CAS Number863774-58-7
Synonyms4-(3-Hydroxyphenyl)-7,7-dimethyl-2-thioxo-2,3,4,6,7,8-hexahydro-5(1H)-quinazolinone; Rac-Dimethylenastron; DIMETHYLENASTRON; 4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-2,3,4,6,7,8-hexahydroquinazolin-5(1H)-one; 2,3,4,6,7,8-Hexahydro-4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-5(1H)-quinazolinone
Molecular FormulaC16H18N2O2S
Molecular Weight302.39
Purity≥95 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point475.6±55.0 °C at 760 mmHg
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 863774-58-7 |
| Catalog No. | 2A-1198810 |
| Chinese Name | 2,3,4,6,7,8-六氢-4-(3-羟基苯基)-7,7-二甲基-2-硫代-5(1H)-喹唑啉酮 |
| Synonyms | 4-(3-Hydroxyphenyl)-7,7-dimethyl-2-thioxo-2,3,4,6,7,8-hexahydro-5(1H)-quinazolinone; Rac-Dimethylenastron; DIMETHYLENASTRON; 4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-2,3,4,6,7,8-hexahydroquinazolin-5(1H)-one; 2,3,4,6,7,8-Hexahydro-4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-5(1H)-quinazolinone |
| Molecular Formula | C16H18N2O2S |
| Molecular Weight | 302.39 |
| Purity | ≥95 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 475.6±55.0 °C at 760 mmHg |
| Appearance | solid |
| Storage Condition | 2-8℃ |
| Application | Dimethylenastron is a potent Eg5 inhibitor with an IC50 value of 200 nM. |
| MDL Number | MFCD09264157 |
| SMILES | S=C1NC(C3=C(N1)CC(CC3=O)(C)C)c2cc(ccc2)O |
| InChI | 1S/C16H18N2O2S/c1-16(2)7-11-13(12(20)8-16)14(18-15(21)17-11)9-4-3-5-10(19)6-9/h3-6,14,19H,7-8H2,1-2H3,(H2,17,18,21) |
| InChI Key | RUOOPLOUUAYNPY-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/200752_1_863774_58_7.pdf |
| Bioactivity | Dimethylenastron is a potent Eg5 inhibitor, with an IC50 of 200 nM. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Kinesin Signaling Pathways >> Cytoskeleton >> Kinesin Research Areas >> Cancer Target Eg5:200 nM (IC50) In Vitro Dimethylenastron is a potent Eg5 inhibitor, with an IC50 of 200 nM. Dimethylenastron exhibits no inhibition of five other kinesin subfamilies (kinesin 1/4/7/10 and one ungrouped-originating from 4 different organisms). Dimethylenastron (0.5, 1 μM) causes accumulation of cells in G2/M in HeLa cells[1]. Dimethylenastron (3 and 10 μM) concentration-dependently suppresses the migratory ability of the cancer cells in PANC1 pancreatic cancer cells after treatment for 24 h, but does not inhibit the proliferation of cancer cells at 24 h until 72 h. Dimethylenastron also reduces invasion ability of the cancer cells[2]. In Vivo Dimethylenastron (1.0 µmol) induces a milder scarring but the length of bleb survival is not significantly prolonged compared with the control group. Dimethylenastron (1.0 µmol) reveals a markedly reduced ratio of intraocular pressure and a milder, but not obviously reduced, subconjunctival fibrotic reaction in the rabbits treated with glaucoma filtration surgery[3]. Cell Assay Cell invasion in response to Dimethylenastron is carried out by transwell assays. The upper surface of the transwell filters is coated with matrigel or fibronectin. Cells suspended in 200 μL serum-free media are added to the chamber, and the chamber is placed in a 24-well plate containing complete medium. After 24 h of incubation at 37°C, the filters are gently taken out and matrigel on the upper surface of the filters is removed by cotton swabs. Cells on the underside of transwell filters are fixed with 4% paraformaldehyde for 30 min, stained with 0.1% crystal violet for 10 min, and then photographed. For quantitative assessment, the number of invading cells is counted in five random fields per filter. The extent of cell invasion is quantified as the number of invading cells in the drug-treatment group divided by the number of invading cells in the control group[2]. Animal Admin Just after the conjunctival suture is closed, a metallic needle (30 G) is inserted into the subconjunctival space at the nasal margin of the superior rectus muscle and injection of one of the following agents is delivered: The rabbits receive either no adjuvant after the surgery in the control group, one unilateral subconjunctival injection of Dimethylenastron (1.0 µmol, 3.0 µmol) or of the vehicle (DMSO, 99.9%, 10 mg/mL) alone at baseline, which means an injection directly after surgery and in two further groups additionally at days 3 and 7 thereafter (1.0 µmol, 3.0 µmol)[3]. References [1]. Gartner M, et al. Development and biological evaluation of potent and specific inhibitors of mitotic Kinesin Eg5. Chembiochem. 2005 Jul;6(7):1173-7. [2]. Sun XD, et al. Dimethylenastron suppresses human pancreatic cancer cell migration and invasion in vitro via allosteric inhibition of mitotic kinesin Eg5. Acta Pharmacol Sin. 2011 Dec;32(12):1543-8. [3]. Lüke J, et al. The effect of adjuvant dimethylenastron, a mitotic Kinesin Eg5 inhibitor, in experimental glaucoma filtration surgery. Curr Eye Res. 2010 Dec;35(12):1090-8. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 475.6±55.0 °C at 760 mmHg Molecular Formula C16H18N2O2S Molecular Weight 302.391 Flash Point 241.4±31.5 °C Exact Mass 302.108887 PSA 93.45000 LogP 2.47 Vapour Pressure 0.0±1.2 mmHg at 25°C Index of Refraction 1.674 InChIKey RUOOPLOUUAYNPY-UHFFFAOYSA-N SMILES CC1(C)CC(=O)C2=C(C1)NC(=S)NC2c1cccc(O)c1 Storage condition 2-8℃ |
| Use of | Dimethylenastron is a potent Eg5 inhibitor, with an IC50 of 200 nM. Properties Name 4-(3-hydroxyphenyl)-7,7-dimethyl-2-sulfanylidene-3,4,6,8-tetrahydro-1H-quinazolin-5-one Synonym More Synonyms Dimethylenastron Biological Activity Description Dimethylenastron is a potent Eg5 inhibitor, with an IC50 of 200 nM. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Kinesin Signaling Pathways >> Cytoskeleton >> Kinesin Research Areas >> Cancer Eg5:200 nM (IC50) In Vivo Dimethylenastron (1.0 µmol) induces a milder scarring but the length of bleb survival is not significantly prolonged compared with the control group. Dimethylenastron (1.0 µmol) reveals a markedly reduced ratio of intraocular pressure and a milder, but not obviously reduced, subconjunctival fibrotic reaction in the rabbits treated with glaucoma filtration surgery[3]. References [2]. Sun XD, et al. Dimethylenastron suppresses human pancreatic cancer cell migration and invasion in vitro via allosteric inhibition of mitotic kinesin Eg5. Acta Pharmacol Sin. 2011 Dec;32(12):1543-8. [3]. Lüke J, et al. The effect of adjuvant dimethylenastron, a mitotic Kinesin Eg5 inhibitor, in experimental glaucoma filtration surgery. Curr Eye Res. 2010 Dec;35(12):1090-8. Chemical & Physical Properties Molecular Formula C16H18N2O2S Exact Mass 302.108887 PSA 93.45000 Index of Refraction 1.674 InChIKey RUOOPLOUUAYNPY-UHFFFAOYSA-N Storage condition 2-8℃ |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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