39562-25-9

Basic information

• Product Name: Isopropyl 2-(3-nitrobenzylidene)acetoacetate
• Synonyms: (E)-ISOPROPYL 2-(3-NITROBENZYLIDENE)-3-OXOBUTANOATE;ISOPROPYL 2-(M-NITROBENZYLIDENE)-ACETOACETATE;Isopropyl-2-(3-Nitrobenzolidene)Acetoacetate;Isopropyl 2-(3-nitrobenzylidene)-3-oxobutanoate;2-(3-Nitrobenzylidene)-3-oxobutyric acid isopropyl ester;2-(3-Nitrobenzylidene)acetoacetic acid isopropyl ester;α-Acetyl-3-nitrobenzeneacrylic acid isopropyl ester;Isopropyl 2-(3-nitrobenzylidene)acetoacetate
• CAS NO: 39562-25-9
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.27
• EINECS: 1312995-182-4
• Mol File: 39562-25-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 404.9 °C at 760 mmHg
• Flash Point: 167.3 °C
• Appearance: /
• Density: 1.229 g/cm³
• Vapor Pressure: 9.11E-07mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Isopropyl 2-(3-nitrobenzylidene)acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl 2-(3-nitrobenzylidene)acetoacetate(39562-25-9)
• EPA Substance Registry System: Isopropyl 2-(3-nitrobenzylidene)acetoacetate(39562-25-9)

Safety Data

• Hazardous Substances Data: 39562-25-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H15NO5/c1-9(2)20-14(17)13(10(3)16)8-11-5-4-6-12(7-11)15(18)19/h4-9H,1-3H3

Upstream product

• 542-08-5 isopropyl acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 75530-68-6 nilvadipine 
• 123524-52-7 azelnidipine 

Relevant articles and documents

Noncovalently Functionalized Commodity Polymers as Tailor-Made Additives for Stereoselective Crystallization

Stereoselective inhibition of the nucleation and crystal growth of one enantiomer aided by “tailor-made” polymeric additives is an efficient method to obtain enantiopure compounds. However, the conventional preparation of polymeric additives from chiral monomers are laborious and limited in structures, which impedes their rapid optimization and applicability. Herein, we report a “plug-and-play” strategy to facilitate synthesis by using commercially available achiral polymers as the platform to attach various chiral small molecules as the recognition side-chains through non-covalent interactions. A library of supramolecular polymers made up of two vinyl polymers and six small molecules were applied with seeds in the selective crystallization of seven racemates in different solvents. They showed good to excellent stereoselectivity in yielding crystals with high enantiomeric purities in conglomerates and racemic compound forming systems. This convenient, low-cost modular synthesis strategy of polymeric additives will allow for high-efficient, economical resolution of various racemates on different scales.

ITH14001, a CGP37157-Nimodipine Hybrid Designed to Regulate Calcium Homeostasis and Oxidative Stress, Exerts Neuroprotection in Cerebral Ischemia

During brain ischemia, oxygen and glucose deprivation induces calcium overload, extensive oxidative stress, neuroinflammation, and, finally, massive neuronal loss. In the search of a neuroprotective compound to mitigate this neuronal loss, we have designed and synthesized a new multitarget hybrid (ITH14001) directed at the reduction of calcium overload by acting on two regulators of calcium homeostasis; the mitochondrial Na+/Ca2+ exchanger (mNCX) and L-type voltage dependent calcium channels (VDCCs). This compound is a hybrid of CGP37157 (mNCX inhibitor) and nimodipine (L-type VDCCs blocker), and its pharmacological evaluation revealed a moderate ability to selectively inhibit both targets. These activities conferred concentration-dependent neuroprotection in two models of Ca2+ overload, such as toxicity induced by high K+ in the SH-SY5Y cell line (60% protection at 30 μM) and veratridine in hippocampal slices (26% protection at 10 μM). It also showed neuroprotective effect against oxidative stress, an activity related to its nitrogen radical scavenger effect and moderate induction of the Nrf2-ARE pathway. Its Nrf2 induction capability was confirmed by the increase of the expression of the antioxidant and anti-inflammatory enzyme heme-oxygenase I (3-fold increase). In addition, the multitarget profile of ITH14001 led to anti-inflammatory properties, shown by the reduction of nitrites production induced by lipopolysaccharide in glial cultures. Finally, it showed protective effect in two acute models of cerebral ischemia in hippocampal slices, excitotoxicity induced by glutamate (31% protection at 10 μM) and oxygen and glucose deprivation (76% protection at 10 μM), reducing oxidative stress and iNOS deleterious induction. In conclusion, our hybrid derivative showed improved neuroprotective properties when compared to its parent compounds CGP37157 and nimodipine.

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.