20802-15-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 5580, 1968 DOI: 10.1021/ja01022a048

InChI:InChI=1/C12H13NO2/c1-14-10-4-3-9(7-11(10)15-2)12(8-13)5-6-12/h3-4,7H,5-6H2,1-2H3

Upstream product

• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 107-04-0 1-Bromo-2-chloroethane 
• 96-49-1 [1,3]-dioxolan-2-one 

Downstream Products

• 862821-16-7 1-(3,4-dimethoxyphenyl)cyclopropanecarboxylic acid 
• 20802-16-8 1-(3,4-dimethoxyphenyl)cyclopropanecarbaldehyde 
• 862821-17-8 N-(3-(1H-imidazol-1-yl)propyl)-1-(3,4-dimethoxyphenyl)cyclopropanecarboxamide 

Relevant academic research and scientific papers

Discovery of Conformationally Restricted Human Glutaminyl Cyclase Inhibitors as Potent Anti-Alzheimer's Agents by Structure-Based Design

Alzheimer's disease (AD) is an incurable, progressive neurodegenerative disease whose pathogenesis cannot be defined by one single element but consists of various factors; thus, there is a call for alternative approaches to tackle the multifaceted aspects of AD. Among the potential alternative targets, we aim to focus on glutaminyl cyclase (QC), which reduces the toxic pyroform of β-amyloid in the brains of AD patients. On the basis of a putative active conformation of the prototype inhibitor 1, a series of N-substituted thiourea, urea, and α-substituted amide derivatives were developed. The structure-activity relationship analyses indicated that conformationally restrained inhibitors demonstrated much improved QC inhibition in vitro compared to nonrestricted analogues, and several selected compounds demonstrated desirable therapeutic activity in an AD mouse model. The conformational analysis of a representative inhibitor indicated that the inhibitor appeared to maintain the Z-E conformation at the active site, as it is critical for its potent activity.

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Inhibitors for human glutaminyl cyclase by structure based design and bioisosteric replacement

The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer's disease. The hallmark of this principle is the prevention of the formation of Aβ 3,11(pE)-40,42, as these Aβ-speci

NOVEL GENES RELATED TO GLUTAMINYL CYCLASE

Novel glutaminyl-peptide cyclotransferase-like proteins (QPCTLs), which are isoenzymes of glutaminyl cyclase (QC, EC 2.3.2.5), and to isolated nucleic acids coding for these isoenzymes, all of which are useful for the discovery of new therapeutic agents,

The first potent inhibitors for human glutaminyl cyclase: Synthesis and structure-activity relationship

The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)- 3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.

Efficient cyclopropanation of active methylene compounds. A serendipitous discovery

Cyclopropanation of active methylene compounds has been achieved in good yields with ethylene carbonate as the cyclopropanating agent in the presence of a simple base.

SUBSTITUTED UREA-OCTAHYDROINDOLS AS ANTAGONISTS OF MELANIN CONCENTRATING HORMONE RECEPTOR 1 (MCH1R)

The invention relates to compounds of the general formula (I). (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, and X are as defined in the description, or pharmaceutically acceptable salts, hydrates, geometrical isomers, racemates, tautomers, optical isomers, N-oxides and prodrug forms thereof. The compounds may be used for the treatment or prophylaxis of disorders related to the MCH1R receptor and for modulation of appetite. The invention also relates to such use as well as to pharmaceutical formulations comprising a compound of formula (I).

Substituted urea-octatydroindols as antagonists of melanin concentrating hormone receptor 1 (MCH1R)

The invention relates to compounds of the general formula (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar, and X are as defined in the description, or a pharmaceutically acceptable salt, hydrates, geometrical isomers, racemates, tautomers, optical isomers, N-oxides and prodrug forms thereof. The compounds may be used for the treatment or prophylaxis of disorders related to the MCH1R receptor and for modulation of appetite. The invention also relates to such use as well as to pharmaceutical formulations comprising a compound of formula (I).