153747-01-4

Basic information

• Product Name: (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE
• Synonyms: (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE;2-[4-(Aminomethyl)-1-piperidyl]isoindoline-1,3-dione
• CAS NO: 153747-01-4
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 259.3
• Mol File: 153747-01-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE(153747-01-4)
• EPA Substance Registry System: (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE(153747-01-4)

Safety Data

• Hazardous Substances Data: 153747-01-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE is used as a building block for the synthesis of various pharmaceuticals and biologically active compounds. Its structural characteristics make it a valuable component in creating new and effective drugs.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE serves as a research tool for the development of novel drugs and therapeutics. Its potential biological activities and chemical properties contribute to the advancement of medical treatments.
Used in Drug Discovery:
(PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE is utilized in drug discovery processes, where its unique structure may lead to the identification of new therapeutic targets and the creation of innovative pharmaceutical agents.
Overall, (PHTHALIMIDO-4-AMINOMETHYL)PIPERIDINE is a versatile chemical compound with a wide range of applications in chemistry and medicine, particularly in the development and synthesis of new pharmaceuticals and therapeutics.

Upstream product

• 136918-14-4 phthalimide 
• 7144-05-0 4-Aminomethylpiperidine 
• 85-44-9 phthalic anhydride 

Downstream Products

• 88915-26-8 4-aminomethyl-1-benzylpiperidine 
• 1136534-48-9 C₂₂H₃₀N₂O₄S 
• 1136473-56-7 C₂₀H₃₀N₄O₄S 
• 1136605-48-5 C₂₅H₃₀N₂O₄S 
• 1136716-49-8 C₂₂H₃₀N₂O₅S 
• 1136603-74-1 C₂₂H₃₀N₂O₄S 

Relevant articles and documents

Donepezil-based hybrids as multifunctional anti-Alzheimer's disease chelating agents: Effect of positional isomerization

The intricate and multifactorial nature of Alzheimer's disease (AD) requires the development of compounds able to hit different pathophysiological targets, such as cholinergic dysfunction, deposits of amyloid beta (Aβ) peptide and metal dyshomeostasis. In order to continue the search for new anti-AD drugs, a design strategy was once more followed based on repositioning donepezil (DNP) drug, by ortho-attaching a benzylpiperidine mimetic of DNP moiety to a hydroxyphenyl-benzimidazole (BIM) chelating unit (compound 1). Herein, compound 1 and a positional isomer 2 are compared in terms of their potential multiple properties: both present good acetylcholinesterase (AChE) inhibition (low μmolar range) and are moderate/good inhibitors of Aβ self- and Cu-mediated aggregation, the inhibition process being mainly due to ligand intercalation between the β-sheets of the fibrils; compound 1 has a higher chelating capacity towards Cu2+ and Zn2+ (pCu = 14.3, pZn = 6.4, pH 7.4, CL/CM = 10, CM = 10?6 M) than 2 (pCu = 10.7, pZn = 6.3), attributed to its ability to establish a tridentate (N,O,O) coordination to the metal ion. Both compounds are eligible as drug candidates for oral administration but compound 1 shows improved neuroprotective role by completely preventing Aβ-induced cell toxicity.

Novel donepezil?arylsulfonamide hybrids as multitarget-directed ligands for potential treatment of Alzheimer?s disease

Alzheimer’s disease (AD) is one of the most devastating neurodegenerative disorders, characterized by multiple pathological features. Therefore, multi-target drug discovery has been one of the most active fields searching for new effective anti-AD therapies. Herein, a series of hybrid compounds are reported which were designed and developed by combining an aryl-sulfonamide function with a benzyl-piperidine moiety, the pharmacophore of donepezil (a current anti-AD acetylcholinesterase AChE inhibitor drug) or its benzyl-piperazine analogue. The in vitro results indicate that some of these hybrids achieve optimized activity towards two main AD targets, by displaying excellent AChE inhibitory potencies, as well as the capability to prevent amyloid-β (Aβ) aggregation. Some of these hybrids also prevented Aβ-induced cell toxicity. Significantly, drug-like properties were predicted, including for blood-brain permeability. Compound 9 emerged as a promising multi-target lead compound (AChE inhibition (IC50 1.6 μM); Aβ aggregation inhibition 60.7%). Overall, this family of hybrids is worthy of further exploration, due to the wide biological activity of sulfonamides.

Donepezil structure-based hybrids as potential multifunctional anti-Alzheimer’s drug candidates

A new series of multifunctional hybrids, based on the structure of the donepezil (DNP) drug, have been developed and evaluated as potential anti Alzheimer’s disease (AD) agents. The rationale of this study was the conjugation of a benzylpiperidine/benzylpiperazine moiety with derivatives of bioactive heterocyclics (benzimidazole or benzofuran), to mimic the main structure of DNP and to endow the hybrids with additional relevant properties such as inhibition of amyloid beta (Aβ) peptide aggregation, antioxidant activity and metal chelation. Overall, they showed good activity for AChE inhibition (IC50=4.0–30.0?μΜ) and moderate ability for inhibition of Aβ1–42 self-mediated aggregation. The hybrids containing chelating groups showed improvement in the inhibition of Cu-induced Aβ42 aggregation and the antioxidant capacity. Moreover, neuroprotective effects of these compounds were evidenced in neuroblastoma cells after Aβ1–42 induced toxicity. Structure–activity relationship allowed the identification of some promising compounds and the main determinant structural features for the targeted properties.

Transamidation of carboxamides catalyzed by Fe(III) and water

The highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is described. The reaction is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III), and the results show that the presence of water is crucial. The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope. An example of its use is an intramolecular application in the synthesis of 2,3-dihydro-5H-benzo[b]-1,4- thiazepin-4-one, which is the bicyclic core of diltiazem and structurally related drugs (Budriesi, R.; Cosimelli, B.; Ioan, P.; Carosati, E.; Ugenti, M. P.; Spisani, R. Curr. Med. Chem. 2007, 14, 279-287). A plausible mechanism that explains the role of water is proposed on the basis of experimental observations and previous mechanistic suggestions for transamidation reactions catalyzed by transition metals such as copper and aluminum. This methodology represents a significant improvement over other existing methods; it can be performed in air and with wet or technical grade solvents.

Synthesis of polyamine derivatives having non-hypotensive Ca2+-permeable AMPA receptor antagonist activity

In order to obtain non-hypotensive and Ca2+-permeable AMPA receptor antagonists, we have synthesized a series of 1,4-bis(4-piperidinylmethyl)diaminobutanes. Compounds 13b, c, f had desirable properties.

Synthesis of diaminobutane derivatives as potent Ca2+-permeable AMPA receptor antagonists

We synthesized diaminobutane derivatives as potent Ca2+-permeable AMPA receptor antagonists with non-hypotensive activity. Compound 10c showed selective Ca2+-permeable AMPA receptor antagonist activity and neuroprotective effects in transient global ischemia models in gerbils.