78436-46-1

Basic information

• Product Name: 1-{3-[1-(p-chlorobenzoyl-5-methoxy-2-methyl)-indolacetyl]}-imidazole
• Synonyms: 1-{3-[1-(p-chlorobenzoyl-5-methoxy-2-methyl)-indolacetyl]}-imidazole
• CAS NO: 78436-46-1
• Molecular Weight: 407.856
• Mol File: 78436-46-1.mol

Chemical Properties

• CAS DataBase Reference: 1-{3-[1-(p-chlorobenzoyl-5-methoxy-2-methyl)-indolacetyl]}-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-{3-[1-(p-chlorobenzoyl-5-methoxy-2-methyl)-indolacetyl]}-imidazole(78436-46-1)
• EPA Substance Registry System: 1-{3-[1-(p-chlorobenzoyl-5-methoxy-2-methyl)-indolacetyl]}-imidazole(78436-46-1)

Safety Data

• Hazardous Substances Data: 78436-46-1(Hazardous Substances Data)

Upstream product

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 78458-11-4 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-2'-hydroxy-diethyloxide 
• 157769-09-0 [1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethyl ester 
• 78458-27-2 N-{2-[4-Amino-3-bromo-5-(N-ethyl-cyclohexylaminomethyl)-benzoyloxy]-ethyl}-N'-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethyl}-piperazine 
• 786593-70-2 N-{2-[4-Amino-3-bromo-5-(N-ethyl-cyclohexylaminomethyl)benzoyloxy]-ethyl}-N-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethyl}-ethylamine 
• 773006-98-7 1-[4-Amino-3-bromo-5-(N-ethyl-cycloheptylaminomethyl)benzoyloxy]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 785728-50-9 1-[4-Amino-3-bromo-5-(4-methyl-piperazinomethyl)-benzoyloxy]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 753401-73-9 1-(4-Amino-3-bromo-5-piperidinomethyl-benzoyloxy)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 789442-03-1 1-(4-Amino-3-bromo-5-pyrrolidinomethyl-benzoyloxy)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 705918-43-0 1-[4-Amino-3-bromo-5-(N-ethyl-cyclopentylaminomethyl)benzoyloxy]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 727351-87-3 1-[4-Amino-3-bromo-5-(N-cyclohexyl-methylaminomethyl)benzoyloxy]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 777009-60-6 1-(4-Amino-3-bromo-5-cyclohexylaminomethyl-benzoyloxy)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 756428-52-1 1-(4-Amino-3-bromo-5-tert.butylaminomethyl-benzoyloxy)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 790160-00-8 1-[4-Amino-3-bromo-5-(N-methyl-n-propylaminomethyl)benzoyloxy]-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 
• 686256-06-4 1-(4-Amino-3-bromo-5-isopropylaminomethyl-benzoyloxy)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-ethane 

Relevant articles and documents

Synthesis and stability of two indomethacin prodrugs

The purpose of this study was to synthesize and study the in vitro enzymatic and non-enzymatic hydrolysis of indomethacin-TEG ester and amide prodrugs. It was found that the ester conjugate 10 was comparatively stable between pH 3 and 6 (half-life >90 h),

Synthesis and pharmacological evaluation of oligoethylene ester derivatives as indomethacin oral prodrugs

Five indomethacin oligoethylene ester derivatives (3-7) were synthesized and evaluated for their anti-inflammatory, analgesic, and ulcerogenic activity after oral administration. The molecular weight of the oligoethylene glycols used for synthesizing esters 3-7 ranged from 106 to 282. The chemical and enzymatic stabilities of esters 3-7 were evaluated in pH 7.4 and 2.0 buffers and in human plasma, respectively. All the prodrugs showed a good stability both in pH 7.4 phosphate buffer and in pH 2.0 buffer, and they were readily hydrolyzed by human plasma. Esters 3-7 showed an anti-inflammatory activity, determined as the percent inhibition of carrageenan-induced edema, similar to that of indomethacin, although at higher doses. From writhing test results, we observed that all the prodrugs exhibited better or similar analgesic activity compared to indomethacin. Esters 3-7 were significantly less irritating to the gastric mucosa than indomethacin, after oral administration, and esters 3-5 did not show any ulcerogenic activity, although they were administered at higher doses than indomethacin.

ESTERS OF 1-p-CHLOROBENZOYL-5-METHOXY-2-METHYL-3-INDOLYLACETIC ACID

Reactions of imidazolide of 1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indolylacetic acid, prepared from the acid and N,N'-carbonyldiimidazole, with the optically active forms of 2-phenyl-3-hydroxypropane acid and with the inactive forms of p-chloro-, p-isopropyl- and p-isobutyl-2-phenyl-3-hydroxypropane acids gave the corresponding esters.The compounds were tested for antiinflammatory activity.