3529-08-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Aminopropyl)piperidine is used as a reactant for the synthesis of various chemotypes that target different diseases and conditions. Its application reason is due to its unique structure, which can be modified and functionalized to create diverse bioactive compounds.
1. As a reactant for the synthesis of chemotypes that inhibit Botulinum neurotoxin serotype A light chain, P. falciparum Malaria, and Ebola filovirus, 1-(3-Aminopropyl)piperidine contributes to the development of potential treatments for these diseases.
2. It is also used in the synthesis of membrane targeting antibiotics, which can help combat antibiotic-resistant bacteria.
3. In the field of neuroscience, 1-(3-Aminopropyl)piperidine is used as a reactant for the synthesis of 5-HT3A receptor antagonists, which have potential applications in treating conditions like anxiety, depression, and nausea.
4. Additionally, it is used in the synthesis of histamine H3 antagonists, which can be beneficial in the treatment of cognitive disorders and sleep-wake regulation.
5. Berberine derivatives, which are synthesized using 1-(3-Aminopropyl)piperidine, are used for the stabilization of G-quadruplex DNA and downregulation of the oncogene c-myc, potentially offering new avenues for cancer treatment.
6. Lastly, 1-(3-Aminopropyl)piperidine is used as a reactant for the incorporation of basic side chains into the cryptolepine scaffold, which enhances its antimalarial activity, providing a potential solution to combat drug-resistant malaria.

Upstream product

• 110-89-4 piperidine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 3088-41-3 3-(piperidin-1-yl)propionitrile 
• 71-36-3 butan-1-ol 
• 76439-26-4 1,3-dipiperidino-propene 
• 4733-45-3 2-(3-(piperidin-1-yl)-propyl)isoindoline-1,3-dione 
• 503-29-7 azetidine 
• 1458-63-5 N-(3-chloropropyl)-piperidine 
• 107-13-1 acrylonitrile 
• 7052-81-5 3-(1-piperidinyl)-1-acetylpropylamine 

Downstream Products

• 37905-61-6 2-methyl-3-(3-piperidin-1-yl-propyl)-3H-quinazolin-4-one 
• 112819-20-2 2,5-bis-(3-piperidino-propylamino)-[1,4]benzoquinone 
• 115581-68-5 2-nitro-N-(3-piperidino-propyl)-aniline 
• 107773-39-7 N-mesityl-N'-(3-piperidino-propyl)-urea 
• 855396-09-7 N-(4-chloro-2-nitro-phenyl)-N'-(3-piperidino-propyl)-oxalamide 
• 107420-28-0 diethyl-(2-chloro-benzyl)-{3-[(3-piperidino-propylaminooxalyl)-amino]-propyl}-ammonium; chloride 
• 111585-13-8 (2-chloro-benzyl)-(3-piperidino-propyl)-amine 
• 107919-00-6 3,4,5-trimethoxy-benzoic acid-(3-piperidino-propylamide) 
• 23061-67-8 N-phenyl-N'-(3-piperidino-propyl)-thiourea 
• 94801-82-8 (3-piperidino-propyl)-veratryl-amine 
• 111584-72-6 (4-chloro-benzyl)-(3-piperidino-propyl)-amine 
• 111163-12-3 4-chloro-2-[(3-piperidino-propylamino)-methyl]-phenol 
• 97753-68-9 (2,4-dichloro-benzyl)-(3-piperidino-propyl)-amine 
• 110051-64-4 3,4,5-trimethoxy-trans-cinnamic acid-(3-piperidino-propylamide) 

Relevant academic research and scientific papers

New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis

Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.

Continuous-Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α-Dideutero Amines

A simple and efficient continuous flow methodology has been developed for hydrogenation and reductive deuteration of nitriles to yield primary amines and also valuable α,α-dideutero analogues. Raney nickel proved to be a useful catalyst for the transformation of a wide range of nitriles under reasonably mild conditions with excellent deuterium incorporation (>90 %) and quantitative conversion. Among known model compounds, three new deuterated primary amines were prepared. The large-scale synthesis of deuterated tryptamine was also carried out to deliver 1.1 g product under flow conditions.

Structure-activity relationship study of hypoxia-activated prodrugs for proteoglycan-targeted chemotherapy in chondrosarcoma

Due to an abundant chondrogenic, poorly vascularized and particularly hypoxic extracellular matrix, chondrosarcoma, a malignant cartilaginous tumour, is chemo- and radio-resistant. Surgical resection with wide margins remains the mainstay of treatment. To address the lack of therapy, our strategy aims to increase anticancer drugs targeting and delivery in the tumour, by leveraging specific chondrosarcoma hallmarks: an extensive cartilaginous extracellular matrix, namely the high negative fixed charge density and severe chronic hypoxia. A dual targeted therapy for chondrosarcoma was investigated by conjugation of a hypoxia-activated prodrug (HAP) to quaternary ammonium (QA) functions which exhibit a high affinity for polyanionic sites of proteoglycans (PGs), the major components of the chondrosarcoma extracellular matrix. Based on preclinical results, an imidazole prodrug, ICF05016, was identified and provided the basis for a lead optimization study. A series of 27 QA-phosphoramide mustard conjugates, differing by the type of QA function and the length of the alkyl linker, was yielded by a common multi-step sequence involving phosphorylation of a key 2-nitroimidazole alcohol. Then, a screening was realized by surface plasmon resonance technology to assess biomolecular interactions between QA derivatives and aggrecan, the most abundant PG in chondrosarcoma. Results revealed that affinity depends more on the type of QA function, than on the linker length. Moreover, the presence of a benzyl group enhanced affinity to aggrecan. Twelve compounds were shortlisted and evaluated for antiproliferative activity (i.e., growth inhibiting concentration 50), under normoxic and hypoxic conditions using the human extraskeletal myeloid chondrosarcoma cell line (HEMC-SS). For all prodrugs, hypoxic selectivity was maintained and even increased, compared with the lead. From this study, compound 31f emerged as the most effective PG-targeted HAPs with a dissociation constant of 2.10 μM in the SPR experiment, a hypoxia cytotoxicity ratio of 24 and an efficient reductive cleavage under chemical and enzymatic conditions.

Synthesis and antitumor activity of 5-bromo-7-azaindolin-2-one derivatives containing a 2,4-dimethyl-1H-pyrrole-3-carboxamide moiety

We report herein the design and synthesis of a series of novel 5-bromo-7-azaindolin-2-one derivatives containing a 2,4-dimethyl-1H-pyrrole-3-carboxamide moiety. These newly synthesized derivatives were evaluated for in vitro activity against selected cancer cell lines by MTT assay. Results revealed that some compounds exhibit broad-spectrum antitumor potency, and the most active compound 23p (IC50: 2.357-3.012 μM) was found more potent than Sunitinib (IC50: 31.594-49.036 μM) against HepG2, A549 and Skov-3, respectively.

OMEGA-AMINOALKYLAMIDES OF (R)-2-ARYL-PROPIONIC ACIDS AS INHIBITORS OF THE CHEMOTAXIS OF POLYMORPHONUCLEATE AND MONONUCLEATE CELLS

no abstract published

STAT3-Hif1α signal pathway inhibitor and its application in anti-tumor

The invention discloses an STAT3-Hif1 alpha signal pathway inhibitor and application in tumor resistance thereof. The structural general formula of the compound is shown as formula I, wherein R1 and R2 are one of amino, alkyl amino of C1-6, aryl of C5-7, heterocyclic aryl of C5-10, and arylamino of C6-10. Specifically, the heterocyclic aryl is one of pyrrolyl, imidazolyl, furyl, thienyl, pyridyl, benzothiophene, benzofuran, indolyl, benzimidazolyl and benzothiazolyl, n is 2 or 3, and X is an oxygen atom. The STAT3-Hif1 alpha signal pathway inhibitor provided by the invention overcomes the problems of current p-STAT3/Hif1 alpha signal pathway inhibitors in the aspects of inhibition efficiency, broad-spectrum, toxicity and the like. The STAT3-Hif1 alpha signal pathway inhibitor provided by the invention can be preferably used as an anticancer drug molecule and for development of related treatment methods. The anticancer drug molecule prepared according to the invention can show the superior performance of high efficiency, low toxicity, simultaneous action on multiple target points, and wide scope of application. (Formula I).

CINNAMIC ACID AMIDE DERIVATIVE

The present invention provides a cinnamic acid amide derivative having an excellent analgesic action. The cinnamic acid amide derivative of the present invention is a compound showing excellent analgesic actions to not only a nociceptive pain model animal but also a neuropathic pain model animal, which is very useful as an agent for treating various pain diseases showing acute or chronic pains or neuropathic pains.

Incorporation of basic side chains into cryptolepine scaffold: Structure-antimalarial activity relationships and mechanistic studies

The synthesis of cryptolepine derivatives containing basic side-chains at the C-11 position and their evaluations for antiplasmodial and cytotoxicity properties are reported. Propyl, butyl, and cycloalkyl diamine side chains significantly increased activity against chloroquine-resistant Plasmodium falciparum strains while reducing cytotoxicity when compared with the parent compound. Localization studies inside parasite blood stages by fluorescence microscopy showed that these derivatives accumulate inside the nucleus, indicating that the incorporation of a basic side chain is not sufficient enough to promote selective accumulation in the acidic digestive vacuole of the parasite. Most of the compounds within this series showed the ability to bind to a double-stranded DNA duplex as well to monomeric hematin, suggesting that these are possible targets associated with the observed antimalarial activity. Overall, these novel cryptolepine analogues with substantially improved antiplasmodial activity and selectivity index provide a promising starting point for development of potent and highly selective agents against drug-resistant malaria parasites.

Solution-phase parallel synthesis of novel membrane-targeted antibiotics

The increase in the incidence of antibiotic-resistant infections is a major concern to healthcare workers and requires the development of novel antibacterial agents. Recently, we described a series of benzophenonecontaining antibiotics which displayed activity against antibiotic-resistant bacteria. We have shown that these agents function by disrupting the bacterial membrane. To further explore these compounds, a practical and efficient solution-phase parallel synthesis method was developed which allowed us to prepare combinatorial libraries of these agents. Using this method, we prepared 218 compounds in 58 reactions. All of the compounds were characterized by HPLC and MALDI-TOF mass spectrometry. Analysis of this library for antibacterial activity identified six compounds which displayed MTC values of 2.0 mg/T. against Staphylococcus aureus. Examination of the structure-function relationships of these agents revealed that cationic groups were required and that cyclic, aliphatic amines were crucial for activity. Using the information generated here, we speculate on how the various structural features of the molecule are necessary for the interaction with the bacterial membrane.

USE OF (R) AND (S)-2-ARYL-PROPIONIC ACID DERIVATIVES AS ANTISEPTIC AGENTS

The present invention relates to the use of amides of (R) and (S)-2-aryl- propionic acids as antiseptic agents. The present invention also provides a pharmaceutical preparation including compounds of formula (I), having antiseptic properties for the treatment of gastrointestinal, muco-epidermal and epidermal infections. The present invention is related to pharmaceutical compositions containing an antiseptic agent carried in a suitable vehicle to provide mouthwashes, tablets, solutions, gels, creams and others. The formulations are applied topically to sites of gastrointestinal, muco-epidermal or epidermal infections. Compounds of present invention can be useful in the treatment of nausea, vomiting, bloating, diarrhea, constipation and oropharyngeal, esophageal, vaginal, rectal, nasal and other mucosal infections.