Losartan Carboxaldehyde

Base Information

• Chemical Name: Losartan Carboxaldehyde
• CAS No.: 114798-36-6
• Molecular Formula: C22H21ClN6O
• Molecular Weight: 420.901
• Hs Code.: 2933290000
• UNII: KJ52CU0VV6
• DSSTox Substance ID: DTXSID80150855
• Nikkaji Number: J424.221A
• Wikidata: Q27282284
• Metabolomics Workbench ID: 42501
• ChEMBL ID: CHEMBL308493
• Mol file: 114798-36-6.mol

Synonyms:2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-imidazole-5-carboxaldehyde;EXP 132;EXP 3179;EXP-132;EXP-3179;EXP132;EXP3179

Chemical Property of Losartan Carboxaldehyde

Chemical Property:

• Melting Point: 84-86°C
• Boiling Point: 666.7±65.0 °C(Predicted)
• PKA: 4.16±0.10(Predicted)
• PSA: 89.35000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 4.58700
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 420.1465370
• Heavy Atom Count: 30
• Complexity: 546

Purity/Quality:

98%Min ^*data from raw suppliers

Losartan Carboxaldehyde-d3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)C=O)Cl
• Description: Losartan carboxaldehyde is an intermediate aldehyde metabolite of the angiotensin II type 1 receptor antagonist, losartan . It does not block angiotensin receptors, but instead inhibits endothelial cyclooxygenase (COX)-2 expression, thereby exerting anti-inflammatory actions. At 1 μM in vitro, losartan carboxaldehyde has also been shown to block the upregulation of intercellular adhesion molecule (ICAM)-1 mRNA and COX-dependent generation of thromboxane A2 and prostaglandin F2α . Losartan carboxaldehyde can also act as a partial agonist (EC50 = 17.1 μM) of the insulin-sensitizing peroxisome proliferator-activated receptor γ in vitro.
• Uses: A metabolite of Losartan. An intermediate in the synthesis of the EXP 3174 A labelled intermediate in the synthesis of the EXP 3174, a metabolite of Losartan Losartan carboxaldehyde is an intermediate aldehyde metabolite of the angiotensin II type 1 receptor antagonist, losartan . It does not block angiotensin receptors, but instead inhibits endothelial cyclooxygenase (COX)-2 expression, thereby exerting anti-inflammatory actions. At 1 μM in vitro, losartan carboxaldehyde has also been shown to block the upregulation of intercellular adhesion molecule (ICAM)-1 mRNA and COX-dependent generation of thromboxane A2 and prostaglandin F2α . Losartan carboxaldehyde can also act as a partial agonist (EC50 = 17.1 μM) of the insulin-sensitizing peroxisome proliferator-activated receptor γ in vitro.[Cayman Chemical]

Technology Process of Losartan Carboxaldehyde

There total 32 articles about Losartan Carboxaldehyde 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: 100.0%

2-butyl-4-chloro-1-({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]-biphenyl-4-yl}-methyl)imidazole-5-carbaldehyde (1307853-51-5) → 2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde (114798-36-6)

Guidance literature:

2-butyl-4-chloro-1-({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]-biphenyl-4-yl}-methyl)imidazole-5-carbaldehyde; With methoxybenzene; trifluoroacetic acid; at 20 - 80 ℃; for 13h;

With potassium hydroxide; In water; toluene;

DOI:10.1021/jo202041e

Reference yield: 94.0%

lorsartan (114798-26-4) → 2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde (114798-36-6)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 - 50 ℃; for 6h; Alkaline conditions;

Reference yield: 78.0%

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde (133910-00-6) → 2-n-butyl-5-chloro-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid (124750-92-1) + EXP 3179 (114798-36-6)

Guidance literature:

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde; With sodium cyanide; manganese(IV) oxide; ethanol; acetic acid; for 21h; Reflux;

With sodium hydroxide; In ethanol; water; for 3h; Reflux;

With hydrogenchloride; In water; pH=3 - 4;

DOI:10.1016/j.ejmech.2012.01.043

upstream raw materials:

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde

cozaar

2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline

2-Cyano-4'-methylbiphenyl

Downstream raw materials:

lorsartan

1-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde O-methyl oxime

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde

Refernces

• 1、 Meyer, Maxime,Foulquier, Sébastien,Dupuis, Fran?ois,Flament, Stéphane,Grimaud, Linda,Henrion, Daniel,Lartaud, Isabelle,Monard, Gérald,Grillier-Vuissoz, Isabelle,Boisbrun, Michel. "Synthesis and evaluation of new designed multiple ligands directed towards both peroxisome proliferator-activated receptor-γ and angiotensin II type 1 receptor". . p. 334 - 352. Retrieved 2018.
• 2、 -. "SYNTHESIS OF DEUTERATED ALDEHYDES". Paragraph 00192. . Retrieved 2021/03/13.