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Merck
CN

SML2862

MC1742

≥98% (HPLC)

Synonym(s):

5-(4-(Biphenyl-4-yl)-6-oxo-1,6-dihydropyrimidin-2-ylthio)-N-hydroxypentanamide, 5-[(4-[1,1′-Biphenyl]-4-yl-1,6-dihydro-6-oxo-2-pyrimidinyl)thio]-N-hydroxypentanamide, MC 1742, MC-1742

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About This Item

Empirical Formula (Hill Notation):
C21H21N3O3S
CAS Number:
1776116-74-5
Molecular Weight:
395.47
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD30290158

Key Documents

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SMILES string

S(CCCCC(=O)NO)c1[nH][c](cc(n1)c2ccc(cc2)c3ccccc3)=O

InChI

1S/C21H21N3O3S/c25-19(24-27)8-4-5-13-28-21-22-18(14-20(26)23-21)17-11-9-16(10-12-17)15-6-2-1-3-7-15/h1-3,6-7,9-12,14,27H,4-5,8,13H2,(H,24,25)(H,22,23,26)

InChI key

AOFVDNFTELWRHV-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Histone deacetylases inhibitor against class I (HDAC1/2/3/8), IIB (HDAC6/10), IV (HDAC11) HDACs with anti-cancer and HIV latency reativation potency.
MC1742 is a uracil-based hydroxyamide (UBHA) that acts as a subtype-selective histone deacetylases (HDACs) inhibitor (IC50: class I HDAC1/2/3/8 = 100/110/20/610 nM, class IIB HDAC6/10 = 7/40 nM, class IV HDAC11 = 100 nM, class IIA HDAC4/5/7/9 >50 μM). MC1742 exerts greater antiproliferation potency than SAHA in sarcoma cancer stem cell (CSC) cultures (MC1742/SAHA IC50 in μM = 0.25/1/RD, 1.12/1.13//MG-63, 1.4/3.92/SK-ES-1 post 72-hr treatment) and effectively reactivates HIV from latency (EC50 = 350 nM; JLAT 10.6 cells) by upregulating histone acetylation at the HIV promoter without activating T cells.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000109361
0000109362
0000103048

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Elleard Fw Heffern et al.
Journal of virus eradication, 5(2), 84-91 (2019-06-14)
Current antiretroviral therapy can suppress HIV replication, increase CD4 count and result in increased lifespan. However, it cannot eradicate the virus due to the presence of latent provirus in cellular reservoirs, such as resting CD4+ T cells. Using combination latency-reversing
Gemma Di Pompo et al.
Journal of medicinal chemistry, 58(9), 4073-4079 (2015-04-24)
Musculoskeletal sarcomas are aggressive malignancies of bone and soft tissues often affecting children and adolescents. Histone deacetylase inhibitors (HDACi) have been proposed to counteract cancer stem cells (CSCs) in solid neoplasms. When tested in human osteosarcoma, rhabdomyosarcoma, and Ewing's sarcoma
Tokuhiro Chano et al.
American journal of cancer research, 6(4), 859-875 (2016-05-18)
The glycolytic-based metabolism of cancers promotes an acidic microenvironment that is responsible for increased aggressiveness. However, the effects of acidosis on tumour metabolism have been almost unexplored. By using capillary electrophoresis with time-of-flight mass spectrometry, we observed a significant metabolic

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