88594-08-5

Usage

InChI:InChI=1/C21H24N4O12/c1-12(37-25(32)33)11-35-21(27)18-14(3)22-13(2)17(20(26)34-8-5-9-36-24(30)31)19(18)15-6-4-7-16(10-15)23(28)29/h4,6-7,10,12,19,22H,5,8-9,11H2,1-3H3

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 88488-52-2 2-nitrooxypropyl acetoacetate 
• 152809-64-8 2-nitrooxypropyl 2-(3-nitrobenzylidene) acetoacetate 
• 107431-60-7 3-nitrooxopropyl 2-(3-nitrobenzylidene)acetoacetate 
• 121486-75-7 (S)-(+)-1,4-dihydro-2,6-dimethyl-5-<(3-nitrooxypropoxy)carbonyl>-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 121486-81-5 (S)-(+)-2-nitrooxypropanol 
• 121486-82-6 (R)-(-)-2-nitrooxypropanol 
• 121486-77-9 (R)-(-)-1,4-dihydro-2,6-dimethyl-5-<(3-nitrooxypropoxy)carbonyl>-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 20266-74-4 1-hydroxy-2-nitrooxy-propane 
• 103434-76-0 (+/-)-1,4-dihydro-2,6-dimethyl-5-<(3-nitrooxypropoxy)carbonyl>-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 88488-49-7 3-nitrooxypropyl acetoacetate 

Relevant academic research and scientific papers

Novel 2-amino-1,4-dihydropyridine calcium antagonists. I. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having nitroxyalkoxycarbonyl groups at 3- and/or 5-position

Novel 2-amino-1,4-dihydropyridine derivatives, which contain nitroxy-alkoxycarbonyl groups at the 3- and/or 5-position, were synthesized and their pharmaceutical effect was evaluated in spontaneously hypertensive rats. The structure-activity relationships are discussed in terms of potency, onset-rapidity, and duration of antihypertensive activity. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced on either side of an ester chain.

Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates

Several 3-(2-cyanoethyl)-1,4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1,4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.

Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing nitrooxyalkylester moieties at the 3- and 5-positions

We have synthesized new 1,4-dihydropyridine derivatives having nitrooxyalkylester moieties at the 3- and 5-positions in order to develop potent and long-lasting vasodilators. The antihypertensive activities of these compounds were compared with that of nifedipine. One of them, 2- nitrooxypropyl 3-nitrooxypropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro- 3,5-pyridinedicarboxylate (CD-349) was selected for further development. The structure-activity relationship is discussed.