78299-53-3

Basic information

• Product Name: Tiacrilast
• Synonyms: Tiacrilast;(E)-3-(6-(Methylthio)-4-oxo-3(4H)-quinazolinyl)-2-propenoic acid;Ro 223747;(E)-3-[6-(Methylthio)-4-oxo-3(4H)-quinazolinyl]propenoic acid;(E)-3-[6-(Methylthio)-4-oxoquinazolin-3(4H)-yl]propenoic acid
• CAS NO: 78299-53-3
• Molecular Formula: C12H10N2O3S
• Molecular Weight: 262.288
• Mol File: 78299-53-3.mol

Chemical Properties

• Boiling Point: 499.3°C at 760 mmHg
• Flash Point: 255.8°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 8.67E-11mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: Tiacrilast(CAS DataBase Reference)
• NIST Chemistry Reference: Tiacrilast(78299-53-3)
• EPA Substance Registry System: Tiacrilast(78299-53-3)

Safety Data

• Hazardous Substances Data: 78299-53-3(Hazardous Substances Data)

Usage

Uses

Used in Dermatology:
Tiacrilast is used as a topical cream for the treatment of atopic dermatitis, a chronic inflammatory skin disease. It is effective in reducing the severity of symptoms such as itching, redness, and dryness by inhibiting the production of inflammatory mediators and promoting the healing of the skin barrier. Despite its demonstrated effectiveness, Tiacrilast may cause side effects like skin irritation and a burning sensation at the application site, necessitating further research to understand its full potential benefits and risks.

InChI:InChI=1/C12H10N2O3S/c1-18-8-2-3-10-9(6-8)12(17)14(7-13-10)5-4-11(15)16/h2-7H,1H3,(H,15,16)/b5-4+

Upstream product

• 78299-51-1 6-(methylthio)quinazolin-4(3H)-one 
• 76745-74-9 2-amino-5-(methylsulfanyl)benzoic acid 
• 68701-32-6 5-methylthio-2-nitrobenzoic acid 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 78299-52-2 trans-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid methyl ester 

Relevant articles and documents

(E)-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acids, a new series of antiallergy agents

A series of substituted (E)-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acids was prepared and evaluated in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. Alkoxy, alkylthio, and isopropyl substituents at the 6- or 8-positions provided highly potent compounds. Conversion to the Z isomer, reduction of the side chain double bond, or reduction of the quinazoline ring resulted in substantial loss of activity. Among the analogues that exhibited oral activity in the PCA test, (E)-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid was the most potent.

Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives

Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives of the formula STR1 wherein R1 is hydrogen, lower alkyl, lower cycloalkyl, lower alkoxy, hydroxy, halo, lower alkykthio, lower alkylsulfinyl, lower alkylsulfonyl, di-(C1 -C7)alkyl-N(CH2)n O-- or 2-hydroxyethoxy; R2 is hydrogen, lower alkyl or lower alkoxy; R3 is hydroxy, lower alkoxy, di-(C1 -C7)alkyl-N(CH2)n O-- or di-(C1 -C7)alkyl-N(CH2)n NH--; and n is 2 to 7; provided that at least one of R1 and R2 is other than hydrogen, when R3 is hydroxy, a salt thereof with a pharmaceutically acceptable base, or when R3 is di-(C1 -C7)alkyl-N(CH2)n O-- or di-(C1 -C7)alkyl-N(CH2)n NH--, a salt thereof with a pharmaceutically acceptable acid, and a process for the preparation thereof, are described. The compounds of formula I are useful as agents in the prevention of allergic reactions.