30653-83-9

Basic information

• Product Name: parsalmide
• Synonyms: parsalmide;5-Amino-N-butyl-2-(2-propynyloxy)benzamide;MY-41-6;Parsal;5-Amino-N-butyl-2-(2-propyn-1-yloxy)benzamide
• CAS NO: 30653-83-9
• Molecular Formula: C₁₄H₁₈N₂O₂
• Molecular Weight: 246.308
• EINECS: 250-274-2
• Mol File: 30653-83-9.mol

Chemical Properties

• Melting Point: 83-85℃
• Boiling Point: 389.31°C (rough estimate)
• Flash Point: 210.3°C
• Appearance: /
• Density: 1.107
• Vapor Pressure: 2.13E-07mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• PKA: pKa (aq soln, 20°) 4.6 ±0.03
• CAS DataBase Reference: parsalmide(CAS DataBase Reference)
• NIST Chemistry Reference: parsalmide(30653-83-9)
• EPA Substance Registry System: parsalmide(30653-83-9)

Safety Data

• Hazardous Substances Data: 30653-83-9(Hazardous Substances Data)

Usage

Originator

Parsalmide,Shanghai Lansheng Corporation

Manufacturing Process

5-Acetylamino-2-acetoxybenzoyl chloride was obtained by reaction of 5acetylamino-2-acetoxy-benzoic acid with thionylchloride.5-Acetylamino-N-butyl-2-hydroxybenzamide was produced in the result of treatment of 5-acetylamino-2-acetoxybenzoyl chloride with butylamine in the presence of sodium hydroxide5-Acetamino-N-(n-butyl)-2-propargyloxybenzamide was obtained by reaction of 5-acetylamino-N-butyl-2-hydroxybenzamide with propargylbromide in the presence of sodium, isopropyl alcohol and sulfuric acid. 28.8 g (0.1 mole) 5-acetamino-N-(n-butyl)-2-propargyloxybenzamide in 320 ml of 4 N sulfuric acid was heated, under stirring, at 90°-95°C for 2 h. The clear solution was cooled and its pH adjusted to 1 with 1 N NaOH; after filtering, further alkali was subsequently added until a pH of 10 was obtained. At this point the product was separated by filtration and recrystallized from ethanol at 60°C to give 16.6 g (a yield of 68%) of chromatographically pure 5-amino-N-(n-hutyl)-2-propargyloxybenzamide; melting point 85°-87°C.

Therapeutic Function

Muscle relaxant, Antiinflammatory, Analgesic

InChI:InChI=1/C14H18N2O2/c1-3-5-8-16-14(17)12-10-11(15)6-7-13(12)18-9-4-2/h2,6-7,10H,3,5,8-9,15H2,1H3,(H,16,17)

Upstream product

• 68505-93-1 N-Butyl-5-nitro-2-(2-propynyloxy)-benzamide 
• 68505-92-0 N-butyl-2-chloro-5-nitro-benzamide 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 51-59-2 N-Acetyl-5-aminosalicylic acid 
• 6382-44-1 5-acetamido-N-butylsalicylamide 
• 89-57-6 5-Aminosalicylic Acid 
• 6382-58-7 5-Acetylamino-N-butyl-2-prop-2-ynyloxy-benzamide 

Downstream Products

• 1395396-81-2 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(prop-2-ynyloxy)benzamide 
• 1395397-31-5 5-(2-(piperidin-1-yl)acetamido)-N-butyl-2-(prop-2-ynyloxy)benzamide 
• 1395396-50-5 5-(2-bromoacetamido)-N-butyl-2-propargyloxybenzamide 

Relevant articles and documents

Synthesis of benzamide derivatives and their evaluation as antiprion agents

A new set of 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide and 5-(2-(piperidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide derivatives were synthesized in which as structural features the 2-(1-pyrrolidinyl)- or 2-(1-piperidyl)acetylamino group or a diphenylether moiety are associated to a benzamide scaffold. Their binding affinity for human PrPC and inhibition of its conversion into PrPSc were determined in vitro; moreover, the antiprion activity was assayed by inhibition of PrPSc accumulation in scrapie-infected mouse neuroblastoma cells (ScN2a) and scrapie mouse brain (SMB) cells. The results clearly indicate the benzamide derivatives as attractive lead compounds for the development of potential therapeutic agents against prion disease.

Synthesis of substituted benzamides as anti-inflammatory agents that inhibit preferentially cyclooxygenase 1 but do not cause gastric damage

Parsalmide (5-amino-N-butyl-2-(2-propynyloxy) benzamide) (5a), is a non-steroidal anti-inflammatory drug (NSAID), commercialised in Italy until 1985 with the brand name of Synovial, that has been widely used to treat arthritic patient. In addition, it was shown to spare gastric mucosa. Here we have synthesised a series of novel substituted benzamides, related to Parsalmide, and have evaluated their activity in vitro on COX-1 and COX-2 as well as in vivo in the carrageenin-induced rat paw edema, a classical in vivo anti-inflammatory assay. Compounds 5b, 11a and 11b, which showed a favourable profile in vitro and in vivo, were screened in comparison with Parsalmide for gastrointestinal (GI) tolerability in vivo in the rat. Results obtained showed that Parsalmide and compound 11b inhibited both COX-1 and COX-2 in vitro as well as they were active in vivo. Both compounds were devoid of gastric effect at the efficacious dose. In addition, both prevented indomethacin-induced gastric damage. Thus, these compounds may guide the definition of a new leading structure with anti-inflammatory activity that may allow designing new safer NSAIDs.