112776-37-1

Usage

InChI:InChI=1/C9H10NO2P/c13-5-10-4-7-1-2-8-9(3-7)12-6-11-8/h1-3,5H,4,6,13H2/b10-5+

Upstream product

• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 20747-42-6 piperonal-(Z)-oxime 

Downstream Products

• 112776-42-8 1-Benzo[1,3]dioxol-5-ylmethyl-2,2-dichloro-3-phenyl-aziridine 
• 1235889-67-4 (2R,5R)-dimethyl 1-(benzo[d][1,3]dioxol-5-ylmethyl)-5-(4-methoxyphenyl)-2-phenylpyrrolidine-3,3-dicarboxylate 
• 1023023-78-0 3-(benzo[d][1,3]dioxol-5-ylmethyl)-2-phenylthiazolidin-4-one 
• 112776-46-2 N-Benzo[1,3]dioxol-5-ylmethyl-2-chloro-2-phenyl-acetamide 
• 112776-49-5 8-Phenyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-7-one 
• 135509-04-5 (3R,4S)-3-(4-Allyl-2-methoxy-phenoxy)-1-benzo[1,3]dioxol-5-ylmethyl-4-phenyl-azetidin-2-one 
• 135508-93-9 1-Benzo[1,3]dioxol-5-ylmethyl-3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-phenyl-azetidin-2-one 
• 135509-03-4 (3R,4S)-1-Benzo[1,3]dioxol-5-ylmethyl-3-(2-isopropyl-5-methyl-phenoxy)-4-phenyl-azetidin-2-one 

Relevant academic research and scientific papers

Synthesis of chromeno[3,4-b]piperazines by an enol-ugi/reduction/cyclization sequence

Keto piperazines and aminocoumarins are privileged building blocks for the construction of geometrically constrained peptides and therefore valuable structures in drug discovery. Combining these two heterocycles provides unique rigid polycyclic peptidomimetics with drug-like properties including many points of diversity that could be modulated to interact with different biological receptors. This work describes an efficient multicomponent approach to condensed chromenopiperazines based on the novel enol-Ugi reaction. Importantly, this strategy involves the first reported post-condensation transformation of an enol-Ugi adduct.

Synthesis, characterization, biological evaluation, and molecular docking studies of some piperonyl-based 4-thiazolidinone derivatives

Heterocyclic compounds are of particular importance among pharmacologically active compounds. In this study, some piperonyl-based 4-thiazolidinone derivatives (2a–i) were synthesized and characterized by spectroscopic assays. All molecules were tested as enzyme inhibitory factors. These compounds were effective inhibitors of the enzymes acetylcholinesterase (AChE), α-glycosidase (α-Gly), and the human carbonic anhydrase I and II isoforms (hCA I and II), with Ki values in the range of 8.90–66.51 nM for α-Gly, 94.8–289.5 nM for hCA I, 106.3–304.6 nM for hCA II, and 0.55–2.36 nM for AChE. The synthesized molecules were also studied theoretically. Molecular docking calculations were performed to investigate the interaction between the target protein and molecules. CA inhibitor compounds have been clinically used for almost 60 years as antiglaucoma and diuretic drugs. The inhibition of the AChE enzyme results in the blockage of ACh hydrolysis. On the contrary, the design of inhibitor compounds or/and modulators for AChE is of major interest as it is one of the most popular tools to prevent Alzheimer's disease.

Synthesis of polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a one-pot (Ugi-3CR/aza diels-alder/N-acylation/aromatization/SN2) process. A suitable alternative towards novel Aza-analogues of falipamil

We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4b]pyridin-5-ones in 33 and 34%, and a couple of Falipamil aza-analogues in 30 and 35% overall yields. It is worth highlighting the good substrate scope found, because final products are furnished with alkyl, aryl, and heterocyclic substituents. The use of chain-ring tautomerizable isocyanides (as key reagents for the Ugi-type three component reaction) allowed for a rapid and efficient assembly of the polysubstituted oxindoles, which were used in situ toward the complex products, conferring features like robustness, sustainability, and the one-pot approach to this synthetic methodology.

Highly efficient iron phthalocyanine catalyzed oxidative synthesis of imines from alcohols and amines

An efficient iron phthalocyanine catalyzed method was developed for direct oxidative coupling of alcohols with amines to afford corresponding imines. The present protocol is applicable to various substituted aromatic and aliphatic alcohols and amines. The reaction is believed to proceed via activation of alcohols by iron phthalocyanines through Lewis acid-base interaction to form aldehydes, which by nucleophilic attack of amines are converted into the corresponding imines.

Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: Reaction development and mechanistic insights

An enantioselective preparation of 2,5-cis-disubstituted pyrrolidines has been achieved via a dynamic kinetic asymmetric transformation (DyKAT) of racemic donor-acceptor cyclopropanes and (E)-aldimines. Mechanistic studies suggest that isomerization of the aldimine or resultant iminium to the Z geometry is not a pathway that furnishes the observed 2,5-cis-disubstituted products.

Phosphatase inhibitors. III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase

Further investigation of the structural requirements of a series of benzylphosphonic acid inhibitors of human prostatic acid phosphatase has led to the highly potent series of α-aminobenzylphosphonic acids. The α-benzylaminobenzylphosphonic acid, with an IC50 = 4 nM, exhibited a 3500-fold improvement in potency over the carbon analogue, α-phenylethyl. The enhanced potency may be due to a combination of four favorable interactions including those with the phosphate binding region, the presence the hydrophobic moieties of the benzylamino and phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the α-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution on the α-amino group led to great reductions in potency.

Synthesis of monocyclic &β-lactams incorporating an essential oil constituent in the ring

A series of new monocyclic β-lactams has been prepared using acyl chlorides derived from 1-menthol, thymol and eugenol and Schiff bases derived from aromatic aldehydes and amines, and their antibacterial activity determined.The compounds have been charact