127641-07-0

Usage

Uses

Used in Asymmetric Synthesis:
2,5-Diazabicyclo[2.2.1]heptane,2-(phenylmethyl)-,(1S,4S)-(9CI) is used as a chiral ligand in asymmetric synthesis, enabling the production of enantiomerically pure compounds. Its unique structure and properties make it a valuable tool in the synthesis of chiral molecules, which are essential in pharmaceuticals, agrochemicals, and other industries.
Used in Resolving Racemic Mixtures:
As a resolving agent, 2,5-Diazabicyclo[2.2.1]heptane,2-(phenylmethyl)-,(1S,4S)-(9CI) is employed to separate enantiomers in racemic mixtures. This is crucial for obtaining pure enantiomers, which often exhibit different biological activities and are required for various applications, including drug development and synthesis of chiral compounds.
Used in Chemical Transformations:
2,5-Diazabicyclo[2.2.1]heptane,2-(phenylmethyl)-,(1S,4S)-(9CI) is used to form complexes with metal ions, which can be utilized in different chemical transformations. Its ability to coordinate with metal ions allows for the development of new catalytic systems and the enhancement of existing ones, further expanding its applications in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,5-Diazabicyclo[2.2.1]heptane,2-(phenylmethyl)-,(1S,4S)-(9CI) is used as a chiral ligand for the synthesis of enantiomerically pure drugs. The production of single enantiomers is essential for ensuring the desired therapeutic effects and minimizing potential side effects associated with the presence of both enantiomers.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 2,5-Diazabicyclo[2.2.1]heptane,2-(phenylmethyl)-,(1S,4S)-(9CI) is used for the synthesis of chiral agrochemicals, such as pesticides and herbicides. The ability to produce enantiomerically pure compounds ensures the effectiveness and safety of these products in agricultural applications.

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 
• 100944-15-8 (1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide 
• 2584-71-6 cis-hydroxy-D-proline 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 57850-05-2 (2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine 
• 141850-60-4 (2S,4R)-(1-tosyl-4-(tosyloxy)pyrrolidin-2-yl)methyl 4-methylbenzenesulfonate 
• 114676-59-4 (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride 
• 125109-59-3 (2R,4S)-4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid 
• 116143-08-9 (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine 
• 118354-72-6 (1R,4R)-2-(4-tolylsulfonyl)-5-(phenylmethyl)-2,5-diazabicyclo<2.2.1>heptane 

Downstream Products

• 132666-68-3 (1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane 
• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 848441-96-3 2-[5-benzyl-(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-N-(2,6-dimethylphenyl)acetamide 

Relevant academic research and scientific papers

Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation

The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity

Identification of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamate-nitrostyrene hybrid as potent antiproliferative and apoptotic inducing agent against cervical cancer cell lines

The present study seeks to describe the design and synthesis of six new Michael adducts of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamate with nitrostyrenes and their in vitro antiproliferative activity against human cervical cancer cell lines [HeLa (HPV 18 positive), CaSki (HPV 16 positive) and ViBo (HPV negative) cervical cancer cell lines]. Virtual screening of the physicochemical properties of all compounds have also been presented. All the compounds exploited significant antiproliferative activity on the three cervical cancer cell lines. Compound 8a was found to be most potent, displaying in vitro antiproliferative activity against HeLa, CaSki and ViBo cervical cancer cell lines superior to Cisplatin and Paclitaxel with IC50 values 0.99 ± 0.007, 2.36 ± 0.016 and 0.73 ± 0.002 μM respectively. In addition, compound 8a did not trigger the necrosis cell death to the test cancer cell lines. Further mechanistic study revealed that compound 8a could inhibit the cancer cell proliferation by inducing apoptosis through caspase-3 activation. Moreover, cell cycle analysis indicated that compound 8a could arrest the cell cycle at the G1 phase for HeLa and CaSki cancer cells. At the predetermined IC50 values on cancer cells, compound 8a did not induce any necrotic (cytotoxic) death to the normal human lymphocytes. In the present design, (1S,4S)-2,5-diazabicyclo[2.2.1]heptane system was found to be superior than the piperazine counterpart 11.

Multicomponent synthesis of some new (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamates and their in vitro anti-proliferative activity against CaSki, MDA-MB-231 and SK-Lu-1 tumour cells as apoptosis inducing agents without necrosis

Identification of a new class of antitumor agent capable to induce apoptosis without triggering necrotic cell death event is challenging. The present communication describes the multicomponent synthesis of seven new (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamates and their in vitro antiproliferative activity on cervical cancer cell line (CaSki), breast cancer cell line (MDA-MB231), lung cancer cell line (SK-Lu-1) and human lymphocytes. Among the synthesized dithiocarbamates, compound 9e displayed significant antiproliferative activity without inducing any necrotic cell death (both on tumour cells and lymphocytes) and induced apoptosis in tumor cells by the caspase dependent apoptotic pathway. The compound 9e also exhibited greater tumor selectivity than human lymphocytes. In silico ADME predictions revealed that compound 9e has the potential to be developed as a drug candidate. Rapid chemical modifications of this lead are thus highly necessary for further investigation as a drug like safer antitumor candidate and also to achieve compounds with better activity profile.

Agents for treatment of brain ischemia

A series of 5-halopyrimidin-2-ylpiperazinylalkyl derivatives having useful anti-ischemic properties for treatment and prevention of dirorders resulting from brain and/or spinal cord anoxia.