39629-88-4

Usage

Uses

1-(4-Hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

InChI:InChI=1/C11H11NO4/c13-9-3-1-8(2-4-9)12-6-7(11(15)16)5-10(12)14/h1-4,7,13H,5-6H2,(H,15,16)/p-1/t7-/m1/s1

Upstream product

• 97-65-4 2-methylenesuccinic acid 
• 123-30-8 4-amino-phenol 
• 75-03-6 ethyl iodide 
• 133748-30-8 methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate 

Downstream Products

• 133748-30-8 methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate 
• 847985-99-3 (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester 
• 133748-40-0 Methyl 4-[1-(4-benzyloxyphenyl)-2-pyrrolidon-4-yl]methoxybenzoate 
• 133748-36-4 Methyl 4-[1-(4-n-propoxyphenyl)-2-pyrrolidon-4-yl]methoxybenzoate 
• 133748-38-6 Methyl 4-[1-(4-isopropoxyphenyl)-2-pyrrolidon-4-yl]methoxybenzoate 
• 133748-33-1 Methyl 4-[1-(4-ethoxyphenyl)-2-pyrrolidon-4-yl]methoxybenzoate 
• 1026175-84-7 Methanesulfonic acid 1-(4-benzyloxy-phenyl)-5-oxo-pyrrolidin-3-ylmethyl ester 
• 133749-63-0 methyl 4-<1-(4-hydroxyphenyl)-2-oxo-pyrrolidin-4-yl>-methyloxybenzoate 
• 1026256-96-1 Methanesulfonic acid 5-oxo-1-(4-propoxy-phenyl)-pyrrolidin-3-ylmethyl ester 
• 1026434-94-5 Methanesulfonic acid 1-(4-ethoxy-phenyl)-5-oxo-pyrrolidin-3-ylmethyl ester 
• 133748-39-7 methyl 1-(4-benzyloxyphenyl)-5-oxo-3-pyrrolidinecarboxylate 
• 73422-75-0 1-(4-Benzyloxyphenyl)-4-hydroxymethyl-2-pyrrolidone 
• 1027063-61-1 Methanesulfonic acid 1-(4-isopropoxy-phenyl)-5-oxo-pyrrolidin-3-ylmethyl ester 
• 133748-37-5 methyl 1-(4-isopropoxyphenyl)-5-oxo-3-pyrrolidinecarboxylate 

Relevant academic research and scientific papers

Analgesic and anticancer activity of benzoxazole clubbed 2-pyrrolidinones as novel inhibitors of monoacylglycerol lipase

Ten benzoxazole clubbed 2-pyrrolidinones (11–20) as human monoacylglycerol lipase inhibitors were designed on the criteria fulfilling the structural requirements and on the basis of previously reported inhibitors. The designed, synthesized, and characterized compounds (11–20) were screened against monoacylglycerol lipase (MAGL) in order to find potential inhibitors. Compounds 19 (4-NO2 derivative) and 20 (4-SO2 NH2 derivative), with an IC50 value of 8.4 and 7.6 nM, were found most active, respectively. Both of them showed micromolar potency (IC50 value above 50 μM) against a close analogue, fatty acid amide hydrolase (FAAH), therefore considered as selective inhibitors of MAGL. Molecular docking studies of compounds 19 and 20 revealed that carbonyl of 2-pyrrolidinone moiety sited at the oxyanion hole of catalytic site of the enzyme stabilized with three hydrogen bonds (~2 ?) with Ala51, Met123, and Ser122, the amino acid residues responsible for the catalytic function of the enzyme. Remarkably, the physiochemical and pharmacokinetic properties of compounds 19 and 20, computed by QikProp, were found to be in the qualifying range as per the proposed guideline for good orally bioactive CNS drugs. In formalin-induced nociception test, compound 20 reduced the pain response in acute and late stages in a dose-dependent manner. They significantly demonstrated the reduction in pain response, having better potency than the positive control gabapentin (GBP), at 30 mg/kg dose. Compounds 19 and 20 were submitted to NCI, USA, for anticancer activity screening. Compounds 19 (NSC: 778839) and 20 (NSC: 778842) were found to have good anticancer activity on SNB-75 cell line of CNS cancer, exhibiting 35.49 and 31.88% growth inhibition (% GI), respectively.

Pyrrolidin-2-one linked benzofused heterocycles as novel small molecule monoacylglycerol lipase inhibitors and antinociceptive agents

Eighteen pyrrolidin-2-one linked benzothiazole, and benzimidazole derivatives (10–27) were designed and synthesized. The structure of the compounds was confirmed by elemental and spectral (IR, 1H-NMR and MS) data analysis. All the compounds wer

Synthesis of a novel and potent small-molecule antagonist of PAC1 receptor for the treatment of neuropathic pain

We recently identified novel small-molecule antagonists of the PACAP type I (PAC1) receptor using docking-based in silico screening followed by in vitro/vivo pharmacological assays. In the present study, we synthesized 18 novel derivatives based on the structure of PA-9, a recently developed antagonist of the PAC1 receptor, with a view to obtain a panel of compounds with more potent antagonistic and analgesic activities. Among them, compound 3d showed improved antagonistic activities. Intrathecal injection of 3d inhibited both pituitary adenylate cyclase-activating polypeptide (PACAP) and spinal nerve ligation-induced mechanical allodynia. The effects were more potent than PA-9. Compound 3d also showed anti-allodynic effects following oral administration. Hence, our results suggest that 3d may become an orally available analgesic in the treatment of the neuropathic pain.

PYRROLIDONE DERIVATIVES AS MAOB INHIBITORS

Racemic or enantiomerically pure 4-pyrrolidino derivatives of the formula (I), processes for their preparation, pharmaceutical compositions comprising said derivatives, and their use in the prevention and treatment of a disease which is mediated by a mono

Synthesis of 4-methyloxybenzoic acids and related compounds, and their inhibitory capacities toward fatty-acid and sterol biosynthesis

The synthesis of a series of 4-methyloxybenzoic acids and related compounds, and their evaluation for inhibitory capacity toward fatty-acid and sterol biosyntheses using rats' liver slices in vitro and rabbits

Phenylcarboxylic acid derivatives having hetero ring

Phenylcarboxylic acid derivatives having a hetero ring in the substituent of the formula: STR1 wherein R1 is halogen, alkyl, cycloalkyl, hydroxy, alkoxy, phenoxy which has a substituent selected from halogen and alkyl, carboxyl, alkylsulfonyloxy, phenylsulfonyloxy optionally substituted by halogen, alkylsulfonyloxyalkoxy, amino, alkanoylamino, benzoylamino, alkenyloxy, phenylalkoxyalkoxy, hydroxyalkoxy, phenylalkoxy having optionally 1 to 3 substituents selected from halogen, alkyl and alkoxy, halogenoalkyl, cycloalkyloxy optionally substituted by hydroxy, alkoxy substituted by cycloalkyl having optionally hydroxy substituent, imidazolylalkyl or imidazolylalkoxy; k is 0 or 1 to 3; or (R1)k is alkylenedioxy; A is alkylene or alkylenoxy; l is 0 or 1; B is methylene or carbonyl; m is 0 or 1; D is alkylene; E is alkylene or alkenylene; n is 0 or 1; and R2 is hydrogen or alkyl, or a salt thereof, which have fatty acid synthesis-inhibitory activity, cholesterol synthesis-inhibitory activity and are useful as antilipidemic agent, prophylactic and treating agent of arteriosclerosis, prophylactic and treating agent of obesity, antidiabetics.