132666-68-3

Usage

Uses

Used in Medicinal Chemistry:
(1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is used as a potential ligand for biological receptors or as an enzyme inhibitor in medicinal chemistry. Its bicyclic amine structure and functional groups may contribute to its pharmacological activities.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is used as a starting material or intermediate in the synthesis of various drug candidates. The steric hindrance provided by the tert-butyl and benzyl groups, along with the compound's lipophilicity, may influence its biological activity and make it a promising candidate for drug development.
Used in Drug Design:
(1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate is used as a structural motif in drug design to explore its potential as a therapeutic agent. Its unique structure and functional groups may offer new opportunities for the development of novel drugs with improved efficacy and selectivity.

Upstream product

• 61478-27-1 (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine 
• 62-53-3 aniline 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 100-39-0 benzyl bromide 
• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 100944-15-8 (1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 127641-07-0 (1S,4S)-N-Benzyl-2,5-diazabicyclo-[2.2.1]heptane 
• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 51-35-4 4R-4-hydroxyproline 
• 100-46-9 benzylamine 
• 133628-17-8 (2S,4R)-4-(methanesulfonyloxy)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 5260-20-8 (1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrochloride 
• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 1217827-86-5 (1S,4S)-2-benzyl-2,5-diazabicyclo[2.2.1]heptane hydrochloride 

Relevant academic research and scientific papers

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

The present invention provides compounds of formula (I): wherein all of the variables are as defined herein. These compounds are inhibitors of indoleamine 2,3-dioxygenase (IDO), which may be used as medicaments for the treatment of proliferative disorders, such as cancer, viral infections and/or autoimmune diseases.

Method for preparing (1S, 4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

The invention discloses a method for preparing (1S, 4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane. The method comprises the following steps: (1) preparing an intermediate I by using N-Boc-trans-4-hydroxy-L-proline methyl ester as a raw material; (2) preparing an intermediate II by reacting the intermediate I with an organic base and a sulfonylating reagent; (3) preparing an intermediate III from the intermediate II and benzylamine; and (4) finally preparing (1S, 4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane by debenzylating the intermediate III. The method provided by the invention simplifies reaction steps, reduces raw material cost and time cost, has high product yield, tends to purify and amplify production, and can reduce waste discharge.

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.

A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane

The rigid piperazine homologue 2,5-diazabicyclo[2.2.1]heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route features a Staudinger reduction of an azide to facilitate a transannular cyclisation.

The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents

A series of non-basic building blocks was synthesized and introduced to the C7 position of the quinolone nucleus 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid to afford the corresponding fluoroquinolones in 46-85% yield. The antibacterial activity of these new fluoroquinolones was evaluated using a standard broth microdilution technique. The sulfur-containing quinolone, 7-(2-thia-5-azabicyclo[2.2.1]heptan-5-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid exhibited a superior antibacterial activity against quinolone-susceptible and multidrug-resistant strains in comparison with the clinically used fluoroquinolones ciprofloxacin and vancomycin, especially to the Streptococcus pneumonia and multidrug-resistant S. pneumonia clinical isolates. Crown Copyright

Synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes

A new method is proposed for the synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes from 1-(tertbutoxycarbonyl)-4-tosyloxy-2-(tosyloxymethyl)pyrrolidine. 1H NMR spectroscopy indicated multiple conformations of 2-(tert-butoxycarbonyl)-2,5-

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.