CAS 92-78-4 | Naphthol AS-E

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Common Name	Naphthol AS-E
CAS Number	92-78-4	Molecular Weight	297.73600
Density	1.399 g/cm3	Boiling Point	416.5ºC at 760 mmHg
Molecular Formula	C₁₇H₁₂ClNO₂	Melting Point	255°C
MSDS	/	Flash Point	205.7ºC

Names

Name	N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide
Synonym	More Synonyms

Naphthol AS-E BiologicalActivity

Description	Naphthol AS-E is a potent and cell-permeable inhibitor of KIX-KID interaction. Naphthol AS-E directly binds to the KIX domain of CBP (Kd:8.6 µM), blocks the interaction between the KIX domain and the KID domain of CREB with IC50 of 2.26 µM. Naphthol AS-E can be used for cancer research.
Related Catalog	Research Areas >>CancerSignaling Pathways >>Epigenetics >>Histone AcetyltransferaseSignaling Pathways >>Epigenetics >>Epigenetic Reader Domain
Target	KIX-KID:2.26 μM (IC50)
In Vitro	CREB (cyclic AMP-response element-binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors. CREB can not be activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through the kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP. In a cell-based CREB Renilla luciferase reporter assay, Naphthol AS-E inhibits CREB-mediated gene transcription with an IC50 of 2.29 µM. In HEK293T-based complementation assay, Naphthol AS-E dose-dependently inhibited Renilla luciferase activity with an IC50 of 2.9 µM by directly binding to CBP's KIX domain (Kd ~8.6 µM using a recombinant KIX). Naphthol AS-E exhibits low µM activity in inhibiting the proliferation of all these cancer cells, which is consistent with its cellular CREB inhibition potency. The average GI50 values for A549, MCF-7, MDA-MB-231 and MDA-MB-468 are approximately 2.9µM, 2.81µM, 2.35µM and 1.46µM, respectively. Naphthol AS-E (2.5 µM-10 µM; 48 hours) decreases the expression of anti-apoptotic protein Bcl-2. The expression of VEGF is also decreased.
References	[1]. Fuchun Xie, et al. Synthesis and Evaluation of an O-Aminated Naphthol AS-E as a Prodrug of CREB-mediated Gene Transcription Inhibition. Lett Org Chem. 2013 Jun;10(5):380-384. [2]. Bingbing X Li, et al. Discovery of a small-molecule inhibitor of the KIX-KID interaction. Chembiochem. 2009 Nov 23;10(17):2721-4.

Chemical & Physical Properties

Density	1.399 g/cm3
Boiling Point	416.5ºC at 760 mmHg
Melting Point	255°C
Molecular Formula	C₁₇H₁₂ClNO₂
Molecular Weight	297.73600
Flash Point	205.7ºC
Exact Mass	297.05600
PSA	49.33000
LogP	4.52410
Index of Refraction	1.735
InChIKey	OHAXNCGNVGGWSO-UHFFFAOYSA-N
SMILES	O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2cc1O

Safety Information

Hazard Codes	Xn
Risk Phrases	R42/43:May cause sensitization by inhalation and skin contact .
Safety Phrases	S7-S36-S24/25
WGK Germany	3
RTECS	MR0176000
HS Code	29053980

Customs

HS Code	2924299090
Summary	2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Synonyms

MFCD00021639

Amanil Naphthol AS-E

Cibanaphthol RC

3-hydroxy-naphthalene-2-carboxylic acid 4-chloro-anilide

3-Hydroxy-[2]naphthoesaeure-(4-chlor-anilid)

naphthol AS-E

EINECS 202-189-7

Naphtoelan E

Naphtazol E

Naphtanilide E

4'-Chloro-3-hydroxy-2-naphthanilide

Sanatol E

3-hydroxy-[2]naphthoic acid-(4-chloro-anilide)

Daito Grounder E

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