Formamide,N-[(1E)-2-(2,5-dihydroxyphenyl)ethenyl]-

Names

[ Name ]:
Formamide,N-[(1E)-2-(2,5-dihydroxyphenyl)ethenyl]-

[Synonym ]:
N-[2-(2,5-dihydroxyphenyl)ethenyl]formamide
FORMAMIDE,N-(2-(2,5-DIHYDROXYPHENYL)ETHENYL)-,(E)
(E)-N-(2-(2,5-Dihydroxyphenyl)ethenyl)formamide
(2-formamidovinyl)-2,5-dihydroxybenzene
Erbstatin

Biological Activity

[Description]:

Erbstatin, a EGFR kinase inhibitor, possesses antineoplastic effect[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> JAK/STAT Signaling >> EGFR

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR

[In Vitro]

Erbstatin不抑制EGF与其受体的结合，但是会抑制EGFR复合物的内吞作用，而且该化合物不会抑制A431细胞中EGF刺激的磷脂酰肌醇代谢[2]。 Erbstatin引起人小细胞肺癌（SCLC）细胞形态学凋亡和DNA断裂[3]。

[References]

[1]. Shigeki Kobayashi, et al. Diastereomer-specific effects of double-stranded peptides conjugated with -L-Tyr-L-Phe- or -L-Tyr-D-Phe- residues on tyrosine phosphorylation and inhibition of src(ts)NRK, A431, MCF-7, and DU145 cell growth. Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1585-92.

[2]. M Toi, et al. Antineoplastic effect of erbstatin on human mammary and esophageal tumors in athymic nude mice. Eur J Cancer. 1990;26(6):722-4.

[3]. S Simizu, et al. Involvement of hydrogen peroxide production in erbstatin-induced apoptosis in human small cell lung carcinoma cells. Cancer Res. 1996 Nov 1;56(21):4978-82.

Chemical & Physical Properties

[ Density]:
1.343g/cm3

[ Boiling Point ]:
517.5ºC at 760mmHg

[ Molecular Formula ]:
C₉H₉NO₃

[ Molecular Weight ]:
179.17

[ Flash Point ]:
266.8ºC

[ Exact Mass ]:
179.05800

[ PSA ]:
69.56000

[ LogP ]:
1.84130

[ Vapour Pressure ]:
2.48E-11mmHg at 25°C

[ Index of Refraction ]:
1.667

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KD9500000

CHEMICAL NAME :: Formamide, N-(2-(2,5-dihydroxyphenyl)ethenyl)-, (E)-

CAS REGISTRY NUMBER :: 100827-28-9

LAST UPDATED :: 199109

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C9-H9-N-O3

MOLECULAR WEIGHT :: 179.19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 15 mg/L

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 78,329,1987

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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