tacedinaline   Click here for help

GtoPdb Ligand ID: 8367

Synonyms: CI-994 | CI994
Compound class: Synthetic organic
Comment: Tacedinaline inhibits the histone deacetylase enzyme HDAC1 [6], and is reported to have antitumour activity in preclinical studies [2,4-5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 84.22
Molecular weight 269.12
XLogP 1.43
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
Isomeric SMILES CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
InChI InChI=1S/C15H15N3O2/c1-10(19)17-12-8-6-11(7-9-12)15(20)18-14-5-3-2-4-13(14)16/h2-9H,16H2,1H3,(H,17,19)(H,18,20)
InChI Key VAZAPHZUAVEOMC-UHFFFAOYSA-N
References
1. Bradner JE, West N, Grachan ML, Greenberg EF, Haggarty SJ, Warnow T, Mazitschek R. (2010)
Chemical phylogenetics of histone deacetylases.
Nat. Chem. Biol., 6 (3): 238-243. [PMID:20139990]
2. Gediya LK, Belosay A, Khandelwal A, Purushottamachar P, Njar VC. (2008)
Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts.
Bioorg. Med. Chem., 16 (6): 3352-60. [PMID:18166465]
3. Liu L, Chen B, Qin S, Li S, He X, Qiu S, Zhao W, Zhao H. (2010)
A novel histone deacetylase inhibitor Chidamide induces apoptosis of human colon cancer cells.
Biochem. Biophys. Res. Commun., 392 (2): 190-5. [PMID:20060381]
4. Loprevite M, Tiseo M, Grossi F, Scolaro T, Semino C, Pandolfi A, Favoni R, Ardizzoni A. (2005)
In vitro study of CI-994, a histone deacetylase inhibitor, in non-small cell lung cancer cell lines.
Oncol. Res., 15 (1): 39-48. [PMID:15839304]
5. LoRusso PM, Demchik L, Foster B, Knight J, Bissery MC, Polin LM, Leopold 3rd WR, Corbett TH. (1996)
Preclinical antitumor activity of CI-994.
Invest New Drugs, 14 (4): 349-56. [PMID:9157069]
6. Methot JL, Chakravarty PK, Chenard M, Close J, Cruz JC, Dahlberg WK, Fleming J, Hamblett CL, Hamill JE, Harrington P et al.. (2008)
Exploration of the internal cavity of histone deacetylase (HDAC) with selective HDAC1/HDAC2 inhibitors (SHI-1:2).
Bioorg. Med. Chem. Lett., 18 (3): 973-8. [PMID:18182289]