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Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate is a synthetic organic compound belonging to the benzothiazine derivatives class. It is characterized by a benzothiazine ring with a carboxylate ester and a methyl group, which contribute to its pharmacological properties. Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate is known for its potential biological activities, such as anti-inflammatory, anti-cancer, and anti-bacterial properties, and is actively being studied for its pharmaceutical potential.

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  • 188614-01-9 Structure
  • Basic information

    1. Product Name: Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate
    2. Synonyms: Methyl-3-Oxo-3,4-Dihydro-2H-1,;Methyl 3,4-dihydro-3-oxo-2H-benzo[b][1,4]thiazine-6-carboxylate;Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate;Methyl 3,4-dihydro-3-oxo-2H-1,4-benzothiazine-6-carboxylate;methyl 3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate;2-Methyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate;Methyl 3-Oxo-2H-1,4-benzothiazine-6-carboxylate;3-keto-4H-1,4-benzothiazine-6-carboxylic acid methyl ester
    3. CAS NO:188614-01-9
    4. Molecular Formula: C10H9NO3S
    5. Molecular Weight: 223.25
    6. EINECS: N/A
    7. Product Categories: Esters;API intermediates;Heterocycle intermediates;Fused Ring Systems
    8. Mol File: 188614-01-9.mol
  • Chemical Properties

    1. Melting Point: 180-182°
    2. Boiling Point: 435.7 °C at 760 mmHg
    3. Flash Point: 217.3 °C
    4. Appearance: /Solid
    5. Density: 1.343g/cm3
    6. Vapor Pressure: 8.58E-08mmHg at 25°C
    7. Refractive Index: 1.605
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate(CAS DataBase Reference)
    11. NIST Chemistry Reference: Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate(188614-01-9)
    12. EPA Substance Registry System: Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate(188614-01-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 188614-01-9(Hazardous Substances Data)

188614-01-9 Usage

Uses

Used in Pharmaceutical Research and Drug Development:
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate is used as a chemical compound in pharmaceutical research and drug development due to its potential biological activities and therapeutic applications.
Used in Anti-inflammatory Applications:
In the pharmaceutical industry, Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate is used as an anti-inflammatory agent for its potential to alleviate inflammation and associated symptoms.
Used in Anti-cancer Applications:
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate is used as an anti-cancer agent in the pharmaceutical industry, leveraging its potential to target and inhibit cancer cell growth and proliferation.
Used in Anti-bacterial Applications:
In the pharmaceutical industry, Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate is used as an anti-bacterial agent to combat bacterial infections and reduce the spread of antibiotic-resistant strains.

Check Digit Verification of cas no

The CAS Registry Mumber 188614-01-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,8,6,1 and 4 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 188614-01:
(8*1)+(7*8)+(6*8)+(5*6)+(4*1)+(3*4)+(2*0)+(1*1)=159
159 % 10 = 9
So 188614-01-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO3S/c1-14-10(13)6-2-3-8-7(4-6)11-9(12)5-15-8/h2-4H,5H2,1H3,(H,11,12)

188614-01-9 Well-known Company Product Price

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  • Alfa Aesar

  • (H64467)  Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, 97%   

  • 188614-01-9

  • 1g

  • 431.0CNY

  • Detail
  • Alfa Aesar

  • (H64467)  Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, 97%   

  • 188614-01-9

  • 5g

  • 1617.0CNY

  • Detail
  • Alfa Aesar

  • (H64467)  Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, 97%   

  • 188614-01-9

  • 25g

  • 6468.0CNY

  • Detail

188614-01-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 3-oxo-4H-1,4-benzothiazine-6-carboxylate

1.2 Other means of identification

Product number -
Other names Methyl 3-Oxo-2H-1,4-benzothiazine-6-carboxylate

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:188614-01-9 SDS

188614-01-9Relevant articles and documents

The discovery of potent small molecule activators of human STING

Pryde, David C.,Middya, Sandip,Banerjee, Monali,Shrivastava, Ritesh,Basu, Sourav,Ghosh, Rajib,Yadav, Dharmendra B.,Surya, Arjun

supporting information, (2020/10/09)

The adaptor protein STING plays a major role in innate immune sensing of cytosolic nucleic acids, by triggering a robust interferon response. Despite the importance of this protein as a potential therapeutic target for serious unmet medical conditions inc

SMALL MOLECULE STING ANTAGONISTS

-

Page/Page column 83-84, (2021/08/20)

The present invention relates to compounds of formula (I). The compounds maybe used to antagonise the Stimulator of Interferon Genes (STING) protein and may thereby treat liver fibrosis, fatty liver disease, non-alcoholic steatohepatitis (NASH), pulmonary fibrosis, lupus, sepsis, rheumatoid arthritis (RA), type I diabetes, STING- associated vasculopathy with onset in infancy (SAVI), Aicardi-Goutieres syndrome (AGS), familial chilblain lupus (FCL), systemic lupus erythematosus (SLE), retinal vasculopathy, neuroinflammation, systemic inflammatory response syndrome, pancreatitis, cardiovascular disease, renal fibrosis, stroke and age-related macular degeneration (AMD).

Facile synthesis of 1,4-benzothiazin-3-ones from Cu-catalyzed coupling of 2-iodoanilines and 2-mercaptoacetate

Huang, Wei-Sheng,Xu, Rongsong,Dodd, Rory,Shakespeare, William C.

, p. 5214 - 5216 (2013/09/02)

A novel synthesis of 1,4-benzothiazin-3-ones was developed from Cu-catalyzed coupling of readily available substituted 2-iodoanilines with 2-mercaptoacetate. The new method offers clear advantages over existing approaches for its one-step simple operation, wider reaction scope, and moderate to excellent isolated yields.

Discovery of a Plasmodium falciparum Glucose-6-phosphate Dehydrogenase 6-phosphogluconolactonase Inhibitor (R,Z)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2- (2-fluorobenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxamide (ML276) that reduces parasite growth in vitro

Preuss, Janina,Malone, Patrick,Peddibhotla, Satyamaheshwar,Hedrick, Michael P.,Hershberger, Paul,Gosalia, Palak,Milewski, Monika,Li, Yujie Linda,Sugarman, Eliot,Hood, Becky,Suyama, Eigo,Nguyen, Kevin,Vasile, Stefan,Sergienko, Eduard,Mangravita-Novo, Arianna,Vicchiarelli, Michael,McAnally, Danielle,Smith, Layton H,Roth, Gregory P.,Diwan, Jena,Chung, Thomas D.Y.,Jortzik, Esther,Rahlfs, Stefan,Becker, Katja,Pinkerton, Anthony B.,Bode, Lars

supporting information, p. 7262 - 7272 (2012/11/07)

A high-throughput screen of the NIH's MLSMR collection of ~340000 compounds was undertaken to identify compounds that inhibit Plasmodium falciparum glucose-6-phosphate dehydrogenase (Pf G6PD). PfG6PD is important for proliferating and propagating P. falciparum and differs structurally and mechanistically from the human orthologue. The reaction catalyzed by glucose-6-phosphate dehydrogenase (G6PD) is the first, rate-limiting step in the pentose phosphate pathway (PPP), a key metabolic pathway sustaining anabolic needs in reductive equivalents and synthetic materials in fast-growing cells. In P. falciparum, the bifunctional enzyme glucose-6-phosphate dehydrogenase-6- phosphogluconolactonase (Pf GluPho) catalyzes the first two steps of the PPP. Because P. falciparum and infected host red blood cells rely on accelerated glucose flux, they depend on the G6PD activity of PfGluPho. The lead compound identified from this effort, (R,Z)-N-((1-ethylpyrrolidin-2-yl)methyl)-2-(2- fluorobenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbox-amide, 11 (ML276), is a submicromolar inhibitor of PfG6PD (IC50 = 889 nM). It is completely selective for the enzyme's human isoform, displays micromolar potency (IC50 = 2.6 μM) against P. falciparum in culture, and has good drug-like properties, including high solubility and moderate microsomal stability. Studies testing the potential advantage of inhibiting Pf G6PD in vivo are in progress.

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