Temocaprilat

Base Information

• Chemical Name: Temocaprilat
• CAS No.: 110221-53-9
• Molecular Formula: C21H24N2O5S2
• Molecular Weight: 448.564
• UNII: 2D6A12Q12R
• DSSTox Substance ID: DTXSID60891350
• Wikidata: Q27108393
• NCI Thesaurus Code: C75023
• ChEMBL ID: CHEMBL300841
• Mol file: 110221-53-9.mol

Synonyms:RS 5139;RS-5139;temocaprilat;temocaprilate

Chemical Property of Temocaprilat

Chemical Property:

• Appearance/Colour: White to Off-White Solid
• Vapor Pressure: 3.18E-23mmHg at 25°C
• Melting Point: >2300C (dec)
• Refractive Index: 1.665
• Boiling Point: 743.6oCat760mmHg
• PKA: 2.09±0.10(Predicted)
• Flash Point: 403.5oC
• PSA: 160.48000
• Density: 1.41g/cm³
• LogP: 2.82220
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 448.11266422
• Heavy Atom Count: 30
• Complexity: 614

Purity/Quality:

99% ^*data from raw suppliers

Temocaprilat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(SCC(C(=O)N1CC(=O)O)NC(CCC2=CC=CC=C2)C(=O)O)C3=CC=CS3
• Isomeric SMILES: C1[C@H](SC[C@@H](C(=O)N1CC(=O)O)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C3=CC=CS3
• Description: Temocaprilat is an inhibitor of angiotensin-converting enzyme (ACE; IC50 = 3.6 nM for rabbit lung ACE). It inhibits contraction of isolated rat aorta induced by angiotensin I with an IC50 value of 7.6 nM. Temocaprilat (1-30 μg/kg, i.v.) inhibits angiotensin I-induced pressor responses in anesthetized rats in a dose-dependent manner.
• Uses: Antihypertensive Antihypertensive.

Technology Process of Temocaprilat

There total 15 articles about Temocaprilat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

temocapril Hydrochloride (110221-44-8) → [3H]-Temocaprilat (110221-53-9)

Guidance literature:

With sodium hydroxide; for 16h; Ambient temperature;

DOI:10.1021/jm00394a009

Reference yield:

ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → [3H]-Temocaprilat (110221-53-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 80 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

3: 94 percent / NaH / dimethylformamide / 5 h / Ambient temperature

4: 78 percent / 4 N aq. HCl / dioxane / 16 h / Ambient temperature

5: 96 percent / 1 N aq. NaOH / 16 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; sodium hydride; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a009

Reference yield:

temocapril (111902-57-9) → ethanol (64-17-5) + [3H]-Temocaprilat (110221-53-9)

Guidance literature:

With Tris-HCl buffer; human liver carboxylesterase pI 4.5; at 37 ℃; pH=7.4; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1248/bpb.20.869

upstream raw materials:

temocapril Hydrochloride

temocapril

1-(2-thienyl)-2-nitroethene

(E)-2-oxo-4-phenyl-3-butenoic acid

Refernces

• 1、 Yanagisawa, Hiroaki,Ishihara, Sadao,Ando, Akiko,Kanazaki, Takuro,Miyamoto, Shuichi,et al.. "Angiotensin-Converting Enzyme Inhibitors: Perhydro-1,4-thiazepin-5-one Derivatives". . p. 1984 - 1991. Retrieved 2007/10/02.