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
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
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 Nov	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 Oct	11605659
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 Jun 6	12036369
Structure-activity relationships in the acronycine series.	2002 Sep	12171551
Covalent binding to glutathione of the DNA-alkylating antitumor agent, S23906-1.	2003 Jul	12823555
Synthesis and cytotoxic activity of some new azapyranoxanthenone aminoderivatives.	2003 Oct 15	14527556
A transesterification reaction is implicated in the covalent binding of benzo[b]acronycine anticancer agents with DNA and glutathion.	2004 Jan 2	14697766
Synthesis and cytotoxic and antitumor activity of 1,2-dihydroxy-1,2-dihydrobenzo[b]acronycine diacid hemiesters and carbamates.	2004 Mar	14993749
Synthesis and cytotoxic activity of pyranocarbazole analogues of ellipticine and acronycine.	2004 May	15133204
Generation of replication-dependent double-strand breaks by the novel N2-G-alkylator S23906-1.	2006 Jul 15	16849567
Synthesis, antitumor activity, and mechanism of action of benzo[a]pyrano[3,2-h]acridin-7-one analogues of acronycine.	2006 Jun 1	16722658
[From acronycine to benzo-[b]-acronycine derivatives: potent antitumor agents].	2007 Jan	17645109
Structure-activity relationships in the acronycine and benzo[b]acronycine series: role of the pyran ring.	2008 Dec	18342404
Fused xanthone derivatives as antiproliferative agents.	2009 Jan	19149484
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 Feb	19926174

Patents

Name

Type

Language

ACRONINE

Official Name

English

acronine [INN]

Common Name

English

COMPOUND 42339

Code

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