166591-85-1

Basic information

• Product Name: 2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID
• Synonyms: 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;REF DUPL: 2-N-Boc-1,2,3,4-Tetrahydro-isoquinoline-1-carboxylic acid;2-Boc-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid;N-Boc-1,2,3,4-Tetrahydro-isoquinoline-1-carboxylic acid;MG 310;3,4-Dihydro-1,2(1H)-isoquinolinedicarboxylic acid 2-(1,1-dimethylethyl) ester
• CAS NO: 166591-85-1
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.318
• Mol File: 166591-85-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 436.7 °C at 760 mmHg
• Flash Point: 217.9 °C
• Appearance: /
• Density: 1.222 g/cm³
• Vapor Pressure: 2.12E-08mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• PKA: 3.49±0.20(Predicted)
• CAS DataBase Reference: 2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID(166591-85-1)
• EPA Substance Registry System: 2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID(166591-85-1)

Safety Data

• Hazardous Substances Data: 166591-85-1(Hazardous Substances Data)

Usage

General Description

2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID is a chemical compound with a BOC-protected amino acid group attached to a tetrahydroisoquinoline ring. It is commonly used in the synthesis of peptides and pharmaceutical compounds. The BOC group provides protection for the amine functionality, allowing for selective reactions at other sites on the molecule. The tetrahydroisoquinoline ring is a versatile scaffold that can be functionalized in a variety of ways, making this compound useful for the development of new drug candidates and chemical probes. Its unique structure and reactivity make it a valuable building block in organic synthesis and medicinal chemistry.

InChI:InChI=1/C15H19NO4/c1-15(2,3)20-14(19)16-9-8-10-6-4-5-7-11(10)12(16)13(17)18/h4-7,12H,8-9H2,1-3H3,(H,17,18)

Upstream product

• 486-73-7 1-isoquinolinecarboxylic acid 
• 124-38-9 carbon dioxide 
• 1359987-43-1 O-tert-butyl 1-(tributylstannyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 41034-52-0 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1359987-62-4 2-(tert-butyl) 1-methyl 3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate 
• 1239902-84-1 C₂₅H₃₂BrN₃O₄ 
• 439287-50-0 1-(2,6-dimethyl-phenylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

PHENOXYETHYL CYCLIC AMINE DERIVATIVES AND THEIR ACTIVITY AS EP4 RECEPTOR MODULATORS

The present invention provides a compound of the Formula (I): wherein X, R, R1,R2,R3, R4,R5,R6, R7, R8, and R9 are as defined herein, or a pharmaceutically acceptable salt thereof.

Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(α-methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the α-methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg-1, TD50 = 36.4 mg kg-1, PI = 6.3). Replacement of the piperidine ring of 1 by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man.

Highly selective tripeptide thrombin inhibitors

Tripeptide aldehydes such as Boc-D-Phe-Pro-Arg-H (5l) exhibit potent direct inhibition of thrombin. This distinction offers important insight for the design of more potent and selective serine protease inhibitors which may be useful pharmacological tools and hold promise for development of clinically useful agents. The structure-activity relationships (SAR) on a series of anticoagulant peptides with high selectivity for the enzyme thrombin are discussed. The SAR is centered on a series of di- and tripeptide arginine aldehydes based on the structure of 5l. The structural and conformational role of the amino acid residue in position 1 was investigated by substitution with conformationally restricted aromatic amino acids, aromatic acids, and a dipeptide isostere containing the ψ[CH2N] amide bond replacement. Many of these peptides demonstrate potent antithrombotic activity along with selectivity toward thrombin, determined by comparison of in vitro inhibitory effects on trypsin, plasmin, factor Xa, and tissue plasminogen activator. Compound 5f, D-1-Tiq-Pro-Arg-H · sulfate is highly active and the most selective tripeptide aldehyde inhibitor of thrombin reported to date.