Oxindole

Modify Date: 2024-01-02 16:07:04

Oxindole Structure
Oxindole structure
Common Name Oxindole
CAS Number 59-48-3 Molecular Weight 133.147
Density 1.3±0.1 g/cm3 Boiling Point 312.8±45.0 °C at 760 mmHg
Molecular Formula C8H7NO Melting Point 123-128 °C(lit.)
MSDS Chinese USA Flash Point 190.0±18.0 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Oxindole


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

 Names

Name indolin-2-one
Synonym More Synonyms

 Oxindole 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
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.

 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

 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
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

 Customs

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

 Articles31

More 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...

 Synonyms

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
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