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| CAS No.: | 319460-85-0 |
|---|---|
| Name: | Axitinib |
| Molecular Structure: | |
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| Formula: | C22H18N4OS |
| Molecular Weight: | 386.477 |
| Synonyms: | AG013736;Benzamide,N-methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1H-indazol-6-yl]thio]-; |
| EINECS: | 638-771-6 |
| Density: | 1.35 g/cm3 |
| Melting Point: | 213-215 °C |
| Boiling Point: | 668.9 °C at 760 mmHg |
| Flash Point: | 358.3 °C |
| Appearance: | Off-white solid |
| Hazard Symbols: | Xn,N |
| Risk Codes: | 22-50/53 |
| Safety: | 60-61 |
| PSA: | 95.97000 |
| LogP: | 5.03000 |
axitinib
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In neat (no solvent) for 0.75h; Milling; | 99% |
| With toluene-4-sulfonic acid In methanol; water at 64℃; for 1 - 5h; Product distribution / selectivity; | 98% |
| With toluene-4-sulfonic acid In methanol; water at 65℃; for 4h; Reagent/catalyst; Inert atmosphere; | 95.4% |
axitinib
| Conditions | Yield |
|---|---|
| With 1,2-diaminopropan In 1-methyl-pyrrolidin-2-one at 40 - 70℃; for 1h; | 95% |
axitinib
| Conditions | Yield |
|---|---|
| In methanol; acetic acid at 60℃; | 92% |
| Stage #1: 6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridin-2-yl)ethenyl]indazole ethylacetate solvate With toluene-4-sulfonic acid In ethanol at 82℃; for 14h; Stage #2: With sodium hydrogencarbonate In ethanol; water at 20℃; for 2h; |
axitinib
| Conditions | Yield |
|---|---|
| In NaHCO3; ethyl acetate at 65℃; | 92% |
2-vinylpyridine
2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide
axitinib
| Conditions | Yield |
|---|---|
| Stage #1: 2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide With palladium diacetate; acetic anhydride; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1-methyl-pyrrolidin-2-one at 25 - 50℃; Inert atmosphere; Stage #2: 2-vinylpyridine In 1-methyl-pyrrolidin-2-one at 50 - 95℃; for 12h; | 70.68% |
| With tris-(o-tolyl)phosphine; lithium bromide; palladium diacetate In 2,4-dichlorophenoxyacetic acid dimethylamine at 110℃; for 25h; Product distribution / selectivity; Heck Reaction; | |
| With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; tris-(o-tolyl)phosphine; lithium bromide; palladium diacetate In DMA at 110℃; for 25h; Product distribution / selectivity; Inert atmosphere; |
| Conditions | Yield |
|---|---|
| With triethylamine In neat (no solvent) at 100℃; for 24h; Heck Reaction; Green chemistry; | 70% |
2-mercapto-N-methylbenzamide
axitinib
| Conditions | Yield |
|---|---|
| With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 48h; Inert atmosphere; Reflux; | 54% |
2-vinylpyridine
axitinib
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: palladium diacetate; triethylamine; triphenylphosphine; tetrabutylammomium bromide; sodium bromide / neat (no solvent) / 1.5 h / Milling 2: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / neat (no solvent) / 0.83 h / Milling 3: toluene-4-sulfonic acid / neat (no solvent) / 0.75 h / Milling View Scheme |
2-vinylpyridine
axitinib
| Conditions | Yield |
|---|---|
| Stage #1: 2-vinylpyridine; N-1 Boc 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide for 2h; Heck Reaction; Stage #2: With tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 100℃; Stage #3: With trifluoroacetic acid Product distribution / selectivity; |
axitinib
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at 20 - 65℃; for 18h; Purification / work up; |
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1. Introduction of Axitinib
Axitinib is one kind of white crystalline powder or off-white solid. The IUPAC name of Axitinib is N-methyl-2-[[3-[(E)-2-pyridin-2-ylethenyl]-1H-indazol-6-yl]sulfanyl]benzamide. The product's categories are All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Protein Kinase Inhibitors and Activators. It is a small molecule tyrosine kinase inhibitor under development by Pfizer. Axitinib can soluble in DMSO at 33 mg/mL; soluble in ethanol at 1.7 mg/mL with warming; very poorly soluble in water; maximum solubility in plain water is estimated to be about 10-50 µM; buffers, serum, or other additives may increase or decrease the aqueous solubility.
2. Properties of Axitinib
Physical properties about Axitinib are:
(1)ACD/LogP: 4.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.14; (4)ACD/LogD (pH 7.4): 4.15; (5)ACD/BCF (pH 5.5): 830.65; (6)ACD/BCF (pH 7.4): 834.47; (7)ACD/KOC (pH 5.5): 4273.12; (8)ACD/KOC (pH 7.4): 4292.77; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 76.32 Å2; (13)Index of Refraction: 1.728; (14)Molar Refractivity: 113.45 cm3; (15)Molar Volume: 284.8 cm3; (16)Polarizability: 44.97×10-24 cm3; (17)Surface Tension: 75.2 dyne/cm; (18)Density: 1.35 g/cm3; (19)Flash Point: 358.3 °C; (20)Enthalpy of Vaporization: 98.31 kJ/mol; (21)Boiling Point: 668.9 °C at 760 mmHg; (22)Vapour Pressure: 9.35E-18 mmHg at 25°C.
3. Structure Descriptors of Axitinib
(1)SMILES:O=C(NC)c4ccccc4Sc1ccc2c(c1)nnc2\C=C\c3ncccc3
(2)InChI:InChI=1/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+
(3)InChIKey:RITAVMQDGBJQJZ-FMIVXFBMBT
(4)Std. InChI:InChI=1S/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+
(5)Std. InChIKey:RITAVMQDGBJQJZ-FMIVXFBMSA-N
4. Uses of Axitinib
Axitinib (AG-013736) is an oral, potent, and selective inhibitor of vascular endothelial growth factor receptors 1 (VEGFR-1), 2 (VEGFR-2), and 3 (VEGFR-3), platelet derived growth factor receptor (PDGFR), and cKIT (CD117). Axitinib inhibits many targets which is including VEGFR-1, VEGFR-2, VEGFR-3, platelet derived growth factor receptor (PDGFR), and cKIT (CD117). It also can inhibit growth of breast cancer in xenograft models and has been successful in trials with renal cell carcinoma (RCC) and several other tumor types. A Phase II clinical trial showed good response in combination chemotherapy with gemcitabine for advanced pancreatic cancer.
