1160247-75-5

Basic information

• Product Name: 1'-(TERT-BUTOXYCARBONYL)SPIRO[CHROMENE-2,4'-PIPERIDINE]-4-CARBOXYLIC ACID
• Synonyms: 1'-(TERT-BUTOXYCARBONYL)SPIRO[CHROMENE-2,4'-PIPERIDINE]-4-CARBOXYLIC ACID;Spiro[2H-1-benzopyran-2,4'-piperidine]-1',4-dicarboxylic acid, 1'-(1,1-diMethylethyl) ester;spiro[chromene-2,4'-piperidine]-4-carboxylic acid;1-(Tert-Butoxycarbonyl)Spiro[Chromene-2,4-Piperidine]-4-Carboxylic Acid(WX105092)
• CAS NO: 1160247-75-5
• Molecular Formula: C19H23NO5
• Molecular Weight: 345.38962
• Mol File: 1160247-75-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1'-(TERT-BUTOXYCARBONYL)SPIRO[CHROMENE-2,4'-PIPERIDINE]-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1'-(TERT-BUTOXYCARBONYL)SPIRO[CHROMENE-2,4'-PIPERIDINE]-4-CARBOXYLIC ACID(1160247-75-5)
• EPA Substance Registry System: 1'-(TERT-BUTOXYCARBONYL)SPIRO[CHROMENE-2,4'-PIPERIDINE]-4-CARBOXYLIC ACID(1160247-75-5)

Safety Data

• Hazardous Substances Data: 1160247-75-5(Hazardous Substances Data)

Usage

General Description

1'-(tert-butoxycarbonyl)spiro[chromene-2,4'-piperidine]-4-carboxylic acid is a chemical compound with a spirocyclic structure containing a chromene and piperidine moiety. It is often used as a building block in the synthesis of various pharmaceuticals and biologically active molecules. The tert-butoxycarbonyl (Boc) group acts as a protecting group for the amine functionality in organic synthesis, allowing for selective reactions to occur. The carboxylic acid group provides an opportunity for further functionalization or conjugation with other molecules. 1'-(tert-butoxycarbonyl)spiro[chromene-2,4'-piperidine]-4-carboxylic acid is of interest in drug discovery and chemical biology due to its potential as a versatile intermediate for the synthesis of diverse chemical entities with biological activities.

Upstream product

• 1207163-67-4 tert-butyl 1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 1024604-94-1 tert-butyl 4-hydroxy-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 849928-22-9 tert-butyl 4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
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Relevant articles and documents

Whole cell screen based identification of spiropiperidines with potent antitubercular properties

Abstract Whole cell based screens to identify hits against Mycobacterium tuberculosis (Mtb), carried out under replicating and non-replicating (NRP) conditions, resulted in the identification of multiple, novel but structurally related spiropiperidines with potent antitubercular properties. These compounds could be further classified into three classes namely 3-(3-aryl-1,2,4-oxadiazol-5-yl)-1′-alkylspiro[indene-1,4′-piperidine] (abbr. spiroindenes), 4-(3-aryl-1,2,4-oxadiazol-5-yl)-1′-alkylspiro[chromene-2,4′-piperidine] (abbr. spirochromenes) and 1′-benzylspiro[indole-1,4′-piperidin]-2(1H)-one (abbr. spiroindolones). Spiroindenes showed ≥4 log10 kill (at 2-12 μM) on replicating Mtb, but were moderately active under non replicating conditions. Whole genome sequencing efforts of spiroindene resistant mutants resulted in the identification of I292L mutation in MmpL3 (Mycobacterial membrane protein Large), required for the assembly of mycolic acid into the cell wall core of Mtb. MIC modulation studies demonstrated that the mutants were cross-resistant to spirochromenes but not to spiroindolones. This Letter describes lead identification efforts to improve potency while reducing the lipophilicity and hERG liabilities of spiroindenes. Additionally, as deduced from the SAR studies, we provide insights regarding the new chemical opportunities that the spiroindolones can offer to the TB drug discovery initiatives.