103816-19-9

Basic information

• Product Name: 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE
• Synonyms: 1-CHLOROCARBONYL-4-PIPERIDINOPERIDINE;forMyl[4-(piperidin-1-yl)piperidin-1-yl]chloranuide;4-Piperidinopiperidine-1-carbonyl chloride;4-Piperidinopiperidine-1-carbonyl chloride
• CAS NO: 103816-19-9
• Molecular Formula: C₁₁H₁₉ClN₂O
• Molecular Weight: 230.73
• EINECS: 1592732-453-0
• Mol File: 103816-19-9.mol

Chemical Properties

• Melting Point: 60-64°C
• Boiling Point: 344.5±31.0 °C(Predicted)
• Appearance: /
• Density: 1.184±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.19±0.20(Predicted)
• CAS DataBase Reference: 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE(103816-19-9)
• EPA Substance Registry System: 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE(103816-19-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 103816-19-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE is used as a reactant for the synthesis of various pharmaceutical compounds, including:
1. Macrocyclic ureas as selective Chk1 inhibitors: These inhibitors play a crucial role in the regulation of cell cycle checkpoints, particularly in the context of cancer therapy. By targeting Chk1, these macrocyclic ureas can help in the development of novel anticancer drugs.
2. Etoposide prodrug for dual prodrug-enzyme antitumor therapy: Etoposide is a widely used chemotherapeutic agent. The development of a prodrug version with 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE can enhance the drug's selectivity and efficacy, making it a valuable addition to cancer treatment strategies.
3. Phosphodiesterase 4 (PDE4) inhibitors: PDE4 inhibitors are known for their anti-inflammatory and immunomodulatory properties. They are being investigated for the treatment of various conditions, including chronic obstructive pulmonary disease (COPD), asthma, and inflammatory bowel disease (IBD). 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE can be used as a reactant in the synthesis of these inhibitors, potentially leading to the development of new therapeutic agents.
4. Camptothecin analogs: Camptothecin is a potent anticancer alkaloid that has been used in the development of several chemotherapy drugs. The synthesis of camptothecin analogs using 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE can result in the creation of novel compounds with improved pharmacological properties and reduced side effects.

Upstream product

• 4897-50-1 4-piperidinopiperidin 
• 503-38-8 trichloromethyl chloroformate 
• 143254-82-4 4-piperidinopiperidine-1-carbonyl chloride hydrochloride 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 1181081-94-6 2-{[(5Z)-2-(1,2-diazinan-1-yl)-4-sulfanylidene-4,5-dihydro-1,3-thiazol-5-ylidene]methyl}-5-fluorophenyl 4-(piperidin-1-yl)piperidine-1-carboxylate 
• 100286-90-6 irinotecan hydrochloirde 
• 136572-09-3 irinotecan hydrochloride trihydrate 
• 103816-16-6 10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin 
• 1309982-12-4 23-(1,4'-bipiperidine-1-carbonyloxy)betulinic acid 

Relevant articles and documents

Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities

Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.

Dopamine D5 receptor agonists as well as preparation and application thereof

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PODOPHYLLOTOXIN DERIVATIVES AND THEIR USE

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COMPOUNDS FOR INHIBITING CANCER AND VIRUS

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Design, synthesis and anti-inflammatory effects of novel 9-O-substituted-berberine derivatives

Berberine, an isoquinoline alkaloid in many medicinal herbs, has been found to possess broad pharmacological activities. A series of novel C-9-O-substituted-berberine derivatives have been synthesized and their anti-inflammatory effects evaluated both in vitro and in vivo. Compared to berberine, the new synthetic berberine derivatives 3i and 5e exhibit significantly improved inhibitory activities against the release of NO, TNF-α and IL-6. Furthermore, derivatives 3i and 5e were found to inhibit more effectively the migration of neutrophils and primitive macrophage in transgenic zebrafish larvae with injury-provoked inflammation. Pre-treatment with derivatives 3i or 5e could lead to a concentration-dependent decrease in nuclear factor-κB (NF-κB) p65 and NF-κB inhibitor α (IκBα) phosphorylation and inducible nitric oxide synthase (iNOS) expression in lipopolysaccharide (LPS)-induced RAW264.7 cells, which suggested that the anti-inflammatory activities of berberine derivatives 3i and 5e are related to their suppression of the NF-κB signal pathway.

PROCESS FOR THE PREPARATION OF 7-ETHYL-10-[4- (1-PIPERIDINO)- 1-PIPERIDINO] CARBONYLOXY-CAMPTOTHECIN HYDROCHLORIDE TRIHYDRATE

The present invention relates to process for the preparation of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothecin hydrochloride trihydrate and process for the isolation of 1-chlorocarbonyl-4-piperidinopiperidine and novel crystalline form of 1-chlorocarbonyl-4-piperidinopiperidine and 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothecin.

Process for the preparation of 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxy-camptothecin hydrochloride trihydrate

The present invention relates to process for the preparation of 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxy-camptothecin hydrochloride trihydrate and process for the isolation of 1-chlorocarbonyl-4-piperidinopiperidine and novel crystalline form of 1-chlorocarbonyl-4-piperidinopiperidine and 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxy-camptothecin.

Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives

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