2096992-22-0

Basic information

• Product Name: tert-butyl(3-(cyanomethyl)bicyclo[1.1.1]pentan-1-yl)carbamate
• CAS NO: 2096992-22-0
• Molecular Weight: 222.28
• Mol File: 2096992-22-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: tert-butyl(3-(cyanomethyl)bicyclo[1.1.1]pentan-1-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl(3-(cyanomethyl)bicyclo[1.1.1]pentan-1-yl)carbamate(2096992-22-0)
• EPA Substance Registry System: tert-butyl(3-(cyanomethyl)bicyclo[1.1.1]pentan-1-yl)carbamate(2096992-22-0)

Safety Data

• Hazardous Substances Data: 2096992-22-0(Hazardous Substances Data)

Upstream product

• 83249-10-9 3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid 
• 773837-37-9 sodium cyanide 
• 1638765-26-0 (3-(hydroxymethyl)bicyclo[1.1.1]pent-1-yl)carbamic acid tert-butyl ester 
• 5399-02-0 heptadecanenitrile 
• 676371-64-5 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid methyl ester 
• 10442-39-4 tetra-n-butylammonium cyanide 

Relevant articles and documents

Discovery of Potent and Orally Available Bicyclo[1.1.1]pentane-Derived Indoleamine-2,3-dioxygenase 1 (IDO1) Inhibitors

Indoleamine-2,3-dioxygenase 1 (IDO1) inhibition and its combination with immune checkpoint inhibitors like pembrolizumab have drawn considerable attention from both academia and the pharmaceutical industry. Here, we describe the discovery of a novel class of highly potent IDO1 heme-displacing inhibitors featuring a unique bicyclo[1.1.1]pentane motif. Compound 1, evolving from an ALIS (automated ligand identification system) hit, exhibited excellent potency but lacked the desired pharmacokinetic profile due to extensive amide hydrolysis of the benzamide moiety. Replacing the central phenyl ring in 1 with a bicyclo[1.1.1]pentane bioisostere effectively circumvented the amide hydrolysis issue, resulting in the discovery of compound 2 with a favorable overall profile such as excellent potency, selectivity, pharmacokinetics, and a low predicted human dose.

NOVEL [1.1.1] BICYCLO COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE INHIBITORS

Disclosed herein are compounds of formula (I) which are inhibitors of an IDO enzyme: (I). Also disclosed herein are uses of the compounds in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising these compounds. Further disclosed herein are uses of the compositions in the potential treatment or prevention of an IDO-associated disease or disorder.

BICYCLIC COMPOUNDS AND THEIR USE IN THE TREATMENT OF CANCER

The present disclosure is directed to novel compounds of Formula I and pharmaceutically acceptable salts, solvates, solvates of the salt and prodrugs thereof, useful in the prevention (e.g., delaying the onset of or reducing the risk of developing) and treatment (e.g., controlling, alleviating, or slowing the progression of) of cancer, including glioblastoma, bone cancer, head and neck cancer, melanoma, basal cell carcinoma, squamous cell carcinoma, adenocarcinoma, oral cancer, esophageal cancer, gastric cancer, intestinal cancer, colon cancer, bladder cancer, hepatocellular carcinoma, renal cell carcinoma, pancreatic cancer, ovarian cancer, cervical cancer, lung cancer, breast cancer, and prostate cancer. The compounds of the disclosure are selective antagonists of the EP4 receptor and useful treatment of various diseases that may be ameliorated with blockade of PGE2-mediated signaling.