74711-43-6

Basic information

• Product Name: 10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid
• Synonyms: Zaltoprofen/ 10,11-Dihydro-alpha-Methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid;Zaltoprofen, >=99%;10,11-dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid;ZALTOPROFEN;Salafapinon;Soleton;Dibenzo(B,F)thiepin-2-acetic acid, 10,11-dihydro-alpha-methyl-10-oxo-;Einecs 277-973-5
• CAS NO: 74711-43-6
• Molecular Formula: C17H14O3S
• Molecular Weight: 298.36
• EINECS: 277-973-5
• Product Categories: Inhibitors;Zaltoprofen;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74711-43-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 129-1310C
• Boiling Point: 500.5 °C at 760 mmHg
• Flash Point: 256.5 °C
• Appearance: off-white to pale yellow crystalline solid
• Density: 1.329 g/cm³
• Vapor Pressure: 7.72E-11mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.21±0.10(Predicted)
• Merck: 14,10112
• CAS DataBase Reference: 10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid(74711-43-6)
• EPA Substance Registry System: 10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid(74711-43-6)

Safety Data

• RTECS: HQ2526700
• Hazardous Substances Data: 74711-43-6(Hazardous Substances Data)

Usage

Description

10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid is a complex organic compound with a unique chemical structure, characterized by its off-white to pale yellow solid appearance. It belongs to the class of dibenzothiepin derivatives and possesses a wide range of potential applications due to its chemical properties and pharmacological activities.

Uses

Used in Pharmaceutical Industry:
10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid is used as a non-steroidal anti-inflammatory drug (NSAID) for its ability to inhibit bradykinin-induced pain responses without directly blocking bradykinin receptors. This unique mechanism of action makes it a valuable compound for the development of novel anti-inflammatory medications.
Used in Chiral Chemistry and Drug Development:
The anti-inflammatory activity of 10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid is primarily attributed to its (S)-enantiomer. This highlights the importance of chirality in drug development, as the (S)-enantiomer is responsible for the desired therapeutic effects. This property can be exploited in the design and synthesis of more effective and selective drugs, potentially leading to improved treatment options for various inflammatory conditions.
Used in Chemical Research:
As a member of the dibenzothiepin family, 10,11-Dihydro-alpha-methyl-10-oxo-dibenzo[b,f]thiepin-2-acetic acid can be utilized in chemical research to explore the structure-activity relationships within this class of compounds. This knowledge can be applied to the development of new drugs with improved pharmacological profiles and reduced side effects.

InChI:InChI=1/C17H14O3S/c1-10(17(19)20)11-6-7-15-12(8-11)9-14(18)13-4-2-3-5-16(13)21-15/h2-8,10H,9H2,1H3,(H,19,20)

Upstream product

• 103918-73-6 5-(1-propanoyl)-2-phenylthiophenyl acetic acid 
• 107234-77-5 methyl 5-(1-methoxycarbonylethyl)-2-phenylthiophenylacetate 
• 115441-83-3 methyl ester zaltoprofen 
• 144-55-8 sodium hydrogencarbonate 
• 83237-49-4 2-(3-carboxymethyl-4-phenylthiophenyl)propionic acid 

Relevant articles and documents

Reshaping the active pocket of esterase Est816 for resolution of economically important racemates

Bacterial esterases are potential biocatalysts for the production of optically pure compounds. However, the substrate promiscuity and chiral selectivity of esterases usually have a negative correlation, which limits their commercial value. Herein, an efficient and versatile esterase (Est816) was identified as a promising catalyst for the hydrolysis of a wide range of economically important substrates with low enantioselectivity. We rationally designed several variants with up to 11-fold increased catalytic efficiency towards ethyl 2-arylpropionates, mostly retaining the initial substrate scope and enantioselectivity. These variants provided a dramatic increase in efficiency for biocatalytic applications. Based on the best variant Est816-M1, several variants with higher or inverted enantioselectivity were designed through careful analysis of the structural information and molecular docking. Two stereoselectively complementary mutants, Est816-M3 and Est816-M4, successfully overcame and even reversed the low enantioselectivity, and several 2-arylpropionic acid derivatives with highEvalues were obtained. Our results offer potential industrial biocatalysts for the preparation of structurally diverse chiral carboxylic acids and further lay the foundation for improving the catalytic efficiency and enantioselectivity of esterases.

Cu(ii)-catalyzed sulfide construction: both aryl groups utilization of intermolecular and intramolecular diaryliodonium salt

A sulfur-iodine exchange protocol of diaryliodonium salts with inorganic sulfur salt was developed. Both aryl groups in the diaryliodonium salt were fully exerted in this transformation. Five- to eight-membered sulfur-containing heterocycles were achieved. Note that [1]benzothieno-[3,2-b][1]benzothiophene (BTBT) (an organic field-effect transistor (OFET) material) and Zaltoprofen were efficiently established through this method.

A method for preparation of ibuprofen

The invention relates to a preparation method for Zaltoprofen, and discloses a method for preparing Zaltoprofen. The method comprises the following steps: using 5-(1-propionyl)-2-thiophenyl phenylacetic acid as an initiator; preparing the Zaltoprofen through rearrangement, hydrolysis and cyclization. The rearrangement of the 5-(1-propionyl)-2-thiophenyl phenylacetic acid adopts illumination to heat; the illumination function is embedded into atom, has an effect on electron, and reduces activation energy required by reaction; reaction efficiency is high; meanwhile, the illumination function enables iodine to sublimate into gas state; the iodine in gas state can be in contact with substrate fully; the reaction is more complete and quick; influence on the rearrangement reaction of methyl iodide is reduced; yield coefficient is higher; the method is simple to operate, environmentally friendly, and suitable for industrial production.