849928-22-9

Basic information

• Product Name: 4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN
• Synonyms: N-Boc-spiro[2H-1-benzopyran-2,4'-piperidine]4(3H)-one;Spiro[2H-1-benzopyran-2,4'-piperidine]-1'-carboxylic acid, 3,4-dihydro-4-oxo-, 1,1-diMethylethyl ester;4-Oxo-2-spiro(N-Boc-piperidin-4-yl)-benzopyran;tert-butyl 4-oxospiro[chromane-2,4'-piperidine]-1'-carboxylate;4-Oxo-2-spiro(N-Boc-piperidine-4-yl)benzopyran - O6086
• CAS NO: 849928-22-9
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.383
• Mol File: 849928-22-9.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 456.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -0.88±0.20(Predicted)
• CAS DataBase Reference: 4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN(849928-22-9)
• EPA Substance Registry System: 4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN(849928-22-9)

Safety Data

• Hazardous Substances Data: 849928-22-9(Hazardous Substances Data)

Usage

General Description

4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN, also known as BOC-piperidin-4-one-2-spiro-3'-(9H-xanthene)-3,4-(1H,5H)-dione, is a chemical compound that belongs to the family of benzopyrans. It contains a spiro moiety and a piperidine ring that is protected by a BOC (tert-butyloxycarbonyl) group. 4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN has potential applications in medicinal chemistry and drug development due to its unique structural features and potential biological activities. Additionally, the spirocyclic structure of 4-OXO-2-SPIRO(N-BOC-PIPERIDINE-4-YL)-BENZOPYRAN confers it with interesting physicochemical properties, making it a valuable building block for the synthesis of novel pharmaceutical compounds.

Upstream product

• 119-61-9 benzophenone 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 118-93-4 o-hydroxyacetophenone 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 136081-84-0 spiro[chroman-2,4'-piperidin]-4-one 
• 911228-63-2 tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 1160247-75-5 1'-(tert-butoxycarbonyl)spiro[chromene-2,4'-piperidine]-4-carboxylic acid 
• 1394028-93-3 (3,4-dimethoxyphenyl)-(4-phenylspiro[chromane-2,4'-piperidine]-1'-yl)methanone 
• 1394031-01-6 (3,4-dimethoxyphenyl)-(4-phenylspiro[chromene-2,4'-piperidine]-1'-yl)methanone 
• 1394031-00-5 4-phenylspiro[chromene-2,4'-piperidine] hydrochloride 
• 1013335-23-3 tert-butyl 4-phenylspiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 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 

Relevant articles and documents

Spirocyclic sulfonamides with carbonic anhydrase inhibitory and anti-neuropathic pain activity

A novel series of 4-oxo-spirochromane bearing primary sulfonamide group were synthetized as Carbonic Anhydrase inhibitors (CAIs) and tested for their management of neuropathic pain. Indeed, CAs have been recently validated as novel therapeutic targets in neuropathic pain. All compounds, here reported, showed strong activity against hCA II and hCA VII with KI values in the low or sub-nanomolar range. Two compounds (6d and 6l) showed good neuropathic pain attenuating effects and longer duration than drug reference acetazolamide in an animal model of oxaliplatin induced neuropathy.

From PARP1 to TNKS2 inhibition: A structure-based approach

Tankyrases (TNKSs) have recently gained great consideration as potential targets in Wnt/β-catenin pathway-dependent solid tumors. Previously, we reported the 2-mercaptoquinazolin-4-one MC2050 as a micromolar PARP1 inhibitor. Here we show how the resolution of the X-ray structure of PARP1 in complex with MC2050, combined with the computational investigation of the structural differences between TNKSs and PARP1/2 active sites, provided the rationale for a structure-based drug design campaign that with a limited synthetic effort led to the discovery of the bis-quinazolinone 5 as a picomolar and selective TNKS2 inhibitor, endowed with antiproliferative effects in a colorectal cancer cell line (DLD-1) where the Wnt pathway is constitutively activated.

Design, Synthesis, and Structure-Activity Relationship of Novel Spiropyrimidinamines as Fungicides against Pseudoperonospora cubensis

Harmful fungus and the developed resistance to available fungicides seriously threaten the yield and quality of crops; thus, the search for new, highly efficient, and resistance-overcoming fungicides remains a quite urgent goal of agricultural scientists. In this study, a series of novel spiropyrimidinamine derivatives were designed and synthesized by employing the intermediate derivatization method (IDM). Their structures were identified by 1H NMR, elemental analyses, and MS spectra. The structure of compound 5 was further confirmed by X-ray diffraction. Bioassays indicated that a number of the title compounds exhibited some fungicidal activities against Pseudoperonospora cubensis. Especially, compound 5 displayed excellent activity (EC50 = 0.422 mg/L), significantly higher than those of the commercialized fungicides cyazofamid, flumorph, and diflumetorim. The structure-activity relationship was also discussed. It was concluded that compound 5 with super fungicidal potency and a novel structure is a promising agrochemical fungicide candidate for further development.