120210-48-2

Basic information

• Product Name: TENIDAP
• Synonyms: TENIDAP;AKOS 91367;5-Chloro-2，3-dihydro-2-oxo-3-(2-thenoyl)-1H-indole-1-carboxamide;CP66248,CP-66248-2;(3Z)-5-Chloro-2,3-dihydro-3-(hydroxy-2-thienylMethylene)-2-oxo-1H-indole-1-carboxaMide;(Z)-5-Chloro-2,3-dihydro-3-(hydroxy-2-thienylMethylene)-2-oxo-1H- indole-1-carboxaMide
• CAS NO: 120210-48-2
• Molecular Formula: C14H9ClN2O3S
• Molecular Weight: 320.75
• Mol File: 120210-48-2.mol

Chemical Properties

• Melting Point: 230° (dec)
• Boiling Point: 523.9°Cat760mmHg
• Flash Point: 270.7°C
• Appearance: faint yellow to dark yellow/
• Density: 1.58g/cm³
• Vapor Pressure: 7.42E-13mmHg at 25°C
• Refractive Index: 1.756
• Storage Temp.: Store at +4°C
• Solubility: DMSO: soluble1mg/mL, clear (warmed)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: TENIDAP(CAS DataBase Reference)
• NIST Chemistry Reference: TENIDAP(120210-48-2)
• EPA Substance Registry System: TENIDAP(120210-48-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 120210-48-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TENIDAP is used as an anti-inflammatory agent for the treatment of conditions such as osteoarthritis and rheumatoid arthritis. It helps in alleviating pain and inflammation by inhibiting the formation of pro-inflammatory arachidonic acid metabolites in human peripheral polymorphonuclear leukocytes.
Used in Inflammatory Conditions Treatment:
TENIDAP is used as a therapeutic agent for managing inflammation in various conditions. Its preferential inhibition of COX-1 makes it a suitable choice for reducing inflammation without causing significant side effects associated with other NSAIDs that inhibit both COX-1 and COX-2 enzymes.

Biological Activity

NSAID that preferentially inhibits COX-1 (IC 50 values are < 0.03, 1.2 and > 30 μ M for COX-1, COX-2 and 5-lipoxygenase respectively). Inhibits formation of pro-inflammatory arachidonic acid metabolites in isolated human peripheral polymorphonuclear leukocytes. Opener of inward rectifying hK IR 2.3 channel (EC 50 = 402 nM).

InChI:InChI=1/C14H9ClN2O3S/c15-7-3-4-9-8(6-7)11(13(19)17(9)14(16)20)12(18)10-2-1-5-21-10/h1-6,19H,(H2,16,20)

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 197776-03-7 5-chloro-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole 
• 197776-00-4 phenyl 5-chloro-2-[(phenoxycarbonyl)oxy]-1H-indole-1-carboxylate 
• 255712-72-2 (Z)-5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole 
• 255712-71-1 (Z)-5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-1-methoxycarbonyl-2-oxo-2,3-dihydroindole 
• 197776-09-3 5-chloro-1-methoxycarbonyl-2-oxo-2,3-dihydroindole 
• 255712-65-3 5-chloro-1-phenoxycarbonyl-2-(thenoyloxy)indole 
• 17630-75-0 5-chloro-indolin-2-one 

Relevant articles and documents

New practical synthesis of tenidap

The development of a new, practical synthesis to tenidap is described. N,O-Dialkoxy(aryloxy)carbonylation of 5-chloro-2-oxo-2,3-dihydroindole, followed by removal of the O-alkoxy-(aryloxy)carbonyl group gave 1-[alkoxy(aryloxy)carbonyl]-5-chloro-2-oxo-2,3-dihydroindoles in good yields. The latter compounds were thenoylated in the 3-position. The role of DMAP in the acylation reaction is discussed. The structures of the thenoylated products and their enolate salts were investigated both in solution and solid phases. Ammonolysis of 5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3- dihydroindole afforded the corresponding 1-carbamoyl derivative (tenidap) in high yield. The corresponding 1-ethoxy- and 1-methoxycarbonyl derivatives could not be similarly transformed to tenidap; loss of the alkoxycarbonyl moiety occurred instead of carbamoylation.

New routes to oxindole derivatives

A new, practical synthesis of the antirheumatic oxindole derivative, tenidap, has been elaborated. The new approach has initiated studies on the mechanism of the acylation reactions of oxindoles. Methods have been developed for the synthesis of 1-[alkoxy(or aryloxy)carbonyl]- and 1,3-di[alkoxy(or aryloxy)carbonyl]oxindoles starting from oxindoles. The route designed for tenidap has provided a facile access to several analogues, too. On another front, new reaction conditions are described, which turn Wenkert's synthesis of 3-alkyloxindoles (by Raney nickel induced alkylation of oxindoles with alcohols) into a highly efficient synthetic tool. The method has been extended to the synthesis of 3-alkyloxindoles from isatins and to the preparation of 3-(ω-hydroxyalkyl)oxindoles from oxindoles and isatins. Springer-Verlag 2004.