151907-80-1

Basic information

• Product Name: (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• Synonyms: (1R,4S)-(+)-4-(BOC-AMINO)-2-CYCLOPENTENE-1-CARBOXYLIC ACID;(+)-(1R,4S)-N-T-BUTOXYCARBONYL-1-AMINOCYCLOPENT-2-ENE-4-CARBOXYLIC ACID;(1R,4S)-(-)-4-AMINOCYCLOPENT-2-ENE-1-CARBOXYLIC ACID, N-BOC PROTECTED;(1R,4S)-(-)-4-(TERT-BUTOXYCARBONYL)AMINOCYCLOPENT-2-ENE-1-CARBOXYLIC ACID;(+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENE-4-CARBOXYLIC ACID;(+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID;(+)-(1R,4S)-N-BOC-GAMMA-HOMOCYCLOLEU-2-ENE;(+)-(1S,4R)-N-BOC-1-AMINOCYCLOPENT-2-ENE-4-CARBOXYLIC ACID
• CAS NO: 151907-80-1
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• Product Categories: Unusual amino acids;Alicyclic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 151907-80-1.mol

Chemical Properties

• Melting Point: 152°C
• Boiling Point: 382.284 °C at 760 mmHg
• Flash Point: 184.999 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.18
• Vapor Pressure: 6.65E-07mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C
• PKA: 4.31±0.40(Predicted)
• BRN: 6177417
• CAS DataBase Reference: (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID(151907-80-1)
• EPA Substance Registry System: (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID(151907-80-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 151907-80-1(Hazardous Substances Data)

Usage

Chemical Properties

off-white crystalline powder

InChI:InChI=1/C11H17NO4/c1-11(2,3)16-10(15)12-8-5-4-7(6-8)9(13)14/h4-5,7-8H,6H2,1-3H3,(H,12,15)(H,13,14)/t7-,8+/m0/s1

Upstream product

• 200002-41-1 (-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate] 
• 108999-93-5 (1SR,4RS)-4-[(tert-butyloxycarbonyl)amino]cyclopent-2-enecarboxylic acid 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 134003-04-6 (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid 

Downstream Products

• 153011-43-9 (1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate 
• 625126-75-2 benzyl (1S,3R)-3-amino-1-isopropylcyclopentanecarboxylate hydrochloride 
• 625128-83-8 C₂₁H₃₁NO₄ 
• 693245-54-4 (1S,3R)-benzyl-(N-BOC-3-amino)-cyclopentanecarboxylate 
• 625098-82-0 C₂₃H₃₀F₃NO₄ 
• 765297-57-2 C₁₃H₁₇NO₂*ClH 
• 625098-85-3 C₂₃H₂₈F₃NO₄ 
• 625098-83-1 (1S,4R)-1-amino-4-benzyloxycarbonyl-cyclopent-2-ene hydrochloride 
• 625098-81-9 C₂₁H₃₁NO₃ 
• 625098-78-4 benzyl (1S,3R)-3-[(diphenylmethylene)amino]cyclopentanecarboxylate 
• 625098-84-2 C₁₈H₂₃NO₃ 
• 130931-85-0 (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 862120-91-0 C₁₈H₂₃NO₄ 
• 251326-99-5 (1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester 

Relevant articles and documents

PRODUCTION OF TRANS-4-AMINOCYCLOPENT-2-ENE-1-CARBOXYLIC ACID DERIVATIVES

Methods of producing compositions of trans-4-amino-2-cyclopentene-1-carboxylic acid derivatives are described. Also described is an amine salt of a compound having formula A, having components present in both cis and trans structures.

AMINOCYCLOPENTYL PYRIDOPYRAZINONE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of Formula I and Formula II (wherein A, E, j, k, m, n, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R15, R16, R17, R18, R19, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, X, Y and Z are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.

NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESS FOR THEIR PREPARATION

The present invention relates to novel compounds useful as dipeptidyl peptidase IV (DPP-IV) inhibitors of the formula: (I) wherein Y is -S(O)m, -CH2-, CHF, or -CF2; m is 0, 1, or 2; X is a bond, C1-C5 alkyl (e.g., -CH2-), or -C(=0)-; the dotted line [----] in the carbocyclic ring represents an optional double bond; R1 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl, substituted or unsubstituted heteroarylalkyl, CN, -COOR3, CONR3R4, -OR3, -NR3R4, or NR3COR3; R2 is hydrogen, cyano, COOH, or an isostere of a carboxylic acid (such as SO3H, CONOH, B(OH)2, PO3R3R4, SO2NR3R4, tetrazole, -COOR3, -CONR3R4, NR3COR4, or -COOCOR3).

NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS; PROCESSES FOR THEIR PREPARATION AND COMPOSITIONS THEREOF

The present invention relates to novel dipeptidyl peptidase IV (DPP-IV) inhibitors or general formula (1) useful for treating diabetes, non-insulin dependent diabetes mellitus, impaired glucose tolerance, inflammatory bowel disease, ulcerative colitis,Chron’s disease, obesity, and metabolic syndrome.

TETRAHYDROPYRANYL CYCLOPENTYL 1-SUBSTITUTED AND 1,1-DISUBSTITUTED TETRAHYDROISOQUINOLINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of Formula I: I (wherein n, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R15, R16, Y and Z are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.

Use of hydrolases for the synthesis of cyclic amino acids

The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I

AMINOCYCLOPENTYL FUSED HETEROTRICYLICAMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of formulae (I and II) (wherein A, D, E. X, l, m, n and R through R are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modul

TETRAHYDROPYRANYL CYCLOPENTYL TETRAHYDROISOQUINOLINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of the formula I: I(wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, X, n and the dashed line are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

Inhibition and substrate activity of conformationally rigid vigabatrin analogues with γ-aminobutyric acid aminotransferase

Several cyclopentene GABA analogues were synthesized as conformationally rigid analogues of the epilepsy drug vigabatrin and tested as inhibitors and substrates of γ-aminobutyric acid aminotransferase (GABA-AT). None of these compounds produced time-dependent inhibition. (1R,4S)-(+)-4-Amino-2- cyclopentene-1-carboxylic acid ((+)-3), (4R)-(-)-4-amino-1-cyclopentene-1- carboxylic acid ((-)-4), and d,l-3-amino-1-cyclopentene-1-carboxylic acid (6) are good substrates. The K(m) and k(cat) values for the latter two compounds are very similar to those of GABA, suggesting that they bind in an orientation similar to that of GABA. The K(m) value for (+)-3 is 24 times lower than that for GABA, although its k(cat) value is only one-fourth that for GABA; nonetheless, it is a better substrate for GABA-AT than is GABA. All of these compounds, as well as the enantiomers of 3 and 4 and d,l-trans-4- amino-2-cyclopentene-1-carboxylic acid (5), are competitive inhibitors of GABA-AT. These results demonstrate the effects of the carboxylate group orientation and the stereochemistry of the amino and carboxylate groups on the substrate activity and inhibitor activity, and this should be important to the future design of inhibitors of GABA-AT.

Development of the Biocatalytic Resolution of 2-azabicyclohept-5-en-3-one as an entry to Single-Enantiomer Carbocyclic Nucleosides

For the resolution of the bicyclic lactam 2-azabicyclohept-5-en-3-one, efficient whole cell biocatalysts have been identified and from these, enzymes (lactamases) have been isolated.While the two enzymes obtained act on different enantiomers of the lactam, either can be used in scaleable processes to obtain synthons for carbocyclic nucleosides having the natural configuration.