Home Carbonyls Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester

Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester

CAS No.:
209783-80-2
Catalog Number:
AG002KDZ
Molecular Formula:
C21H20N4O3
Molecular Weight:
376.4085
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
95%
In Stock USA
United States
$73
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10mg
95%
In Stock USA
United States
$103
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50mg
95%
In Stock USA
United States
$169
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100mg
95%
In Stock USA
United States
$219
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200mg
95%
In Stock USA
United States
$336
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500mg
95%
In Stock USA
United States
$603
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1g
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In Stock USA
United States
$1069
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Product Description
Catalog Number:
AG002KDZ
Chemical Name:
Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester
CAS Number:
209783-80-2
Molecular Formula:
C21H20N4O3
Molecular Weight:
376.4085
MDL Number:
MFCD08272435
IUPAC Name:
pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate
InChI:
InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
InChI Key:
INVTYAOGFAGBOE-UHFFFAOYSA-N
SMILES:
O=C(OCc1cccnc1)NCc1ccc(cc1)C(=O)Nc1ccccc1N
UNII:
1ZNY4FKK9H
NSC Number:
706995
Properties
Complexity:
508  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
376.154g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
376.416g/mol
Monoisotopic Mass:
376.154g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
106A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2  
Literature
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Class I histone deacetylase inhibitor entinostat suppresses regulatory T cells and enhances immunotherapies in renal and prostate cancer models. PloS one 20120101
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The histone-deacetylase inhibitor MS-275 and the CDK-inhibitor CYC-202 promote anti-tumor effects in hepatoma cell lines. Oncology reports 20081101
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Evaluation of the in vitro and in vivo antitumor activity of histone deacetylase inhibitors for the therapy of retinoblastoma. Clinical cancer research : an official journal of the American Association for Cancer Research 20080515
Potentiation of reactive oxygen species is a marker for synergistic cytotoxicity of MS-275 and 5-azacytidine in leukemic cells. Leukemia research 20080501
Novel uracil-based 2-aminoanilide and 2-aminoanilide-like derivatives: histone deacetylase inhibition and in-cell activities. Bioorganic & medicinal chemistry letters 20080415
MS-275 synergistically enhances the growth inhibitory effects of RAMBA VN/66-1 in hormone-insensitive PC-3 prostate cancer cells and tumours. British journal of cancer 20080408
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Acute-myeloid-leukemia-targeted toxins kill tumor cells by cell-type-specific mechanisms and synergize with TRAIL to allow manipulation of the extent and mechanism of tumor cell death. Leukemia 20080301
Histone deacetylase inhibitors in lymphoma and solid malignancies. Expert review of anticancer therapy 20080301
Regulation of arginase-1 expression in macrophages by a protein kinase A type I and histone deacetylase dependent pathway. Journal of cellular biochemistry 20080201
Histone deacetylase inhibitors induce growth arrest and apoptosis of HTLV-1-infected T-cells via blockade of signaling by nuclear factor kappaB. Leukemia research 20080201
Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. The Biochemical journal 20080115
Antiproliferative activities of a library of hybrids between indanones and HDAC inhibitor SAHA and MS-275 analogues. Bioorganic & medicinal chemistry letters 20071115
Novel aminophenyl benzamide-type histone deacetylase inhibitors with enhanced potency and selectivity. Journal of medicinal chemistry 20071115
Histone deacetylase inhibitors induce cell death and enhance the apoptosis-inducing activity of TRAIL in Ewing's sarcoma cells. Journal of cancer research and clinical oncology 20071101
Histone deacetylase inhibitors suppress TF-kappaB-dependent agonist-driven tissue factor expression in endothelial cells and monocytes. The Journal of biological chemistry 20070928
Phase I trial of MS-275, a histone deacetylase inhibitor, administered weekly in refractory solid tumors and lymphoid malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research 20070915
Histone deacetylase inhibitor MS-275 alone or combined with bortezomib or sorafenib exhibits strong antiproliferative action in human cholangiocarcinoma cells. World journal of gastroenterology 20070907
Trithiocarbonates: exploration of a new head group for HDAC inhibitors. Bioorganic & medicinal chemistry letters 20070901
Relationship between embryonic histonic hyperacetylation and axial skeletal defects in mouse exposed to the three HDAC inhibitors apicidin, MS-275, and sodium butyrate. Toxicological sciences : an official journal of the Society of Toxicology 20070801
Antitumor activity of the histone deacetylase inhibitor MS-275 in prostate cancer models. The Prostate 20070801
Synergistic in vivo antitumor effect of the histone deacetylase inhibitor MS-275 in combination with interleukin 2 in a murine model of renal cell carcinoma. Clinical cancer research : an official journal of the American Association for Cancer Research 20070801
Histone deacetylase inhibitors affect dendritic cell differentiation and immunogenicity. Clinical cancer research : an official journal of the American Association for Cancer Research 20070701
Bispyridinium dienes: histone deacetylase inhibitors with selective activities. Journal of medicinal chemistry 20070517
MAGE-A9 mRNA and protein expression in bladder cancer. International journal of cancer 20070515
Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid. Bioorganic & medicinal chemistry letters 20070415
Phase 1 and pharmacologic study of MS-275, a histone deacetylase inhibitor, in adults with refractory and relapsed acute leukemias. Blood 20070401
Anti-rheumatic activities of histone deacetylase (HDAC) inhibitors in vivo in collagen-induced arthritis in rodents. British journal of pharmacology 20070401
The histone deacetylase inhibitors depsipeptide and MS-275, enhance TRAIL gene therapy of LNCaP prostate cancer cells without adverse effects in normal prostate epithelial cells. Cancer gene therapy 20070301
A liquid chromatography/tandem mass spectrometry assay to quantitate MS-275 in human plasma. Journal of pharmaceutical and biomedical analysis 20070117
Measuring cytotoxicity: a new perspective on LC50. Anticancer research 20070101
MS-275, a potent orally available inhibitor of histone deacetylases--the development of an anticancer agent. The international journal of biochemistry & cell biology 20070101
HDAC inhibitors induce apoptosis in glucocorticoid-resistant acute lymphatic leukemia cells despite a switch from the extrinsic to the intrinsic death pathway. The international journal of biochemistry & cell biology 20070101
Antiproliferative and proapoptotic effects of histone deacetylase inhibitors on gastrointestinal neuroendocrine tumor cells. Endocrine-related cancer 20061201
Factors affecting the pharmacokinetic profile of MS-275, a novel histone deacetylase inhibitor, in patients with cancer. Investigational new drugs 20060901
Substituted N-(2-aminophenyl)-benzamides, (E)-N-(2-aminophenyl)-acrylamides and their analogues: novel classes of histone deacetylase inhibitors. Bioorganic & medicinal chemistry letters 20060801
Ex vivo therapy of malignant melanomas transplanted into organotypic brain slice cultures using inhibitors of histone deacetylases. Acta neuropathologica 20060801
Experimental therapy of malignant gliomas using the inhibitor of histone deacetylase MS-275. Molecular cancer therapeutics 20060501
Curcumin is an inhibitor of p300 histone acetylatransferase. Medicinal chemistry (Shariqah (United Arab Emirates)) 20060301
Interspecies differences in plasma protein binding of MS-275, a novel histone deacetylase inhibitor. Cancer chemotherapy and pharmacology 20060201
Anticancer activity of MS-275, a novel histone deacetylase inhibitor, against human endometrial cancer cells. Anticancer research 20060101
Bombesin/gastrin-releasing peptide receptor antagonists increase the ability of histone deacetylase inhibitors to reduce lung cancer proliferation. Journal of molecular neuroscience : MN 20060101
Histone deacetylase inhibitors in cancer therapy. Cancer investigation 20060101
Histone deacetylase inhibitors promote osteoblast maturation. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20051201
Targeting epigenetic changes in acute myeloid leukemia. Clinical advances in hematology & oncology : H&O 20051101
Early clinical data and potential clinical utility of novel histone deacetylase inhibitors in prostate cancer. Clinical prostate cancer 20050901
Blockade of histone deacetylase inhibitor-induced RelA/p65 acetylation and NF-kappaB activation potentiates apoptosis in leukemia cells through a process mediated by oxidative damage, XIAP downregulation, and c-Jun N-terminal kinase 1 activation. Molecular and cellular biology 20050701
[A new target of cancer therapy: advances in the study of histone deacetylase]. Yao xue xue bao = Acta pharmaceutica Sinica 20050701
In vivo imaging of retinoic acid receptor beta2 transcriptional activation by the histone deacetylase inhibitor MS-275 in retinoid-resistant prostate cancer cells. The Prostate 20050615
Phase I and pharmacokinetic study of MS-275, a histone deacetylase inhibitor, in patients with advanced and refractory solid tumors or lymphoma. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050610
Epigenetic modulation of retinoic acid receptor beta2 by the histone deacetylase inhibitor MS-275 in human renal cell carcinoma. Clinical cancer research : an official journal of the American Association for Cancer Research 20050501
Histone deacetylase inhibitors and cancer: from cell biology to the clinic. European journal of cell biology 20050301
Peak shape improvement of basic analytes in capillary liquid chromatography. Journal of separation science 20050201
Histone deacetylase inhibitor pharmacodynamic analysis by multiparameter flow cytometry. Annals of clinical and laboratory science 20050101
Enhancement of xenograft tumor radiosensitivity by the histone deacetylase inhibitor MS-275 and correlation with histone hyperacetylation. Clinical cancer research : an official journal of the American Association for Cancer Research 20040915
Histone deacetylase inhibitor enhances the anti-leukemic activity of an established nucleoside analogue. Cancer biology & therapy 20040801
The histone deacetylase inhibitor MS-275 induces caspase-dependent apoptosis in B-cell chronic lymphocytic leukemia cells. Leukemia 20040701
Histone deacetylase inhibitors FK228, N-(2-aminophenyl)-4-[N-(pyridin-3-yl-methoxycarbonyl)amino- methyl]benzamide and m-carboxycinnamic acid bis-hydroxamide augment radiation-induced cell death in gastrointestinal adenocarcinoma cells. International journal of cancer 20040610
Determination of MS-275, a novel histone deacetylase inhibitor, in human plasma by liquid chromatography-electrospray mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040525
The histone deacetylase inhibitor MS-275 interacts synergistically with fludarabine to induce apoptosis in human leukemia cells. Cancer research 20040401
(2-amino-phenyl)-amides of omega-substituted alkanoic acids as new histone deacetylase inhibitors. Bioorganic & medicinal chemistry letters 20040105
Enhanced radiation-induced cell killing and prolongation of gammaH2AX foci expression by the histone deacetylase inhibitor MS-275. Cancer research 20040101
Synthesis and biological evaluation of 3-(4-substituted-phenyl)-N-hydroxy-2-propenamides, a new class of histone deacetylase inhibitors. Journal of medicinal chemistry 20031218
Identification of novel isoform-selective inhibitors within class I histone deacetylases. The Journal of pharmacology and experimental therapeutics 20031101
Inhibition of PI-3 kinase sensitizes human leukemic cells to histone deacetylase inhibitor-mediated apoptosis through p44/42 MAP kinase inactivation and abrogation of p21(CIP1/WAF1) induction rather than AKT inhibition. Oncogene 20030918
The histone deacetylase inhibitor MS-275 promotes differentiation or apoptosis in human leukemia cells through a process regulated by generation of reactive oxygen species and induction of p21CIP1/WAF1 1. Cancer research 20030701
Induction of fetal hemoglobin expression by the histone deacetylase inhibitor apicidin. Blood 20030301
Gene expression profiling of multiple histone deacetylase (HDAC) inhibitors: defining a common gene set produced by HDAC inhibition in T24 and MDA carcinoma cell lines. Molecular cancer therapeutics 20030201
Trifluoromethyl ketones as inhibitors of histone deacetylase. Bioorganic & medicinal chemistry letters 20021202
MS-27-275, an inhibitor of histone deacetylase, has marked in vitro and in vivo antitumor activity against pediatric solid tumors. Cancer research 20021101
Sulfonamide anilides, a novel class of histone deacetylase inhibitors, are antiproliferative against human tumors. Cancer research 20020801
Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group. Bioorganic & medicinal chemistry letters 20020520
Transcriptional regulation of the transforming growth factor beta type II receptor gene by histone acetyltransferase and deacetylase is mediated by NF-Y in human breast cancer cells. The Journal of biological chemistry 20020215
MS-275, a histone deacetylase inhibitor, selectively induces transforming growth factor beta type II receptor expression in human breast cancer cells. Cancer research 20010201
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