N-(Carboxymethyl)acridone
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N-(Carboxymethyl)acridone
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CAS No:
38609-97-1
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Formula:
C15H11NO3
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Chemical Name:
N-(Carboxymethyl)acridone
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Synonyms:
10(9H)-Acridineacetic acid,9-oxo-;9-Oxo-10(9H)-acridineacetic acid;N-(Carboxymethyl)acridone;10-(Carboxymethyl)-9-acridinone;9-Oxo-10-acridineacetic acid;L 1;N-(Carboxymethyl)-9-acridone;Acridone-N-acetic acid;Cridanimod;10-CMA;2-(9-Oxo-9,10-dihydroacridin-10-yl)acetic acid;2-(9-Oxoacridin-10-yl)acetic acid
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CAS No:
Description
Cridanimod is a small-molecule immunomodulator and interferon inducer[1]. Cridanimod is a potent progesterone receptor (PR) activator mediated through induction of IFNα and IFNβ expression[2].
Cridanimod is a member of acridines. It derives from an acridone.|Cridanimod is a small molecule that can increase progesterone receptor (PR) expression, with potential antineoplastic adjuvant activity. Upon intramuscular administration, 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. In addition, this agent is able to increase the production and release of interferon (IFN) alpha and beta. PR is often downregulated in endometrial cancer and makes it resistant to progestin-mediated hormone therapy.
N-(Carboxymethyl)acridone Basic Attributes
253.25
253.25
1312995-182-4
X91E9EME19
DTXSID6046557
C77948
L - Antineoplastic and immunomodulating agents
2933990090
Safety Information
NONH for all modes of transport
3
36/37/38
26
AR7190000
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Agents that promote the production and release of interferons. They include mitogens, lipopolysaccharides, and the synthetic polymers Poly A-U and Poly I-C. Viruses, bacteria, and protozoa have been also known to induce interferons. (See all compounds classified as Interferon Inducers.)
10(9H)-acridineacetic acid, 9-oxo-
N-(Carboxymethyl)acridone Use and Manufacturing
The synthesis method comprises the following steps:29.2 g of [Pmim] OH ionic liquid was added in a three-necked flask equipped with a condensing reflux at room temperature, 19.5g acridone, stirring evenly after adding 11.3 g of chloroacetic acid, the control temperature of 25 stirring reaction 12h after standing at room temperatureThe residue was then washed with 25 ml of methanol and dried to give 24.2 g of acridone acetate (yield: 95.7percent).39percent acridone (2 mol), N-tetrabutylammonium bromide (TBAB) 19.34g (0.06mol), 265 g (2.8 mol) of chloroacetic acid was added to a 1000 mL three-necked flask.Add 500 mL of organic solvent DMF and stir at 80 ° C to dissolve.Further, 100 mL of a 60 wtpercent NaOH aqueous solution was added, and after heating at 80 ° C for 3 hours, The reaction was stopped, allowed to cool to room temperature, and the reaction system was poured into 300 mL of ice water.A large amount of yellow solid precipitates were precipitated, allowed to stand overnight, suction filtered, and washed with ice water.That is, a wet intermediate is obtained; 500 mL of a 30 wtpercent NaOH aqueous solution is added to the wet intermediate, Dissolve and stir at room temperature, filter, and wash with 100 mL of 30 wtpercent NaOH aqueous solution.Combine the washing solution, add concentrated hydrochloric acid to adjust the pH value between 4 and 5.There is a large amount of yellow solid precipitates, Allow to stand overnight, suction filtration, wash with ice water, Drying, 474 g of acridinone acetate product was obtained, and the yield was 93.5percent.The purity by HPLC was 99.2percent.
Pre-column derivatization reagent for amino acids in HPLC fluorescence determination method
Computed Properties
Molecular Weight:253.25
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:253.07389321
Monoisotopic Mass:253.07389321
Topological Polar Surface Area:57.6
Heavy Atom Count:19
Complexity:356
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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