ACRONINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H19NO3
Molecular Weight	321.3698
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C=CC(C)(C)O2)C3=C1C(=O)C4=C(C=CC=C4)N3C

InChI

InChIKey=SMPZPKRDRQOOHT-UHFFFAOYSA-N

InChI=1S/C20H19NO3/c1-20(2)10-9-13-15(24-20)11-16(23-4)17-18(13)21(3)14-8-6-5-7-12(14)19(17)22/h5-11H,1-4H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5458379 | https://www.ncbi.nlm.nih.gov/pubmed/6616497 | https://www.ncbi.nlm.nih.gov/pubmed/15960428

Acronine is an acridone alkaloid isolated from the bark of Acronychia bauri Schott, scrub ash indigenous to Australia. It possesses broad-spectrum activity against experimental neoplasms. Acronine has been studied in the treatment of multiple myeloma. Acronine analogues also possess cytotoxic and antitumor activity.

Approval Year

PubMed

Title	Date	PubMed
The NER proteins XPC and CSB, but not ERCC1, regulate the sensitivity to the novel DNA binder S23906: implications for recognition and repair of antitumor alkylators.	2010-08-01	20399198
Identification of thymidylate synthase as a potential therapeutic target for lung cancer.	2010-07-27	20628382
An unusual DNA binding compound, S23906, induces mitotic catastrophe in cultured human cells.	2010-03-28	19758748
Synthesis and cytotoxic activity of psorospermin and acronycine analogues in the 3-propyloxy-acridin-9(10H)-one and -benzo[b]acridin-125H-one series.	2010-02	19926174
Influence of the stereoisomeric position of the reactive acetate groups of the benzo[b]acronycine derivative S23906-1 on its DNA alkylation, helix-opening, cytotoxic, and antitumor activities.	2009-12	19752199
Acronycine derivatives: a promising series of anticancer agents.	2009-09	19594412
4'-Chloro-3',5'-dimethoxy-acetanilide.	2009-04-22	21583893
[Effect of peroxisome proliferators activated receptor gamma and its ligand on airway mucus hypersecretion in rats].	2009-04	19576043
Antitumor psoropermum xanthones and sarcomelicope acridones: privileged structures implied in DNA alkylation.	2009-03-27	19191562
Synthesis, cytotoxic activity, and DNA binding properties of antitumor cis-1,2-dihydroxy-1,2-dihydrobenzo[b]acronycine cinnamoyl esters.	2009-03-01	19217791
Fused xanthone derivatives as antiproliferative agents.	2009-01	19149484
Structure-activity relationships in the acronycine and benzo[b]acronycine series: role of the pyran ring.	2008-12	18342404
Synthesis, cytotoxic activity, and mechanism of action of furo[2,3-c]acridin-6-one and benzo[b]furo[3,2-h]acridin-6-one analogues of psorospermin and acronycine.	2008-11-27	18947222
2,2-dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties.	2008-09	18806949
Synthesis and cytotoxic activity of dimeric analogs of acronycine in the benzo[b]pyrano[3,2-h]acridin-7-one series.	2007-05	17473459
[From acronycine to benzo-[b]-acronycine derivatives: potent antitumor agents].	2007-01	17645109
Synthesis and cytotoxic activity of benzo[a]pyrano[3,2-h] and [2,3-i]xanthone analogues of psorospermine, acronycine, and benzo[a]acronycine.	2006-08	16880654
Generation of replication-dependent double-strand breaks by the novel N2-G-alkylator S23906-1.	2006-07-15	16849567
Synthesis, antitumor activity, and mechanism of action of benzo[a]pyrano[3,2-h]acridin-7-one analogues of acronycine.	2006-06-01	16722658
Design, synthesis and antiproliferative activity of some new azapyranoxanthenone aminoderivatives.	2006-01	16300857
Synthesis and cytotoxic activity of acronycine analogues in the benzo[c]pyrano[3,2-h]acridin-7-one and naphtho[1,2-b][1,7] and [1,10]-phenanthrolin-7(14H)-one series.	2005-12	16327185
Design, synthesis, and cytotoxic activity of Michael acceptors and enol esters in the benzo[b]acronycine series.	2005-08	16079520
Antimalarial activity of thioacridone compounds related to the acronycine alkaloid.	2005-03-01	15698783
Synthesis, biological evaluation, and molecular modeling of novel thioacridone derivatives related to the anticancer alkaloid acronycine.	2005-02-01	15653336
[Structure activity relationships and mechanism of action of antitumor benzo[b]acronycine antitumor agents].	2005-01	15803100
[Acronycine revisited: development of benzo[b]acronycine antitumor agents].	2005-01	15803099
Covalent binding of antitumor benzoacronycines to double-stranded DNA induces helix opening and the formation of single-stranded DNA: unique consequences of a novel DNA-bonding mechanism.	2005-01	15657355
Structure-activity relationship studies of new acronine analogues as suggested by molecular descriptors.	2005	15960428
Benzo[b]acronycine derivatives: a novel class of antitumor agents.	2004-08	15276298
Synthesis and cytotoxic activity of pyranocarbazole analogues of ellipticine and acronycine.	2004-05	15133204
Design of novel antitumor DNA alkylating agents: the benzacronycine series.	2004-03	15032716
Synthesis and cytotoxic and antitumor activity of 1,2-dihydroxy-1,2-dihydrobenzo[b]acronycine diacid hemiesters and carbamates.	2004-03	14993749
A transesterification reaction is implicated in the covalent binding of benzo[b]acronycine anticancer agents with DNA and glutathion.	2004-01-02	14697766
Synthesis and cytotoxic activity of some new azapyranoxanthenone aminoderivatives.	2003-10-15	14527556
Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues.	2003-07-03	12825945
Covalent binding to glutathione of the DNA-alkylating antitumor agent, S23906-1.	2003-07	12823555
Synthesis of 6-dialkylaminoalkylamino pyrano[2,3-c]acridones and benzo[b]pyrano[3,2-h]acridones: soluble acronycine analogues with increased cytotoxic activity.	2003	12659419
Structure-activity relationships in the acronycine series.	2002-09	12171551
Alkylation of guanine in DNA by S23906-1, a novel potent antitumor compound derived from the plant alkaloid acronycine.	2002-08-06	12146956
[New antitumor agents in the acronycine series].	2002-07	12378151
Design, synthesis, and antiproliferative activity of some new pyrazole-fused amino derivatives of the pyranoxanthenone, pyranothioxanthenone, and pyranoacridone ring systems: a new class of cytotoxic agents.	2002-06-06	12036369
Design and synthesis of some new pyranoxanthenone aminoderivatives with cytotoxic activity.	2002-06-03	12031316
Acronycine derivatives as promising antitumor agents.	2002-06	12045455
Induction of apoptosis in HL-60 leukemia and B16 melanoma cells by the acronycine derivative S23906-1.	2002-04-15	11996885
Induction of cyclin E and inhibition of DNA synthesis by the novel acronycine derivative S23906-1 precede the irreversible arrest of tumor cells in S phase leading to apoptosis.	2001-12	11723246
Synthesis, cytotoxic activity, NMR study and stereochemical effects of some new pyrano[3,2-b]thioxanthen-6-ones and pyrano[2,3-c]thioxanthen-7-ones.	2001-11	11597459
1-Oxo-2-hydroxy-1,2-dihydroacronycine: a useful synthon in the acronycine series for the introduction of amino substituents at 6-position and for the conversion into isopropylfuroacridones.	2001-10	11605659
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653
Anti-herpesvirus activity of citrusinine-I, a new acridone alkaloid, and related compounds.	1989-08	2556960
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Name

Type

Language

COMPOUND 42339

Preferred Name

English

ACRONINE

Official Name

English

acronine [INN]

Common Name

English

ACRONINE [HSDB]

Common Name

English

COMPOUND-42339

Code

English

NSC-403169

Code

English

3,12-Dihydro-6-methoxy-3,3,12-trimethyl-7H-pyrano[2,3-c]acridin-7-one

Systematic Name

English

ACRONINE [USAN]

Common Name

English

7H-PYRANO(2,3-C)ACRIDIN-7-ONE, 3,12-DIHYDRO-6-METHOXY-3,3,12-TRIMETHYL-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2163