ChemicalBook > CAS DataBase List > Acronine

Acronine

Product Name
Acronine
CAS No.
7008-42-6
Chemical Name
Acronine
Synonyms
Acronine;NSC-403169;NCI-C 01536;Compound 42339;Acronycine (Acronine);3,12-Dihydro-6-methoxy-3,3,12-trimethyl-7H-pyrano[2,3-c]acridin-7-one;7H-Pyrano[2,3-c]acridin-7-one,3,12-dihydro-6-methoxy-3,3,12-trimethyl-;3,3,12-Trimethyl-6-methoxy-7,12-dihydro-3H-pyrano[2,3-c]acridine-7-one
CBNumber
CB71177962
Molecular Formula
C20H19NO3
Formula Weight
321.37
MOL File
7008-42-6.mol
More
Less

Acronine Property

Melting point:
175-176℃
Boiling point:
460.13°C (rough estimate)
Density 
1.202±0.06 g/cm3 (20 ºC 760 Torr)
refractive index 
1.5600 (estimate)
pka
-2.43±0.40(Predicted)
Water Solubility 
2.7mg/L(25 ºC)
EPA Substance Registry System
Acronycine (7008-42-6)
More
Less

Safety

Hazardous Substances Data
7008-42-6(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

TRC
Product number
A191225
Product name
Acronycine
Packaging
1mg
Price
$165
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0010615
Product name
ACRONINE
Purity
95.00%
Packaging
5MG
Price
$505.67
Updated
2021/12/16
More
Less

Acronine Chemical Properties,Usage,Production

Originator

Acronine ,ZYF Pharm Chemical

Uses

Antineoplastic.

Definition

ChEBI: An alkaloid antineoplastic agent isolated from Acronychia baueri.

Manufacturing Process

The acridone alkaloids constitute a small group of natural products found exclusively in the Rutaceae family of higher plants. A sustained interest in this field has been due to the reported activity of acronycine a constituent of Acronnychia baueri and Vepris amphody as an anti-tumor agent.
There are different methods of the synthetic preparation of acronycine (W. M. Bandaranayake et al., J. Chem. Soc. Perkin 1, 998 (1968); J. Hlubucek et al.; Aust. J. Chem. 23, 1881 (1970). One of them is described below. Friedel- Crafts condensation between 2-nitrobenzoyl chloride and 3,5- dimethoxyphenol.
2-Nitrobenzoyl chloride (12 g) and AlCl3, (anhyd., 13 g) were dissolved in dry ether (50 ml) and this mixture added to a solution of 3.5-dimethoxyphenol (5 g) in dry ether 150 ml) at 0°C and the final mixture stirred at 0°C for 3 hours, brought to 20°C and stirred for a further 3 h. Diluted HCl and ice were added and the product extracted with EtOAc (3x50 ml), this extract was washed with aq. NaHCO3, water, dried (MgSO4), filtered and evaporated under reduced pressure to yield a dark red oil. This oil was treated with 2 M aq. NaOH. (100 ml) for 1 h., acidified with diluted HCl and re-extracted with EtOAc which gave, after a similar work up, a paled red oil (5.0 g). Thin layer chromatography (TLC) showed three components one of which was the starting phenol. Column chromatography (150 g silica gel) and elution with benzene:petrol ether 40°-60°C (1:1) followed by increasing polarity of solvents (benzene through chloroform to chloroform:ether (4:1) gave 59 fractions. Fractions 1-12 were combined to gave a solid, which crystallized from benzene to give 4,6-dimethoxy-2-hydroxy-2-nitrobenzophenone, MP: 198°-199°C. Fractions 13-21 were discarded. Fractions 22-42 were combined (0.3 g), crystallized from benzene and the product added to that obtained from fractions 43-59 which crystallized from benzene to give 2,6-dimethoxy- 7-hydroxy-2-nitrobenzophenone (0.5 g) MP: 175°-177°C. Condensation of 3-chloro-3-methylbutyne with 2,6-dimethoxy-7-hydroxy-2- nitrobenzophenone:
A solution of the above benzophenone (2 g) and excess 3-chloro-3- methylbutyne (4.5 g) in dry DMF (60 ml) containing anhydrous K2CO3 (4 g) and dry KI (2 g) was stirred and heated at 65°C for 14 hours (under N2). The mixture was cooled, diluted with water, acidified, extracted with chloroform (3x50 ml) and the extract was worked up in the usual way (including a NaOH wash) to give an oil, which was redissolved in DMF (20 ml) and heated at 130°C, under N2, for 7 h whence most of the starting material had disappeared. The solvent was removed under reduced pressure to give a product (0.62 g) which was purified by preparative layer chromatography on silica gel to give 6-(2-nitrobehzoyl)-5,7-dimethoxy-2,2-dimethylchromene (0.22 g) which crystallized from EtOH, MP: 92°-93°C.
6-(2-Aminobenzoyl)-5,7-dimethoxy-2,2-dimethylchromene (0.2 g) was dissolved in EtOH (30 ml) containing water (5 ml) and ammonium chloride (1 g) and Zn mossy (1.5 g) was added in portions and the mixture stirred at room temperature for 5 days. The solution was filtered, evaporated to dryness under reduced pressure and the residue dissolved in EtOAc (25 ml) and worked up in the usual way to give a solid (0.19 g). It crystallised from EtOH with MP: 123°-126°C.
Cyclization of aminodimethylchromenylbenzophenone: 6-(2-aminobenzoyl)- 5,7-dimethoxy-2,2-dimethylchromene (0.12 g) was dissolved in DMSO (8 ml) and NaH (0.06 g) added, the mixture was stirred for 6 days at room temperature. A further addition of NaH (0.06 g) was made and the solution heated to 50°C for 0.5 h whence it was poured into water, extracted with EtOAc and worked up in the usual way to give a crude mixture (0.11 g; components). Separation of this mixture on plate (silica gel:benzene:EtOAc, 10:4) gave band 1 (Rf 0.45: 38 mg) identified as starting material. Band 2 (Rf 0.32: 42 mg; 43%) which crystallized from ethylacetate as des-Nmethylisoacronycine, MP: 293°-295°C. Band 3 (Rf 0.10; 29 mg, 29%) crystallized from ethyl acetate as des-N-methylacronycine. MP: 237°-240°C.
Des-N-methylacronycine (14 mg) was dissolved in dry acetone (10 ml), anhydrous K2CO3 (1 g), and MeI (2 ml) added and the mixture refluxed for 11 hours. The solution was filtered and the solvents evaporated to give a solid (12 mg) which after purification on TLC, gave acronycine which crystallized from aqueous MeOH, MP: 171°-173°C. This product showed identical U.V. and Rf characterization when compared with acronycine and had an accurate mass measurement of 321.1368. C20H19NO3, required: 321.1364. UV and 1H NMR spectrum confirmed the structures of all described compounds.

Therapeutic Function

Antineoplastic

General Description

Yellow powder.

Air & Water Reactions

Water insoluble.

Reactivity Profile

Amines, like Acronine, are weak chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Acronine emits toxic fumes.

Fire Hazard

Flash point data for Acronine are not available. Acronine is probably combustible.

Acronine Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Acronine Suppliers

Sichuan Wei Keqi Biological Technology Co., Ltd.
Tel
028-81700200 18116577057
Fax
028-81705658
Email
3003855609@qq.com
Country
China
ProdList
7887
Advantage
56
Shanghai Yongye Biotechnology Co., Ltd.
Tel
86-021-61559134 15921386130
Fax
021-55068248
Email
3423497944@qq.com
Country
China
ProdList
8144
Advantage
55
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
Shanghai ChengShao Biological Technology Co., Ltd.
Tel
021-61847300 13341622919
Fax
021-61847300
Email
shcss01@163.com
Country
China
ProdList
4808
Advantage
58
Hubei Jusheng Technology Co.,Ltd.
Tel
18871490254
Fax
027-59599243
Email
linda@hubeijusheng.com
Country
CHINA
ProdList
28172
Advantage
58
Zhejiang Lianshuo Biotechnology Co., Ltd.
Tel
18616526224
Email
lianshuo@vip.126.com
Country
China
ProdList
9607
Advantage
58
Shanghai Fusheng Industrial Co., LTD
Tel
021-52961053 13524666654
Email
3004902811@qq.com
Country
China
ProdList
9724
Advantage
58
Foshan Treasure Biotechnology Co., Ltd
Tel
0757-85921206 18520245316
Email
2329783215@qq.com
Country
China
ProdList
12661
Advantage
58
Chengdu Push Bio-Technology Co., Ltd.
Tel
18080489829
Email
3004654993@qq.com
Country
China
ProdList
9209
Advantage
58
Nanjing Shangshu Biotechnology Co., Ltd
Tel
18266960953 18266960953
Email
907697096@qq.com
Country
China
ProdList
3033
Advantage
58

7008-42-6, AcronineRelated Search:


  • Acronine
  • 3,12-Dihydro-6-methoxy-3,3,12-trimethyl-7H-pyrano[2,3-c]acridin-7-one
  • 3,3,12-Trimethyl-6-methoxy-7,12-dihydro-3H-pyrano[2,3-c]acridine-7-one
  • Compound 42339
  • NSC-403169
  • NCI-C 01536
  • Acronycine (Acronine)
  • 7H-Pyrano[2,3-c]acridin-7-one,3,12-dihydro-6-methoxy-3,3,12-trimethyl-
  • 7008-42-6