Home Other Building Blocks 3-(2-methoxyethyl)-2-methyl-4,9-dioxo-1-(pyrazin-2-ylmethyl)naphtho[2,3-d]imidazol-1-ium bromide

3-(2-methoxyethyl)-2-methyl-4,9-dioxo-1-(pyrazin-2-ylmethyl)naphtho[2,3-d]imidazol-1-ium bromide

CAS No.:
781661-94-7
Catalog Number:
AG0036ME
Molecular Formula:
C20H19BrN4O3
Molecular Weight:
443.2939
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$96
- +
5mg
≥98%
1 week
United States
$135
- +
10mg
98%
1 week
United States
$173
- +
25mg
≥98%
1 week
United States
$348
- +
50mg
98%
1 week
United States
$540
- +
100mg
98%
1 week
United States
$740
- +
Product Description
Catalog Number:
AG0036ME
Chemical Name:
3-(2-methoxyethyl)-2-methyl-4,9-dioxo-1-(pyrazin-2-ylmethyl)naphtho[2,3-d]imidazol-1-ium bromide
CAS Number:
781661-94-7
Molecular Formula:
C20H19BrN4O3
Molecular Weight:
443.2939
MDL Number:
MFCD11983133
IUPAC Name:
1-(2-methoxyethyl)-2-methyl-3-(pyrazin-2-ylmethyl)benzo[f]benzimidazol-3-ium-4,9-dione;bromide
InChI:
InChI=1S/C20H19N4O3.BrH/c1-13-23(9-10-27-2)17-18(24(13)12-14-11-21-7-8-22-14)20(26)16-6-4-3-5-15(16)19(17)25;/h3-8,11H,9-10,12H2,1-2H3;1H/q+1;/p-1
InChI Key:
QBIYUDDJPRGKNJ-UHFFFAOYSA-M
SMILES:
COCCn1c(C)[n+](c2c1C(=O)c1ccccc1C2=O)Cc1cnccn1.[Br-]
UNII:
7H5Q4J1CM5
Properties
Complexity:
571  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
442.064g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
443.301g/mol
Monoisotopic Mass:
442.064g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
78A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
YM155 as an inhibitor of cancer stemness simultaneously inhibits autophosphorylation of epidermal growth factor receptor and G9a-mediated stemness in lung cancer cells. PloS one 20170101
Prevention of BMS-777607-induced polyploidy/senescence by mTOR inhibitor AZD8055 sensitizes breast cancer cells to cytotoxic chemotherapeutics. Molecular oncology 20140501
Inhibition of pluripotent stem cell-derived teratoma formation by small molecules. Proceedings of the National Academy of Sciences of the United States of America 20130827
Sepantronium bromide (YM155) enhances response of human B-cell non-Hodgkin lymphoma to rituximab. The Journal of pharmacology and experimental therapeutics 20121001
Survivin is a therapeutic target in Merkel cell carcinoma. Science translational medicine 20120509
The survivin suppressant YM155 potentiates chemosensitivity to gemcitabine in the human pancreatic cancer cell line MiaPaCa-2. Anticancer research 20120501
A phase II study of YM155, a novel small-molecule suppressor of survivin, in castration-resistant taxane-pretreated prostate cancer. Annals of oncology : official journal of the European Society for Medical Oncology 20120401
Overcoming erlotinib resistance in EGFR mutation-positive non-small cell lung cancer cells by targeting survivin. Molecular cancer therapeutics 20120101
Mcl-1 downregulation by YM155 contributes to its synergistic anti-tumor activities with ABT-263. Biochemical pharmacology 20111101
YM155, a selective survivin suppressant, inhibits tumor spread and prolongs survival in a spontaneous metastatic model of human triple negative breast cancer. International journal of oncology 20110901
Antitumor activity of YM155, a selective small-molecule survivin suppressant, alone and in combination with docetaxel in human malignant melanoma models. Clinical cancer research : an official journal of the American Association for Cancer Research 20110815
YM155, a novel survivin suppressant, enhances taxane-induced apoptosis and tumor regression in a human Calu 6 lung cancer xenograft model. Anti-cancer drugs 20110601
Survivin inhibition is critical for Bcl-2 inhibitor-induced apoptosis in hepatocellular carcinoma cells. PloS one 20110101
Marked anti-tumour activity of the combination of YM155, a novel survivin suppressant, and platinum-based drugs. British journal of cancer 20100629
Characterization of human organic cation transporter 1 (OCT1/SLC22A1)- and OCT2 (SLC22A2)-mediated transport of 1-(2-methoxyethyl)-2-methyl-4,9-dioxo-3-(pyrazin-2-ylmethyl)- 4,9-dihydro-1H-naphtho[2,3-d]imidazolium bromide (YM155 monobromide), a novel small molecule survivin suppressant. Drug metabolism and disposition: the biological fate of chemicals 20100101
Phase I study of YM155, a novel survivin suppressant, in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20090601
Carrier-mediated uptake of 1-(2-methoxyethyl)-2-methyl-4,9-dioxo-3-(pyrazin-2-ylmethyl)-4,9-dihydro-1H-naphtho[2,3-d]imidazolium bromide (YM155 monobromide), a novel small-molecule survivin suppressant, into human solid tumor and lymphoma cells. Drug metabolism and disposition: the biological fate of chemicals 20090301
Survivin expression in primary malignant melanoma of the esophagus. Scandinavian journal of gastroenterology 20090101
Phase I and pharmacokinetic study of YM155, a small-molecule inhibitor of survivin. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20081110
Liquid chromatography-electrospray tandem mass spectrometric assay suitable for quantitation of YM155, a novel small-molecule survivin suppressant, in dog plasma. Biomedical chromatography : BMC 20080701
Properties