1-methylisatin

Names

[ CAS No. ]:
2058-74-4

[ Name ]:
1-methylisatin

[Synonym ]:
INDOLE-2,3-DIONE,1-METHYL
1-Methyl-indole-2,3-dione
1-Methyl-1H-indole-2,3-dione
1H-Indole-2,3-dione, 1-methyl-
N-methylindol-2,3-dione
1-Methylindole-2,3-dione
N-methylisatin
1-methylindoline-2,3-dione
OL-57
EINECS 218-164-9
1-methylisatin
1-Methyl-2,3-indolinedione
N-methylindole-2,3-dione
MFCD00005812
1-methylindole-2,3(1H)-dione
N-Methylindoline-2,3-dione
1H-Indole-2,3-dione,1-methyl

Biological Activity

[Description]:

1-Methylisatin is a potent and selective CE (carboxylesterases) inhibitor, with Kis of 38.2 and 5.38 µM for hiCE and hCE1, respectively. 1-Methylisatin interacts with Hb (human adult hemoglobin) by hydrophobic binding and electrostatic attraction. 1-Methylisatin can be used in the study of regulation of drug metabolism in vivo[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[Target]

hiCE:38.2 μM (Ki)

hCE1:5.38 μM (Ki)

[References]

[1]. Hyatt JL, et al. Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. J Med Chem. 2007 Apr 19;50(8):1876-85.

[2]. Mandal P, et al. Fluorescence spectroscopic characterization of the interaction of human adult hemoglobin and two isatins, 1-methylisatin and 1-phenylisatin: a comparative study. J Phys Chem B. 2009 Nov 12;113(45):14904-13.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
294.3±23.0 °C at 760 mmHg

[ Melting Point ]:
130-133 °C(lit.)

[ Molecular Formula ]:
C₉H₇NO₂

[ Molecular Weight ]:
161.157

[ Flash Point ]:
137.4±15.0 °C

[ Exact Mass ]:
161.047684

[ PSA ]:
37.38000

[ LogP ]:
0.58

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.607

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL7939000

CHEMICAL NAME :: Indole-2,3-dione, 1-methyl-

CAS REGISTRY NUMBER :: 2058-74-4

BEILSTEIN REFERENCE NO. :: 0128280

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H7-N-O2

MOLECULAR WEIGHT :: 161.17

WISWESSER LINE NOTATION :: T56 BNVVJ B1

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 :: 685 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 15,858,1981

Safety Information

[ Symbol ]:

GHS05, GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P301 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S26-S39-S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
NL7939000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Fluorescence spectroscopic characterization of the interaction of human adult hemoglobin and two isatins, 1-methylisatin and 1-phenylisatin: a comparative study.

J. Phys. Chem. B 113(45) , 14904-13, (2009)

In this report, steady state and time-resolved fluorescence along with circular dichroism (CD) spectroscopic, FTIR, and anisotropy investigations were made to reveal the nature of the interactions bet...

The hydrolysis of N-methylisatin: on how a simple rate-pH profile may mislead.

Drug Des. Discov. 11(3) , 223-30, (1994)

Alkaline hydrolysis of the title isatin 4 in unbuffered solution obeys a rate law such that kobs varies; is directly proportional to [OH-]2 at pH 10 changes smoothly to kobs varies; is directly propor...

Straightforward stereoselective synthesis of spiro-epoxyoxindoles.

Org. Lett. 9(9) , 1745-8, (2007)

[reaction: see text] The in situ preparation of a sulfonium ylide reagent achieved the highly diastereoselective epoxidation of isatins, so that a new and straightforward access to biologically signif...