132666-68-3

Basic information

• Product Name: (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
• Synonyms: (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;(1S,4S)-5-(Phenylmethyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester;2,5-Diazabicyclo[2.2.1]heptane-2-carboxylic acid, 5-(phenylMethyl)-, 1,1-diMethylethyl ester, (1S,4S)-;tert-butyl (1S,4S)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;(1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(WXC05820)
• CAS NO: 132666-68-3
• Molecular Formula: C₁₇H₂₄N₂O₂
• Molecular Weight: 288.38
• Mol File: 132666-68-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 377.392 °C at 760 mmHg
• Flash Point: 182.04 °C
• Appearance: /
• Density: 1.140
• CAS DataBase Reference: (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(132666-68-3)
• EPA Substance Registry System: (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate(132666-68-3)

Safety Data

• Hazardous Substances Data: 132666-68-3(Hazardous Substances Data)

Usage

General Description

The chemical "(1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate" is a compound with a molecular formula of C18H25N2O2. It is a derivative of diazabicyclo[2.2.1]heptane, a bicyclic amine structure. The compound contains a tert-butyl group, a benzyl group, and a carboxylate group, which are all important functional groups in organic chemistry. (1S,4S)-tert-butyl 5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate may have potential applications in medicinal chemistry, as bicyclic amines and their derivatives are known to have various pharmacological activities, including as both ligands for biological receptors and as enzyme inhibitors. Additionally, the tert-butyl and benzyl groups could provide steric hindrance and enhance the compound's lipophilicity, potentially affecting its biological activity.

Upstream product

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• 24424-99-5 di-tert-butyl dicarbonate 
• 127641-07-0 (1S,4S)-N-Benzyl-2,5-diazabicyclo-[2.2.1]heptane 
• 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 
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• 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 

Downstream Products

• 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 
• 5260-20-8 (1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrochloride 

Relevant articles and documents

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.

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.

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.