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Methyl 1-acetyl-2-oxoindoline-6-carboxylate is an organic compound that serves as a crucial reagent in the synthesis of Nintedanib, an angiokinase inhibitor. It plays a significant role in the development of pharmaceuticals targeting various medical conditions.

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  • 676326-36-6 Structure
  • Basic information

    1. Product Name: Methyl 1-acetyl-2-oxoindoline-6-carboxylate
    2. Synonyms: Methyl 1-acetyl-2-oxoindoline-6-carboxylate;1-Acetyl-2,3-dihydro-2-oxo-1H-indole-6-carboxylic acid methyl ester;1-acetyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester
    3. CAS NO:676326-36-6
    4. Molecular Formula: C12H11NO4
    5. Molecular Weight: 233
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 676326-36-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 489.5±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.330
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: -1.94±0.20(Predicted)
    10. CAS DataBase Reference: Methyl 1-acetyl-2-oxoindoline-6-carboxylate(CAS DataBase Reference)
    11. NIST Chemistry Reference: Methyl 1-acetyl-2-oxoindoline-6-carboxylate(676326-36-6)
    12. EPA Substance Registry System: Methyl 1-acetyl-2-oxoindoline-6-carboxylate(676326-36-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 676326-36-6(Hazardous Substances Data)

676326-36-6 Usage

Uses

Used in Pharmaceutical Industry:
Methyl 1-acetyl-2-oxoindoline-6-carboxylate is used as a key reagent for the preparation of Nintedanib (N478290), an angiokinase inhibitor. methyl 1-acetyl-2-oxoindoline-6-carboxylate is utilized in the treatment of idiopathic pulmonary fibrosis, a chronic and progressive lung disease characterized by scarring of lung tissue.
Additionally, methyl 1-acetyl-2-oxoindoline-6-carboxylate contributes to the inhibition of blood vessel formation, a process that is essential for the growth and metastasis of cancer cells. This property makes it a valuable component in the development of cancer therapies, potentially assisting in the prevention of tumor growth and spread by disrupting the formation of new blood vessels that supply nutrients to cancer cells.

Check Digit Verification of cas no

The CAS Registry Mumber 676326-36-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 6,7,6,3,2 and 6 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 676326-36:
(8*6)+(7*7)+(6*6)+(5*3)+(4*2)+(3*6)+(2*3)+(1*6)=186
186 % 10 = 6
So 676326-36-6 is a valid CAS Registry Number.

676326-36-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 1-acetyl-2-oxo-3H-indole-6-carboxylate

1.2 Other means of identification

Product number -
Other names QC-1090

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:676326-36-6 SDS

676326-36-6Relevant articles and documents

Harnessing affinity-based protein profiling to reveal a novel target of nintedanib

Chen, Xiong,Li, Manru,Li, Menglin,Wang, Dongmei,Zhang, Jinlan

supporting information, p. 3139 - 3142 (2021/04/02)

Nintedanib (BIBF1120), a triple angiokinase inhibitor, was first approved for idiopathic pulmonary fibrosis (IPF) therapy and is also efficacious for lung carcinoma, and interstitial lung diseases, far beyond its inhibition of VEGFR/PDGFR/FGFR. We identified tripeptidyl-peptidase 1 (TPP1) as one of the direct targets of nintedanib employing the affinity-based protein profiling (AfBPP) technique. This may be a new mechanism for nintedanib's role different from tyrosine kinase inhibition.

ALK5 INHIBITOR CONJUGATES AND USES THEREOF

-

Paragraph 0191-0193, (2021/07/17)

The present disclosure relates to targeted drug conjugates comprising ALK5 inhibitors and targeting moieties that direct the ALK5 inhibitors to cells involved in fibrosis and cancer, for example myofibroblasts, activated fibroblasts and transitioning fibr

Method for preparing nintedanib ethanesulfonate

-

Paragraph 0021; 0040-0042; 0049-0051; 0058-0060, (2020/11/12)

The invention discloses a method for preparing nintedanib ethanesulfonate. The method comprises the following steps: carrying out acylation reaction on 2-oxoindole-6-methyl formate and acetic anhydride to obtain 1-acetyl-2-oxoindoline -6-methyl formate; condensing with trimethyl orthobenzoate to generate 1-acetyl-3-(methoxyphenyl methylene)-2-oxoindoline-6-methyl formate, and finally reacting withN-(4-aminophenyl)-N, 4-dimethyl-1-piperazinecarboxamide; under the condition of not separating a main product, adding an alkali for deprotection to generate nintedanib, and finally salifying with ethanesulfonic acid to generate the nintedanib ethanesulfonate. The method has the advantages of mild reaction conditions, simple process operation and high yield, can obtain the nintedanib ethanesulfonate with the purity of 100% without refining, and is suitable for industrial production.

Preparation method of dihydroindolone derivative and intermediate thereof

-

Paragraph 0071-0095, (2020/09/23)

The invention provides a dihydroindolone derivative represented by a formula I, and a preparation method of an intermediate of the dihydroindolone derivative. The preparation method of the dihydroindole derivative intermediate comprises the following steps: enabling 2-oxoindole-6-methyl formate and acetic anhydride to react in methylbenzene under the heating condition of 100 DEG C to 110 DEG C toobtain 1-acetyl-2-oxodihydroindolone-6-methyl formate. The preparation method of the indolinone derivative comprises the following steps: (1) carrying out a condensation reaction on 1-acetyl-2-oxodihydroindolone-6-methyl formate and trimethyl orthobenzoate or triethyl orthobenzoate to obtain a compound represented by a formula IV; (2) enabling the compound represented by the formula IV to react with N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazine-1-yl) acetamide to obtain a compound represented by a formula V; and (3) deprotecting the compound represented by the formula V to obtain the compound represented by the formula I.

ANTIBODY-ALK5 INHIBITOR CONJUGATES AND THEIR USES

-

Paragraph 0183-0185, (2020/02/06)

The present disclosure relates to antibody-drug conjugates comprising ALK5 inhibitors and their uses.

ANTIBODY-ALK5 INHIBITOR CONJUGATES AND THEIR USES

-

Paragraph 0199-0201, (2020/06/07)

The present disclosure relates to antibody-drug conjugates comprising ALK5 inhibitors and their uses.

ANTIB0DY-ALK5 INHIBITOR CONJUGATES AND THEIR USES

-

Paragraph 0188-0190, (2021/01/21)

The present disclosure relates to antibody-drug conjugates comprising ALK5 inhibitors and their uses.

SYNTHESIS OF A 2-INDOLINONE DERIVATIVE KNOWN AS INTERMEDIATE FOR PREPARING NINTEDANIB

-

Page/Page column 4; 6-8, (2019/06/13)

The invention discloses the preparation method of methyl (E)-1-acetyl-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylatefrom methyl 2-oxoindoline-6-carboxylate using high reaction temperatures and a reaction solvent enabling azeotropic removal of acetic acid during the reaction.

A METHOD FOR PREPARING METHYL (Z)-3-[[4-[METHYL[2-(4-METHYL-1-PIPERAZINYL)ACETYL] AMINO]PHENYL]AMINO]PHENYLMETHYLENE)-OXINDOLE-6-CARBOXYLATE (INTEDANIB, NINTEDANIB)

-

Page/Page column 7, (2017/02/24)

The invention relates to a method of synthesizing methyl (Z)-3-[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl] amino]phenyl] amino]phenylmethylene)-oxindole-6-carboxylate of formula (1), known under the generic name of intedanib or nintedanib. The present method comprises a) a reaction of methyl oxindole-6-carboxylate with acetic anhydride at a temperature of 130 - 140°C, providing methyl 1-acetyl-oxindole-6-carboxylate; b) a reaction of methyl 1-acetyl-oxindole-6-carboxylate of with trimethyl orthobenzoate and acetic anhydride in the presence of toluene, providing methyl (E)-1-acetyl-3-(methoxyphenylmethylene)-oxindole-6-carboxylate; c) a reaction (E)-1-acetyl-3-(methoxyphenylmethylene)-oxindole-6-carboxylate with N-(4-aminophenyl)-N,4-dimethyl-1-piperazine acetamide and subsequently with an alkali hydroxide or alkali alkoxide in methanol or ethanol without isolation of the intermediate, providing methyl (Z)-3-[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl]amino]phenyl] amino]phenylmethylene)-oxindole-6-carboxylate, wherein the reaction is conducted at a temperature of 50 to 100°C. (1)

Discovery of a potent inhibitor of MELK that inhibits expression of the anti-apoptotic protein Mcl-1 and TNBC cell growth

Edupuganti, Ramakrishna,Taliaferro, Juliana M.,Wang, Qiantao,Xie, Xuemei,Cho, Eun Jeong,Vidhu, Fnu,Ren, Pengyu,Anslyn, Eric V.,Bartholomeusz, Chandra,Dalby, Kevin N.

, p. 2609 - 2616 (2017/04/06)

Despite recent advances in molecularly directed therapy, triple negative breast cancer (TNBC) remains one of the most aggressive forms of breast cancer, still without a suitable target for specific inhibitors. Maternal embryonic leucine zipper kinase (MELK) is highly expressed in TNBC, where level of overexpression correlates with poor prognosis and an aggressive disease course. Herein, we describe the discovery through targeted kinase inhibitor library screening, and structure-guided design of a series of ATP-competitive indolinone derivatives with subnanomolar inhibition constants towards MELK. The most potent compound, 17, inhibits the expression of the anti-apoptotic protein Mcl-1 and proliferation of TNBC cells exhibiting selectivity for cells expressing high levels of MELK. These studies suggest that further elaboration of 17 will furnish MELK-selective inhibitors with potential for development in preclinical models of TNBC and other cancers.

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