183673-66-7

Basic information

• Product Name: 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
• Synonyms: 1-(TERT-BUTOXYCARBONYL)-4-([(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO)PIPERIDINE-4-CARBOXYLIC ACID;1-(TERT-BUTOXYCARBONYL)-4-FLUORENYLMETHOXYCARBONYLAMINOPIPERIDINE-4-CARBOXYLIC ACID;1-N-BOC-4-N-FMOC-AMINO-4-CARBOXYLIC-PIPERIDINE;1-N-BOC-4-N-FMOC-AMINOPIPERIDINE-4-CARBOXYLIC ACID;1-BOC-4-FMOC-PIP-OH;1-BOC-4-(FMOC-AMINO)-PIPERIDINE-4-CARBOXYLIC ACID;1-BOC-PIPERIDINE-4-FMOC-AMINO-4-CARBOXYLIC ACID;4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
• CAS NO: 183673-66-7
• Molecular Formula: C₂₆H₃₀N₂O₆
• Molecular Weight: 466.53
• Product Categories: amino acids;FMOC;Amino Acid Derivatives;Others;Peptide Synthesis;Unnatural Amino Acid Derivatives;Amino Acids & Derivatives;Heterocycles
• Mol File: 183673-66-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 80-82 °C
• Boiling Point: 569.36°C (rough estimate)
• Flash Point: 351.6 °C
• Appearance: white to cream crystalline powder or chunks
• Density: 1.2464 (rough estimate)
• Vapor Pressure: 3.37E-18mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.80±0.20(Predicted)
• CAS DataBase Reference: 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER(183673-66-7)
• EPA Substance Registry System: 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER(183673-66-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 183673-66-7(Hazardous Substances Data)

Usage

Description

4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER is a complex organic compound with a chemical structure that features a fluorenylmethoxycarbonylamino group attached to a piperidine core, which is further connected to a dicarboxylic acid moiety. This molecule is esterified with a tert-butyl group, which may contribute to its stability and reactivity in various chemical reactions. It is a white to cream crystalline powder or chunks, indicating its solid-state physical appearance.

Uses

Used in Pharmaceutical Industry:
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows it to be a valuable building block in the synthesis of complex molecules with potential therapeutic applications.
Used in Peptide Synthesis:
In the field of peptide chemistry, this compound serves as a key component in the preparation of synthetic peptide amides. It is particularly useful for the development of kappa opioid receptor agonists, which are important for the treatment of pain, pruritis, and inflammation associated with a variety of diseases.
Used in the Synthesis of Water-Soluble Peptides:
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER is also utilized in the synthesis of cyclic α,α-disubstituted amino acids. These amino acids are crucial for the preparation of water-soluble, highly helical peptides, which have potential applications in drug design and delivery due to their unique structural and functional properties.

InChI:InChI=1/C26H30N2O6/c1-25(2,3)34-24(32)28-14-12-26(13-15-28,22(29)30)27-23(31)33-16-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-11,21H,12-16H2,1-3H3,(H,27,31)(H,29,30)/p-1

Upstream product

• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 183673-71-4 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 13625-39-3 1,3,8-triaza-spiro[4.5]decan-2,4-dione 
• 183673-70-3 tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate 
• 183673-68-9 1-tert-butyloxycarbonylpiperidine-4-spiro-5'-(1',3'-bis(tertbutyloxy-carbonyl))hydantoin 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 877273-27-3 C₃₇H₄₁N₃O₇ 
• 406235-17-4 tert-butyl 4-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-4-(hydroxymethyl)piperidine-1-carboxylate 
• 161529-14-2 (R)-3-(9H-fluoren-9-ylmethyloxycarbonylamino)-4-hydroxybutyric acid tert-butyl ester 
• 1059175-69-7 tert-butyl 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(3,5-bis(trifluoromethyl)phenylcarbamoyl)piperidine-1-carboxylate 
• 1246024-65-6 Fmoc(BocApi)2OBn 
• 1246024-63-4 Fmoc(BocApi)OBn 
• 1352083-21-6 4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-methylpiperidine-4-carboxylic acid 

Relevant articles and documents

4-Aminopiperidine-4-carboxylic acid: A cyclic α,α-disubstituted amino acid for preparation of water-soluble highly helical peptides

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Spiro compound

The invention discloses a spiro compound, application thereof and a pharmaceutical composition containing the spiro compound. The structure of the compound is shown as a formula I, and the compound has a good inhibition effect on RET kinase.

Exploration of N-(2-aminoethyl)piperidine-4-carboxamide as a potential scaffold for development of VEGFR-2, ERK-2 and Abl-1 multikinase inhibitor

VEGFR, ERK and Abl had been respectively identified as good drug targets, and their crosstalk also had been well elaborated. Multitarget drugs were more advantageous for cancer treatment, however, no inhibitors simultaneously acting on the three proteins were developed due to their structural diversities. Herein, N-(4-((2-(2-(naphthaen-1-yl)acetamido)ethyl)carbamoyl)piperidin-4-yl)-6- (trifluoromethyl)nicotinamide (NEPT, 6a) was discovered as an active scaffold against VEGFR-2, ERK-2 and Abl-1 kinases through the combination of support vector machine, similarity searching and molecular docking. NEPT and its derivatives were synthesized by convenient routine, their in vitro anti-proliferative abilities against human liver cancer cell line HepG2 were preliminarily evaluated. A representative compound 6b showed an IC50 value of 11.3 μM and induced significant HepG2 cells apoptosis. Besides, these compounds displayed better anti-proliferative abilities against K562 cells (a cell line with typical hyperactivity of the above multikinases), for example compound 6b exhibited an IC50 value of 4.5 μM. Based on hepatotoxicity case reports of Abl inhibitors, cytotoxicity of synthetic compounds against normal liver cell lines (QSG7701 and HL7702) was studied, 6b had a similar toxic effect with positive control imatinib, and most compounds showed less than 35% inhibition activities at 100 μM. Molecular docking study disclosed interactions of 6b with VEGFR-2, ERK-2 and Abl-1 kinases, respectively. Our data suggested the biological activities of 6b may derived from collaborative effects of VEGFR-2, ERK-2 and Abl-1 inhibition.