862686-31-5

Basic information

• Product Name: tert-butyl [(3S)-(4-nitrophenyl)pyrrolidin-3-yl]carbamate
• CAS NO: 862686-31-5
• Molecular Weight: 307.349
• Mol File: 862686-31-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl [(3S)-(4-nitrophenyl)pyrrolidin-3-yl]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl [(3S)-(4-nitrophenyl)pyrrolidin-3-yl]carbamate(862686-31-5)
• EPA Substance Registry System: tert-butyl [(3S)-(4-nitrophenyl)pyrrolidin-3-yl]carbamate(862686-31-5)

Safety Data

• Hazardous Substances Data: 862686-31-5(Hazardous Substances Data)

Upstream product

• 122536-76-9 3(S)-(tert-butoxycarbonylamino)pyrrolidine 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 1232361-11-3 C₂₆H₂₉N₃O₆S 
• 1291057-78-7 1-benzo[b]thiophen-3-yl-3-[1-(4-nitrophenyl)-(S)-pyrrolidin-3-ylamino]propan-1-one 
• 202267-29-6 3(S)-amino-1-(4-nitro)phenylpyrrolidine 

Relevant articles and documents

Synthesis and Structure–Activity Relationship of Thioacetamide-Triazoles against Escherichia coli

Infections due to Gram-negative bacteria are increasingly dangerous due to the spread of multi-drug resistant strains, emphasizing the urgent need for new antibiotics with alternative modes of action. We have previously identified a novel class of antibacterial agents, thioacetamide-triazoles, using an antifolate targeted screen and determined their mode of action which is dependent on activation by cysteine synthase A. Herein, we report a detailed examination of the anti-E. coli structure–activity relationship of the thioacetamide-triazoles. Analogs of the initial hit compounds were synthesized to study the contribution of the aryl, thioacetamide, and triazole sections. A clear structure–activity relationship was observed generating compounds with excellent inhibition values. Substitutions to the aryl ring were generally best tolerated, including the introduction of thiazole and pyridine heteroaryl systems. Substitutions to the central thioacetamide linker section were more nuanced; the introduction of a methyl branch to the thioacetamide linker substantially decreased antibacterial activity, but the isomeric propionamide and N-benzamide systems retained activity. Changes to the triazole portion of the molecule dramatically decreased the antibacterial activity, further indicating that 1,2,3-triazole is critical for potency. From these studies, we have identified new lead compounds with desirable in-vitro ADME properties and in-vivo pharmacokinetic properties.

5-Cyclic amine-3-arylsulfonylindazoles as novel 5-HT6 receptor antagonists

Novel 5-cyclic amine-3-arylsulfonylindazoles were prepared, and several analogues within this class have been identified as high-affinity 5-HT 6 receptor ligands with improved pharmacokinetic and pharmacological properties. One selected example, 18b, showed good brain penetrability and a generally favorable pharmacokinetic profile with procognitive efficacy in the rat novel object recognition assay. The synthesis and structure-activity relationship of this potent class are discussed.