Aranidipine

Base Information

• Chemical Name: Aranidipine
• CAS No.: 86780-90-7
• Molecular Formula: C₁₉H₂₀N₂O₇
• Molecular Weight: 388.377
• UNII: 4Y7UR6X2PO
• DSSTox Substance ID: DTXSID9048649
• Wikipedia: Aranidipine
• Wikidata: Q4784109
• NCI Thesaurus Code: C73022
• Pharos Ligand ID: Q5LBW4US71VW
• Metabolomics Workbench ID: 152261
• ChEMBL ID: CHEMBL2104030
• Mol file: 86780-90-7.mol

Synonyms:aranidipine;methyl 2-oxopropyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid;MPC 1304;MPC-1304

Chemical Property of Aranidipine

Chemical Property:

• Vapor Pressure: 2.56E-11mmHg at 25°C
• Melting Point: 155°
• Refractive Index: 1.555
• Boiling Point: 530 °C at 760 mmHg
• PKA: 2.56±0.70(Predicted)
• Flash Point: 274.3 °C
• PSA: 127.52000
• Density: 1.284 g/cm³
• LogP: 2.98680
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 388.12705098
• Heavy Atom Count: 28
• Complexity: 748

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

Aranidipine(MPC1304) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OCC(=O)C)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
• Description: Aranidipine was launched in Japan as an antihypertensive agent. Its pharmacological effects are similar to other dihydropyridine derivatives, e.g., nefidipine, however, it is more potent and longer lasting. This is partially due to the fact that its initial metabolite (ketone reduction) is just as effective as the parent compound. Aranidipine exerts its activity by blocking Ca+2 entry during depolarization via L-type voltagegated Ca channels. This causes decreased levels of intracellular Ca which leads to enhanced relaxation of smooth and cardiac muscle. It is a selective α2-adrenoreceptor antagonist which inhibits vasoconstrictive responses. As a dihydropyridine derivative, it can be synthesized via a modified Hantsch synthesis. While sold as a racemate, the (S)-enantiomer is 150 times more active than the (R)- antipode.
• Therapeutic Function: Antihypertensive

Technology Process of Aranidipine

There total 9 articles about Aranidipine 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: 92.0%

2,2-ethylenedioxypropyl methyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate (86780-89-4) → aranidipine (86780-90-7,330783-93-2,330783-94-3)

Guidance literature:

With acetic acid; In water; for 10h; Heating;

DOI:10.1248/cpb.34.1589

Reference yield: 75.8%

methyl 2-(2'-nitrobenzylidene)acetoacetate (39562-27-1) + 3-amino-2-crotonic acid 2,2-ethylenedioxy propyl ester (86780-81-6) → aranidipine (86780-90-7,330783-93-2,330783-94-3)

Guidance literature:

In ethanol; Reflux;

Reference yield:

3-amino-2-crotonic acid 2,2-ethylenedioxy propyl ester (86780-81-6) → aranidipine (86780-90-7,330783-93-2,330783-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / ethanol / 10 h / Heating

2: 92 percent / AcOH / H₂O / 10 h / Heating

With acetic acid; In ethanol; water;

DOI:10.1248/cpb.34.1589

upstream raw materials:

2,2-ethylenedioxypropyl methyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

methyl 2-(2'-nitrobenzylidene)acetoacetate

acetoacetic acid methyl ester

3-amino-2-crotonic acid 2,2-ethylenedioxy propyl ester

Refernces

• 1、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.
• 2、 Ohno,Komatsu,Mizukoshi,Ichihara,Nakamura,Morishima,Sumita. "Synthesis of asymmetric 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates with vasodilating and antihypertensive activities". . p. 1589 - 1606. Retrieved 2007/10/02.