117570-53-3

Basic information

• Product Name: 5,6-Dimethylxantheonone-4-acetic acid
• Synonyms: 5,6-dimethylxanthenoneacetic acid;5,6-Dimethylxantheonone-4-acetic acid;DMXAA;vadimezan;(5,6-DIMETHYL-9-OXO-XANTHEN)-4-ACETIC ACID;5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid;5,6-Dimethylxanthenone-4-acetic acid;NSC-640488
• CAS NO: 117570-53-3
• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29
• Product Categories: Inhibitors
• Mol File: 117570-53-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 259-261 °C
• Boiling Point: 520.9 °C at 760 mmHg
• Flash Point: 197.1 °C
• Appearance: light brown/solid
• Density: 1.321 g/cm³
• Vapor Pressure: 1.12E-11mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: 2-8°C
• Solubility: DMSO: 17 mg/mL, soluble
• PKA: 4.21±0.10(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 5,6-Dimethylxantheonone-4-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dimethylxantheonone-4-acetic acid(117570-53-3)
• EPA Substance Registry System: 5,6-Dimethylxantheonone-4-acetic acid(117570-53-3)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: ZD5536200
• Hazardous Substances Data: 117570-53-3(Hazardous Substances Data)

Usage

Description

DMXAA (117570-53-3) is a STING (Stimulator of Interferon Genes) agonist selective for mouse STING.1,2 Intratumoral administration of DMXAA resulted in tumor regression and complete rejection in mouse xenografts.3 Tumor regression induced by DMXAA results from a cascade of cellular events which include disruption of tumor vasculature followed by the release of chemokines which trigger the recruitment of immune cells.4 DMXAA induced expression of IFN-β resulting in a striking expansion of leukemia-specific T cells extending survival in two acute myeloid leukemia models.5

Uses

Different sources of media describe the Uses of 117570-53-3 differently. You can refer to the following data:
1. Vadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models.
2. Vadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models. It is a substrate for the immune adaptor protein STING in mice.

Definition

ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.

General Description

5,6-dimethylxanthenone-4-acetic acid (DMXAA) is a flavone acetic acid derivative. It acts as a vascular disrupting agent (VDA), which damages tumor vasculature and stimulates an anti-tumor immune response. It stimulates hemorrhagic necrosis.

Biochem/physiol Actions

DMXAA is an apoptosis inducer; anti-vascular.

References

1) Prantner et al. (2012), 5,6-Dimethylzanthenone-4-acetic acid (DMXAA) activates stimulator of interferon gene (STING)-dependent innate immune pathways and is regulated by mitochondrial membrane potential; J. Biol. Chem., 287 39776 2) Conlon et al. (2013), Mouse, but not human STING, binds and signals in response to the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid; J. Immunol., 190 5216 3) Corrales et al. (2015), Direct Activation of STING in the Tumor Microenvironment Leads to Potent and Systemic Tumor Regression and immunity; Cell Rep., 11 1018 4) Weiss et al. (2017), The STING agonist DMXAA triggers a cooperation between T lymphocytes and myeloid cells that leads to tumor regression; Oncoimmunology, 6 e1346765 5) Curran et al. (2016), STING Pathway Activation Stimulates Potent Immunity Against Acute Myeloid Leukemia; Cell Rep., 15 2357

InChI:InChI=1/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19)

Synthetic route

2-(7-bromo-5,6-dimethyl-9-oxo-9H-xanthene-4-yl) acetic acid (1021381-69-0) → vadimezan (117570-53-3)

Conditions	Yield
With palladium on activated charcoal; hydrogen	99%
With palladium on activated charcoal; hydrogen In methanol under 760.051 Torr;	85%

2-<2-(carboxymethyl)phenoxy>-3,4-dimethylbenzoic acid (117570-93-1) → vadimezan (117570-53-3)

Conditions	Yield
With sulfuric acid In water at 80℃; for 0.166667h;	95%
With sulfuric acid In water at 80℃; for 0.166667h;	70%
With sulfuric acid In water for 2h; Heating;	64.4%

3,4-dimethyl-2-nitrobenzaldehyde + 2-Hydroxyphenylacetic acid (614-75-5) → vadimezan (117570-53-3)

Conditions	Yield
With potassium phosphate; triphenylphosphine; copper dichloride In toluene at 110℃; for 24h; Reagent/catalyst;	83%

ethyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate (1415114-04-3) → vadimezan (117570-53-3)

Conditions	Yield
With water; sodium hydroxide In methanol at 40℃; Darkness;	75%
Stage #1: ethyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate With water; sodium hydroxide at 40℃; Darkness; Stage #2: With acetic acid In water Darkness;

(2-hydroxyphenyl)acetic acid disodium salt (117571-22-9) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / tris[2-(2-methoxyethoxy)ethyl]amine; CuCl / dimethylformamide / 4 h / 85 °C 2: 87 g / H2SO4 / H2O / 0.92 h / 90 °C View Scheme

potassium; 2-iodo-3,4-dimethyl-benzoate → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / tris[2-(2-methoxyethoxy)ethyl]amine; CuCl / dimethylformamide / 4 h / 85 °C 2: 87 g / H2SO4 / H2O / 0.92 h / 90 °C View Scheme

6,7-dimethylisatin (20205-43-0) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / KOH, KCl, 27percent H2O2 / 20 °C 2: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 3: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 4: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

2,3-dimethyl-α-isonitrosoacetanilide (6579-44-8) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 65 percent / CH3SO3H / 70 - 80 °C 2: 65 percent / KOH, KCl, 27percent H2O2 / 20 °C 3: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 4: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 5: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

2-amino-3,4-dimethylbenzoic acid (50419-58-4) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 2: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 3: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

3,4-dimethyl-2-iodobenzoic acid (129833-31-4) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 2: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

2,3-Dimethylaniline (87-59-2) → vadimezan (117570-53-3)

Conditions

Yield

Multi-step reaction with 6 steps 1: Na2SO4, hydroxylamine sulfate, concd. HCl / H2O 2: 65 percent / CH3SO3H / 70 - 80 °C 3: 65 percent / KOH, KCl, 27percent H2O2 / 20 °C 4: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 5: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 6: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

2,3-Dimethylphenol (526-75-0) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium / methanol / 12 h / 100 °C 2.1: Tris(3,6-dioxaheptyl)amine; copper(l) chloride / dimethyl sulfoxide / 4 h / 85 °C 2.2: pH 2 - 3 3.1: sulfuric acid / water / 0.5 h / 90 °C 4.1: caesium carbonate / palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 24 h / 80 °C 5.1: water; sodium hydroxide / 40 °C / Darkness 5.2: Darkness View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate; copper dichloride; triphenylphosphine / toluene / 24 h / 110 °C 2: bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate; 18-crown-6 ether; potassium phosphate / 12 h / 160 °C / Inert atmosphere 3: sodium hydroxide; water / methanol / 40 °C / Darkness View Scheme

4-bromo-5,6-dimethylxanthone (1035912-43-6) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: caesium carbonate / palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 24 h / 80 °C 2.1: water; sodium hydroxide / 40 °C / Darkness 2.2: Darkness View Scheme

3-bromo-2-(2,3-dimethylphenoxy)-benzoic acid (1035912-41-4) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / water / 0.5 h / 90 °C 2.1: caesium carbonate / palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 24 h / 80 °C 3.1: water; sodium hydroxide / 40 °C / Darkness 3.2: Darkness View Scheme

3-bromo-2-iodo benzoic acid potassium salt → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Tris(3,6-dioxaheptyl)amine; copper(l) chloride / dimethyl sulfoxide / 4 h / 85 °C 1.2: pH 2 - 3 2.1: sulfuric acid / water / 0.5 h / 90 °C 3.1: caesium carbonate / palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 24 h / 80 °C 4.1: water; sodium hydroxide / 40 °C / Darkness 4.2: Darkness View Scheme

2-iodo-3-bromobenzoic acid (503821-94-1) → vadimezan (117570-53-3)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: potassium hydroxide / water / 12 h / 100 °C 2.1: Tris(3,6-dioxaheptyl)amine; copper(l) chloride / dimethyl sulfoxide / 4 h / 85 °C 2.2: pH 2 - 3 3.1: sulfuric acid / water / 0.5 h / 90 °C 4.1: caesium carbonate / palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 24 h / 80 °C 5.1: water; sodium hydroxide / 40 °C / Darkness 5.2: Darkness View Scheme

sodium 2,3-xylenolate (37621-79-7) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Tris(3,6-dioxaheptyl)amine; copper(l) chloride / dimethyl sulfoxide / 4 h / 85 °C 1.2: pH 2 - 3 2.1: sulfuric acid / water / 0.5 h / 90 °C 3.1: caesium carbonate / palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 24 h / 80 °C 4.1: water; sodium hydroxide / 40 °C / Darkness 4.2: Darkness View Scheme

(2-hydroxyphenyl)acetic acid disodium salt (117571-22-9) + potassium; 2-iodo-3,4-dimethyl-benzoate → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: Tris(3,6-dioxaheptyl)amine; copper(l) chloride / dimethyl sulfoxide / 8 h / Heating; Inert atmosphere 2: sulfuric acid / water / 2 h / Heating View Scheme

3,4-dimethylbenzoic acid (619-04-5) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; N-Bromosuccinimide / 12 h / 20 °C 2: trichlorophosphate; zinc(II) chloride / 0.67 h / 85 °C / Microwave irradiation 3: hydrogen; palladium on activated charcoal / methanol / 760.05 Torr View Scheme

2,5-dibromo-3,4-dimethylbenzoic acid (6514-83-6) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate; zinc(II) chloride / 0.67 h / 85 °C / Microwave irradiation 2: hydrogen; palladium on activated charcoal / methanol / 760.05 Torr View Scheme

2,3-dichlorobenzylaldehyde (6334-18-5) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate; copper dichloride; triphenylphosphine / toluene / 24 h / 110 °C 2: bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate; 18-crown-6 ether; potassium phosphate / 12 h / 160 °C / Inert atmosphere 3: sodium hydroxide; water / methanol / 40 °C / Darkness View Scheme

3,4-dimethylbenzaldehyde (5973-71-7) → vadimezan (117570-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate / 1.5 h / -5 - 0 °C 2: potassium phosphate; copper dichloride; triphenylphosphine / toluene / 24 h / 110 °C View Scheme

1-Phenylethanol (98-85-1, 13323-81-4) + vadimezan (117570-53-3) → 1-phenylethyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	99.4%

propan-1-ol (71-23-8) + vadimezan (117570-53-3) → propyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	98.7%

methanol (67-56-1) + vadimezan (117570-53-3) → methyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate (1035912-44-7)

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	98.6%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 23℃; for 3h;	88%

vadimezan (117570-53-3) + GlyOEt*HCl (459-73-4) → ethyl 2-(2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetamido)acetate (1415113-38-0)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	96.5%

vadimezan (117570-53-3) + butan-1-ol (71-36-3) → butyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	95.8%

ethanol (64-17-5) + vadimezan (117570-53-3) → ethyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate (1415114-04-3)

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	95.4%

3-amino-propionic acid ethyl ester (924-73-2) + vadimezan (117570-53-3) → ethyl 3-(2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetamido)propanoate (1415113-39-1)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	92.4%

vadimezan (117570-53-3) + cyclohexanol (108-93-0) → cyclohexyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	90.6%

n-heptan1ol (111-70-6) + vadimezan (117570-53-3) → 2-(5,6-dimethylxanthone-4-yl)acetic acid heptyl ester (1415113-18-6)

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	87.8%
With diphenylammonium trifluoromethanesulfonate In toluene Reflux;	87.8%

i-Amyl alcohol (123-51-3) + vadimezan (117570-53-3) → isopentyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	87.4%

8-methyl-1-nonanol (55505-26-5) + vadimezan (117570-53-3) → 8-methylnonyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetat

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	87.1%

vadimezan (117570-53-3) + benzyl alcohol (100-51-6) → 2-(5,6-dimethylxanthone-4-yl)acetic acid benzyl ester (1415113-22-2)

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	81.7%

pentan-1-ol (71-41-0) + vadimezan (117570-53-3) → pentyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	80.6%

vadimezan (117570-53-3) + aniline (62-53-3) → 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)-N-phenylacetamide (1415113-26-6)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	80%

vadimezan (117570-53-3) + p-aminoethylbenzoate (94-09-7) → 4-(2-(5,6-dimethylxanthone-4-yl)acetamido)benzoic acid ethyl ester (1415113-40-4)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	79.3%

4-phenyl-butan-1-ol (3360-41-6) + vadimezan (117570-53-3) → 4-phenylbutyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	78.7%

1-octadecanol (112-92-5) + vadimezan (117570-53-3) → 2-(5,6-dimethylxanthone-4-yl)acetic acid octadecyl ester (1415113-19-7)

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	73.7%

vadimezan (117570-53-3) + isopropyl alcohol (67-63-0) → isopropyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	73.4%

vadimezan (117570-53-3) → 2,2-dideutero-2-(1,2,3,7,8-pentadeutero-9-oxo-5,6-bis(trideuteromethyl)-9H-xanthen-4-yl)acetic acid (1222125-89-4)

Conditions	Yield
Stage #1: vadimezan With [D]-sodium hydroxide; hydrogen; water-d2; platinum on carbon; palladium 10% on activated carbon at 180℃; for 96h; Sealed tube; Stage #2: With hydrogenchloride In water pH=3;	68%

1-Heptylamine (111-68-2) + vadimezan (117570-53-3) → 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)-N-heptylacetamide

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	66.4%

propylamine (107-10-8) + vadimezan (117570-53-3) → 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)-N-propylacetamide (1415113-24-4)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	64.9%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide Heating;	64.9%

vadimezan (117570-53-3) + m,p-dichloroaniline (95-76-1) → N-(3,4-dichlorophenyl)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetamide (1415113-29-9)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	58.6%

vadimezan (117570-53-3) + allyl alcohol (107-18-6) → 2-(5,6-dimethylxanthone-4-yl)acetic acid allyl ester (1415113-20-0)

Conditions	Yield
With diphenylammonium trifluoromethanesulfonate In toluene for 2h; Reflux;	57.7%

vadimezan (117570-53-3) + 3-chloro-aniline (108-42-9) → N-(3-chlorophenyl)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetamide (1415113-28-8)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 24h;	55.7%

3,4-dihydro-12-O-(3'-hydroxypropyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one + vadimezan (117570-53-3) → 3,4-dihydro-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one-12-O-propyl 5,6-dimethylxanthone-4-acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	52.4%

3,4-dihydro-12-O-(4'-hydroxybutyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one + vadimezan (117570-53-3) → 3,4-dihydro-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one-12-O-butyl 5,6-dimethylxanthone-4-acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	52.4%
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	51.3%

Upstream product

• 117570-93-1 2-<2-(carboxymethyl)phenoxy>-3,4-dimethylbenzoic acid 
• 1021381-69-0 2-(7-bromo-5,6-dimethyl-9-oxo-9H-xanthene-4-yl) acetic acid 
• 1415114-04-3 ethyl 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetate 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 5973-71-7 3,4-dimethylbenzaldehyde 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 6514-83-6 2,5-dibromo-3,4-dimethylbenzoic acid 
• 619-04-5 3,4-dimethylbenzoic acid 
• 117571-22-9 (2-hydroxyphenyl)acetic acid disodium salt 
• 37621-79-7 sodium 2,3-xylenolate 
• 503821-94-1 2-iodo-3-bromobenzoic acid 
• 1035912-41-4 3-bromo-2-(2,3-dimethylphenoxy)-benzoic acid 
• 1035912-43-6 4-bromo-5,6-dimethylxanthone 
• 526-75-0 2,3-Dimethylphenol 

Downstream Products

• 1415113-44-8 N'-(2-hydroxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-46-0 N'-(4-hydroxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-48-2 N'-(3-methoxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-50-6 N'-(4-methoxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-52-8 N'-(5-chloro-2-hydroxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-54-0 N'-(3,4,5-trimethoxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-55-1 N'-(3,4-dihydroxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-57-3 N'-(4-hydroxy-3-methoxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-59-5 N'-(4-hydroxy-3-methoxy-2-nitrobenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-61-9 N'-(3-hydroxy-4-methoxybenzylidene)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazide 
• 1415113-67-5 (R)-1-(2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetyl)-4-(1-phenylethyl)thiosemicarbazide 
• 1415113-69-7 (S)-1-(2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetyl)-4-(1-phenylethyl)thiosemicarbazide 
• 1415113-22-2 2-(5,6-dimethylxanthone-4-yl)acetic acid benzyl ester 
• 1415113-23-3 2-(5,6-dimethylxanthone-4-yl)acetic acid-(4-chlorobenzyl)ester 

Relevant articles and documents

Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists

STING (Stimulator of Interferon Genes) has become a focal point in immunology research and a target in drug discovery. The discovery of a potent human-STING agonist is expected to revolutionize current anti-virus or cancer immunotherapy. Inspired by the structure and function of murine STING-specific agonists (DMXAA and CMA), we rationally designed and synthesized four series of novel compounds for the enhancement of human sensitivity. In the cell-based assay, we identified six compounds from all the synthetic small molecules: 2g, 9g, and 12b are STING agonists that are efficacious across species, and all have the skeleton of acridone; 1b, 1c, and 12c just function in the murine STING pathway. Notably, 12b exhibits the best activity among the six agonists, and its inductions of both human and murine STING-dependent signalling are similar to that of 2′3′-cGAMP, which is a well-known STING inducer. While a protein assay indicated that 2 g, 9 g, and 12b could activate the pathway by directly binding human STING, 12b also displayed the strongest binding affinity. Additionally, our studies show that 12b can induce faster, more powerful, and more durable responses of assorted cytokines in a native system than 2′3′-cGAMP. Consequently, our team is the first to successfully modify murine STING agonists to obtain human sensitivity, and these results suggest that 12b is a potent direct-human-STING agonist. Additionally, the acridone analogues demonstrate tremendous potential in the treatment of tumours or viral infections.

Compound as DMXAA-Pyranoxanthone well as preparation method and application thereof

The invention discloses a DMXAA-Pyranoxanthone heterozygous compound with an anti-tumor effect and a preparation method and application thereof. The DMXAA-Pyranoxanthone heterozygous compound adopts the structural formula shown as a formula I. The preparation method comprises the following steps: preparing DMXAA in three steps, preparing pyranoxanthone in two steps, and combining the DMXAA and the pyranoxanthone into the DMXAA-Pyranoxanthone heterozygous compound in two steps. The DMXAA-Pyranoxanthone heterozygous compound and a DMXAA/pyranoxanthone combined medicine have excellent in-vitro tumor cell proliferation inhibiting activity on breast cancer cells, liver cancer cells, leukemia cells, and can induce apoptosis of tumor cells through multiple targets. The DMXAA-Pyranoxanthone heterozygous compound and the DMXAA/pyranoxanthone combined medicine can be applied to preparation of cancer treating medicines.

5,6-DIMETHYL XANTHONE-4-ACETIC ACID DERIVATIVES AND METHOD OF PREPARING THE SAME

A method of preparation of 5,6-dimethylxanthone-4-acetic acid (DMXAA) and derivatives thereof. The derivatives are represented by formula (I), wherein R represents totally 1 to 2 substitutes at 1, 2, 3, 7, and 8 position selected from a lower alkyl, halogen, CF3, CN, NO2, NH2, CH2COOH, OR2, OH, NHSO2R2, SR2, CH2CONHR2 or NHR2, and R2 represents a lower alkyl, or a lower alkyl having OH, NH2, or OCH3. The invention further provides a pharmaceutical composition having such derivatives used as excellent antitumor and antibacterial agents.