Olprinone - CAS 106730-54-5
Catalog number: 106730-54-5
Category: Inhibitor
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Molecular Formula:
C14H10N4O
Molecular Weight:
250.26
COA:
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Targets:
Phosphodiesterase (PDE)
Description:
Olprinone(Loprinone) is a selective phosphodiesterase 3 (PDE3) inhibitor.
Purity:
>98%
MSDS:
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InChIKey:
JPAWFIIYTJQOKW-UHFFFAOYSA-N
InChI:
InChI=1S/C14H10N4O/c1-9-12(6-11(7-15)14(19)17-9)10-2-3-13-16-4-5-18(13)8-10/h2-6,8H,1H3,(H,17,19)
Canonical SMILES:
CC1=C(C=C(C(=O)N1)C#N)C2=CN3C=CN=C3C=C2
1. Synthesis of imidazo[1,2-a]pyridines: a decade update
Avik Kumar Bagdi, Sougata Santra, Kamarul Monir and Alakananda Hajra*. Chem. Commun., 2015, 51, 1555—1575
Imidazopyridine, the imidazole moiety fused with the pyridine ring, is an important biologically active nitrogen containing heterocycle. Among the various imidazopyridine derivatives, the imidazo[1,2-a]pyridine moiety is the most important in the area of natural products and pharmaceuticals. These derivatives show a wide range of biological activities such as anti-fungal, antiinflammatory, antitumor, antiviral, antibacterial, antiprotozoal, antipyretic, analgesic, antiapoptotic, hypnoselective, and anxioselective activities. They also act as b-amyloid formation inhibitors, GABA and benzodiazepine receptor agonists, and cardiotonic agents. There are several drugs such as zolpidem (1, used in the treatment of insomnia), alpidem (2, as an anxiolytic agent),olprinone (3, for the treatment of acute heart failure), zolimidine (4, used for the treatment of peptic ulcer), necopidem and saripidem (5 and 6, both work as an anxiolytic agent) available in the market which contain the imidazo[1,2-a]pyridine moiety (Fig. 1). The optically active GSK812397 is a drug for the treatment of HIV infection. The antibiotic drug Rifaximin also contains this fused heterocyclic moiety.
2. Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C–H bonds with DMSO using molecular oxygen
Hua Cao,* Sai Lei, Naiying Li, Longbin Chen. Chem. Commun., 2015, 51, 1823—1825
Our recent efforts included the construction of imidazo[1,2-a]-pyridines by direct C–H functionalization or the multicomponent reaction. Imidazo[1,2-a]pyridine and its derivatives as important fine chemicals have been found to be key structural units in many natural products and drugs, such as zolpidem, alpidem, zolimidine, olprinone, saripidem, and necopidem, and exhibit a broad range of biological activities. There has been long-standing interest in the development of new and efficient transformation for the synthesis of imidazo[1,2-a]pyridines due to their great important applications. In continuation of our interest in preparing imidazo[1,2-a]pyridine derivatives by direct C–H functionalization, we reported a novel and facile copper-catalyzed C-3 formylation of imidazo[1,2-a]pyridines with DMSO utilizing molecular oxygen as the terminal oxidant.
3. Ruthenium-catalyzed direct C-3 oxidative olefination of imidazo[1,2-a]pyridines
Haiying Zhan, Limin Zhao,* Naiying Li, Longbin Chen, Jingyun Liu, Jinqiang Liao and Hua Cao*. RSC Adv.,2014, 4, 32013–32016
We are particularly interested in the development of new catalytic transformation that exploit selective C–H functionalization to elaborate simple imidazo[1,2-a]pyridines to useful products. Imidazo[1,2-a]pyridine rings are among the most important heterocyclic structural motifs. It has been found to be key structural units inmany pharmaceuticals and exhibited a wide range of biological activities, such as zolpidem, zolimidine, and alpidem, necopidem, olprinone, and divalpon. Thus, the development of short and facile routes for the construction of imidazo[1,2-a]pyridine compounds through transition-metal-catalyzed functionalizations has received intensive attention. Among thesemetal, Pd, Au, Ag, and Cu is the favorable catalysts for the preparation of imidazo[1,2-a]pyridine derivatives. transition-metal-catalyzed transformation has been developed for the synthesis of imidazo[1,2-a]pyridine derivatives during the last few years, there has only been a rare example for the direct oleflnation of imidazo[1,2-a]pyridine.
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CAS 106730-54-5 Olprinone

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