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. Many of them are naturally occurring alkaloids.
Compounds with three aromatic rings in linear arrangement with a SULFUR in the center ring.
Acridines are heterocyclic aromatic organic compounds containing two nitrogen atoms at positions 1 and 3 of a planar, unsaturated ring system, which have been widely used in chemotherapy and have also found applications in dye industries and fluorescence microscopy.

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)

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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)

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"Acridones" are a class of chemical compounds that contain a heterocyclic ring structure consisting of a benzene ring fused to a pyrimidine ring. The name "acridone" refers to the parent compound of this class, which is 9-phenylacridine or dibenzo[b,f]pyrimidine-7(8H)-one.

Acridones have been studied for their potential medicinal properties, including their antimicrobial, antiviral, and antitumor activities. However, some acridones have also been found to be toxic or carcinogenic, so their use in medical applications is limited.

In a medical context, "acridones" may refer to a specific class of drugs that are derived from the parent compound and have been investigated for their potential therapeutic uses. It is important to note that each drug or chemical compound should be evaluated on its own merits and in the context of its specific medical use, as generalizations about a entire class of compounds can be misleading.

Thioxanthenes are a group of heterocyclic organic compounds that contain a thioxanthene nucleus, which is a six-membered ring containing five carbon atoms and one sulfur atom. Thioxanthenes are structurally related to phenothiazines and have been used in the synthesis of various pharmaceutical drugs, particularly antipsychotic medications.

In medical terms, thioxanthenes refer to a class of antipsychotic drugs that are used to treat various psychiatric disorders such as schizophrenia and related conditions. These drugs work by blocking dopamine receptors in the brain, which helps to reduce the symptoms of psychosis such as hallucinations, delusions, and disordered thinking.

Some examples of thioxanthene antipsychotics include chlorprothixene, thiothixene, and flupenthixol. Like other antipsychotic medications, thioxanthenes can have side effects such as extrapyramidal symptoms (EPS), which are movement disorders that can cause stiffness, tremors, or spasms. Other potential side effects of thioxanthenes may include sedation, orthostatic hypotension, and weight gain.

Acridines are a class of heterocyclic aromatic organic compounds that contain a nucleus of three fused benzene rings and a nitrogen atom. They have a wide range of applications, including in the development of chemotherapeutic agents for the treatment of cancer and antibacterial, antifungal, and antiparasitic drugs. Some acridines also exhibit fluorescent properties and are used in research and diagnostic applications.

In medicine, some acridine derivatives have been found to intercalate with DNA, disrupting its structure and function, which can lead to the death of cancer cells. For example, the acridine derivative proflavin has been used as an antiseptic and in the treatment of certain types of cancer. However, many acridines also have toxic side effects, limiting their clinical use.

It is important to note that while acridines have potential therapeutic uses, they should only be used under the supervision of a qualified healthcare professional, as they can cause harm if not used properly.

... can be synthesized by heating fenamic acid. One of the first who were able to prove the compound's existence was Karl ... Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. The molecule is planar ... 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 ...
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 ...
... 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". 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 ...
C. F. H. Allen, G. H. W. McKee (1939). "Acridone". Organic Syntheses. 19: 6. doi:10.15227/orgsyn.019.0006. H.B. Goodbrand; Nan- ...
doi:10.1002/14356007.a20_371.(subscription required) Smith, J. Anthony; West, Richard M.; Allen, Malcolm (2004). "Acridones and ...
It may be prepared from acridone. There's also a route from toluene: v t e (Articles without EBI source, Articles without KEGG ...
This enzyme participates in acridone alkaloid biosynthesis. Eilert U, Wolters B (1989). "Elicitor induction of S-adenosyl-L- ...
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 ...
The 2016 rematch between Solomon and Cohen was notably acrid. One article suggested that Cohen's operatives had stolen ...
"In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum". Antimicrobial Agents and ...
Patented: November 30, 1948 Soluble vat dyes of the acridone series. William B. Hardy and Elizabeth M. Hardy, Bound Brook. ...
Waffo, AF; Coombes, PH; Crouch, NR; Mulholland, DA; El Amin, SM; Smith, PJ (2007). "Acridone and furoquinoline alkaloids from ...
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- ...
In one experimental setup the hydrophobic matrix is RP silica gel (C18) and the anchor is acridone. Acridone is N-alkylated and ...
A series of furanoacridones and two acridone alkaloids (arborinine and evoxanthine) have been isolated from R. graveolens. It ...
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 ...
This enzyme participates in 3 metabolic pathways: carbazole degradation, benzoate degradation via coa ligation, and acridone ...
The name indicates that the compounds are a fusion of acridone and quinoline, although they are not made that way. Classically ...
... acridones (1-hydroxy-3-methoxy-10-methylacridon-9-one, 1-hydroxy-10-methylacridon-9-one, zanthozolin), and aromatic and ...
... 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- ...
... acridone Most members of this class are unstable towards self-condensation, however some important examples do exist as ...
The lignan sesamin, the N-isobutylamide γ-sanshool, the acridone alkaloids 1-hydroxy-3-methoxy-N-methylacridone, arborinine, ...
The molecular formula C13H9NO (molar mass: 195.22 g/mol, exact mass: 195.0684 u) may refer to: Acridone CR gas, or ...
Acridone can be synthesized by heating fenamic acid. One of the first who were able to prove the compounds existence was Karl ... Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. The molecule is planar ... 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 Quinacridone [Wiki] Quino[2,3-b]acridin. e-7,14-dione, 5,12-. dihydro- [ACD/Index Name] ...
Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 25,. 166-187.. Mukherjee, P. K., (2019). Chapter 6 - Extraction ...
P. Belmont, J. Bosson, T. Godet, and M. Tiano, "Acridine and acridone derivatives, anticancer properties and synthetic methods ...
Rutaceae) used traditionally by Akamba tribe in Kenya yielded three acridone alkaloids, a furoquinoline alkaloid and two ... Rutaceae) used traditionally by Akamba tribe in Kenya yielded three acridone alkaloids, a furoquinoline alkaloid and two ... Rutaceae) used traditionally by Akamba tribe in Kenya yielded three acridone alkaloids, a furoquinoline alkaloid and two ...
New Acridone Alkaloids from Citrus junos Tanaka. Motoharu Ju-ichi,* Mami Inoue, Kuniko Aoki, and Hiroshi Furukawa. ... Two new acridone alkaloids, junosine (1) and 5-methoxynoracronycine (2), were isolated from the bark of Citrus junos (Rutaceae ...
Well what the group at Oregon noticed was that if they took an Acridone which is a tricyclic molecule and had a particular ... What they did with that is engineered the Acridone ring system to have its own antimalarial activity. ...
Prenylated Acridones from Atalantia monophylla DC. and Their Aromatase Inhibition and Cytotoxic Activities. Phytochemistry 2020 ... Prenylated Acridones from Atalantia monophylla DC. and Their Aromatase Inhibition and Cytotoxic Activities. Phytochemistry 2020 ...
Acridones - Preferred Concept UI. M0508131. Scope note. Compounds based on acridone, which have three linear rings, with the ... Compounds based on acridone, which have three linear rings, with the center ring containing a ring nitrogen and a keto oxygen ...
Multi spectroscopic and molecular simulation studies of propyl acridone binding to calf thymus DNA in the presence of ...
... acridone and quinacridone (US 2007/0252517 A1). ...
Introduction of a fluorine atom into the acridone cycle results in an increase of the fluorescence quantum yield and decay time ...
Artículo Acridones As Antiviral Agents: Synthesis, Chemical and Biological Properties Sepúlveda, Claudia Soledad ; Fascio, ... Artículo Antiviral activity of an N-allyl acridone against dengue virus Mazzucco, María Belén ; Talarico, Laura Beatriz ; ...
N10-Substituted Acridones as DNA-Intercalating Agents. J. Chem. Res. 2020, 44, 410-425.. ... N10-Substituted Acridones as DNA-Intercalating Agents. J. Chem. Res. 2020, 44, 410-425. ...
9(10H)-ACRIDONE. 578-95-0. More. 9-Oxo-10(9H)-acridineacetic acid. 38609-97-1. More. Allyl iodide. 556-56-9. More. Diacetone-D- ...
ID: GO:0008441 Type: http://bio2vec.net/ontology/gene_function Label: 3\(2\),5\-bisphosphate nucleotidase activity Synonyms: 3\(2\), 5\-bisphosphate nucleotidase activity Alternative IDs: als API: GO SPARQL: GO ...
ID: GO:0047774 Type: http://bio2vec.net/ontology/gene_function Label: cis-2-enoyl-CoA reductase (NADPH) activity Synonyms: cis-2-enoyl-CoA reductase (NADPH) activity Alternative IDs: als API: GO SPARQL: GO ...
The scale of the project is: an annual output of 100 tons of iodide, 3 tons of erlotinib hydrochloride, 10 tons of acridone ... Acridone acetate Production Contamination:. ① exhaust gas: organized exhaust gas: condensation, acidification ring, alkaline ...
Inclusion Complexes of Acridone and Its Semicarbazone Derivative With β- Cyclodextrin: - A Thermodynamic, Spectral and ...
Quin Acridone Purple Blue 593 2. *Quin Acridone Purple Red 592 2 ...
A toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. It is the first parasympathomimetic substance ever studied and causes profound parasympathetic activation that may end in convulsions and death. The specific antidote is atropine ...
Gonzalez-Garcia, M.C., et al., Coupled Excited-State Dynamics in N-Substituted 2-Methoxy-9-Acridones. Front. Chem., (2019). 7: ...
Acridone, Thioxanthone, Xanthone and Phenazine Derivatives OR Radical ,, Radical mechanism by ROS formation ,, Polynitroarenes ... Acridone, Thioxanthone, Xanthone and Phenazine Derivatives OR Non-covalent interaction ,, DNA intercalation ,, Aminoacridine ...
Acridone synthase (ACS) catalyzes the committed condensing reaction of acridone biosynthesis yielding 1,3-dihydroxy-N- ... From the lyophilized cell material nine acridones and three acridone-monoglucosides have been isolated which were found for the ... Acridone Alkaloids from Cell Suspension Cultures of Thamnosma montana. Baumert, A; Maier, W; Matern, U; Schmidt, J; Schumann, B ... Differential regulation and distribution of acridone synthase in Ruta graveolens. Junghanns, K T; Kneusel, R E; Gröger, D; ...
PFASs: polyfluoroalkyl substances, MASH: 10-methyl-acridone-2-sulfonohydrazide.. 6. Analytical methods for α-keto acids and 2- ...
Acridine/acridone-carborane conjugates as strong DNA-binding agents with anticancer potential. D. Różycka, A. Kowalczyk, M. ...
Synthesis, cytotoxicity, and docking based analysis of acridone-N-acetamides as AKT kinase inhibitors. 3129. -. 3144. ...
Design, Synthesis and Property Study of Bispiropyran Switchable Molecule Based on Acridone [J]. Acta Chim. Sinica, 2016, 74(8 ...
His study looks at the intersection of Biophysics and topics like Förster resonance energy transfer with Acridone, Carbon ... His Biophysics research incorporates elements of Acridone, Lipid bilayer, Antibiotic resistance and Förster resonance energy ...
  • Rutaceae) used traditionally by Akamba tribe in Kenya yielded three acridone alkaloids, a furoquinoline alkaloid and two triterpenoids. (academicjournals.org)
  • Chemical studies on this genus have led to the isolation of an extensive array of coumarins and alkaloids (including acridones, carbazoles, furoquinolines, and indoles) [16] . (jse.ac.cn)
  • Ruta graveolens) essential oil in a clear glass vial A series of furanoacridones and two acridone alkaloids (arborinine and evoxanthine) can be isolated from Ruta graveolens. (greenmattersec.com)
  • Acridone constitutes the scaffold of some synthetic compounds with diverse pharmacological activities. (wikipedia.org)
  • 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. (bvsalud.org)
  • Introduction of a fluorine atom into the acridone cycle results in an increase of the fluorescence quantum yield and decay time whereas immobilization in a rigid polymer matrix (polystyrene) further extends the lifetime up to 18 ns. (advion.com)
  • His study looks at the intersection of Biophysics and topics like Förster resonance energy transfer with Acridone, Carbon chemistry, Dual fluorescence and Drug resistance. (research.com)
  • 3-Chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone has shown promise as an antimalarial drug. (wikipedia.org)
  • What they did with that is engineered the Acridone ring system to have its own antimalarial activity. (chemistryworld.com)
  • Techasakul, S. Synthesis, Cytotoxicity Evaluation, and Molecular Modeling Studies of 2,N10-Substituted Acridones as DNA-Intercalating Agents. (cri.or.th)
  • Multi spectroscopic and molecular simulation studies of propyl acridone binding to calf thymus DNA in the presence of electromagnetic force [med. (emf-portal.org)
  • 3-Chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone has shown promise as an antimalarial drug. (wikipedia.org)
  • We compared AOX activity in rhesus monkeys, guinea pigs, and humans using phthalazine and N -[2-(dimethylamino)ethyl]acridone-4-carboxamide (DACA) as substrates and raloxifene as an inhibitor. (aspetjournals.org)
  • A simple and sensitive method for the determination of free fatty acids (FFAs) using acridone ́ 9 ́ ethyl ́ p ́ toluenesulfonate (AETS) as a fluorescence derivatization reagent by high performance liquid chromatography (HPLC) has been developed. (virginia.edu)
  • 15. A new acridone with antifungal properties against Candida spp. (nih.gov)
  • Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive intramolecular cross-aldol condensation. (unboundmedicine.com)
  • Thermal dimerization of the acridone alkaloid noracronycine ( 2 ) leads to Diels-Alder adducts ( 3 ) and ( 4 ), possessing a rearranged structure. (heterocycles.jp)