148928-15-8

Basic information

• Product Name: FMOC-ISONIPECOTIC ACID
• Synonyms: RARECHEM AR PA 0004;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-PIPERIDINE-4-CARBOXYLIC ACID;N-(9-FLUORENYLMETHOXYCARBONYL)-HEXAHYDROISONICOTINIC ACID;N-(9-FLUORENYLMETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID;N-(9-FLUORENYLMETHYLOXYCARBONYL)-PIPERIDINE-4-CARBOXYLIC ACID;N-(9-FLUORENYLMETHYLOXYCARBONYL)-ISONIPECOTIC ACID;N-ALPHA-FMOC-PIPERIDINE-4-CARBOXYLIC ACID;BUTTPARK 154\50-71
• CAS NO: 148928-15-8
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.39574
• EINECS: 2017-001-1
• Product Categories: Amino Acids
• Mol File: 148928-15-8.mol

Chemical Properties

• Melting Point: ~190 °C (dec.)
• Boiling Point: 561.624 °C at 760 mmHg
• Flash Point: 293.46 °C
• Appearance: White/Powder
• Density: 1.293
• Vapor Pressure: 1.89E-13mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• PKA: 4.54±0.20(Predicted)
• BRN: 7722550
• CAS DataBase Reference: FMOC-ISONIPECOTIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-ISONIPECOTIC ACID(148928-15-8)
• EPA Substance Registry System: FMOC-ISONIPECOTIC ACID(148928-15-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 148928-15-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
FMOC-ISONIPECOTIC ACID is used as a building block for the synthesis of anti-thrombotic peptide libraries. Its incorporation into peptide structures aids in the development of novel therapeutic agents that can help prevent blood clot formation, which is a critical factor in the treatment and management of various cardiovascular diseases.
Additionally, FMOC-ISONIPECOTIC ACID can be utilized in other applications within the pharmaceutical industry, such as the synthesis of other bioactive peptides or as a component in drug delivery systems, due to its versatile chemical properties and reactivity.

InChI:InChI=1/C21H21NO4/c23-20(24)14-9-11-22(12-10-14)21(25)26-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-8,14,19H,9-13H2,(H,23,24)

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 5984-56-5 piperidine-4-carboxylic acid hydrochloride 
• 498-94-2 isonipecotic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 905592-96-3 C₃₂H₃₈FN₇O₄ 
• 905593-01-3 C₃₃H₃₈F₃N₇O₄ 
• 905593-06-8 C₃₂H₃₉N₇O₄ 
• 905593-11-5 C₃₂H₃₈N₈O₆ 
• 1252806-71-5 5-isoxazoyl-Cha-Ile-(piperidin-3-yl)-(4-[aminomethyl]piperidin-1-yl)methanone 
• 816464-43-4 9H-fluoren-9-ylmethyl 4-[(3-amino-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridin-2-yl)carbonyl]piperidine-1-carboxylate 

Relevant articles and documents

Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture

The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.

Radical-Mediated Activation of Esters with a Copper/Selectfluor System: Synthesis of Bulky Amides and Peptides

Herein, we describe a new approach for the activation of esters via a radical-mediated process enabled by a copper/Selectfluor system. A variety of para-methoxybenzyl esters derived from bulky carboxylic acids and amino acids can be easily converted into the corresponding acyl fluorides, directly used in the one-pot synthesis of amides and peptides. As a proof of concept, this method was applied to the iterative formation of sterically hindered amide bonds.

IMIDAZOTRIAZINONE COMPOUNDS

The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9 and pharmaceutically acceptable salt thereof. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4′-dimethoxytrityl protection in the presence of trityl linkers

An N-protection protocol employing the 4,4′-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.

Diaminopropionic acid derivatives

A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.

A Constrained Diketopiperazine as a New Scaffold for the Synthesis of Peptidomimetics

As a new scaffold for peptidomimetic synthesis, a highly constrained bifunctional diketopiperazine, 4, has been prepared by smooth N-alkylation with tert-butyl bromoacetate. As a first application, we describe herein the synthesis of new peptidomimetics of the Arg-Gly-Asp (RGD) sequence. The product 30, which shows a selective platelet-aggregation inhibiting activity, can be used as a lead for the preparation of more potent products.

DNA-binding ligands from peptide libraries containing unnatural amino acids

An unnatural peptide-based library, bound on a solid support, was screened for double-stranded-DNA (dsDNA)-binding ligands. For this purpose, fluorescein and rhodamine were used to label the single-stranded oigodeoxynucleotides. Beads containing products with affinity to dsDNA turned red in visible light and fluoresced yellow in UV light. A similar technique can be used for the selection of ligands which bind to a hairpin RNA, using a monolabelled oligoribonucleotide. The screening process revealed a high structure-affinity relationship in the successful products. Only six out of the twelve unnatural amino acids were selected, with the repeated appearance of AlaU, Sar and the secondary amino acids (Hyp, Inp). The affinity and selectivity for the target was determined using a DNase I protection assay.

Low molecular weight peptidomimetic growth hormone secretagogues

The present invention comprises growth hormone releasing peptides/peptidomimetics (GHRP) capable of causing release of growth hormone from the pituitary. Compositions containing the GHRP's of this invention are used to promote growth in mammals either alone or in combination with other growth promoting compounds, especially IGF-1. In a method of this invention GHRP's in combination with IGF-1 are used to treat Type II diabetes. An exemplary compound of this invention is provided below. STR1