9-Oxo-10(9H)-acridineacetic acid Chemical Properties

Melting point:

~289 °C (dec.)

Boiling point:

486.6±34.0 °C(Predicted)

Density 

1.362

storage temp. 

Sealed in dry,Room Temperature

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

form 

Solid

pka

3.69±0.10(Predicted)

color 

Pale Yellow to Light Yellow

λmax

410nm(H2O)(lit.)

BRN 

227508

InChI

InChI=1S/C15H11NO3/c17-14(18)9-16-12-7-3-1-5-10(12)15(19)11-6-2-4-8-13(11)16/h1-8H,9H2,(H,17,18)

InChIKey

UOMKBIIXHQIERR-UHFFFAOYSA-N

SMILES

C1=C2C(N(CC(O)=O)C3=C(C2=O)C=CC=C3)=CC=C1

CAS DataBase Reference

38609-97-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

AR7190000

HS Code 

2933.99.8290

9-Oxo-10(9H)-acridineacetic acid Usage And Synthesis

Definition

Acriridone derivatives have become a research hotspot in the field of medicine in recent years due to their good antibacterial, anti-inflammatory, anti-malarial, and anti-cancer activities. This type of compound has a rigid planar structure of a macrocyclic conjugated system and can be embedded or Electrostatic attraction binds to DNA. Among them, 9-aminoacridine derivatives have good pharmacological and biological activities, and some of them have been used clinically as DNA embedding reagents. As an important pharmaceutical intermediate, 9-Oxo-10(9H)-acridineacetic acid has also received increasing attention. Cridanimod (9-Oxo-10(9H)-acridineacetic acid) is a potent progesterone receptor (PR) activator mediated through induction of IFNα and IFNβ expression. Cridanimod is a small-molecule immunomodulator and interferon inducer.

Description

9-Oxo-10(9H)-acridineacetic acid , also known as Cridanimod or XBIO-101, is a small molecule that can increase progesterone receptor (PR) expression, with potential antineoplastic adjuvant activity. Cridanimod is able to induce the expression of PR in endometrial cancer. This could increase the sensitivity of endometrial cancer cells to progestin monotherapy. In combination with a progestin, cancer cells could be eradicated through increased PR-mediated signaling, leading to an inhibition of luteinizing hormone (LH) release from the pituitary gland, via a negative feedback mechanism, and, eventually, an inhibition of estrogen release from the ovaries. This leads to an inhibition of cellular growth in estrogen-dependent tumor cells.

Uses

9-Oxo-10(9H)-acridineacetic acid is a reagent for pre-column derivatization of amino acids for fluorescent determination in HPLC and it is also a building block in pharmaceutics.

Definition

ChEBI: Cridanimod is a member of acridines. It is functionally related to an acridone.

Synthesis

The synthetic method consisted of the following steps: 29.2 g of [Pmim]OH ionic liquid was added to a three-necked flask equipped with a condensation reflux device, followed by the addition of 19.5 g of acridinone and 11.3 g of chloroacetic acid, which was homogenized by stirring at room temperature. The reaction mixture was allowed to stand at room temperature and then reacted under stirring conditions for 12 hours. After completion of the reaction, the residue was washed with 25 mL of methanol and dried to give 24.2 g of 2-(9-oxoacridin-10(9H)-yl)acetic acid in 95.7% yield.

storage

Store at +4°C

References

[1] Patent: CN104592115, 2017, B. Location in patent: Paragraph 0016; 0017; 0018
[2] Patent: CN108456166, 2018, A. Location in patent: Paragraph 0030; 0044; 0045; 0047; 0050; 0051; 0072
[3] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 2, p. 211 - 214

9-Oxo-10(9H)-acridineacetic acid(38609-97-1)Related Product Information

• Glycine
• 2-ETHOXY-6,9-DIAMINOACRIDINE
• Amsacrine hydrochloride
• 6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE
• 9(10H)-ACRIDONE
• Basic Orange 14
• Ethyl 2-(Chlorosulfonyl)acetate
• Ethyl acetate
• Quinacridone
• Folic acid
• Citric acid
• Ascoric Acid
• Chloroacetic acid
• Acetic anhydride
• CARBAZINE
• 10-METHYL-9(10H)-ACRIDONE
• (DIPHENYLAMINO)ACETIC ACID
• Camedon