Acridones
Thioxanthenes
Interactions of antitumor triazoloacridinones with DNA. (1/13)
Triazoloacridinones (TA) are a new group of potent antitumor compounds, from which the most active derivative, C-1305, has been selected for extended preclinical trials. This study investigated the mechanism of TA binding to DNA. Initially, for selected six TA derivatives differing in chemical structures as well as cytotoxicity and antitumor activity, the capability of noncovalent DNA binding was analyzed. We showed that all triazoloacridinones studied stabilized the DNA duplex at a low-concentration buffer but not at a salt concentration corresponding to that in cells. DNA viscometric studies suggested that intercalation to DNA did not play a major role in the mechanism of the cytotoxic action of TA. Studies involving cultured cells revealed that triazoloacridinone C-1305 after previous metabolic activation induced the formation of interstrand crosslinks in DNA of some tumor and fibroblast cells in a dose dependent manner. However, the detection of crosslink formation was possible only when the activity of topoisomerase II in cells was lowered. Furthermore, it was impossible to validate the relevance of the ability to crosslink DNA to biological activity of TA derivatives. (+info)Design, synthesis, and evaluation of 10-N-substituted acridones as novel chemosensitizers in Plasmodium falciparum. (2/13)
A series of novel 10-N-substituted acridones, bearing alkyl side chains with tertiary amine groups at the terminal position, were designed, synthesized, and evaluated for the ability to enhance the potency of quinoline drugs against multidrug-resistant (MDR) Plasmodium falciparum malaria parasites. A number of acridone derivatives, with side chains bridged three or more carbon atoms apart between the ring nitrogen and terminal nitrogen, demonstrated chloroquine (CQ)-chemosensitizing activity against the MDR strain of P. falciparum (Dd2). Isobologram analysis revealed that selected candidates demonstrated significant synergy with CQ in the CQ-resistant (CQR) parasite Dd2 but only additive (or indifferent) interaction in the CQ-sensitive (CQS) D6. These acridone derivatives also enhanced the sensitivity of other quinoline antimalarials, such as desethylchloroquine (DCQ) and quinine (QN), in Dd2. The patterns of chemosensitizing effects of selected acridones on CQ and QN were similar to those of verapamil against various parasite lines with mutations encoding amino acid 76 of the P. falciparum CQ resistance transporter (PfCRT). Unlike other known chemosensitizers with recognized psychotropic effects (e.g., desipramine, imipramine, and chlorpheniramine), these novel acridone derivatives exhibited no demonstrable effect on the uptake or binding of important biogenic amine neurotransmitters. The combined results indicate that 10-N-substituted acridones present novel pharmacophores for the development of chemosensitizers against P. falciparum. (+info)Antitumour properties of acridone alkaloids on a murine lymphoma cell line. (3/13)
The aim of the present study was to investigate the anticancer properties of a set of furanoacridone alkaloids, arborinine and evoxanthine, including the inhibitory effect of P-glycoprotein (Pgp) and the apoptosis-inducing capacity. The tested alkaloids were evaluated for multidrug resistance (MDR)-reversing activity on human Pgp-transfected L5178 mouse lymphoma cells, using the rhodamine-123 (Rh-123) assay. The antiproliferative effects of natural compounds and their interactions with doxorubicin were determined in MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assays. Apoptosis-inducing activity was additionally measured by means of dual annexin V and propidium iodide staining. RT-PCR was used to test the expression of Pgp mRNA after acridone treatment. All of the acridones investigated increased the accumulation of Rh-123. Gravacridonetriol and gravacridonediol monomethyl ether increased the antiproliferative effect of doxorubicin on resistant L5178 cells. Treatment with these agents resulted in a decrease in Pgp mRNA levels. Naturally occurring acridone alkaloids exhibit a beneficial combination of anticancer effects and, accordingly, the acridone skeleton can be considered useful in the design of novel antiproliferative agents. (+info)A new acridone alkaloid from Micromelum integerrimum. (4/13)
A new acridone alkaloid, 1,3-dihydroxy-4-methoxy-10-methylacridone (1), was isolated from leaves of the plant Micromelum integerrimum, together with two known carbazole alkaloids, glycozolinol (2) and methyl carbazole-3-carboxylate (3). Their structures were elucidated by extensive spectroscopic analysis. (+info)Fluorescent properties of acridonyl group in DNA duplex. (5/13)
(+info)Isolation of acridone alkaloids and N-[(4-monoterpenyloxy)phenylethyl]-substituted sulfur-containing propanamide derivatives from Glycosmis parva and their anti-herpes simplex virus activity. (6/13)
Six acridone alkaloids including a new glycosparvarine (1), three limonoids, and four N-[(4-monoterpenyloxy)phenylethyl]-substituted sulfur-containing propanamide derivatives including two new species, (+)-S-deoxydihydroglyparvin (10) and (+)-S-deoxytetrahydroglyparvin (11), were isolated from the branches and the leaves of Glycosmis parva CRAIB collected in the east of Thailand. Antiviral activity evaluation of isolates against herpes simplex virus (HSV) type 1 and 2 disclosed that two acridone alkaloids, glycosparvarine (1) and glycofolinine (4), showed moderate inhibitory activities with 50% effective concentration (EC50) of 348 microM and 151 microM, respectively; as well, (+)-S-deoxydihydroglyparvin (10) exhibited anti-HSV activity at the lower concentration. (+info)Natural and synthetic acridines/acridones as antitumor agents: their biological activities and methods of synthesis. (7/13)
Acridine derivatives constitute a class of compounds that are being intensively studied as potential anticancer drugs. Acridines are well-known for their high cytotoxic activity; however, their clinical application is limited or even excluded because of side effects. Numerous synthetic methods are focused on the preparation of target acridine skeletons or modifications of naturally occurring compounds, such as acridone alkaloids, that exhibit promising anticancer activities. They have been examined in vitro and in vivo to test their importance for cancer treatment and to establish the mechanism of action at both the molecular and cellular level, which is necessary for the optimization of their properties so that they are suitable in chemotherapy. In this article, we review natural and synthetic acridine/acridone analogs, their application as anticancer drugs and methods for their preparation. (+info)Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes. (8/13)
(+info)Application of Palladium-Mediated Diarylamine Synthesis and Directed Remote Metalation (DreM) in the Synthesis of Acridones,...
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Fenamic acid
"Acridone". Organic Syntheses. 2: 6. doi:10.15227/orgsyn.019.0006. (Articles without KEGG source, Articles with changed EBI ... 17 Fenamic acid can be synthesized from 2-chlorobenzoic acid and can be converted into acridone. Gupta, PK. Drug ...
Ullmann condensation
C. F. H. Allen, G. H. W. McKee (1939). "Acridone". Organic Syntheses. 2: 6. doi:10.15227/orgsyn.019.0006. H.B. Goodbrand; Nan- ... an intermediate in the preparation of acridone: Aryl iodides are favored arylating agents. The catalyst used is formed from ...
Diethylsuccinoylsuccinate
doi:10.1002/14356007.a20_371.(subscription required) Smith, J. Anthony; West, Richard M.; Allen, Malcolm (2004). "Acridones and ...
Lucigenin
It may be prepared from acridone. There's also a route from toluene: v t e (Articles without EBI source, Articles without KEGG ...
Anthranilate N-methyltransferase
This enzyme participates in acridone alkaloid biosynthesis. Eilert U, Wolters B (1989). "Elicitor induction of S-adenosyl-L- ...
Acridine
Another classic method for the synthesis of acridones is the Lehmstedt-Tanasescu reaction. In enzymology, an acridone synthase ... Media related to Acridine at Wikimedia Commons Synthesis of acridone in Organic Syntheses 19:6; Coll. Vol. 2:15 [1] from o- ... by heating salicylaldehyde with aniline and zinc chloride or by distilling acridone (9-position a carbonyl group) over zinc ... which are readily transformed by the action of alkaline potassium ferricyanide to N-alkyl acridones. Acridine and its ...
Mark B. Cohen
The 2016 rematch between Solomon and Cohen was notably acrid. One article suggested that Cohen's operatives had stolen ...
Furoquinoline alkaloid
"In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum". Antimicrobial Agents and ...
Elizabeth Hardy (chemist)
Patented: November 30, 1948 Soluble vat dyes of the acridone series. William B. Hardy and Elizabeth M. Hardy, Bound Brook. ...
Evoxine
Waffo, AF; Coombes, PH; Crouch, NR; Mulholland, DA; El Amin, SM; Smith, PJ (2007). "Acridone and furoquinoline alkaloids from ...
I-motif DNA
Acridone derivative stabilizes the c-myc i-motif structure with no significant interaction with G4 in order to downregulate the ... These include IMC-48, IMC-76, Nitidine, NSC309874, acridone derivative, and PBP1. IMC-48 stabilizes the bcl-2 structure of i- ...
Noncovalent solid-phase organic synthesis
In one experimental setup the hydrophobic matrix is RP silica gel (C18) and the anchor is acridone. Acridone is N-alkylated and ...
Ruta graveolens
A series of furanoacridones and two acridone alkaloids (arborinine and evoxanthine) have been isolated from R. graveolens. It ...
Anthranilate-CoA ligase
This enzyme participates in 3 metabolic pathways: carbazole degradation, benzoate degradation via coa ligation, and acridone ...
Lehmstedt-Tanasescu reaction
Lehmsted-Tănăsescu acridone synthesis and Lehmsted-Tanasescu acridone synthesis. In the first step of the reaction mechanism ... The Lehmstedt-Tanasescu reaction is a method in organic chemistry for the organic synthesis of acridone derivatives (3) from a ... leads to the N-nitroso acridone 11 via intermediates 9 en 10. The N-nitroso group is removed by an acid in the final step. The ...
Quinacridone
The name indicates that the compounds are a fusion of acridone and quinoline, although they are not made that way. Classically ...
Zanthoxylum
... acridones (1-hydroxy-3-methoxy-10-methylacridon-9-one, 1-hydroxy-10-methylacridon-9-one, zanthozolin), and aromatic and ...
List of EC numbers (EC 2)
... acridone synthase EC 2.3.1.160: vinorine synthase EC 2.3.1.161: lovastatin nonaketide synthase EC 2.3.1.162: taxadien-5α-ol O- ...
Aminoaldehydes and aminoketones
... acridone Most members of this class are unstable towards self-condensation, however some important examples do exist as ...
T35
... acridone, an antimalarial drug This disambiguation page lists articles associated with the same title formed as a letter-number ...
Zanthoxylum gilletii
The lignan sesamin, the N-isobutylamide γ-sanshool, the acridone alkaloids 1-hydroxy-3-methoxy-N-methylacridone, arborinine, ...
C13H9NO
The molecular formula C13H9NO (molar mass: 195.22 g/mol, exact mass: 195.0684 u) may refer to: Acridone CR gas, or ...
Acridone
... is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. It is a yellow solid. ... Acridone can be synthesized by the condensation of aniline and 2-chlorobenzoic acid and subsequently heating of N- ... Acridone constitutes the scaffold of some synthetic compounds with diverse pharmacological activities. 3-Chloro-6-(2- ... C. F. H. Allen & G. H. W. McKee (1939). "Acridone". Organic Syntheses. 19: 6. doi:10.15227/orgsyn.019.0006. Austrian National ...
Acridone synthase
In enzymology, an acridone synthase (EC 2.3.1.159) is an enzyme that catalyzes the chemical reaction 3 malonyl-CoA + N- ... Baumert A, Maier W, Gröger D, Deutzmann R (1994). "Purification and properties of acridone synthase from cell suspension ... Junghanns KT, Kneusel RE, Gröger D, Matern U (1998). "Differential regulation and distribution of acridone synthase in Ruta ... "Native acridone synthases I and II from Ruta graveolens L. form homodimers". FEBS Lett. 448 (1): 135-40. doi:10.1016/S0014-5793 ...
Acridone alkaloids
... are natural products derived from acridone. Acridone alkaloids are found in bark, wood, leaves and roots of ... Acridone alkaloids show a blue-green fluorescence so that they can be detected with UV light. Some alkaloids of this group are ... Entry on Acridone. at: Römpp Online. Georg Thieme Verlag, retrieved 21 April 2020. R. Hänsel, O.Sticher (2007), Pharmakognosie ... This group is named after the acridone. Further members are acronycin, melicopicine and rutacridone, among others: Acronycin ...
Acridone - Wikipedia
Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. It is a yellow solid. ... Acridone can be synthesized by the condensation of aniline and 2-chlorobenzoic acid and subsequently heating of N- ... Acridone constitutes the scaffold of some synthetic compounds with diverse pharmacological activities. 3-Chloro-6-(2- ... C. F. H. Allen & G. H. W. McKee (1939). "Acridone". Organic Syntheses. 19: 6. doi:10.15227/orgsyn.019.0006. Austrian National ...
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Alkaloids1
- The plant contains alkaloids of various structure types, including quinoline, furocholine and alkaloids of the acridone type such as rutacridone. (sauerandsons.com)
Function1
- Phosphorescence of the donor (D) and the delayed fluorescence of the acceptor (A) and their lifetimes have been measured for coumarin 102 (D)-rhodamine B(A) and 9(10H)-acridone (D)-rhodamine 6G(A) dye systems as a function of acceptor concentration. (ias.ac.in)
Derivatives1
- Cholewinski G , Iwaszkiewicz-Grzes D , Trzonkowski P , Dzierzbicka K . Synthesis and biological activity of ester derivatives of mycophenolic acid and acridines/acridones as potential immunosuppressive agents. (wjgnet.com)
Compounds4
- Compounds based on acridone, which have three linear rings, with the center ring containing a ring nitrogen and a keto oxygen opposite to each other. (nih.gov)
- This compound belongs to the class of organic compounds known as acridones. (drugbank.com)
- HN - 2008(2004) BX - Acetogenin Compounds MH - Acridones UI - D054831 MN - D3.132.32 MN - D3.494.46.109 MS - Compounds based on acridone, which have three linear rings, with the center ring containing a ring nitrogen and a keto oxygen opposite to each other. (nih.gov)
- Among them, acridone alkaloids are the most powerful antimicrobial compounds while coumarin inhibits fungal and bacterial development just at high concentrations, while tested gas of rue didn't present such activity. (brain-tumor-cancer-information.com)