results showed that the synthesized compounds 4, 6, 14, and 15 had effective free radical scavenging activity.

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9-[3-(Dimethyloxyamino)propylimino]-1-nitro-9,10-dihydroacridine monohydrate

Abstract: Direct methods were used to solve the structure, and refinement was by full-matrix leastsquares methods. The final weighted R value for 1481 reflexions was 0.100. The acridine nucleus is not planar and the nitro group is twisted out of the plane of the acridine-moiety side ring.

Cited by 18 publications

References 3 publications

Crystal and Molecular Structure of an Acridinedione

Crystal and Molecular Structure of an Acridinedione

Intercalation Model for DNA-Cross Linking in a 1-Nitro-9-aminoacridine Derivative, an Analog of the Antitumor Agent “Ledakrin” (Nitracrine)

Rapid synthesis of novel 1,8-dioxoacridine carboxylic acid derivatives by microwave irradiation and their free radical scavenging activity

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