Oxindole

Names

[ CAS No. ]:
59-48-3

[ Name ]:
Oxindole

[Synonym ]:
Oxindole
3H-Indol-2-ol
2-INDOLINONE
2-indolinon
2-Oxindoline
2-oxo-indoline
EINECS 200-429-5
OXINDOL
indolinone
1,3-Dihydro-2H-indol-2-one
2-Indolone
2H-Indol-2-one, 1,3-dihydro-
Indolin-2-one
2-Oxiindole
MFCD00005711
2-Oxindole
1,3-dihydro-indol-2-one

Biological Activity

[Description]:

Oxindole (Indolin-2-one) is an aromatic heterocyclic building block. 2-indolinone derivatives have become lead compounds in the research of kinase inhibitors.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Cancer

Research Areas >> Metabolic Disease

Research Areas >> Endocrinology

Research Areas >> Inflammation/Immunology

Research Areas >> Infection

Research Areas >> Neurological Disease

[In Vitro]

Oxindole (Indolin-2-one) is a bicyclic structure consisting of a benzene ring fused to 2-pyrrolidone. Substituted indolinones can be referred as ‘privileged structures’ owing to their excellent binding affinity for many receptors and to the number of approved drugs containing this scaffold[1]. Oxindole has been found in tissues and fluids of mammals as well as natural products produced by a range of plants, bacteria and invertebrates. 2-indolinone derivatives possess diverse range of pharmacological activities including anti-cancer, anti-HIV, anti-diabetic, antibacterial, antioxidant, kinase inhibitory, AChE inhibitory, anti-leishmanial, b3 adrenergic receptor agonistic, phosphatase inhibitory, analgesic, spermicidal, vasopressin antagonists, progesterone antagonists, neuroprotection, NMDA blocker and sleep inducing activities[2].

[References]

[1]. Leoni A, et al. 2-Indolinone a versatile scaffold for treatment of cancer: a patent review (2008-2014). Expert Opin Ther Pat. 2016;26(2):149-73.

[2]. Kaur M, et al. Oxindole: A chemical prism carrying plethora of therapeutic benefits. Eur J Med Chem. 2016 Nov 10;123:858-894.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
312.8±45.0 °C at 760 mmHg

[ Melting Point ]:
123-128 °C(lit.)

[ Molecular Formula ]:
C₈H₇NO

[ Molecular Weight ]:
133.147

[ Flash Point ]:
190.0±18.0 °C

[ Exact Mass ]:
133.052765

[ PSA ]:
29.10000

[ LogP ]:
0.61

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.640

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM2080500

CHEMICAL NAME :: 2-Indolinone

CAS REGISTRY NUMBER :: 59-48-3

BEILSTEIN REFERENCE NO. :: 0114692

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C8-H7-N-O

MOLECULAR WEIGHT :: 133.16

WISWESSER LINE NOTATION :: T56 BMV DHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 152,121,1964

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 152,121,1964

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
2811

[ WGK Germany ]:
3

[ RTECS ]:
NM2080500

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
29337900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933790090

[ Summary ]:
2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

Articles

Cytotoxic and antimicrobial evaluations of novel apoptotic and anti-angiogenic spiro cyclic 2-oxindole derivatives of 2-amino-tetrahydroquinolin-5-one.

Arch. Pharm. (Weinheim) 348(2) , 113-24, (2015)

A novel series of cyclic 2-oxindole derivatives incorporating 2-amino-tetrahydroquinolin-5-one were prepared. The structures of the prepared compounds were elucidated using different spectral tools. T...

Synthesis and biological evaluation of new pyridone-annelated isoindigos as anti-proliferative agents.

Molecules 19(9) , 13076-92, (2014)

A selected set of substituted pyridone-annelated isoindigos 3a-f has been synthesized via interaction of 5- and 6-substituted oxindoles 2a-f with 6-ethyl-1,2,9-trioxopyrrolo[3,2-f]quinoline-8-carboxyl...

Synthesis and receptor binding assay of indolin-2-one derivatives as dopamine D4 receptor ligands.

Pharmazie 70 , 511-4, (2015)

Five indolin-2-one derivatives bearing piperazinylbutyl side chains attached to the amide nitrogen were synthesized from 2-indolinone. 1-(4-Bromobutyl)-indolin-2-one was reacted with 1-piperazinecarbo...