78146-26-6

Basic information

• Product Name: 1,4-bis(2,3-epoxypropylamino)-9,10-anthracenedione
• Synonyms: 1,4-bis(2,3-epoxypropylamino)-9,10-anthracenedione
• CAS NO: 78146-26-6
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 0
• Mol File: 78146-26-6.mol

Chemical Properties

• Boiling Point: 648.6°C at 760 mmHg
• Flash Point: 346.1°C
• Appearance: /
• Density: 1.468g/cm³
• Vapor Pressure: 1.04E-16mmHg at 25°C
• Refractive Index: 1.733
• CAS DataBase Reference: 1,4-bis(2,3-epoxypropylamino)-9,10-anthracenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(2,3-epoxypropylamino)-9,10-anthracenedione(78146-26-6)
• EPA Substance Registry System: 1,4-bis(2,3-epoxypropylamino)-9,10-anthracenedione(78146-26-6)

Safety Data

• Hazardous Substances Data: 78146-26-6(Hazardous Substances Data)

Usage

Chemical structure

1,4-bis(2,3-epoxypropylamino)-9,10-anthracenedione

Primary use

Cross-linking agent in the production of epoxy resins

Functional groups

Contains two epoxy functional groups

Core structure

Quinone core structure

Applications

Adhesives, coatings, composites, electronics, and aerospace industries

Known for

High performance and durability

Handling precautions

Potential reactivity and toxicity require careful handling

InChI:InChI=1/C20H18N2O4/c23-19-13-3-1-2-4-14(13)20(24)18-16(22-8-12-10-26-12)6-5-15(17(18)19)21-7-11-9-25-11/h1-6,11-12,21-22H,7-10H2

Upstream product

• 29311-94-2 1,4-bis<(3-chloro-2-hydroxypropyl)amino>-9,10-anthracenedione 
• 128-95-0 1,4-diamino-9,10-anthraquinone 
• 1758-68-5 1,2-diamino-9,10-anthraquinone 
• 106-89-8 epichlorohydrin 
• 75-09-2 dichloromethane 

Downstream Products

• 99788-75-7 1,4-bis(2,3-dihydroxypropylamino)-9,10-anthracenedione 

Relevant articles and documents

Design, synthesis, and antitumor evaluation of novel anthraquinone derivatives

N-alkylated and O-alkylated anthraquinone derivatives with structures analogous to mitoxantrone were synthesized, characterized, and evaluated for their cytotoxic properties against three tumor cell lines (Human Breast Adenocarcinoma MCF-7, Human Cervical Adenocarcinoma HeLa, and Human Glioblastoma M059J) and a normal cell line (human lung fibroblasts GM-07492A). A structure-activity relationship study was carried out to verify the influence of lipophilic chain size on the biological activity of these compounds. The results indicated promising candidates for antineoplastic agents for the cancers evaluated, since these compounds showed significant selectivity and high cytotoxic potential for cancer cells, rather than mitoxantrone, the compound of which is already used in anticancer therapy.

Antitumor Agents-CLXVII. Synthesis and structure-activity correlations of the cytotoxic anthraquinone 1,4-bis-(2,3-epoxypropylamino)-9,10-anthracenedione, and of related compounds

1,4-Bis-(2,3-epoxypropylamino)-9,10-anthracenedione (3) was synthesized in this laboratory and was found to be a potent antitumor agent. Derivatives of this compound containing anthraquinone, naphthoquinone, and quinone skeletons were also prepared and evaluated for in vitro cytotoxic activity in several cell lines. These molecules were designed as bifunctional antitumor agents with the potential to act as (1) intercalating agents due to their planar backbones, and (2) alkylating agents due to the presence of alkylating moieties in their side chains. Compounds with an anthraquinone skeleton and propylamino side chains containing epoxides or halohydrins as the alkylating species showed greater activity than similar compounds with naphthoquinone or quinone skeletons. Compounds without these alkylating functionalities (e.g., with alkene or amino groups) were generally inactive. Hydroxy substitution on the planar skeleton in conjunction with alkylating side chains gave compounds with the most potent cytotoxic activity. The position of the hydroxy groups and side chains could be varied without substantially affecting activity. Activity was retained when an epoxypropyloxy side chain was substituted for the epoxypropylamino side chain in the parent compound.

1,4-bis-(amino-hydroxyalkylamino)-anthraquinones for inhibiting protein kinase C

The present invention provides novel substituted anthraquinones having the formula STR1 wherein R1 and R2 are independently H, alkyl, aryl, or arylalkyl; m and n are independently 1, 2, or 3; X is H, OH, NR3 R4, Cl, Br, I, F, alkyl, aryl alkoxy, aroxy, COOR5, or CONR6 R7 ; R3, R4, R5, R6, and R7 are independently H, lower alkyl or aryl useful for inhibiting protein kinase C and treating conditions related to, or affected by inhibition of protein kinase C, particularly cancer tumors, inflammatory disease, reperfusion injury, and cardiac dysfunctions related to reperfusion injury.

Microbicidal and plant growth regulating compounds

Process comprising the use as a microbicide or plant growth regulator of a compound of the formula STR1 wherein A, B, C and D is each independently selected from the group consisting of O,NR1, CR1 R1, CO, S,SO, and SO2, except for the A-C, C-A, B-D,D-B combinations: O--O, SO--SO, SO2 --SO2, S--O, S--NR2, SONR2, SO--CO, SO2 --CO, SO2 --SO; each group of the groups R1 is independently selected from the group consisting of H and (C1 -C4)alkyl; Y1 and Y2 may each be independently selected from the group consisting of H, (C1 -C4)alkyl, halogen, OR,SOR,SO2 R, SO3 R, CN, CO2 R, COR, CF3, NO2, NHCOR, and OCOR; or alternatively Y1 and Y2 and the carbons to which they are attached may comprise a cyclic structure selected from the group consisting of STR2 where R11 is aryl or (C1 -C4)alkyl X1 to X8 is each independently selected from the group consisting of H, (C1 -C4)alkyl, halogen, OR, SOR, SO2 R, SO3 R, CN,CO2 R, COR, CF3, NO2, NHCOR, and OCOR: and furthermore optionally any pair or pairs of adjacent X's may be in the form of a divalent group attached across the adjacent X position; Z1 and Z2 is each independently selected from the group consisting of NR2, O, S, CR2 R2 where each of the groups R2 is independently selected from the group consisting of H and (C1 -C4)alkyl; each of the groups R3 is independently selected from the group consisting of CO2 R, COR, CN CF3, SOR, SO2 R, (C1 -C4)alkyl and H.