51971-46-1

Usage

Uses

Used in Pharmaceutical Industry:
1-(1,3-dioxoisoindol-2-yl)cyclopentane-1-carboxylic acid is used as a therapeutic agent for neurological disorders due to its ability to modulate the activity of certain enzymes and receptors in the central nervous system. It has been studied for its potential in treating Alzheimer's disease and schizophrenia.
Used in Research and Development:
CPI is used as a research compound to further understand its pharmacological properties and potential applications in the treatment of various neurological disorders. This includes exploring its interactions with biological macromolecules and its effects on enzyme and receptor activities in the central nervous system.

InChI:InChI=1/C14H13NO4/c16-11-9-5-1-2-6-10(9)12(17)15(11)14(13(18)19)7-3-4-8-14/h1-2,5-6H,3-4,7-8H2,(H,18,19)

Upstream product

• 4414-88-4 1H-benzimidazol-2-acetonitrile 
• 51972-37-3 1-phthalimido-cyclopentanecarbonyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 85-44-9 phthalic anhydride 
• 52-52-8 1-amino-1-cyclopentanecarboxylic acid 

Downstream Products

• 862306-54-5 {[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclopentanecarbonyl]-methyl-amino}-phenyl-acetic acid benzyl ester 
• 862306-53-4 {[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclopentanecarbonyl]-methyl-amino}-phenyl-acetic acid methyl ester 

Relevant academic research and scientific papers

General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C?H Bond Lactonization

α-Amino acids represent a valuable class of natural products employed as building blocks in biological and chemical synthesis. Because of the limited number of natural amino acids available, and of their widespread application in proteomics, diagnosis, drug delivery and catalysis, there is an increasing demand for the development of procedures for the preparation of modified analogues. Herein, we show that the use of bioinspired manganese catalysts and H2O2 under mild conditions, provides access to modified α-amino acids via γ-C?H bond lactonization. The system can efficiently target 1°, 2° and 3° γ-C?H bonds of α-substituted and achiral α,α-disubstituted α-amino acids with outstanding site-selectivity, good to excellent diastereoselectivity and (where applicable) enantioselectivity. This methodology may be considered alternative to well-established organometallic procedures.

Development of modifiable bidentate amino oxazoline directing group for Pd-catalyzed arylation of secondary C-H bonds

Abstract A novel bidentate α-amino oxazolinyl directing group has been developed. Different from previous directing groups, this newly designed directing group was easily prepared from amino acids and modified in structure. This auxiliary preferentially effects functionalization at secondary C(sp3)-H bonds, rather than at aryl C(sp2)-H bonds. The diastereoselectivity of direct arylation between geminal secondary C(sp3)-H bonds in linear molecules has also been realized for the first time with a chiral directing group by remote chirality relay. Two diastereoisomers are produced with the same chiral source by changing the substituents of substrates and aryl halides. A new direction: A multifunctional amino oxazoline directing group that is readily available from amino acids, has been developed, which can induce chemo-, regio- and diastereoselectivity in secondary C(sp3)-H arylation reactions. Furthermore, this directing group is removable and modifiable. Steric control and counterions play important roles in the relayed chirality transfer.

Cyclic α-amino acids as precursors for synthesis of 2-amino-3-hetarylpyrrolin-4-ones and their spiro derivatives

α-Aminoisobutanoic acid and some representatives of cyclic α-amino acids were converted to corresponding 1-phthalimido- and N-trifluoroacylated acid chlorides. Treatment of 2-(1H-benzimidazol-2-yl) acetonitrile with 1-phthalimidoacid chlorides in DMF unexpectedly gave 2-(1H-benzimidazol-2-yl)-3-(dimethylamino)-2-propenenitrile. On the other hand, the reaction of hetarylacetonitriles with N-trifluoroacylated acid chlorides gave the desired (3-cyano-2-oxo-3-hetarylpropyl)-2,2,2-trifluoroacetamides that upon detrifluoroacetylation provided the target 2-amino-3-hetarylpyrrolin-4- ones. The acylation of benzoimidazolylamino-pyrrolinones by benzoyl chloride leads to formation of 3-benzoyl-2,3-dihydro-5-phenyl-1H-benzo[4,5]imidazo[1,2-c] pyrrolo[3,2-e]pyrimidin-1-ones. Springer-Verlag 2012.

Enantioselective and diastereoselective synthesis of fluorinated dipeptides by late electrophilic fluorination

A series of optically enriched monofluorinated dipeptides incorporating an α-fluoro-α-amino acid were prepared by enantio- and diastereoselective electrophilic fluorination. This previously unsuccessful approach to fluorinated dipeptides can now be achieved with up to 73:27 enantiomeric ratio and high >98:2 diastereomeric ratio.

Phthalimide derivatives and their use as plant growth regulants

The invention is a novel class of phthalimido derivatives represented by a formula: SPC1 Or SPC2 Wherein W is hydrogen or alkyl C1 -C4 ; X and X' each represent hydrogen, halogen, alkyl C1 -C4, CF3, alkoxy(C1 -C4), benzyloxy, di(C1 -C4)alkylamino, C1 -C4 alkylthio, hydroxy, C1 -C4 alkylsulfonyl, alkanoylamino C1 -C4 or nitro; Y is --COOR3, --CONHR8, --CONR3 R4, --CONHN(R5)2, --CONHN+(R6)3 . halide-, --CN or --COR7 with the proviso that at least one of X and X' is a substituent other than hydrogen; R1 and R2 each represent alkyl C1 -C4 or when taken together with the carbon to which they are attached form cycloalkyl C4 -C11 optionally substituted with methyl; R3 and R4 each represent hydrogen or alkyl C1 -C4 ; R5 and R6 each represent alkyl C1 -C2 ; R7 is halogen and R8 is --CH3 or SPC3 Where Z and Z' are hydrogen, alkyl C1 -C2, halogen, --CF3 or --OCH3, is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring and a method for regulating the growth of plants with these compounds and with compounds having the above structure wherein X and X' each represent hydrogen.