1440-60-4

Usage

Uses

Used in Scientific Research:
2-Chloro-1-Piperidin-1-yl-Ethanone is used as a synthetic intermediate for the preparation of various chemical compounds. Its presence in the structure allows for the creation of a wide range of derivatives, making it a valuable asset in the field of chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-1-Piperidin-1-yl-Ethanone is used as a building block for the development of new drugs. The piperidine ring is a common structural element in many medications, and 2-CHLORO-1-PIPERIDIN-1-YL-ETHANONE's unique features can contribute to the design of novel therapeutic agents.
Used in Chemical Synthesis:
2-Chloro-1-Piperidin-1-yl-Ethanone is employed as a reagent in chemical synthesis processes. Its versatility in forming different chemical bonds and its compatibility with various reaction conditions make it a useful component in the synthesis of complex molecules.

InChI:InChI=1/C7H12ClNO/c8-6-7(10)9-4-2-1-3-5-9/h1-6H2

Upstream product

• 110-89-4 piperidine 
• 79-04-9 chloroacetyl chloride 
• 79-11-8 chloroacetic acid 
• 22118-09-8 2-bromoacetyl chloride 
• 1796-25-4 1-(2-bromoacetyl)piperidine 

Downstream Products

• 101997-49-3 1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-piperidine 
• 15029-30-8 1-cyanoacetylpiperidine 
• 112577-29-4 (4-nitro-benzyl)-(2-oxo-2-piperidino-ethyl)-dipropyl-ammonium; bromide 
• 92032-55-8 1-(N-phenyl-glycyl)-piperidine 
• 92698-91-4 1-[N-(2,6-dimethyl-phenyl)-glycyl]-piperidine 
• 98840-89-2 1-(N-methyl-N-phenyl-glycyl)-piperidine 
• 100875-44-3 1-(N-benzyl-glycyl)-piperidine 
• 34023-69-3 Iodacetopiperidid 
• 52121-08-1 1-[(2-ethylcarbamoylimino-5-nitro-thiazol-3-yl)-acetyl]-piperidine 
• 63238-11-9 4-Amino-2-methylthio-5-thiazol-(N,N-pentamethylencarboxamid) 
• 63238-12-0 4-Amino-2-ethylthio-5-thiazol-(N,N-pentamethylencarboxamid) 
• 63238-13-1 4-Amino-2-benzylthio-5-thiazol-(N,N-pentamethylencarboxamid) 
• 59716-73-3 S-(4,5-Diphenyloxazol-2-yl)-mercaptoacetpiperidid 
• 116078-71-8 (+/-)-1-<5--3-(2-chlorophenyl)-3-cyano-1-oxopentyl>piperidine 

Relevant academic research and scientific papers

Synthesis, Evaluation and Molecular Docking of Thiazolopyrimidine Derivatives as Dipeptidyl Peptidase IV Inhibitors

A series of thiazolopyrimidine derivatives was designed, synthesized and screened for in-vitro inhibition of Dipeptidyl Peptidase IV (DPP IV). The SAR study indicated the influence of substituted chemical modifications on thiazolopyrimidine scaffold. Comp

Conventional and microwave-assisted synthesis of new 1H-benzimidazole-thiazolidinedione derivatives: A potential anticancer scaffold

A series of new benzimidazole bearing thiazolidinedione derivatives has been designed, synthesized by using conventional as well as microwave-assisted methods. Microwave-assisted synthesis caused a significant reduction in the reaction times and improvement in the yields of all the derivatives. All the new synthesized compounds were evaluated for their in vitro cytotoxic potential against selected human cancer cell lines of breast (MDAMB-231), prostate (PC-3), cervical (HeLa), lung (A549) and bone (HT1080) along with a normal kidney cells (HeK-293T). The compounds 17n, 17p and 17q were found to be potent cytotoxic with IC50 values in the range of 0.096–0.63 μM on PC-3, HeLa, A549 and HT1080 cancer cells. Most of the compounds have found to be safe on normal HeK-293T kidney cells in comparison to cancer cells. The treatment of cells with 17p and 17q showed the typical apoptotic morphological features like fragmentation and shrinkage of nuclei. Further, test compounds resulted in inhibition of cell migration through disruption of F-actin protein assembly. Hoechst, DCFH-DA staining, mitochondrial membrane and annexin binding assays revealed that the cancer cell proliferation was inhibited through induction of apoptosis in A549 cells.

A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction

A xanthate-based oxidative radical process for the direct alkylation of the coumarin ring system is presented. In the reaction, a vinylic and unactivated C-H bond of the coumarin system is replaced by an α-acyl functionality under neutral conditions. This reaction has a high reaction site selectivity, which can realize alkylation at the C-3 position. A vinylic and unactivated C-H bond of the coumarin system is replaced by an alkyl functionality trough a xanthate-based radical reaction (DLP = dilauroyl peroxide).

Synthesis of 3-(aminooxoethyl)-6-methyl-1-(thiethan-3-yl)-pyrimidine-2,4-(1H,3H)-diones

A new approach to prepare 2-chloroacetamides has been developed, based on the reaction of chloroacetyl chloride with excess of secondary amines. Alkylation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione with the synthesized 2-chloroacetamides in the presence of potassium carbonate has afforded N 3-acetamido-substituted 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-diones.

Asymmetric synthesis of pochonin e and F, revision of their proposed structure, and their conversion to potent Hsp90 inhibitors

A concise and modular synthesis of pochonin E and F, and their epimers at C-6 established the correct stereochemistry of these two natural products. Several members of the pochonin family have been shown to bind the heat shock protein 90 (Hsp90), which has been the focus of intense drug discovery efforts. Pochonin E and F as well as their epimers were derivatized into the corresponding pochoximes and further modified at the C-6 position. Molecular dynamics simulations, docking studies, and Hsp90 affinity measurements were performed to evaluate the impact of these modifications.

Design, synthesis, and biological evaluation of 2,6,7-substituted pyrrolo[2,3-d]pyrimidines as cyclin dependent kinase inhibitor in pancreatic cancer cells

Pancreatic cancer is a highly malignant tumor, and more effective treatment is urgently needed to lengthen the life of patients. In this paper a class of new 2,6,7-substituted pyrrolo[2,3-d]pyrimidine derivatives of CDK 4/6 inhibitor ribociclib (1) was de

Structure–activity relationship investigation of coumarin–chalcone hybrids with diverse side-chains as acetylcholinesterase and butyrylcholinesterase inhibitors

Chalcones containing tertiary amine side-chains have potent activity as acetylcholinesterase (AChE) inhibitors. However, the effects of the location of the tertiary amine groups as well as of other groups on AChE and butyrylcholinesterase (BChE) activity have not been reported. Here, we report the synthesis and testing of 36 new coumarin–chalcone hybrids (5d–7j, 9d–11f, 12k–13m) against AChE and BChE. The nature and position of the chalcone substituents had major effects on inhibitory activity as well as selectivity for AChE over BChE. Compounds with para-substituted chalcone fragments in which the substituents were choline-like had potent activity against AChE and poor activity against BChE, while ortho-substituted analogs exhibited an opposite effect. Replacement of the terminal amine groups by amide, alkyl or alkenyl groups abrogated activity. Compound 5e showed potent inhibitory activity (IC50=0.15±0.01μmol/L) and good selectivity for AChE over BChE (ratio 27.4), and a kinetic study showed that 5e exhibited mixed-type inhibition against AChE. Computational docking results indicate that 5e binds to Trp 279, Tyr334 and Trp 84 in AChE, but only to Trp 82 in BChE. Overall, the results show that coumarin–chalcone hybrids with choline-like side-chains have promising activity and selectivity against AChE and be promising therapeutic leads for Alzheimer’s disease.

Design and Synthesis of New Aryloxy-linked Dimeric 1,2,3-Triazoles via Click Chemistry Approach: Biological Evaluation and Molecular Docking Study

A quest for more potent new antitubercular agents has prompted to design and synthesize aryloxy-linked dimeric 1,2,3-triazoles (4a–j), from azides (2a-e) and bis(prop-2-yn-1-yloxy)benzene (3a–b) on 1,3-dipolar cycloaddition reaction via copper (I)-catalyzed click chemistry approach with good to better yields. The titled compounds (4a–j) were designed using molecular hybridization approach by assembling various bioactive pharmacophoric fragments in a single molecular framework. All the synthesized compounds have been screened for their in vitro antitubercular, antifungal, and antioxidant activities against their respective strains. Among them, 4h and 4i show the highest antifungal activity, whereas compounds 4h, 4i, and 4j have revealed promising antitubercular activity against their respective strains. In addition to this, most of the synthesized compounds were found as potent antifungal and antioxidant agents. A significant network of bonded and non-bonded interactions stabilized these molecules into the active site of fungal CYP51 that is realized from the obtained well-placed docking poses and the associated thermodynamic interactions with the enzyme. The synthesized compounds have also been analyzed for absorption, distribution, metabolism, and excretion properties.

Synthesis, evaluation and molecular docking of prolyl-fluoropyrrolidine derivatives as dipeptidyl peptidase IV inhibitors

A series of prolyl-fluoropyrrolidine derivatives were designed, synthesized and screened for in vitro inhibition of dipeptidyl peptidase IV. The SAR study revealed the influence of substituted chemical modifications on dipeptidyl peptidase IV inhibitory activity. Among all the compounds screened, compound 9 (IC50 = 0.83 μm) and 10 (IC50 = 0.43 μm) possessing aryl substituted piperazine with acetamide linker resulted as most potent dipeptidyl peptidase IV inhibitors. Both the compounds 9 and 10 resulted significant reduction in glucose excursion during oral glucose tolerance test in streptozotocin-induced diabetic rat model at single dose of 10 mg/kg. Molecular docking studies were performed to illustrate the probable binding mode and interactions of prolyl-fluoropyrrolidine nucleus and its derivatives at binding site of receptor. The fluoropyrrolidine moiety of prolyl-fluoropyrrolidine derivatives occupied S1 pocket as observed in the crystal structure (PDB id: 2FJP). The compounds 9 and 10 were observed to occupy S2 binding pocket and were observed to have interaction with Arg125, Tyr547 and Ser630 acquired through hydrogen bond. The aryl moiety at piperazine ring was found to extend into the cavity and interacted with Arg358. The observed interactions signalled that occupancy of the highly hydrophobic S2 pocket is very crucial for dipeptidyl peptidase IV inhibitory activity. A series of prolyl-fluoropyrrolidine derivatives were synthesized and evaluated for inhibition of dipeptidyl peptidase IV (DPP IV) for treatment of Type 2 diabetes. The binding position of docked compounds (stick rendering) in the binding pocket of DPP IV.

Access to newly functionalized imidazole derivatives: Efficient synthesis of novel 5-amino-2-thioimidazoles using propylphosphonic anhydride (T3P)

We describe here an efficient method to synthesize 5-amino-2-thioimidazole compounds by T3P-mediated cyclization of N-acetamidoisothiourea intermediates. The newly functionalized 5-amino-2-thioimidazole compounds are finally obtained in 5 steps from an amine as starting block.