4858-84-8

Basic information

• Product Name: 1,4-PIPERAZINEDICARBONYL CHLORIDE
• Synonyms: 1,4-PIPERAZINEDICARBONYL CHLORIDE;1,4-piperazinedicarbonyl dichloride
• CAS NO: 4858-84-8
• Molecular Formula: C₆H₈Cl₂N₂O₂
• Molecular Weight: 211.04592
• Mol File: 4858-84-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-PIPERAZINEDICARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-PIPERAZINEDICARBONYL CHLORIDE(4858-84-8)
• EPA Substance Registry System: 1,4-PIPERAZINEDICARBONYL CHLORIDE(4858-84-8)

Safety Data

• Hazardous Substances Data: 4858-84-8(Hazardous Substances Data)

Usage

Functional groups

Piperazine ring, Carbonyl groups, Chloride groups

Appearance

Unknown (not provided in the material)

Physical state

Unknown (not provided in the material)

Reactivity

Reacts with amines and other nucleophiles

Organic synthesis

Introduces piperazine ring structures into molecules

Medicinal chemistry

Versatile building block for producing pharmaceuticals and drugs

Synthesis of peptides

Used in the synthesis of complex organic molecules

Drug development

Important tool in chemical research and development of new medications

Safety

Unknown (not provided in the material, but generally, chemical safety should be considered when handling)

Upstream product

• 110-85-0 piperazine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 
• 108-88-3 toluene 
• 71-43-2 benzene 

Downstream Products

• 6511-92-8 bis(4-nitrophenyl) piperazine-1,4-dicarboxylate 
• 2897-59-8 1,4-bis-(aziridine-1-carbonyl)-piperazine 
• 117688-87-6 Piperazine-1,4-dicarboxylic acid bis-(cyclohexyl-{[(E)-cyclohexylimino]-morpholin-4-yl-methyl}-amide) 

Relevant articles and documents

Prodrugs for nitroreductase based cancer therapy-4: Towards prostate cancer targeting: Synthesis of N-heterocyclic nitro prodrugs, Ssap-NtrB enzymatic activation and anticancer evaluation

In this study, various N-heterocyclic nitro prodrugs (NHN1-16) containing pyrimidine, triazine and piperazine rings were designed and synthesized. The final compounds were identified using FT-IR, 1H NMR, 13C NMR as well as elemental analyses. Enzymatic activities of compounds were conducted by using HPLC analysis to investigate the interaction of substrates with Ssap-NtrB nitroreductase enzyme. MTT assay was performed to evaluate the toxic effect of compounds against Hep3B and PC3 cancer cell lines and healthy HUVEC cell. It was observed that synthesized compounds NHN1-16 exhibited different cytotoxic profiles. Pyrimidine derivative NHN3 and triazine derivative NHN5 can be good drug candidates for prostate cancer with IC50 values of 54.75 μM and 48.9 μM, respectively. Compounds NHN6, NHN10, NHN12, NHN14 and NHN16 were selected as prodrug candidates because of non-toxic properties against three different cell models. The NHN prodrugs and Ssap-NtrB combinations were applied to SRB assay to reveal the prodrug capabilities of these selected compounds. SRB screening results showed that the metabolites of all selected non-toxic compounds showed remarkable cytotoxicity with IC50 values in the range of 1.71–4.72 nM on prostate cancer. Among the tested compounds, especially piperazine derivatives NHN12 and NHN14 showed significant toxic effect with IC50 values of 1.75 nM and 1.79 nM against PC3 cell compared with standart prodrug CB1954 (IC50: 1.71 nM). Novel compounds NHN12 and NHN14 can be considered as promising prodrug candidates for nitroreductase-prodrug based prostate cancer therapy.

Synthesis of acylguanidine analogues: inhibitors of ADP-induced platelet aggregation

Routine screening of compounds for inhibition of ADP-induced platelet aggregation in vitro revealed that 1'-hexamethylenebis[3-cyclohexyl-3-[(cyclohexylimino)(4-morpholinyl)methyl] urea] was active and represented the first example of a bis(acylguanidine) with possible antithrombotic activity. In order to develop a structure-activity relationship for this class of compounds, we synthesized a number of new bis(acylguanidines). These were tested in vitro, and several analogues were also active. Ex vivo testing revealed that compounds 22, 41, 58, and 70-73 were orally active in rats or guinea pigs.